WO2017138755A1 - Heterocyclic compound and organic electroluminescent device containing same - Google Patents
Heterocyclic compound and organic electroluminescent device containing same Download PDFInfo
- Publication number
- WO2017138755A1 WO2017138755A1 PCT/KR2017/001438 KR2017001438W WO2017138755A1 WO 2017138755 A1 WO2017138755 A1 WO 2017138755A1 KR 2017001438 W KR2017001438 W KR 2017001438W WO 2017138755 A1 WO2017138755 A1 WO 2017138755A1
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- WIPO (PCT)
- Prior art keywords
- group
- substituted
- unsubstituted
- divalent
- heterocyclic compound
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 29
- -1 dimethyl fluorenyl group Chemical group 0.000 claims description 51
- 239000011368 organic material Substances 0.000 claims description 47
- 238000002347 injection Methods 0.000 claims description 41
- 239000007924 injection Substances 0.000 claims description 41
- 239000000463 material Substances 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000006267 biphenyl group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 6
- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical group N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 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 claims description 5
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical group N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 4
- FQOBINBWTPHVEO-UHFFFAOYSA-N pyrazino[2,3-b]pyrazine Chemical group N1=CC=NC2=NC=CN=C21 FQOBINBWTPHVEO-UHFFFAOYSA-N 0.000 claims description 4
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 claims description 4
- LSMNCNQKKZSDFC-UHFFFAOYSA-N 2,4-dimethyl-9H-indeno[2,1-d]pyrimidine Chemical group CC=1C2=C(N=C(N=1)C)CC=1C=CC=CC=12 LSMNCNQKKZSDFC-UHFFFAOYSA-N 0.000 claims description 3
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 3
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical group N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 claims description 2
- PYKUKGUIFBFVDR-UHFFFAOYSA-N 4,7-diazapentacyclo[10.7.1.02,11.03,8.016,20]icosa-1(19),2(11),3,5,7,9,12,14,16(20),17-decaene Chemical group C1=CC2=CC=CC(C=3C4=C5N=CC=NC5=CC=3)=C2C4=C1 PYKUKGUIFBFVDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 140
- 150000001875 compounds Chemical class 0.000 description 54
- 125000001424 substituent group Chemical group 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 230000032258 transport Effects 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 16
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- SNAKUPLQASYKTC-AWEZNQCLSA-N (3S)-3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxymethyl]-N-phenylpiperidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC[C@@H]1CN(CCC1)C(=O)NC1=CC=CC=C1 SNAKUPLQASYKTC-AWEZNQCLSA-N 0.000 description 5
- LJHFUFVRZNYVMK-CYBMUJFWSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@@H](CC1)O LJHFUFVRZNYVMK-CYBMUJFWSA-N 0.000 description 5
- LJHFUFVRZNYVMK-ZDUSSCGKSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3S)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@H](CC1)O LJHFUFVRZNYVMK-ZDUSSCGKSA-N 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical compound ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- ITOKSWHFPQBNSE-UHFFFAOYSA-N [1]benzofuro[3,2-d]pyrimidine Chemical group N1=CN=C2C3=CC=CC=C3OC2=C1 ITOKSWHFPQBNSE-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- ZZTFQOIZJMYIIL-UHFFFAOYSA-N benzo[f]quinazoline Chemical group C1=NC=C2C3=CC=CC=C3C=CC2=N1 ZZTFQOIZJMYIIL-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000002219 fluoranthenes Chemical group 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000003246 quinazolines Chemical group 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 2
- AELILXBWWJSIMK-UHFFFAOYSA-N 2-chloro-4-naphthalen-2-ylquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(C=3C=C4C=CC=CC4=CC=3)=C21 AELILXBWWJSIMK-UHFFFAOYSA-N 0.000 description 2
- ICQFFYYMWOOREK-UHFFFAOYSA-N 2-chloro-4-phenyl-[1]benzothiolo[3,2-d]pyrimidine Chemical compound S1C2=C(C3=C1C(C1=CC=CC=C1)=NC(=N3)Cl)C=CC=C2 ICQFFYYMWOOREK-UHFFFAOYSA-N 0.000 description 2
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical group C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 0 c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-[n](c1c2cccc1)c1c2*(cccc2)c2c(-c2c3[n]c(cc(cccc4)c4c4)c4c3ccc2)c1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-[n](c1c2cccc1)c1c2*(cccc2)c2c(-c2c3[n]c(cc(cccc4)c4c4)c4c3ccc2)c1 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008021 deposition Effects 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
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000007774 positive electrode material Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical group N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 2
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IBGUDZMIAZLJNY-UHFFFAOYSA-N 1,4-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=C(Br)C2=C1 IBGUDZMIAZLJNY-UHFFFAOYSA-N 0.000 description 1
- NDXQDKJSFNZMJK-UHFFFAOYSA-N 1-bromo-2-chloronaphthalene Chemical compound C1=CC=CC2=C(Br)C(Cl)=CC=C21 NDXQDKJSFNZMJK-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AELZBFQHFNMGJS-UHFFFAOYSA-N 1h-1-benzosilole Chemical group C1=CC=C2[SiH2]C=CC2=C1 AELZBFQHFNMGJS-UHFFFAOYSA-N 0.000 description 1
- HZKKNNZKUWBKQC-UHFFFAOYSA-N 2,4-dimethyl-5H-indeno[1,2-d]pyrimidine Chemical group CC=1C2=C(N=C(N=1)C)C1=CC=CC=C1C2 HZKKNNZKUWBKQC-UHFFFAOYSA-N 0.000 description 1
- ORPYLLUOBDZSEX-UHFFFAOYSA-N 2-bromo-1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=C(Br)C=CC2=C1 ORPYLLUOBDZSEX-UHFFFAOYSA-N 0.000 description 1
- UCEGSRIJXCCEST-UHFFFAOYSA-N 2-bromo-3-chloronaphthalene Chemical compound C1=CC=C2C=C(Br)C(Cl)=CC2=C1 UCEGSRIJXCCEST-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 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
- 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
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 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
- 240000000662 Anethum graveolens Species 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Definitions
- the present specification relates to a heterocyclic compound and an organic electroluminescent device including the same.
