WO2019190231A1 - Polycyclic compound and organic light emitting diode comprising same - Google Patents
Polycyclic compound and organic light emitting diode comprising same Download PDFInfo
- Publication number
- WO2019190231A1 WO2019190231A1 PCT/KR2019/003653 KR2019003653W WO2019190231A1 WO 2019190231 A1 WO2019190231 A1 WO 2019190231A1 KR 2019003653 W KR2019003653 W KR 2019003653W WO 2019190231 A1 WO2019190231 A1 WO 2019190231A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- substituted
- unsubstituted
- compound
- layer
- Prior art date
Links
- -1 Polycyclic compound Chemical class 0.000 title claims description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 239000000126 substance Substances 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 238000002347 injection Methods 0.000 claims description 41
- 239000007924 injection Substances 0.000 claims description 41
- 239000011368 organic material Substances 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000003277 amino group Chemical group 0.000 claims description 23
- 230000001629 suppression Effects 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000005264 aryl amine group Chemical group 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 150000003974 aralkylamines Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 6
- 125000005377 alkyl thioxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000005165 aryl thioxy group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000005462 imide group Chemical group 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 156
- 239000000463 material Substances 0.000 description 50
- 238000002360 preparation method Methods 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 125000004432 carbon atom Chemical group C* 0.000 description 37
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 27
- 239000008096 xylene Substances 0.000 description 27
- 230000005525 hole transport Effects 0.000 description 16
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 16
- 0 CCCC(CC)C(*C(C)CC*C)C1(C)*(C)(CCC)C*C*1 Chemical compound CCCC(CC)C(*C(C)CC*C)C1(C)*(C)(CCC)C*C*1 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 10
- 125000002950 monocyclic group Chemical group 0.000 description 9
- 125000003367 polycyclic group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 125000005241 heteroarylamino group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004957 naphthylene group Chemical group 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical group C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000006616 biphenylamine group Chemical group 0.000 description 2
- 150000001716 carbazoles Chemical group 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 150000002987 phenanthrenes Chemical group 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- NTYDMFCZXBCEJY-UHFFFAOYSA-N 1-methyl-2-phenylcyclohexa-2,4-dien-1-amine Chemical group CC1(N)CC=CC=C1C1=CC=CC=C1 NTYDMFCZXBCEJY-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 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 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical group CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- MQFYUZCANYLWEI-UHFFFAOYSA-N 4-methylnaphthalen-1-amine Chemical group C1=CC=C2C(C)=CC=C(N)C2=C1 MQFYUZCANYLWEI-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FEEFPEROKIVZHH-CLTKARDFSA-N C=C/C=C\C1C=CC=CC1 Chemical compound C=C/C=C\C1C=CC=CC1 FEEFPEROKIVZHH-CLTKARDFSA-N 0.000 description 1
- RIZHFYOKLDMFJD-UHFFFAOYSA-N CC(C1C=CC=CC1)/N=C(/C1C=CC2c(cccc3)c3SC2C1)\N Chemical compound CC(C1C=CC=CC1)/N=C(/C1C=CC2c(cccc3)c3SC2C1)\N RIZHFYOKLDMFJD-UHFFFAOYSA-N 0.000 description 1
- JMOGURRYIHVGFC-XYKNRCHWSA-N CC[C@@H]1C(C2C=CC=CC2)=NC(NC2=CC=CCC2C2C(SC(C34)C=Cc5c3c(cccc3)c3cc5)=C4C=CC2)NC1C(C=CC1)=CC1c1ccccc1 Chemical compound CC[C@@H]1C(C2C=CC=CC2)=NC(NC2=CC=CCC2C2C(SC(C34)C=Cc5c3c(cccc3)c3cc5)=C4C=CC2)NC1C(C=CC1)=CC1c1ccccc1 JMOGURRYIHVGFC-XYKNRCHWSA-N 0.000 description 1
- FVZANSVZWKUYPH-ZPBILBBLSA-N CC[C@@H]1C(C2C=CC=CC2)NC(N(C2CC=CCC2)C2C=CC3c(c4c(cc5)ccc6c4C=CCC6)c5OC3C2)=N[C@@H]1Cc1cc(C2C=CC=CC2)ccc1 Chemical compound CC[C@@H]1C(C2C=CC=CC2)NC(N(C2CC=CCC2)C2C=CC3c(c4c(cc5)ccc6c4C=CCC6)c5OC3C2)=N[C@@H]1Cc1cc(C2C=CC=CC2)ccc1 FVZANSVZWKUYPH-ZPBILBBLSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NFTRAGGUIJBGHD-UHFFFAOYSA-N N-(9H-fluoren-1-yl)phenanthren-1-amine Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC1=2)NC1=CC=CC=2C3=CC=CC=C3CC1=2 NFTRAGGUIJBGHD-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- ACYWVHCCUGTDEW-UHFFFAOYSA-N N-naphthalen-1-yl-9H-fluoren-1-amine Chemical group C1(=CC=CC2=CC=CC=C12)NC1=CC=CC=2C3=CC=CC=C3CC12 ACYWVHCCUGTDEW-UHFFFAOYSA-N 0.000 description 1
- WJOZUXJBWJTHQQ-UHFFFAOYSA-N N-phenyl-2-(2-phenylphenyl)aniline Chemical group C1(=CC=CC=C1)NC=1C(=CC=CC=1)C=1C(=CC=CC=1)C1=CC=CC=C1 WJOZUXJBWJTHQQ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- YUFCQKOQQSONJN-UHFFFAOYSA-N c(cc1)ccc1-[n]1c(ccc(-[n]2c3ccc(c(cccc4)c4[s]4)c4c3c3c2cccc3)c2)c2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c(ccc(-[n]2c3ccc(c(cccc4)c4[s]4)c4c3c3c2cccc3)c2)c2c2ccccc12 YUFCQKOQQSONJN-UHFFFAOYSA-N 0.000 description 1
- YYCLYVREFDXAJO-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-[n]1c2ccc(c3c(cccc4)c4ccc3[o]3)c3c2c2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-[n]1c2ccc(c3c(cccc4)c4ccc3[o]3)c3c2c2c1cccc2 YYCLYVREFDXAJO-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 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 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NJVSFOMTEFOHMI-UHFFFAOYSA-N n,2-diphenylaniline Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1NC1=CC=CC=C1 NJVSFOMTEFOHMI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HCISEFFYVMEPNF-UHFFFAOYSA-N n-phenyl-9h-fluoren-1-amine Chemical group C=12CC3=CC=CC=C3C2=CC=CC=1NC1=CC=CC=C1 HCISEFFYVMEPNF-UHFFFAOYSA-N 0.000 description 1
- UMGBMWFOGBJCJA-UHFFFAOYSA-N n-phenylphenanthren-1-amine Chemical group C=1C=CC(C2=CC=CC=C2C=C2)=C2C=1NC1=CC=CC=C1 UMGBMWFOGBJCJA-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 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 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical compound N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
Definitions
- the present specification relates to a polycyclic compound and an organic light emitting device including the same.
- an organic light emitting device is a light emitting device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and the organic semiconductor material.
- the organic light emitting device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting element of the form.
- the second is a light emitting device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
- organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
- organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
- Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
- the luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color.
- a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
- the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light.
- the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
- a material forming the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
- a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
- An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
- X is O or S
- L1 and L2 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
- Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substitute
- a is an integer of 0 to 4,
- the first electrode A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
- the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
- the compound according to at least one embodiment may improve the lifespan and / or in the organic light emitting device.
- the compounds described herein can be used as the material of the hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer.
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
- FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 9, a light emitting layer 7, a hole blocking layer 10, an electron injection and transport layer ( 11) and an example of the organic light-emitting device consisting of the cathode 4 are shown.
- the present specification provides a compound represented by the following Formula 1.
- the compound represented by the following formula (1) is used in the organic material layer of the organic light emitting device, the efficiency of the organic light emitting device is always.
- X is O or S
- L1 and L2 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
- Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substitute
- a is an integer of 0 to 4,
- substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.
- substituted or unsubstituted is deuterium; Halogen group; Cyano group; An alkyl group; Cycloalkyl group; Arylamine group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents.
- a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
- examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
- carbon number of an ester group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
- carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
- the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
- the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
- alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-jade Although there exist a tilt group etc., it is not limited to these.
- the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
- the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
- the present invention is not limited thereto.
- the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
- the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
- the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.
- the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
- Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
- Diphenylamine group N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine Groups, N-phenanthrenylfluorenylamine groups, N-biphenylfluorenylamine groups, and the like, but are not limited thereto.
- the N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.
- the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.
- the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N in the amine group.
- examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
- the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
- the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
- arylamine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine Groups, 9-methyl-anthracenylamine groups, diphenyl amine groups, phenyl naphthyl amine groups, biphenyl phenyl amine groups, and the like, but are not limited thereto.
- the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
- the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
- the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
- the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
- Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group).
- the present invention is not limited thereto.
- the aryl group in the alkylaryl group, the aryloxy group, the arylthioxy group, the aryl sulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, and the arylamine group has a description regarding the aforementioned aryl group. Can be applied.
- the alkyl group of the alkylaryl group, the alkylthioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkylamine group, the alkylamine group, and the N-alkylheteroarylamine group may be applied to the description of the aforementioned alkyl group.