- the electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
- the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
- the organic thin film may be composed of a single layer or multiple layers as necessary.
- the material of the organic thin film may have a light emitting function as necessary.
- a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
- a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
- the present specification provides a heterocyclic compound and an organic electroluminescent device including the same.
- An exemplary embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.
- Ar is a substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted arylamine group,
- L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
- R1 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- Two or more adjacent groups of R1 to R4 may combine with each other to form a substituted or unsubstituted ring.
- the present application is 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 aforementioned heterocyclic compound. do.
- the compound according to the exemplary embodiment of the present application may be used in an organic electroluminescent device to lower the driving voltage of the organic electroluminescent device, improve the light efficiency, and improve the life characteristics of the device by thermal stability of the compound.
- FIG. 1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
- FIG. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. An example is shown.
- FIG. 3 is an MS spectrum of Compound 1-17 according to Synthesis Example 2.
- FIG. 4 is an MS spectrum of Compound 1-18 according to Synthesis Example 3.
- FIG. 4 is an MS spectrum of Compound 1-18 according to Synthesis Example 3.
- FIG. 5 is an MS spectrum of Compound 1-45 according to Synthesis Example 5.
- FIG. 6 is an MS spectrum of Compound 4-45 according to Synthesis Example 9.
- the present specification provides a heterocyclic compound represented by Chemical Formula 1.
- 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 substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
- the term "substituted or unsubstituted” is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Alkyl groups; Cycloalkyl group; Alkenyl groups; An alkoxy group; Substituted or unsubstituted phosphine oxide 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, chlorine, bromine or iodine.
- the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50.
- Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
- the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.
- 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, 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 is not limited.
- the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40.
- 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.
- phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
- the aryl group is a monocyclic aryl group
- carbon number is not particularly limited, but preferably 6 to 25 carbon atoms.
- the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
- Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24.
- the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
- the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
- the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S, and the like. have.
- carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60.
- heterocyclic group examples include thiophenyl group, furanyl group, pyrrole group, imidazolyl group, oxazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, acridil group, hydroacrylic Dill groups (e.g., ), Pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, and isoquinolinyl , Indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl
- the condensation structure may be a structure in which an aromatic carbon hydrogen ring is condensed to a corresponding substituent.
- a condensed ring of benzimidazole Etc. but is not limited thereto.
- Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.
- Ra to Rl are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
- Ra to Rl are hydrogen or deuterium.
- Ra to Rl are hydrogen.
- R1 to R4 are hydrogen or deuterium, or two or more adjacent groups combine with each other to form a benzene ring.
- R1 to R4 are hydrogen, or two or more adjacent groups combine with each other to form a benzene ring.
- R5 to R15 are hydrogen or deuterium.
- R5 to R15 are hydrogen.
- L is a direct bond; Substituted or unsubstituted phenylene group; Substituted or unsubstituted naphthalene group; A substituted or unsubstituted divalent triazine group; A substituted or unsubstituted divalent pyrimidine group; A substituted or unsubstituted divalent pyridine group; Substituted or unsubstituted divalent quinoline group; A substituted or unsubstituted divalent quinazoline group; A substituted or unsubstituted divalent benzoquinazolin group; A substituted or unsubstituted divalent quinolsaline group; A substituted or unsubstituted divalent pyridopyrimidine group; A substituted or unsubstituted divalent pyridopyrazine group; Substituted or unsubstituted divalent pteridine group; A substituted or unsubd
- L is a direct bond; Phenylene group; Naphthalene group; Divalent pyridine group; Divalent quinoline groups; Divalent quinazoline group; Divalent benzoquinazolin group; Divalent quinolsaline group; Divalent pyridopyrimidine group; Divalent pyridopyrazine group; Divalent pteridine groups; Divalent pyrazinopyrazine groups; Divalent benzofurypyrimidine group; Divalent benzothienopimidine group; Or a divalent dimethyl indeno pyrimidine group.
- L is a direct bond; Phenylene group; Naphthalene group; Divalent pyridine group; Divalent quinoline groups; Divalent quinazoline group; Divalent benzo [ h ] quinazolin group; Divalent benzo [ f ] quinazolin group; Divalent quinolsaline group; Divalent pyrido [3,2-d] pyrimidine groups; Divalent pyrido [2,3-d] pyrimidine groups; Divalent pyrido [2,3-b] pyrazine groups; Divalent pyrido [3,2-b] pyrazine groups; Divalent pteridine groups; Divalent pyrazino [2,3-b] pyrazine groups; Divalent benzofuro [3,2-d] pyrimidine group; Divalent benzothieno [3,2-d) pimidine group; Or a divalent dimethyl indeno [1,2-d] pyrimidine group.
- Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzoquinazolin group; Substituted or unsubstituted phthalazine group; Substituted or unsubstituted isoquinoline group; Sub
- Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzo [ f ] quinazoline group; Substituted or unsubstituted phthalazine group; Substituted or unsubstituted isoquino
- Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzo [ f ] quinazoline group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted pyrido
- the "substituted or unsubstituted" of Ar is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Alkyl groups; Cycloalkyl group; Alkenyl groups; An alkoxy group; Substituted or unsubstituted phosphine oxide 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 of the substituents are connected, or does not have any substituents.
- the "substituted or unsubstituted" of Ar is deuterium; Cyano group; Substituted or unsubstituted phosphine oxide 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 of the substituents are connected, or does not have any substituents.
- the "substituted or unsubstituted" of Ar is deuterium; Cyano group; Diphenyl phosphine oxide group; Phenyl group; Biphenyl group; Naphthyl group; Dibenzofuran group; And it is substituted with one or two or more substituents selected from the group consisting of dibenzothiophene group or substituted with a substituent to which two or more substituents of the substituent is connected, or means having no substituent.
- the "substituted or unsubstituted" of Ar is deuterium; Phenyl group; Biphenyl group; Naphthyl group; Dibenzofuran group; And it is substituted with one or two or more substituents selected from the group consisting of dibenzothiophene group or substituted with a substituent to which two or more substituents of the substituent is connected, or means having no substituent.
- the compound represented by Chemical Formula 1 is any one selected from the following structural formulas.
- Formula 2A was prepared in the same manner as in Example 1, except that 1-bromo-2-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
- Formula 3A was prepared in the same manner as in Example 1, except that 2-bromo-3-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
- Formula 4A was prepared by the same method as the method of formula 1A of Preparation Example 1, except that 2-bromo-1-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
- the present specification provides an organic electroluminescent device comprising the compound described above.
- the 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.
- the organic material layer of the organic electroluminescent device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
- the organic EL device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
- the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic layers.
- the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
- the thickness of the organic material layer is 1 kPa to 1000 kPa.
- the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host material.
- the organic material layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound, and further includes a dopant compound.
- the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound and the dopant compound in a ratio of 100: 1 to 5: 5.
- the dopant compound may be selected from the following structural formulas.
- the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.
- the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
- the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound.
- the organic electroluminescent device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound.
- the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.
- the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound.
- the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
- heterocyclic compound when the compound is included in each of the two or more electron transport layers, other materials except for the heterocyclic compound may be the same or different from each other.
- the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group or benzocarbazolyl group in addition to the organic material layer including the heterocyclic compound.
- the organic electroluminescent device may be an organic electroluminescent device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
- the organic electroluminescent device may be an organic electroluminescent device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
- FIGS. 1 and 2 For example, the structure of an organic EL device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.
- FIG. 1 illustrates a structure of an organic EL device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
- the compound may be included in the light emitting layer (3).
- FIG. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked.
- the structure of is illustrated.
- the compound may be included in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.
- the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.
- the organic EL device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.
- the organic material layers may be formed of the same material or different materials.
- the organic EL device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Chemical Formula 1.
- the organic EL device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
- a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
- an organic EL device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic EL device.
- the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
- an organic electroluminescent device may be fabricated by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
- the manufacturing method is not limited thereto.
- 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 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); ZnO: Al or SnO 2 : Combination of metals and oxides such as 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 layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer.
- the compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
- the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
- the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
- the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
- the material 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 light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport 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.
- the light emitting layer may include a host material and a dopant material.