- Alkyl thioxy groups include methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thioxy group and the like, and alkyl sulfoxy groups include mesyl, ethyl sulfoxy, propyl sulfoxy and butyl sulfoxy groups.
- the present invention is not limited thereto.
- the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
- the heterocyclic group include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, and the like. It is not limited only to.
- heterocyclic group may be applied except that the heteroaryl group is aromatic.
- heteroaryl group the heteroaryl group of the heteroarylamine group, the description of the aforementioned heterocyclic group may be applied.
- adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted.
- two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
- ring in a substituted or unsubstituted ring in which adjacent groups are bonded to each other, a “ring” means a hydrocarbon ring; Or heterocycle.
- the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.
- the description of the aryl group may be applied except that the aromatic hydrocarbon ring is monovalent.
- the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of N, O, P, S, Si, Se, and the like. can do.
- the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
- X is O or S.
- L1 and L2 are each independently, a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.
- L1 and L2 are each independently, a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
- L1 and L2 are each independently, a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
- L1 and L2 are each independently a substituted or unsubstituted arylene group, it may be any one selected from the following structures.
- A1 and A2 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
- L1 and L2 are each independently a substituted or unsubstituted divalent heterocyclic group, it may be any one selected from the following structures.
- Y1 to Y5 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
- Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted or unsubstituted al
- Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted
- Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted diaryl phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
- Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C60 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 60 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
- Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C30 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 30 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
- Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C20 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 20 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 20 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms containing at least one N.
- Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrene group, Substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazole group, substituted or unsubstituted A substituted amine group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, or a substituted or unsubstituted phosphine oxide
- Ar1 and Ar2 are each independently a phenyl group; Naphthylene group; Biphenyl group; Phenanthrene group; Triphenylene group; A fluorenyl group substituted with a substituent selected from the group consisting of a methyl group and a phenyl group; Dibenzofuran group; Dibenzothiophene group; Carbazole groups unsubstituted or substituted with a phenyl group; A substituted or unsubstituted amine group selected from the group consisting of a phenyl group, a biphenyl group, a naphthylene group and a fluorenyl group substituted with a methyl group; A pyridine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubstituted or substituted with a phenyl group; Triazine group unsubstituted or substituted with a phenyl group;
- Ar1 and Ar2 may be any one selected from the following structures.
- Formula 1 is represented by the following formula (2).
- Chemical Formula 1 is represented by the following Chemical Formula 3 or 4.
- Chemical Formula 1 may be represented by any one of the following structures.
- Compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the production method described below.
- the compound of Formula 1 may be prepared in the core structure as shown in Schemes A to F.
- Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
- the conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
- a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
- the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
- the compound which has the intrinsic property of the introduced substituent can be synthesize
- a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material and the hole suppression layer material used in the manufacture of the organic light emitting device into the core structure to synthesize a material satisfying the requirements of each organic material layer can do.
- the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
- the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
- the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
- the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
- the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole suppression layer, an electron injection layer and the like as an organic material layer.
- the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
- the organic material layer may include an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer may include a compound represented by the formula (1).
- the organic material layer may include a hole injection layer or a hole transport layer
- the hole injection layer or hole transport layer may include a compound represented by the formula (1).
- the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
- the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a dopant of the light emitting layer.
- the organic material layer may include an electron suppression layer, and the electron suppression layer may include a compound represented by Chemical Formula 1.
- the organic material layer may include a hole blocking layer, and the hole blocking layer may include a compound represented by Chemical Formula 1.
- the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds. May be included as the dopant.
- the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant. have.
- the first electrode is an anode
- the second electrode is a cathode
- the first electrode is a cathode and the second electrode is an anode.
- the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
- FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
- the compound may be included in the light emitting layer (3).
- FIG. 2 illustrates an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1.
- the structure is illustrated.
- the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, or the electron transport layer 8.
- the compound is the hole injection layer 5, electron suppression layer 9, light emitting layer 7 or hole blocking It may be included in layer 10.
- the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, an electron suppression layer, a light emitting layer and a hole suppression layer thereon, and then depositing a material that can be used as a cathode thereon.
- PVD metal vapor deposition
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the organic material layer may have a multilayer structure including a hole injection layer, an electron suppression layer, a light emitting layer, a hole suppression layer, and the like, but is not limited thereto and may have a single layer structure.
- the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
- the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
- the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
- the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
- the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
- the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
- a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
- Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
- the emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material.
- the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the electron suppression layer and the hole suppression layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
- Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
- Alq 3 8-hydroxyquinoline aluminum complex
- Carbazole series compounds Dimerized styryl compounds
- BAlq 10-hydroxybenzoquinoline-metal compound
- Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
- the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
- the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- Iridium complex used as the dopant of the light emitting layer is as follows, but is not limited thereto.
- the electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer.
- a material having high mobility to electrons is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
- the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
- a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
- ITO indium tin oxide
- Fischer Co. was used as a detergent
- distilled water was filtered secondly as a filter of Millipore Co. as a distilled water.
- ultrasonic washing was performed twice with distilled water for 10 minutes.
- ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
- the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
- the compound of the following compound HI1 and the following compound HI2 was thermally vacuum deposited to a thickness of 100 kPa so that the ratio of 98: 2 (molar ratio) was formed on the ITO transparent electrode as the anode thus prepared, thereby forming a hole injection layer.
- Compound (1150.) Represented by the following formula HT1 was vacuum deposited on the hole injection layer to form a hole transport layer.
- the compound of Preparation Example 1 was vacuum deposited on the hole transport layer with a film thickness of 50 kV to form an electron suppressing layer.
- the light emitting layer was formed by vacuum depositing the compound represented by the following formula BH and the compound represented by the following formula BD at a weight ratio of 50: 1 on the electron suppressing layer with a film thickness of 200 kPa.
- a hole blocking layer was formed by vacuum depositing a compound represented by the following formula HB1 with a film thickness of 50 kPa on the light emitting layer.
- the compound represented by the following formula ET1 and the compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1: 1 on the hole blocking layer to form an electron injection and transport layer having a thickness of 30 kPa.
- Lithium fluoride (LiF) and aluminum were deposited on the electron injection and transport layer sequentially to a thickness of 12 ⁇ and 1,000 ⁇ to form a cathode.
- the deposition rate of the organic material was maintained at 0.4 to 0.7 ⁇ / sec
- the lithium fluoride of the cathode was maintained at 0.3 ⁇ / sec
- the aluminum was maintained at a deposition rate of 2 ⁇ / sec.
- An organic light-emitting device was manufactured by maintaining ⁇ 7 to 5 ⁇ 10 ⁇ 6 torr.
- An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1.
- An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1.
- the compounds of EB2 and EB3 used in Table 1 below are as follows.
- T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).
- Example 1-1 Preparation Example 1 4.20 6.55 (0.144, 0.045) 240
- Example 1-2 Preparation Example 2 4.11 6.55 (0.142, 0.045) 275
- Example 1-3 Preparation Example 5 4.25 6.44 (0.143, 0.046) 265
- Example 1-4 Preparation Example 7 4.27 6.55 (0.144, 0.045) 250
- Example 1-5 Preparation Example 8
- Example 1-6 Preparation Example 9 4.38 6.57 (0.144, 0.047) 250
- Example 1-7 Preparation Example 13 4.37 6.59 (0.143, 0.046) 265
- Example 1-8 Preparation Example 14 4.36 6.44 (0.144, 0.045) 240 Comparative Example 1-1 EB2 5.02 5.73 (0.142, 0.047) 180 Comparative Example 1-2
- the organic light emitting device using the compound of the present invention as an electron suppressing layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
- Examples 1-1 to 1-8 When phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and arylamines and p-type substituents such as dibenzofuran, dibenzothiophene, and carbazole were used as the electron suppression layer, they showed low voltage, high efficiency, and long life.
- phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and arylamines and p-type substituents such as dibenzofuran, dibenzothiophene, and carbazole were used as the electron suppression layer, they showed low voltage, high efficiency, and long life.
- phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and arylamines and p-type substituents such
- the compound according to the present invention was confirmed that the excellent electron blocking ability can be applied to the organic light emitting device.
- An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the EB1 compound as an electron suppression layer instead of the compound of Preparation Example 1, and using the compound shown in Table 2 below instead of HB1.
- An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the EB1 compound was used as an electron suppression layer instead of the compound of Preparation Example 1, and the following HB2 and HB3 compounds were used as hole blocking layers instead of HB1. It was.
- the compounds of HB2 and HB3 used in Table 2 below are as follows.
- T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).
- Example 2-1 Preparation Example 3 3.51 6.31 (0.143, 0.047) 265
- Example 2-2 Preparation Example 4 3.54 6.25 (0.144, 0.046) 270
- Example 2-3 Preparation Example 6 3.58 6.43 (0.143, 0.045) 280
- Example 2-4 Preparation Example 10 3.53 6.42 (0.144, 0.046) 285
- Example 2-5 Preparation Example 11 3.58 6.46 (0.145, 0.045) 270
- Example 2-6 Preparation Example 12 3.63 6.43 (0.144, 0.046) 265
- Example 2-7 Preparation Example 15 3.63 6.42 (0.143, 0.045) 285 Comparative Example 2-1 HB2 4.17 5.72 (0.139, 0.041) 130 Comparative Example 2-2 HB3 3.95 6.03 (0.141, 0.042) 205
- the organic light emitting device using the compound of the present invention as a hole suppression layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
- Examples 2-1 to 2-7 when phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and a substance linked with n-type substituents of cyanopyrimidine, triazine, pyrimidine, quinazoline and phosphine oxide was used as the electron suppressing layer, It can be seen that the characteristics of low voltage, high efficiency, and long life is shown.