- the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
- the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
- the heterocyclic containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, and the like, but is not limited thereto.
- the electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
- the electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof 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 electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
- suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
- the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
- the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
- fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
- Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
- the hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
- the organic electroluminescent device may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.
- a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
- ITO Indium Tin Oxide
- Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer.
- HT1 700 mW
- HT2 200 mW
- Compound 1-9 and dopant Dp-7 compound were vacuum deposited to a light emitting layer to a thickness of 300 kPa as a host.
- the dopant was used in an amount of 3% by weight based on the total amount of the host and the dopant.
- E1 compound 300 kPa was thermally vacuum deposited sequentially to the electron injection and transport layer.
- An organic electroluminescent device was manufactured by depositing lithium fluoride (LiF) having a thickness of 12 kW and aluminum having a thickness of 2,000 kW sequentially on the electron transport layer to form a cathode.
- LiF lithium fluoride
- the deposition rate of the organic material was maintained at 1 ⁇ / sec
- LiF was 0.2 ⁇ / sec
- the aluminum was maintained at a deposition rate of 3 ⁇ / sec to 7 ⁇ / sec.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-17 was used instead of Compound 1-9 in Example 1.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-18 was used instead of Compound 1-9 in Example 1,
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-19 was used instead of Compound 1-9 in Example 1.
- An organic electroluminescent device organic electroluminescent device organic electroluminescent device organic electroluminescent device group A compound instead of compound 1-9 in Example 1, except that compound 1-45 was used instead of compound 1-9 in Example 1
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that 4-9 was used.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-17 was used instead of Compound 1-9 in Example 1.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-19 was used instead of Compound 1-9 in Example 1.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-45 was used instead of Compound 1-9 in Example 1.
- An organic light emitting diode device was manufactured according to the same method as Example 1 except for using H-1 instead of compound 1-9 in Example 1.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that H-2 was used instead of Compound 1-9 in Example 1.
- An organic electroluminescent device was manufactured in the same manner as in Example 1, except that H-3 was used instead of Compound 1-9 in Example 1.
- Table 1 shows the results of the organic electroluminescent devices produced according to Examples 1 to 9 and Comparative Examples 1 to 3. Voltage, efficiency and emission color are data at 5000 nit luminance. The lifetime was initially measured at 100% and the time at 98%.
- the organic electroluminescent device using the compound of the present invention improved the luminous efficiency while lowering the driving voltage and all showed red light emission. It showed up to 80% more improvement in efficiency than H-1, a comparative material, and had the advantage of driving voltage as a whole.
- Comparative Example 2 and Comparative Example 3 seemed to have the advantages of the driving voltage, the lifespan is less than half the level of Example 5, Comparative Example 1 is similar in life but did not seem to have a great advantage in terms of driving voltage and efficiency. Therefore, the compound of the present invention can be judged to have the advantages of high efficiency, low driving voltage and long life in the organic EL device.
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Abstract
The present specification provides a heterocyclic compound and an organic electroluminescent device containing the same.
Description
본 명세서는 2016년 2월 11일에 한국특허청에 제출된 한국 특허 출원 제10-2016-0015838호의 출원일의 이익을 주장하며, 그 내용은 전부 본 명세서에 포함된다.This specification claims the benefit of the filing date of Korean Patent Application No. 10-2016-0015838 filed with the Korea Intellectual Property Office on February 11, 2016, the entire contents of which are incorporated herein.
본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present specification relates to a heterocyclic compound and an organic electroluminescent device including the same.
전계 발광 소자는 자체 발광형 표시 소자의 일종으로서, 시야각이 넓고, 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. The electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
유기발광소자는 2개의 전극 사이에 유기박막을 배치시킨 구조를 가지고 있다. 이와 같은 구조의 유기발광소자에 전압이 인가되면, 2개의 전극으로부터 주입된 전자와 정공이 유기박막에서 결합하여 쌍을 이룬 후 소멸하면서 빛을 발하게 된다. 상기 유기박막은 필요에 따라 단층 또는 다층으로 구성될 수 있다. The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers as necessary.
유기박막의 재료는 필요에 따라 발광 기능을 가질 수 있다. 예컨대, 유기박막 재료로는 그 자체가 단독으로 발광층을 구성할 수 있는 화합물이 사용될 수도 있고, 또는 호스트-도펀트계 발광층의 호스트 또는 도펀트 역할을 할 수 있는 화합물이 사용될 수도 있다. 그 외에도, 유기박막의 재료로서, 정공주입, 정공수송, 전자블록킹, 정공블록킹, 전자수송 또는 전자주입 등의 역할을 수행할 수 있는 화합물이 사용될 수도 있다.The material of the organic thin film may have a light emitting function as necessary. For example, as the organic thin film material, a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
유기발광소자의 성능, 수명 또는 효율을 향상시키기 위하여, 유기박막의 재료의 개발이 지속적으로 요구되고 있다.In order to improve the performance, lifespan or efficiency of the organic light emitting device, the development of the material of the organic thin film is continuously required.
본 명세서는 헤테로고리 화합물 및 이를 포함하는 유기 전계 발광 소자를 제공한다.The present specification provides a heterocyclic compound and an organic electroluminescent device including the same.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 헤테로환 화합물을 제공한다. An exemplary embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.
[화학식 1][Formula 1]
상기 화학식 1에 있어서, Ar은 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 치환 또는 비치환된 아릴아민기이고, In Formula 1, Ar is a substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted arylamine group,
L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
R1 내지 R15는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고, R1 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R1 내지 R4 중 인접하는 2이상의 기가 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다. Two or more adjacent groups of R1 to R4 may combine with each other to form a substituted or unsubstituted ring.
또한, 본 출원은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 유기물층 중 1 층 이상은 전술한 헤테로환 화합물을 포함하는 것인 유기 전계 발광 소자를 제공한다.In addition, the present application is 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 aforementioned heterocyclic compound. do.
본 출원의 일 실시상태에 따른 화합물은 유기 전계 발광 소자에 사용되어, 유기 전계 발광 소자의 구동전압을 낮추고, 광효율을 향상시키며, 화합물의 열적 안정성에 의하여 소자의 수명 특성을 향상시킬 수 있다. The compound according to the exemplary embodiment of the present application may be used in an organic electroluminescent device to lower the driving voltage of the organic electroluminescent device, improve the light efficiency, and improve the life characteristics of the device by thermal stability of the compound.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)이 순차적으로 적층된 유기 전계 발광 소자의 예를 도시한 것이다. 1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(3), 전자수송층(7) 및 음극(4)이 순차적으로 적층된 유기 전계 발광 소자의 예를 도시한 것이다. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. An example is shown.
도 3은 합성예 2에 따른 화합물 1-17의 MS 스펙트럼이다.3 is an MS spectrum of Compound 1-17 according to Synthesis Example 2. FIG.
도 4는 합성예 3에 따른 화합물 1-18의 MS 스펙트럼이다. 4 is an MS spectrum of Compound 1-18 according to Synthesis Example 3. FIG.
도 5는 합성예 5에 따른 화합물 1-45의 MS 스펙트럼이다.5 is an MS spectrum of Compound 1-45 according to Synthesis Example 5. FIG.
도 6은 합성예 9에 따른 화합물 4-45의 MS 스펙트럼이다.6 is an MS spectrum of Compound 4-45 according to Synthesis Example 9. FIG.
[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: 전자수송층 7: electron transport layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, this specification is demonstrated in detail.
본 명세서는 상기 화학식 1로 표시되는 헤테로환 화합물을 제공한다.The present specification provides a heterocyclic compound represented by Chemical Formula 1.
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 substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 알킬기; 시클로알킬기; 알케닐기; 알콕시기; 치환 또는 비치환된 포스핀 옥사이드기; 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 있다. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Alkyl groups; Cycloalkyl group; Alkenyl groups; An alkoxy group; Substituted or unsubstituted phosphine oxide 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.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되지 않는다. In the present specification, the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.
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, 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, 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 is not limited.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 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 이들에 한정되지 않는다.In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. 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, 포스핀옥사이드기는 구체적으로 디페닐포스핀옥사이드기, 디나프틸포스핀옥사이드 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
본 명세서에서 상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 25인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 24인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
상기 플루오레닐기가 치환되는 경우, 
,
등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted, , Etc., but is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se, Si 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 헤테로고리기의 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오페닐기, 퓨라닐기, 피롤기, 이미다졸릴기, 옥사졸릴기, 트리아졸릴기, 피리딜기, 비피리딜기, 피리미딜기, 트리아지닐기, 아크리딜기, 하이드로아크리딜기(예컨대, 
), 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 디벤조카바졸릴기, 벤조티오페닐기, 디벤조티오페닐기, 벤조퓨라닐기, 디벤조퓨라닐기, 벤조실롤기, 디벤조실롤기, 페난트롤리닐기(phenanthrolinyl group), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 페노티아지닐기, 페노옥사지닐기, 및 이들의 축합구조 등이 있으나, 이들에만 한정되는 것은 아니다. 이외에도 헤테로고리기의 예로서, 술포닐기를 포함하는 헤테로고리 구조, 예컨대, 
등이 있다.In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S, and the like. have. Although carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60. Examples of the heterocyclic group include thiophenyl group, furanyl group, pyrrole group, imidazolyl group, oxazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, acridil group, hydroacrylic Dill groups (e.g., ), Pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, and isoquinolinyl , Indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzo Furanyl group, benzosilol group, dibenzosilol group, phenanthrolinyl group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, phenothiazinyl group, phenooxazinyl group, and Although there exist these condensation structures etc., it is not limited to these. In addition, examples of heterocyclic groups include heterocyclic structures including a sulfonyl group, for example, Etc.