- the compound according to the present invention has excellent hole blocking ability and can be applied to an organic light emitting device.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present specification provides a compound of chemical formula 1 and an organic light emitting diode comprising same.
Description
본 발명은 2018년 03월 28일에 한국특허청에 제출된 한국 특허 출원 제10-2018-0036140의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2018-0036140 filed with the Korea Intellectual Property Office on March 28, 2018, the entire contents of which are incorporated herein.
본 명세서는 다환 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a polycyclic compound and an organic light emitting device including the same.
본 명세서에서, 유기 발광 소자란 유기 반도체 물질을 이용한 발광 소자로서, 전극과 유기 반도체 물질 사이에서의 정공 및/또는 전자의 교류를 필요로 한다. 유기 발광 소자는 동작 원리에 따라 하기와 같이 크게 두 가지로 나눌 수 있다. 첫째는 외부의 광원으로부터 소자로 유입된 광자에 의하여 유기물층에서 엑시톤(exiton)이 형성되고, 이 엑시톤이 전자와 정공으로 분리되고, 이 전자와 정공이 각각 다른 전극으로 전달되어 전류원(전압원)으로 사용되는 형태의 발광 소자이다. 둘째는 2개 이상의 전극에 전압 또는 전류를 가하여 전극과 계면을 이루는 유기 반도체 물질층에 정공 및/또는 전자를 주입하고, 주입된 전자와 정공에 의하여 작동하는 형태의 발광 소자이다.In the present specification, an organic light emitting device is a light emitting device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and the organic semiconductor material. The organic light emitting device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting element of the form. The second is a light emitting device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기 발광 소자는 자발광, 고휘도, 고효율, 낮은 구동 전압, 넓은 시야각, 높은 콘트라스트 등의 특성을 갖는 것으로 알려져 있다.In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows. Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
유기 발광 소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공 주입 재료, 정공 수송 재료, 전자 수송 재료, 전자 주입 재료 등으로 분류될 수 있다. 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료가 있다.Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions. The luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color.
또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도펀트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도펀트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때 호스트의 파장이 도펀트의 파장대로 이동하므로, 이용하는 도펀트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
전술한 유기 발광 소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공 주입 물질, 정공 수송 물질, 발광 물질, 전자 수송 물질, 전자 주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되므로 새로운 재료의 개발이 계속 요구되고 있다.In order to fully exhibit the excellent characteristics of the above-described organic light emitting device, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. The development of new materials continues to be required.
본 명세서에는 다환 화합물 및 이를 포함하는 유기 발광 소자가 기재된다. In the present specification, a polycyclic compound and an organic light emitting device including the same are described.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
화학식 1에 있어서,In Chemical Formula 1,
X는 O 또는 S이고,X is O or S,
L1 및 L2는 각각 독립적으로, 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 and L2 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a는 0 내지 4의 정수이며,a is an integer of 0 to 4,
a가 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하다.When a is 2 or more, the substituents in parentheses are the same as or different from each other.
또한, 본 명세서의 일 실시상태에 따르면, 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.Further, according to one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 및/또는 수명 특성을 향상시킬 수 있다. 특히, 본 명세서에 기재된 화합물은 정공주입층, 정공수송층, 전자억제층, 발광층, 정공저지층, 전자수송층, 전자주입층의 재료로 사용될 수 있다.The compound described herein can be used as the material of the organic material layer of the organic light emitting device. The compound according to at least one embodiment may improve the lifespan and / or in the organic light emitting device. In particular, the compounds described herein can be used as the material of the hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer.
도 1은 기판(1), 양극(2), 발광층(3) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
도 3은 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 전자억제층(9), 발광층(7), 정공저지층(10), 전자주입 및 수송층(11) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 9, a light emitting layer 7, a hole blocking layer 10, an electron injection and transport layer ( 11) and an example of the organic light-emitting device consisting of the cathode 4 are shown.
<부호의 설명><Description of the code>
1: 기판1: substrate
2: 양극2: anode
3: 발광층3: light emitting layer
4: 음극4: cathode
5: 정공주입층5: hole injection layer
6: 정공수송층6: hole transport layer
7: 발광층7: light emitting layer
8: 전자수송층8: electron transport layer
9: 전자억제층9: electron suppression layer
10: 정공저지층10: hole blocking layer
11: 전자주입 및 수송층11: electron injection and transport layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, the present specification will be described in more detail.
본 명세서는 하기 화학식 1로 표시되는 화합물을 제공한다. 하기 화학식 1로 표시되는 화합물을 유기 발광 소자의 유기물층에 사용하는 경우, 유기 발광 소자의 효율이 항상된다.The present specification provides a compound represented by the following Formula 1. When the compound represented by the following formula (1) is used in the organic material layer of the organic light emitting device, the efficiency of the organic light emitting device is always.
[화학식 1] [Formula 1]
상기 화학식 1에 있어서,In Chemical Formula 1,
X는 O 또는 S이고,X is O or S,
L1 및 L2는 각각 독립적으로, 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 and L2 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a는 0 내지 4의 정수이며,a is an integer of 0 to 4,
a가 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하다When a is 2 or more, the substituents in parentheses are the same as or different from each other.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components unless specifically stated otherwise.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents herein are described below, but are not limited thereto.
상기 "치환" 이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 알킬기; 시클로알킬기; 아릴아민기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 도 있다.As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; An alkyl group; Cycloalkyl group; Arylamine group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the substituents are described below, but are not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소(F), 염소(Cl), 브롬(Br) 또는 요오드(I)가 있다.In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
본 명세서에 있어서, 에스테르기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 50인 것이 바람직하다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, although carbon number of an ester group is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 50인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다. Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
본 명세서에 있어서, 아미드기는 아미드기의 질소가 수소, 탄소수 1 내지 30의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, 이소부틸기, tert-부틸기, n-펜틸기, n-헥실기, n-헵틸기, n-옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-jade Although there exist a tilt group etc., it is not limited to these.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 붕소기는 -BR100R101일 수 있으며, 상기 R100 및 R101은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 니트릴기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다.In the present specification, the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서에 있어서, 포스핀옥사이드기는 구체적으로 디페닐포스핀옥사이드기, 디나프틸포스핀옥사이드기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.
본 명세서에 있어서, 아민기는 -NH2; 알킬아민기; N-알킬아릴아민기; 아릴아민기; N-아릴헤테로아릴아민기; N-알킬헤테로아릴아민기 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, N-페닐나프틸아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기, N-페닐나프틸아민기, N-바이페닐나프틸아민기, N-나프틸플루오레닐아민기, N-페닐페난트레닐아민기, N-바이페닐페난트레닐아민기, N-페닐플루오레닐아민기, N-페닐터페닐아민기, N-페난트레닐플루오레닐아민기, N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine Groups, N-phenanthrenylfluorenylamine groups, N-biphenylfluorenylamine groups, and the like, but are not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다.In the present specification, the N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N in the amine group.
명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 2 이상의 아릴기를 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다. In the specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
아릴아민기의 구체적인 예로는 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디페닐 아민기, 페닐 나프틸 아민기, 바이페닐 페닐 아민기 등이 있으나, 이에 한정되는 것은 아니다.Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine Groups, 9-methyl-anthracenylamine groups, diphenyl amine groups, phenyl naphthyl amine groups, biphenyl phenyl amine groups, and the like, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
상기 플루오레닐기가 치환되는 경우, 
, 
등의 스피로플루오레닐기, 
(9,9-디메틸플루오레닐기), 및 
(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted, , Spirofluorenyl groups, such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group). However, the present invention is not limited thereto.
본 명세서에 있어서, 알킬아릴기, 아릴옥시기, 아릴티옥시기, 아릴술폭시기, 아릴포스핀기, 아르알킬기, 아랄킬아민기, 아르알케닐기, 아릴아민기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the alkylaryl group, the aryloxy group, the arylthioxy group, the aryl sulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, and the arylamine group has a description regarding the aforementioned aryl group. Can be applied.
본 명세서에 있어서, 알킬아릴기, 알킬티옥시기, 알킬술폭시기, 아르알킬기, 아랄킬아민기, 알킬아민기, N-알킬헤테로아릴아민기 중 알킬기는 전술한 알킬기에 관한 설명이 적용될 수 있다. 알킬티옥시기로는 메틸티옥시기, 에틸티옥시기, tert－부틸티옥시기, 헥실티옥시기, 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메실, 에틸술폭시기, 프로필술폭시기, 부틸술폭시기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group of the alkylaryl group, the alkylthioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkylamine group, the alkylamine group, and the N-alkylheteroarylamine group may be applied to the description of the aforementioned alkyl group. Alkyl thioxy groups include methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thioxy group and the like, and alkyl sulfoxy groups include mesyl, ethyl sulfoxy, propyl sulfoxy and butyl sulfoxy groups. However, the present invention is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 30이다. 헤테로 고리기의 예로는 예로는 피리딜기, 피롤기, 피리미딜기, 피리다지닐기, 퓨라닐기, 티오페닐기, 이미다졸기, 피라졸기, 디벤조퓨라닐기, 디벤조티오페닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, and the like. It is not limited only to.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.