본 명세서에 있어서, 상기 축합구조는 해당 치환기에 방향족 탄소수소 고리가 축합된 구조일 수 있다. 예컨대, 벤즈이미다졸의 축합고리로서 
등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the condensation structure may be a structure in which an aromatic carbon hydrogen ring is condensed to a corresponding substituent. For example, as a condensed ring of benzimidazole Etc., but is not limited thereto.
본 명세서의 일 실시 상태에 있어서, 상기 화학식 1은 하기 화학식 2 내지 4중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 2 내지 4에 있어서, 상기 Ar, L, 및 R1 내지 R15의 정의는 화학식 1과 같고, In Formulas 2 to 4, Ar, L, and R1 to R15 are the same as defined in Formula 1,
Ra 내지 Rl 은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. Ra to Rl are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
본 명세서의 일 실시 상태에 있어서, Ra 내지 Rl은 수소 또는 중수소이다.In one embodiment of the present specification, Ra to Rl are hydrogen or deuterium.
본 명세서의 일 실시 상태에 있어서, Ra 내지 Rl은 수소이다.In one embodiment of the present specification, Ra to Rl are hydrogen.
본 명세서의 일 실시 상태에 있어서, R1 내지 R4는 수소 또는 중수소이거나, 인접하는 2이상의 기는 서로 결합하여 벤젠고리를 형성한다.In one embodiment of the present specification, R1 to R4 are hydrogen or deuterium, or two or more adjacent groups combine with each other to form a benzene ring.
본 명세서의 일 실시 상태에 있어서, R1 내지 R4는 수소이거나, 인접하는 2이상의 기는 서로 결합하여 벤젠고리를 형성한다.In one embodiment of the present specification, R1 to R4 are hydrogen, or two or more adjacent groups combine with each other to form a benzene ring.
본 명세서의 일 실시 상태에 있어서, 상기 R5 내지 R15는 수소 또는 중수소이다.In one embodiment of the present specification, R5 to R15 are hydrogen or deuterium.
본 명세서의 일 실시 상태에 있어서, R5 내지 R15는 수소이다.In one embodiment of the present specification, R5 to R15 are hydrogen.
본 명세서의 일 실시 상태에 있어서, 상기 L은 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 나프탈렌기; 치환 또는 비치환된 2가의 트리아진기; 치환 또는 비치환된 2가의 피리미딘기; 치환 또는 비치환된 2가의 피리딘기; 치환 또는 비치환된 2가의 퀴놀린기; 치환 또는 비치환된 2가의 퀴나졸린기; 치환 또는 비치환된 2가의 벤조퀴나졸린기; 치환 또는 비치환된 2가의 퀴놀살린기; 치환 또는 비치환된 2가의 피리도피리미딘기; 치환 또는 비치환된 2가의 피리도피라진기; 치환 또는 비치환된 2가의 프테리딘기; 치환 또는 비치환된 2가의 피라지노피라진기; 치환 또는 비치환된 2가의 벤조퓨로피리미딘기; 치환 또는 비치환된 2가의 벤조티에노피미딘기; 또는 치환 또는 비치환된 2가의 디메틸 인데노 피리미딘기이다.In one embodiment of the present specification, L is a direct bond; Substituted or unsubstituted phenylene group; Substituted or unsubstituted naphthalene group; A substituted or unsubstituted divalent triazine group; A substituted or unsubstituted divalent pyrimidine group; A substituted or unsubstituted divalent pyridine group; Substituted or unsubstituted divalent quinoline group; A substituted or unsubstituted divalent quinazoline group; A substituted or unsubstituted divalent benzoquinazolin group; A substituted or unsubstituted divalent quinolsaline group; A substituted or unsubstituted divalent pyridopyrimidine group; A substituted or unsubstituted divalent pyridopyrazine group; Substituted or unsubstituted divalent pteridine group; A substituted or unsubstituted divalent pyrazinopyrazine group; A substituted or unsubstituted divalent benzopuropyrimidine group; A substituted or unsubstituted divalent benzothienopimidine group; Or a substituted or unsubstituted divalent dimethyl indeno pyrimidine group.