본 명세서에 있어서, 헤테로아릴기, 헤테로아릴아민기 중 헤테로아릴기는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. In the present specification, the heteroaryl group, the heteroaryl group of the heteroarylamine group, the description of the aforementioned heterocyclic group may be applied.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오쏘(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한"기로 해석될 수 있다.In the present specification, "adjacent" The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
본 명세서에 있어서, 인접한 기가 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 탄화수소고리; 또는 헤테로고리를 의미한다.In the present specification, in a substituted or unsubstituted ring in which adjacent groups are bonded to each other, a “ring” means a hydrocarbon ring; Or heterocycle.
본 명세서에 있어서, 탄화수소고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.
본 명세서에 있어서, 방향족 탄화수소고리는 1가인 것을 제외하고는 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aryl group may be applied except that the aromatic hydrocarbon ring is monovalent.
본 명세서에 있어서, 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 N, O, P, S, Si 및 Se 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 방향족 헤테로고리는 1가가 아닌 것을 제외하고 상기 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of N, O, P, S, Si, Se, and the like. can do. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
본 명세서의 일 실시상태에 따르면, X 는 O 또는 S이다.According to an exemplary embodiment of the present disclosure, X is O or S.
본 명세서의 일 실시상태에 따르면, L1 및 L2는 각각 독립적으로, 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이다.According to an exemplary embodiment of the present disclosure, L1 and L2 are each independently, a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.
본 명세서의 일 실시상태에 따르면, L1 및 L2는 각각 독립적으로, 직접결합; 치환 또는 비치환된 탄소수 6 내지 60의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 60인 2가의 헤테로고리기이다.According to an exemplary embodiment of the present disclosure, L1 and L2 are each independently, a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 따르면, L1 및 L2는 각각 독립적으로, 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30인 2가의 헤테로고리기이다.According to an exemplary embodiment of the present disclosure, L1 and L2 are each independently, a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, L1 및 L2가 각각 독립적으로, 치환 또는 비치환된 아릴렌기인 경우, 하기의 구조들 중 선택되는 어느 하나일 수 있다.According to an exemplary embodiment of the present disclosure, when L1 and L2 are each independently a substituted or unsubstituted arylene group, it may be any one selected from the following structures.
상기 구조에서, A1 및 A2는 각각 독립적으로 치환 또는 비치환된 알킬기, 또는 치환 또는 비치환된 아릴기이다.In the above structure, A1 and A2 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, L1 및 L2가 각각 독립적으로, 치환 또는 비치환된 2가의 헤테로고리기인 경우, 하기의 구조들 중 선택되는 어느 하나일 수 있다.According to an exemplary embodiment of the present disclosure, when L1 and L2 are each independently a substituted or unsubstituted divalent heterocyclic group, it may be any one selected from the following structures.
상기 구조에서, Y1 내지 Y5는 각각 독립적으로 치환 또는 비치환된 알킬기, 또는 치환 또는 비치환된 아릴기이다.In the above structure, Y1 to Y5 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
본 명세서에서, 
는 결합위치를 나타낸 것이다.In this specification, Indicates the coupling position.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 디아릴포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted diaryl phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 아민기; 치환 또는 비치환된 탄소수 1 내지 60의 알킬아민기; 치환 또는 비치환된 탄소수 6 내지 60의 아랄킬아민기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴아민기; 치환 또는 비치환된 탄소수 12 내지 60의 디아릴포스핀옥사이드기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C60 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 60 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 아민기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기; 치환 또는 비치환된 탄소수 6 내지 30의 아랄킬아민기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴아민기; 치환 또는 비치환된 탄소수 12 내지 30의 디아릴포스핀옥사이드기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C30 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 30 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 아민기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬아민기; 치환 또는 비치환된 탄소수 6 내지 20의 아랄킬아민기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴아민기; 치환 또는 비치환된 탄소수 12 내지 20의 디아릴포스핀옥사이드기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 N을 적어도 하나 포함하는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted C1-C20 alkylamine group; A substituted or unsubstituted aralkylamine group having 6 to 20 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 20 carbon atoms; A substituted or unsubstituted diaryl phosphine oxide group having 12 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms containing at least one N.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 페닐기, 치환 또는 비치환된 나프틸렌기, 치환 또는 비치환된 비페닐기, 치환 또는 비치환된 페난트렌기, 치환 또는 비치환된 트리페닐렌기, 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 디벤조퓨란기, 치환 또는 비치환된 디벤조티오펜기, 치환 또는 비치환된 카바졸기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 피리딘기, 치환 또는 비치환된 피리미딘기, 치환 또는 비치환된 트리아진기, 또는 치환 또는 비치환된 포스핀옥사이드기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrene group, Substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazole group, substituted or unsubstituted A substituted amine group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, or a substituted or unsubstituted phosphine oxide group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 각각 독립적으로, 페닐기; 나프틸렌기; 비페닐기; 페난트렌기; 트리페닐렌기; 메틸기 및 페닐기로 이루어진 군으로부터 선택된 치환기로 치환된 플루오레닐기; 디벤조퓨란기; 디벤조티오펜기; 페닐기로 치환 또는 비치환된 카바졸기; 페닐기, 비페닐기, 나프틸렌기 및 메틸기로 치환된 플루오레닐기로 이루어진 군으로부터 선택된 치환 또는 비치환된 아민기; 페닐기로 치환 또는 비치환된 피리딘기; 페닐기로 치환 또는 비치환된 피리미딘기; 페닐기로 치환 또는 비치환된 트리아진기; 또는 디페닐포스핀옥사이드기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a phenyl group; Naphthylene group; Biphenyl group; Phenanthrene group; Triphenylene group; A fluorenyl group substituted with a substituent selected from the group consisting of a methyl group and a phenyl group; Dibenzofuran group; Dibenzothiophene group; Carbazole groups unsubstituted or substituted with a phenyl group; A substituted or unsubstituted amine group selected from the group consisting of a phenyl group, a biphenyl group, a naphthylene group and a fluorenyl group substituted with a methyl group; A pyridine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubstituted or substituted with a phenyl group; Triazine group unsubstituted or substituted with a phenyl group; Or a diphenylphosphine oxide group.
본 명세서의 일 실시상태에 따르면, Ar1 및 Ar2는 하기의 구조들 중에서 선택되는 어느 하나일 수 있다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 may be any one selected from the following structures.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2로 표시된다.According to an exemplary embodiment of the present specification, Formula 1 is represented by the following formula (2).
[화학식 2][Formula 2]
화학식 2에 있어서,In Chemical Formula 2,
X, L1 및 Ar1의 정의는 상기와 같다.The definitions of X, L1 and Ar1 are as above.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 3 또는 4로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 3 or 4.
[화학식 3][Formula 3]
[화학식 4][Formula 4]
화학식 3 및 4에 있어서,In Chemical Formulas 3 and 4,
X, L1, L2, Ar1 및 Ar2 의 정의는 상기 화학식 1에서와 같다.Definitions of X, L1, L2, Ar1 and Ar2 are the same as in Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 구조들 중 어느 하나로 표시될 수 있다.In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following structures.
본 명세서의 일 실시상태에 따른 화학식 1의 화합물은 후술하는 제조방법으로 제조될 수 있다.Compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the production method described below.
예컨대 상기 화학식 1의 화합물은 하기 반응식 A 내지 F와 같이 코어구조가 제조될 수 있다. 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.For example, the compound of Formula 1 may be prepared in the core structure as shown in Schemes A to F. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
<반응식 A>Scheme A
<반응식 B>Scheme B
<반응식 C>Scheme C
<반응식 D>Scheme D
<반응식 E>Scheme E
<반응식 F>Scheme F
화합물의 컨쥬게이션 길이와 에너지 밴드갭은 밀접한 관계가 있다. 구체적으로, 화합물의 컨쥬게이션 길이가 길수록 에너지 밴드갭이 작아진다. The conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
본 발명에서는 상기와 같이 코어 구조에 다양한 치환기를 도입함으로써 다양한 에너지 밴드갭을 갖는 화합물을 합성할 수 있다. 또한, 본 발명에서는 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 화합물의 HOMO 및 LUMO 에너지 준위도 조절할 수 있다.In the present invention, a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공 주입층 물질, 정공 수송용 물질, 발광층 물질 및 정공 억제층 물질에 주로 사용되는 치환기를 상기 코어 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 합성할 수 있다.Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, by incorporating a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material and the hole suppression layer material used in the manufacture of the organic light emitting device into the core structure to synthesize a material satisfying the requirements of each organic material layer can do.
또한, 본 발명에 따른 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1의 화합물을 포함하는 것을 특징으로 한다.In addition, the organic light emitting device according to the present invention includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
상기 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공 주입층, 정공 수송층, 발광층, 정공 억제층, 전자 주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole suppression layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함할 수 있고, 상기 전자수송층 또는 전자주입층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer may include a compound represented by the formula (1).
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함할 수 있고, 상기 정공주입층 또는 정공수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, the organic material layer may include a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer may include a compound represented by the formula (1).