본 명세서의 일 실시 상태에 있어서, 상기 L은 직접결합; 페닐렌기; 나프탈렌기; 2가의 피리딘기; 2가의 퀴놀린기; 2가의 퀴나졸린기; 2가의 벤조퀴나졸린기; 2가의 퀴놀살린기; 2가의 피리도피리미딘기; 2가의 피리도피라진기; 2가의 프테리딘기; 2가의 피라지노피라진기; 2가의 벤조퓨로피리미딘기; 2가의 벤조티에노피미딘기; 또는 2가의 디메틸 인데노 피리미딘기이다.In one embodiment of the present specification, L is a direct bond; Phenylene group; Naphthalene group; Divalent pyridine group; Divalent quinoline groups; Divalent quinazoline group; Divalent benzoquinazolin group; Divalent quinolsaline group; Divalent pyridopyrimidine group; Divalent pyridopyrazine group; Divalent pteridine groups; Divalent pyrazinopyrazine groups; Divalent benzofurypyrimidine group; Divalent benzothienopimidine group; Or a divalent dimethyl indeno pyrimidine group.
본 명세서의 일 실시 상태에 있어서, 상기 L은 직접결합; 페닐렌기; 나프탈렌기; 2가의 피리딘기; 2가의 퀴놀린기; 2가의 퀴나졸린기; 2가의 벤조[h]퀴나졸린기; 2가의 벤조[f]퀴나졸린기; 2가의 퀴놀살린기; 2가의 피리도[3,2-d]피리미딘기; 2가의 피리도[2,3-d]피리미딘기; 2가의 피리도[2,3-b]피라진기; 2가의 피리도[3,2-b]피라진기; 2가의 프테리딘기; 2가의 피라지노[2,3-b]피라진기; 2가의 벤조퓨로[3,2-d]피리미딘기; 2가의 벤조티에노[3,2-d)피미딘기; 또는 2가의 디메틸 인데노[1,2-d]피리미딘기이다.In one embodiment of the present specification, L is a direct bond; Phenylene group; Naphthalene group; Divalent pyridine group; Divalent quinoline groups; Divalent quinazoline group; Divalent benzo [ h ] quinazolin group; Divalent benzo [ f ] quinazolin group; Divalent quinolsaline group; Divalent pyrido [3,2-d] pyrimidine groups; Divalent pyrido [2,3-d] pyrimidine groups; Divalent pyrido [2,3-b] pyrazine groups; Divalent pyrido [3,2-b] pyrazine groups; Divalent pteridine groups; Divalent pyrazino [2,3-b] pyrazine groups; Divalent benzofuro [3,2-d] pyrimidine group; Divalent benzothieno [3,2-d) pimidine group; Or a divalent dimethyl indeno [1,2-d] pyrimidine group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디메틸플루오레닐기; 치환 또는 비치환된 비스비페닐아민기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 피리미딘기; 치환 또는 비치환된 퀴나졸린기; 치환 또는 비치환된 벤조퀴나졸린기; 치환 또는 비치환된 프탈라진기; 치환 또는 비치환된 이소퀴놀린기;; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 피리도 인돌기; 치환 또는 비치환된 벤조퓨로피리미딘기; 치환 또는 비치환된 벤조티에노피미딘기; 치환 또는 비치환된 플루오란텐기; 치환 또는 비치환된 아세나프토피라진기; 또는 치환 또는 비치환된 아세나프토퀴녹살린기이다.In one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzoquinazolin group; Substituted or unsubstituted phthalazine group; Substituted or unsubstituted isoquinoline group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted pyrido indole group; Substituted or unsubstituted benzofurypyrimidine group; Substituted or unsubstituted benzothienopimidine group; Substituted or unsubstituted fluoranthene group; Substituted or unsubstituted acenaphtopyrazine group; Or a substituted or unsubstituted acenaphthoquinoxaline group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디메틸플루오레닐기; 치환 또는 비치환된 비스비페닐아민기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 피리미딘기; 치환 또는 비치환된 퀴나졸린기; 치환 또는 비치환된 벤조[f]퀴나졸린기; 치환 또는 비치환된 프탈라진기; 치환 또는 비치환된 이소퀴놀린기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 피리도[2,3-b]인돌기; 치환 또는 비치환된 피리도[3,4-b]인돌기; 치환 또는 비치환된 벤조퓨로[3,2-d]피리미딘기; 치환 또는 비치환된 벤조티에노[3,2-d]피미딘기; 치환 또는 비치환된 플루오란텐기; 치환 또는 비치환된 아세나프토[1.2-b]피라진기; 또는 치환 또는 비치환된 아세나프토[1,2-b]퀴녹살린기이다.In one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzo [ f ] quinazoline group; Substituted or unsubstituted phthalazine group; Substituted or unsubstituted isoquinoline group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted pyrido [2,3-b] indole group; A substituted or unsubstituted pyrido [3,4-b] indole group; Substituted or unsubstituted benzofuro [3, 2-d] pyrimidine group; Substituted or unsubstituted benzothieno [3, 2-d] pyrimidine group; Substituted or unsubstituted fluoranthene group; A substituted or unsubstituted acenaphtho [1.2-b] pyrazine group; Or a substituted or unsubstituted acenaphtho [1,2-b] quinoxaline group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디메틸플루오레닐기; 치환 또는 비치환된 비스비페닐아민기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 피리미딘기; 치환 또는 비치환된 퀴나졸린기; 치환 또는 비치환된 벤조[f]퀴나졸린기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 피리도[2,3-b]인돌기; 치환 또는 비치환된 피리도[3,4-b]인돌기; 치환 또는 비치환된 벤조퓨로[3,2-d]피리미딘기; 또는 치환 또는 비치환된 벤조티에노[3,2-d]피미딘기이다. In one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzo [ f ] quinazoline group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted pyrido [2,3-b] indole group; A substituted or unsubstituted pyrido [3,4-b] indole group; Substituted or unsubstituted benzofuro [3, 2-d] pyrimidine group; Or a substituted or unsubstituted benzothieno [3,2-d] pimidine group.