또 하나의 실시 상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층이 상기 화학식 1로 표시되는 화합물을 포함한다. In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
또 하나의 실시 상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함할 수 있다. According to another exemplary embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a dopant of the light emitting layer.
또 하나의 실시 상태에 따르면, 상기 유기물층은 전자억제층을 포함하고, 상기 전자억제층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. According to another exemplary embodiment, the organic material layer may include an electron suppression layer, and the electron suppression layer may include a compound represented by Chemical Formula 1.
또 하나의 실시 상태에 따르면, 상기 유기물층은 정공저지층을 포함하고, 상기 정공저지층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. According to another exemplary embodiment, the organic material layer may include a hole blocking layer, and the hole blocking layer may include a compound represented by Chemical Formula 1.
또 하나의 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 상기 화학식 1로 표시되는 화합물을 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 포함하며, 다른 유기화합물, 금속 또는 금속화합물을 도펀트로 포함할 수 있다.In another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds. May be included as the dopant.
또 하나의 예로서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 상기 화학식 1로 표시되는 화합물을 도펀트로서 포함하고, 형광 호스트 또는 인광 호스트를 포함하며, 이리듐계(Ir) 도펀트와 함께 사용할 수 있다.As another example, the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant. have.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 제2 전극은 음극이다.In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 일 실시상태에 따르면, 상기 제1 전극은 음극이고, 제2 전극은 양극이다.According to another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
본 발명의 유기 발광 소자의 구조는 도 1 및 도 2에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
도 1에는 기판(1) 위에 양극(2), 발광층(3) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(3)에 포함될 수 있다.1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound may be included in the light emitting layer (3).
도 2에는 기판(1) 위에 양극(2), 정공 주입층(5), 정공 수송층(6), 발광층(7), 전자 수송층(8) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공 주입층(5), 정공 수송층(6), 발광층(7) 또는 전자 수송층(8)에 포함될 수 있다.2 illustrates an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. The structure is illustrated. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, or the electron transport layer 8.
도 3은 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 전자억제층(9), 발광층(7), 정공저지층(10), 전자주입 및 수송층(11) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.이와 같은 구조에 있어서, 상기 화합물은 상기 정공 주입층(5), 전자억제층(9), 발광층(7) 또는 정공저지층(10)에 포함될 수 있다.3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 9, a light emitting layer 7, a hole blocking layer 10, an electron injection and transport layer ( 11) and an example of an organic light-emitting device consisting of a cathode 4. In this structure, the compound is the hole injection layer 5, electron suppression layer 9, light emitting layer 7 or hole blocking It may be included in layer 10.
예컨대, 본 발명에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 전자 억제층, 발광층 및 정공 억제층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다.For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, an electron suppression layer, a light emitting layer and a hole suppression layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
상기 유기물층은 정공 주입층, 전자 억제층, 발광층 및 정공 억제층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer may have a multilayer structure including a hole injection layer, an electron suppression layer, a light emitting layer, a hole suppression layer, and the like, but is not limited thereto and may have a single layer structure. In addition, the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO : Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
상기 정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다.As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 전자 억제층과 정공 억제층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the electron suppression layer and the hole suppression layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.As a host material of a light emitting layer, a condensed aromatic ring derivative, a heterocyclic containing compound, etc. are mentioned. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
발광층의 도펀트로 사용되는 이리듐계 착물은 하기와 같으나, 이에 한정되지 않는다.Iridium complex used as the dopant of the light emitting layer is as follows, but is not limited thereto.
상기 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.The electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer. A material having high mobility to electrons is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 명세서를 예시하기 위한 것이며, 본 명세서의 범위가 이들에 의하여 한정되는 것은 아니다.Fabrication of an organic light emitting device including the compound represented by Chemical Formula 1 will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.
제조예 1Preparation Example 1
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A(8.65 g, 23.19mmol), 및 화합물 a1(8.79 g, 22.03 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(2.45 g, 25.51 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.24 g, 0.46 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 260 mL으로 재결정하여 제조예 1(6.88 g, 수율: 46%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound A (8.65 g, 23.19 mmol) and Compound a1 (8.79 g, 22.03 mmol) were completely dissolved in 220 mL of Xylene, followed by the addition of NaOtBu (2.45 g, 25.51 mmol) and Bis (tri- tert -butylphosphine) palladium (0) (0.24 g, 0.46 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, Xylene was concentrated under reduced pressure and recrystallized from 260 mL of ethyl acetate, thereby preparing Preparation Example 1 (6.88 g, yield: 46%).
MS[M+H]+= 693MS [M + H] + = 693
제조예 2Preparation Example 2
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A(7.25 g, 19.44mmol), 및 화합물 a2(5.93 g, 18.47 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(2.05 g, 21.38 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.39 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 제조예 2(7.16 g, 수율: 60%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound A (7.25 g, 19.44 mmol) and Compound a2 (5.93 g, 18.47 mmol) were completely dissolved in 220 mL of Xylene, followed by addition of NaOtBu (2.05 g, 21.38 mmol), followed by Bis. (tri- tert- butylphosphine) palladium (0) (0.20 g, 0.39 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 250 mL of ethyl acetate to prepare Preparation Example 2 (7.16 g, yield: 60%).
MS[M+H]+= 615MS [M + H] + = 615
제조예 3Preparation Example 3
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A(8.16 g, 21.88mmol), 및 화합물 a3(5.55 g, 20.78 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(2.31 g, 24.06 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.22 g, 0.44 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 190 mL으로 재결정하여 제조예 3(8.34 g, 수율: 63%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound A (8.16 g, 21.88 mmol) and Compound a3 (5.55 g, 20.78 mmol) were completely dissolved in 220 mL of Xylene, followed by the addition of NaOtBu (2.31 g, 24.06 mmol), followed by Bis. (tri- tert -butylphosphine) palladium (0) (0.22 g, 0.44 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure and recrystallized from 190 mL of ethyl acetate, thereby preparing Preparation Example 3 (8.34 g, Yield: 63%).
MS[M+H]+= 605MS [M + H] + = 605
제조예 4Preparation Example 4
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A(7.76 g, 20.80mmol), 및 화합물 a4(5.73 g, 19.76 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(2.21 g, 22.88 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.21 g, 0.42 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 260 mL으로 재결정하여 제조예 4(6.98 g, 수율: 53%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound A (7.76 g, 20.80 mmol) and Compound a4 (5.73 g, 19.76 mmol) were completely dissolved in 220 mL of Xylene, followed by the addition of NaOtBu (2.21 g, 22.88 mmol), followed by Bis. (tri- tert -butylphosphine) palladium (0) (0.21 g, 0.42 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, Xylene was concentrated under reduced pressure and recrystallized from 260 mL of ethyl acetate, thereby preparing Preparation Example 4 (6.98 g, yield: 53%).
MS[M+H]+= 628MS [M + H] + = 628
제조예 5Preparation Example 5
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A(6.87 g, 18.42mmol), 및 화합물 a5(8.07 g, 17.51 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(1.95 g, 20.26 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.19 g, 0.37 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 280 mL으로 재결정하여 제조예 5(8.23 g, 수율: 56%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound A (6.87 g, 18.42 mmol) and Compound a5 (8.07 g, 17.51 mmol) were completely dissolved in 220 mL of Xylene, followed by addition of NaOtBu (1.95 g, 20.26 mmol), and Bis (tri- tert -butylphosphine) palladium (0) (0.19 g, 0.37 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, Xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to prepare Preparation Example 5 (8.23 g, yield: 56%).
MS[M+H]+= 799MS [M + H] + = 799
제조예 6Preparation Example 6
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A(9.23 g, 24.75mmol), 및 화합물 a6(9.10 g, 23.51 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(2.62 g, 27.22 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.25 g, 0.49 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 210 mL으로 재결정하여 제조예 6(10.75 g, 수율: 64%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound A (9.23 g, 24.75 mmol) and Compound a6 (9.10 g, 23.51 mmol) were completely dissolved in 220 mL of Xylene, followed by the addition of NaOtBu (2.62 g, 27.22 mmol) and Bis (tri- tert -butylphosphine) palladium (0) (0.25 g, 0.49 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, Xylene was concentrated under reduced pressure and recrystallized from 210 mL of ethyl acetate, thereby preparing Preparation Example 6 (10.75 g, Yield: 64%).
MS[M+H]+= 680MS [M + H] + = 680
제조예 7Preparation Example 7
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B(6.55 g, 18.35mmol), 및 화합물 a7(8.98 g, 17.43 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(1.94 g, 20.18 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.19 g, 0.37 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 210 mL으로 재결정하여 제조예 7(6.08 g, 수율: 42%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound B (6.55 g, 18.35 mmol) and Compound a7 (8.98 g, 17.43 mmol) were completely dissolved in 220 mL of Xylene, followed by addition of NaOtBu (1.94 g, 20.18 mmol), and Bis (tri- tert -butylphosphine) palladium (0) (0.19 g, 0.37 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, Xylene was concentrated under reduced pressure and recrystallized from 210 mL of ethyl acetate to prepare Preparation Example 7 (6.08 g, yield: 42%).
MS[M+H]+= 793MS [M + H] + = 793
제조예 8Preparation Example 8
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B(6.75 g, 18.91mmol), 및 화합물 a8(4.42 g, 17.96 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(2.01 g, 20.80 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.19 g, 0.38 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 270 mL으로 재결정하여 제조예 8(5.11 g, 수율: 52%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound B (6.75 g, 18.91 mmol) and Compound a8 (4.42 g, 17.96 mmol) were completely dissolved in 220 mL of Xylene, followed by addition of NaOtBu (2.01 g, 20.80 mmol), and Bis (tri- tert -butylphosphine) palladium (0) (0.19 g, 0.38 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to prepare Preparation Example 8 (5.11 g, yield: 52%).
MS[M+H]+= 524MS [M + H] + = 524
제조예 9Preparation Example 9
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B(6.22 g, 17.42mmol), 및 화합물 a9(4.34 g, 16.55 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(1.84 g, 19.17 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.18 g, 0.35 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 210 mL으로 재결정하여 제조예 9(4.44 g, 수율: 47%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound B (6.22 g, 17.42 mmol) and Compound a9 (4.34 g, 16.55 mmol) were completely dissolved in 220 mL of Xylene, followed by the addition of NaOtBu (1.84 g, 19.17 mmol), followed by Bis. (tri- tert- butylphosphine) palladium (0) (0.18 g, 0.35 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, Xylene was concentrated under reduced pressure and recrystallized from 210 mL of ethyl acetate to prepare Preparation Example 9 (4.44 g, Yield: 47%).
MS[M+H]+= 540MS [M + H] + = 540
제조예 10Preparation Example 10
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B(5.47 g, 15.32mmol), 및 화합물 a10(5.63 g, 14.56 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(1.62 g, 16.85 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.16 g, 0.31 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 220 mL으로 재결정하여 제조예 10(6.19 g, 수율: 75%)를 제조하였다.Dissolve Compound B (5.47 g, 15.32 mmol), and Compound a10 (5.63 g, 14.56 mmol) in 220 mL of Xylene in a 500 mL round-bottom flask in nitrogen atmosphere, then add NaOtBu (1.62 g, 16.85 mmol) and add Bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.31 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure and recrystallized from 220 mL of ethyl acetate to prepare Preparation Example 10 (6.19 g, yield: 75%).
MS[M+H]+= 665MS [M + H] + = 665
제조예 11Preparation Example 11
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B(7.05 g, 19.75mmol), 및 화합물 a11(5.55 g, 18.76 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(2.09 g, 21.72 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.39 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 270 mL으로 재결정하여 제조예 11(7.28 g, 수율: 60%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound B (7.05 g, 19.75 mmol) and Compound a11 (5.55 g, 18.76 mmol) were completely dissolved in 220 mL of Xylene, followed by addition of NaOtBu (2.09 g, 21.72 mmol), and Bis (tri- tert- butylphosphine) palladium (0) (0.20 g, 0.39 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure and recrystallized from 270 mL of ethyl acetate to prepare Preparation Example 11 (7.28 g, yield: 60%).
MS[M+H]+= 618MS [M + H] + = 618
제조예 12Preparation Example 12
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B(6.88 g, 19.27mmol), 및 화합물 a12(4.39 g, 18.31 mmol)을 Xylene 220 mL에 완전히 녹인 후 NaOtBu(2.04 g, 21.20 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.39 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 230 mL으로 재결정하여 제조예 12(6.07 g, 수율: 56%)를 제조하였다.In a 500 mL round bottom flask in nitrogen atmosphere, Compound B (6.88 g, 19.27 mmol) and Compound a12 (4.39 g, 18.31 mmol) were completely dissolved in 220 mL of Xylene, followed by addition of NaOtBu (2.04 g, 21.20 mmol), and Bis (tri- tert- butylphosphine) palladium (0) (0.20 g, 0.39 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the base was removed by filtration, Xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate, thereby preparing Preparation 12 (6.07 g, Yield: 56%).
MS[M+H]+= 562MS [M + H] + = 562
제조예 13Preparation Example 13
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C(10.69 g, 26.26mmol) 및 화합물 a13(4.87 g, 23.87 mmol)을 Xylene/DMAC 200mL/50mL에 완전히 녹인 후 NaOtBu(2.98 g, 31.03 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 석출된 고체를 filter하고 H2O 500ml로 씻겨주고 감압하여 용매를 제거하여 13-A(8.75 g, 18.12 mmol)를 제조하였다. 얻어진 고체 및 화합물 a14(5.76 g, 19.93 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.63 g, 0.54 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 250 mL로 재결정하여 제조예 13(8.87 g, 71%)를 제조하였다.After dissolving Compound C (10.69 g, 26.26 mmol) and Compound a13 (4.87 g, 23.87 mmol) in Xylene / DMAC 200 mL / 50 mL in a 500 mL round bottom flask under nitrogen atmosphere, NaOtBu (2.98 g, 31.03 mmol) was added. Heat stirring for 3 hours. The precipitated solid was filtered, washed with 500 ml of H 2 O, and the solvent was removed under reduced pressure to prepare 13-A (8.75 g, 18.12 mmol). The obtained solid and compound a14 (5.76 g, 19.93 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (120 mL) was added thereto, followed by tetrakis- (triphenylphosphine) palladium (0.63 g, 0.54 mmol). ) Was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of ethyl acetate to prepare Preparation Example 13 (8.87 g, 71%).
MS[M+H]+= 693MS [M + H] + = 693
제조예 14Preparation Example 14
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 D(7.68 g, 19.64mmol) 및 화합물 a15(4.52 g, 21.61 mmol)을 Xylene/DMAC 200mL/50mL에 완전히 녹인 후 NaOtBu(2.45 g, 25.53 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 석출된 고체를 filter하고 H2O 500ml로 씻겨주고 감압하여 용매를 제거하여 14-A(6.27 g, 12.98 mmol)를 제조하였다. 얻어진 고체 및 화합물 a16(4.12 g, 14.34 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.45 g, 0.39 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 250 mL로 재결정하여 제조예 14(5.88 g, 62%)를 제조하였다.Dissolve Compound D (7.68 g, 19.64 mmol) and Compound a15 (4.52 g, 21.61 mmol) in Xylene / DMAC 200 mL / 50 mL in a 500 mL round bottom flask in nitrogen atmosphere, and then add NaOtBu (2.45 g, 25.53 mmol). Heat stirring for 3 hours. The precipitated solid was filtered, washed with 500 ml of H 2 O, and the solvent was removed under reduced pressure to prepare 14-A (6.27 g, 12.98 mmol). The resulting solid and compound a16 (4.12 g, 14.34 mmol) were completely dissolved in 240 mL of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (120 mL), and tetrakis- (triphenylphosphine) palladium (0.45 g, 0.39 mmol). ) Was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and recrystallized with 250 mL of ethyl acetate to prepare Preparation 14 (5.88 g, 62%).
MS[M+H]+= 725MS [M + H] + = 725
제조예 15Preparation Example 15
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 E(10.69 g, 26.26mmol) 및 화합물 a13(4.87 g, 23.87 mmol)을 Xylene/DMAC 200mL/50mL에 완전히 녹인 후 NaOtBu(2.98 g, 31.03 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 석출된 고체를 filter하고 H2O 500ml로 씻겨주고 감압하여 용매를 제거하여 15-A(8.75 g, 18.12 mmol)를 제조하였다. 얻어진 고체 및 화합물 a17(5.76 g, 19.93 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.63 g, 0.54 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 에틸아세테이트 250 mL로 재결정하여 제조예 15(8.87 g, 71%)를 제조하였다.After dissolving Compound E (10.69 g, 26.26 mmol) and Compound a13 (4.87 g, 23.87 mmol) in Xylene / DMAC 200 mL / 50 mL in a 500 mL round bottom flask under nitrogen atmosphere, NaOtBu (2.98 g, 31.03 mmol) was added. Heat stirring for 3 hours. The precipitated solid was filtered, washed with 500 ml of H 2 O, and the solvent was removed under reduced pressure to prepare 15-A (8.75 g, 18.12 mmol). The resulting solid and compound a17 (5.76 g, 19.93 mmol) were dissolved completely in 240 mL of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (120 mL) was added thereto, followed by tetrakis- (triphenylphosphine) palladium (0.63 g, 0.54 mmol). ) Was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of ethyl acetate to prepare Preparation 15 (8.87 g, 71%).
MS[M+H]+= 726MS [M + H] + = 726
실시예 1-1Example 1-1
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
이렇게 준비된 양극인 ITO 투명 전극 위에 하기 화합물 HI1 및 하기 화합물 HI2의 화합물을 98:2(몰비)의 비가 되도록 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 화학식 HT1으로 표시되는 화합물(1150Å)을 진공 증착하여 정공수송층을 형성하였다. 이어서, 상기 정공수송층 위에 막 두께 50Å으로 앞서 제조한 제조예 1의 화합물을 진공 증착하여 전자억제층을 형성하였다. 이어서, 상기 전자억제층 위에 막 두께 200Å으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 50:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 막 두께 50Å으로 하기 화학식 HB1으로 표시되는 화합물을 진공 증착하여 정공저지층을 형성하였다. 이어서, 상기 정공저지층 위에 하기 화학식 ET1으로 표시되는 화합물과 하기 화학식 LiQ로 표시되는 화합물을 1:1의 중량비로 진공증착하여 30Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. The compound of the following compound HI1 and the following compound HI2 was thermally vacuum deposited to a thickness of 100 kPa so that the ratio of 98: 2 (molar ratio) was formed on the ITO transparent electrode as the anode thus prepared, thereby forming a hole injection layer. Compound (1150.) Represented by the following formula HT1 was vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, the compound of Preparation Example 1 was vacuum deposited on the hole transport layer with a film thickness of 50 kV to form an electron suppressing layer. Subsequently, the light emitting layer was formed by vacuum depositing the compound represented by the following formula BH and the compound represented by the following formula BD at a weight ratio of 50: 1 on the electron suppressing layer with a film thickness of 200 kPa. A hole blocking layer was formed by vacuum depositing a compound represented by the following formula HB1 with a film thickness of 50 kPa on the light emitting layer. Subsequently, the compound represented by the following formula ET1 and the compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1: 1 on the hole blocking layer to form an electron injection and transport layer having a thickness of 30 kPa. Lithium fluoride (LiF) and aluminum were deposited on the electron injection and transport layer sequentially to a thickness of 12 Å and 1,000 Å to form a cathode.
상기의 과정에서 유기물의 증착속도는 0.4 내지 0.7 Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 내지 5×10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at a deposition rate of 2 Å / sec. An organic light-emitting device was manufactured by maintaining −7 to 5 × 10 −6 torr.
실시예 1-2 내지 실시예 1-8Example 1-2 to Example 1-8
제조예 1의 화합물 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1.
비교예 1-1 내지 1-2Comparative Examples 1-1 to 1-2
제조예 1의 화합물 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 사용한 EB2, EB3 의 화합물은 하기와 같다. An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1. The compounds of EB2 and EB3 used in Table 1 below are as follows.
실험예 1Experimental Example 1
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 2에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light emitting diodes manufactured in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).
| 화합물(전자억제층)Compound (electron suppression layer) | 전압(V@10mA/cm2)Voltage (V @ 10mA / cm 2 ) | 효율(cd/A@10mA/cm2)Efficiency (cd / A @ 10mA / cm 2 ) | 색좌표(x,y)Color coordinates (x, y) | T95(hr)T95 (hr) | |
| 실시예 1-1Example 1-1 | 제조예 1Preparation Example 1 | 4.204.20 | 6.556.55 | (0.144, 0.045)(0.144, 0.045) | 240240 |
| 실시예 1-2Example 1-2 | 제조예 2Preparation Example 2 | 4.114.11 | 6.556.55 | (0.142, 0.045)(0.142, 0.045) | 275275 |
| 실시예 1-3Example 1-3 | 제조예 5Preparation Example 5 | 4.254.25 | 6.446.44 | (0.143, 0.046)(0.143, 0.046) | 265265 |
| 실시예 1-4Example 1-4 | 제조예 7Preparation Example 7 | 4.274.27 | 6.556.55 | (0.144, 0.045)(0.144, 0.045) | 250250 |
| 실시예 1-5Example 1-5 | 제조예 8Preparation Example 8 | 4.264.26 | 6.466.46 | (0.143, 0.046)(0.143, 0.046) | 275275 |
| 실시예 1-6Example 1-6 | 제조예 9Preparation Example 9 | 4.384.38 | 6.576.57 | (0.144, 0.047)(0.144, 0.047) | 250250 |
| 실시예 1-7Example 1-7 | 제조예 13Preparation Example 13 | 4.374.37 | 6.596.59 | (0.143, 0.046)(0.143, 0.046) | 265265 |
| 실시예 1-8Example 1-8 | 제조예 14Preparation Example 14 | 4.364.36 | 6.446.44 | (0.144, 0.045)(0.144, 0.045) | 240240 |
| 비교예 1-1Comparative Example 1-1 | EB2EB2 | 5.025.02 | 5.735.73 | (0.142, 0.047)(0.142, 0.047) | 180180 |
| 비교예 1-2Comparative Example 1-2 | EB3EB3 | 4.964.96 | 5.825.82 | (0.141, 0.048)(0.141, 0.048) | 175175 |
상기 표 1에 나타난 바와 같이, 본 발명의 화합물을 전자억제층으로 사용한 유기 발광 소자는, 유기 발광 소자의 효율, 구동 전압 및 안정성 면에서 우수한 특성을 나타내었다.실시예 1-1 내지 1-8에서 phenanthrofurocarbazole 및 phenanthrothienocarbazole를 코어로 가지고 아릴아민 및 디벤조퓨란, 디벤조티오펜, 카바졸 등의 p-type 치환기가 연결된 물질을 전자억제층으로 사용하였을 때 저전압, 고효율, 장수명의 특성을 보이는 것을 알 수 있었다. 이는 아릴아민 및 디벤조퓨란, 디벤조티오펜, 카바졸 이 치환기로 연결되면서 homo값도 깊어지면서 발광층 계면과의 barrier가 줄어들 뿐만 아니라 전자에 대한 안정성도 크게 증가하기 때문으로 보인다.As shown in Table 1, the organic light emitting device using the compound of the present invention as an electron suppressing layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device. Examples 1-1 to 1-8 When phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and arylamines and p-type substituents such as dibenzofuran, dibenzothiophene, and carbazole were used as the electron suppression layer, they showed low voltage, high efficiency, and long life. Could. This is because arylamine, dibenzofuran, dibenzothiophene, and carbazole are connected to the substituents, and the homogeneity is also deepened, which not only reduces the barrier with the interface of the light emitting layer but also greatly increases the electron stability.
상기 표 1의 결과와 같이, 본 발명에 따른 화합물은 전자 차단 능력이 우수하여 유기 발광 소자에 적용 가능함을 확인할 수 있었다.As shown in Table 1, the compound according to the present invention was confirmed that the excellent electron blocking ability can be applied to the organic light emitting device.
실시예 2-1 내지 실시예 2-9Example 2-1 to Example 2-9
제조예 1의 화합물 대신 상기 EB1 화합물을 전자억제층으로 사용하고, HB1 대신 하기 표 2에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the EB1 compound as an electron suppression layer instead of the compound of Preparation Example 1, and using the compound shown in Table 2 below instead of HB1.
비교예 2-1 내지 2-2Comparative Examples 2-1 to 2-2
제조예 1의 화합물 대신 상기 EB1 화합물을 전자억제층으로 사용하고, HB1 대신 하기 HB2 및 HB3의 화합물을 정공저지층으로 사용한 것을 제외하고는, 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 2에서 사용한 HB2, HB3 의 화합물을 하기와 같다. An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the EB1 compound was used as an electron suppression layer instead of the compound of Preparation Example 1, and the following HB2 and HB3 compounds were used as hole blocking layers instead of HB1. It was. The compounds of HB2 and HB3 used in Table 2 below are as follows.
실험예 2Experimental Example 2
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 2에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light emitting diodes manufactured in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).
| 화합물(정공저지층)Compound (hole blocking layer) | 전압(V@20mA/cm2)Voltage (V @ 20mA / cm 2 ) | 효율(cd/A@20mA/cm2)Efficiency (cd / A @ 20mA / cm 2 ) | 색좌표(x,y)Color coordinates (x, y) | T95(hr)T95 (hr) | |
| 실시예 2-1Example 2-1 | 제조예 3Preparation Example 3 | 3.513.51 | 6.316.31 | (0.143, 0.047)(0.143, 0.047) | 265265 |
| 실시예 2-2Example 2-2 | 제조예 4Preparation Example 4 | 3.543.54 | 6.256.25 | (0.144, 0.046)(0.144, 0.046) | 270270 |
| 실시예 2-3Example 2-3 | 제조예 6Preparation Example 6 | 3.583.58 | 6.436.43 | (0.143, 0.045)(0.143, 0.045) | 280280 |
| 실시예 2-4Example 2-4 | 제조예 10Preparation Example 10 | 3.533.53 | 6.426.42 | (0.144, 0.046)(0.144, 0.046) | 285285 |
| 실시예 2-5Example 2-5 | 제조예 11Preparation Example 11 | 3.583.58 | 6.466.46 | (0.145, 0.045)(0.145, 0.045) | 270270 |
| 실시예 2-6Example 2-6 | 제조예 12Preparation Example 12 | 3.633.63 | 6.436.43 | (0.144, 0.046)(0.144, 0.046) | 265265 |
| 실시예 2-7Example 2-7 | 제조예 15Preparation Example 15 | 3.633.63 | 6.426.42 | (0.143, 0.045)(0.143, 0.045) | 285285 |
| 비교예 2-1Comparative Example 2-1 | HB2HB2 | 4.174.17 | 5.725.72 | (0.139, 0.041)(0.139, 0.041) | 130130 |
| 비교예 2-2Comparative Example 2-2 | HB3HB3 | 3.953.95 | 6.036.03 | (0.141, 0.042)(0.141, 0.042) | 205205 |
상기 표 2에 나타난 바와 같이, 본 발명의 화합물을 정공억제층으로 사용한 유기 발광 소자는, 유기 발광 소자의 효율, 구동 전압 및 안정성 면에서 우수한 특성을 나타내었다. 실시예 2-1 내지 2-7에서 phenanthrofurocarbazole 및 phenanthrothienocarbazole를 코어로 가지고 싸이아노피리미딘, 트리아진, 피리미딘, 퀴나졸린 및 포스핀옥사이드의 n-type 치환기가 연결된 물질을 전자억제층으로 사용하였을 때 저전압, 고효율, 장수명의 특성을 보이는 것을 알 수 있었다.상기 표 2의 결과와 같이, 본 발명에 따른 화합물은 정공 차단 능력이 우수하여 유기 발광 소자에 적용 가능함을 확인할 수 있었다.As shown in Table 2, the organic light emitting device using the compound of the present invention as a hole suppression layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device. In Examples 2-1 to 2-7, when phenanthrofurocarbazole and phenanthrothienocarbazole were used as cores and a substance linked with n-type substituents of cyanopyrimidine, triazine, pyrimidine, quinazoline and phosphine oxide was used as the electron suppressing layer, It can be seen that the characteristics of low voltage, high efficiency, and long life is shown. As shown in Table 2, the compound according to the present invention has excellent hole blocking ability and can be applied to an organic light emitting device.
이상을 통해 본 발명의 바람직한 실시예(전자억제층, 정공저지층)에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.Although preferred embodiments of the present invention (electron suppression layer, hole blocking layer) have been described above, the present invention is not limited thereto, and various modifications are made within the scope of the claims and the detailed description of the invention. It is possible and this also belongs to the scope of the invention.
Claims (8)
- 하기 화학식 1로 표시되는 것인 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
화학식 1에 있어서,In Chemical Formula 1,X는 O 또는 S이고,X is O or S,L1 및 L2는 각각 독립적으로, 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며,L1 and L2 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,Ar1 및 Ar2는 각각 독립적으로, 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬술폭시기; 치환 또는 비치환된 아릴술폭시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아르알킬기; 치환 또는 비치환된 아르알케닐기; 치환 또는 비치환된 알킬아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아랄킬아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 아릴포스핀기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,a는 0 내지 4의 정수이며,a is an integer of 0 to 4,a가 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하다.When a is 2 or more, the substituents in parentheses are the same as or different from each other. - 청구항 1에 있어서,The method according to claim 1,상기 화학식 1은 하기 화학식 2로 표시되는 것인 화합물:Formula 1 is a compound represented by the following formula (2):[화학식 2][Formula 2]
화학식 2에 있어서,In Chemical Formula 2,X, L1 및 Ar1의 정의는 상기 화학식 1에서와 같다.Definitions of X, L1 and Ar1 are the same as in Chemical Formula 1. - 청구항 1에 있어서,The method according to claim 1,상기 화학식 1은 하기 화학식 3 또는 4로 표시되는 것인 화합물:Formula 1 is a compound represented by the following formula 3 or 4:[화학식 3][Formula 3]
[화학식 4][Formula 4]
화학식 3 및 4에 있어서,In Chemical Formulas 3 and 4,X, L1, L2, Ar1 및 Ar2 의 정의는 상기 화학식 1에서와 같다.Definitions of X, L1, L2, Ar1 and Ar2 are the same as in Chemical Formula 1. - 청구항 1에 있어서,The method according to claim 1,상기 화학식 1은 하기 구조식들 중에서 선택되는 어느 하나인 것인 화합물:Formula 1 is any one selected from the following structural formula:
.
. - 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 청구항 1 내지 4 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound according to any one of claims 1 to 4. Light emitting element.
- 청구항 5에 있어서,The method according to claim 5,상기 유기물층은 정공주입층 또는 전자억제층을 포함하고, 상기 정공주입층 또는 전자억제층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes a hole injection layer or an electron suppression layer, and the hole injection layer or an electron suppression layer comprises the compound.
- 청구항 5에 있어서,The method according to claim 5,상기 유기물층은 정공저지층 또는 전자주입층을 포함하고, 상기 정공저지층 또는 전자주입층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes a hole blocking layer or an electron injection layer, the hole blocking layer or an electron injection layer is an organic light emitting device comprising the compound.
- 청구항 5에 있어서,The method according to claim 5,상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an emission layer, and the emission layer comprises the compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201980003809.0A CN111051315B (en) | 2018-03-28 | 2019-03-28 | Polycyclic compound and organic light emitting device including the same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20180036140 | 2018-03-28 | ||
| KR10-2018-0036140 | 2018-03-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2019190231A1 true WO2019190231A1 (en) | 2019-10-03 |
Family
ID=68058225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2019/003653 WO2019190231A1 (en) | 2018-03-28 | 2019-03-28 | Polycyclic compound and organic light emitting diode comprising same |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR102168281B1 (en) |
| CN (1) | CN111051315B (en) |
| WO (1) | WO2019190231A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698458A (en) * | 2019-10-30 | 2020-01-17 | 烟台显华化工科技有限公司 | Organic luminescent material and application thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102405810B1 (en) * | 2019-05-20 | 2022-06-08 | 엘티소재주식회사 | Heterocyclic compound and organic light emitting device comprising same |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160089033A (en) * | 2015-01-16 | 2016-07-27 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| KR20170097450A (en) * | 2016-02-18 | 2017-08-28 | 삼성에스디아이 주식회사 | Organic compound and organic optoelectric device and display device |
| KR20170117775A (en) * | 2016-04-14 | 2017-10-24 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20170125555A (en) * | 2016-05-04 | 2017-11-15 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20180020522A (en) * | 2016-08-18 | 2018-02-28 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100924145B1 (en) * | 2008-06-10 | 2009-10-28 | 삼성모바일디스플레이주식회사 | Organic light emitting diode and fabrication method of the same |
| KR101861263B1 (en) * | 2010-12-14 | 2018-05-28 | 에스에프씨 주식회사 | Anthracene deriva tives and organic light-emitting diode including the same |
| KR101835187B1 (en) * | 2015-06-15 | 2018-03-06 | 주식회사 엘지화학 | Multicyclic compound and organic light emitting device comprising the same |
| KR102673941B1 (en) * | 2015-12-28 | 2024-06-11 | 에스에프씨 주식회사 | Novel heterocyclic compounds and organic light-emitting diode including the same |
-
2019
- 2019-03-28 WO PCT/KR2019/003653 patent/WO2019190231A1/en active Application Filing
- 2019-03-28 KR KR1020190035978A patent/KR102168281B1/en active IP Right Grant
- 2019-03-28 CN CN201980003809.0A patent/CN111051315B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160089033A (en) * | 2015-01-16 | 2016-07-27 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| KR20170097450A (en) * | 2016-02-18 | 2017-08-28 | 삼성에스디아이 주식회사 | Organic compound and organic optoelectric device and display device |
| KR20170117775A (en) * | 2016-04-14 | 2017-10-24 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20170125555A (en) * | 2016-05-04 | 2017-11-15 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20180020522A (en) * | 2016-08-18 | 2018-02-28 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698458A (en) * | 2019-10-30 | 2020-01-17 | 烟台显华化工科技有限公司 | Organic luminescent material and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111051315A (en) | 2020-04-21 |
| CN111051315B (en) | 2022-06-14 |
| KR20190113673A (en) | 2019-10-08 |
| KR102168281B1 (en) | 2020-10-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2017043887A1 (en) | Organic electroluminescent element | |
| WO2019190235A1 (en) | Compound and organic light-emitting device comprising same | |
| WO2013154378A1 (en) | Novel nitrogen-containing heterocyclic compound and organic electronic device using same | |
| WO2015016498A1 (en) | Heterocyclic compound and organic light-emitting device comprising same | |
| WO2017131380A1 (en) | Heterocyclic compound and organic light emitting device containing same | |
| WO2015152650A1 (en) | Heterocyclic compound and organic light-emitting element comprising same | |
| WO2017073932A1 (en) | Amine compound and organic light emitting element comprising same | |
| WO2016195406A2 (en) | Heterocyclic compound and organic light emitting device including same | |
| WO2017061779A1 (en) | Amine compound and organic light-emitting device comprising same | |
| WO2014123369A1 (en) | Novel compound and organic electronic element using same | |
| WO2021049840A1 (en) | Heterocyclic compound and organic light-emitting device comprising same | |
| WO2017047977A1 (en) | Heterocyclic compound and organic light emitting diode comprising same | |
| WO2019160315A1 (en) | Heterocyclic compound and organic light emitting device comprising same | |
| WO2020106098A1 (en) | Compound and organic light-emitting diode comprising same | |
| WO2019066607A1 (en) | Heterocyclic compound and organic light emitting device comprising same | |
| WO2020009492A1 (en) | Polycyclic compound and organic light emitting diode comprising same | |
| WO2019164301A1 (en) | Compound and organic light emitting diode comprising same | |
| WO2020096326A1 (en) | Organic light emitting diode | |
| WO2019088751A1 (en) | Compound and organic light emitting device comprising same | |
| WO2020130528A1 (en) | Compound and organic light emitting diode comprising same | |
| WO2020106102A1 (en) | Compound and organic light emitting diode comprising same | |
| WO2019143223A9 (en) | Polycyclic compound and organic light-emitting diode comprising same | |
| WO2019177393A1 (en) | Compound and organic light emitting device comprising same | |
| WO2021066351A1 (en) | Novel compound and organic light-emitting device using same | |
| WO2019190231A1 (en) | Polycyclic compound and organic light emitting diode comprising same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 19775065 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 19775065 Country of ref document: EP Kind code of ref document: A1 |