본 명세서의 일 실시상태에 있어서, 상기 Ar의 "치환 또는 비치환된"은 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 알킬기; 시클로알킬기; 알케닐기; 알콕시기; 치환 또는 비치환된 포스핀 옥사이드기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.In one embodiment of the present specification, the "substituted or unsubstituted" of Ar is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Alkyl groups; Cycloalkyl group; Alkenyl groups; An alkoxy group; Substituted or unsubstituted phosphine oxide 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 of the substituents are connected, or does not have any substituents.
본 명세서의 일 실시상태에 있어서, 상기 Ar의 "치환 또는 비치환된"은 중수소; 시아노기; 치환 또는 비치환된 포스핀 옥사이드기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.In one embodiment of the present specification, the "substituted or unsubstituted" of Ar is deuterium; Cyano group; Substituted or unsubstituted phosphine oxide 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 of the substituents are connected, or does not have any substituents.
본 명세서의 일 실시상태에 있어서, 상기 Ar의 "치환 또는 비치환된"은 중수소; 시아노기; 디페닐 포스핀 옥사이드기; 페닐기; 비페닐기; 나프틸기; 디벤조퓨란기; 및 디벤조티오펜기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.In one embodiment of the present specification, the "substituted or unsubstituted" of Ar is deuterium; Cyano group; Diphenyl phosphine oxide group; Phenyl group; Biphenyl group; Naphthyl group; Dibenzofuran group; And it is substituted with one or two or more substituents selected from the group consisting of dibenzothiophene group or substituted with a substituent to which two or more substituents of the substituent is connected, or means having no substituent.
본 명세서의 일 실시상태에 있어서, 상기 Ar의 "치환 또는 비치환된"은 중수소; 페닐기; 비페닐기; 나프틸기; 디벤조퓨란기; 및 디벤조티오펜기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.In one embodiment of the present specification, the "substituted or unsubstituted" of Ar is deuterium; Phenyl group; Biphenyl group; Naphthyl group; Dibenzofuran group; And it is substituted with one or two or more substituents selected from the group consisting of dibenzothiophene group or substituted with a substituent to which two or more substituents of the substituent is connected, or means having no substituent.
본 명세서의 일 실시 상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 구조식들 중에서 선택되는 어느 하나이다. In one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following structural formulas.
본 명세서의 일 실시상태에 따른 화합물은 후술하는 제조방법으로 제조될 수 있다. Compounds according to one embodiment of the present specification may be prepared by the preparation method described below.
<제조예 1> 화학식 1A의 제조Preparation Example 1 Preparation of Chemical Formula 1A
1) 화학식 1-a의 제조1) Preparation of Chemical Formula 1-a
1,4-디브로모나프탈렌 100.00 g (1.00 eq), (2-나이트로페닐)브로닉 에시드((2-nitrophenyl)boronic acid) 129.45 g (1.1 eq), Pd(PPh3)4 8.14 g (0.01 eq) 를 1,4-디옥산 1.5L 에 녹여 교반한 다음 K2CO3 194.73 g (2.0 eq)를 물 600 ml 에 녹여 첨가 이를 환류하여 교반했다. 2시간 후 반응이 종료되면 유기층을 분리한 뒤 감압하여 용매를 제거했다. 생성물을 CHCl3에 완전히 녹인 후 물로 씻어주고 용액을 50% 정도 감압 농축하고 에탄올을 넣어서 결정을 떨어트리고 여과했다. 이 후 컬럼크로마토그래피를 이용하여 정제했다. 화학식 1-a 237.27 g (수율 91 %)를 얻었다. [M+H]=37110,00 g (1.00 eq) of 1,4-dibromonaphthalene, (2-nitrophenyl) boronic acid 129.45 g (1.1 eq), Pd (PPh 3 ) 4 8.14 g ( 0.01 eq) was dissolved in 1.5 L of 1,4-dioxane and stirred, and then 194.73 g (2.0 eq) of K 2 CO 3 was dissolved in 600 ml of water, and the resultant was refluxed and stirred. After the reaction was completed after 2 hours, the organic layer was separated, and the solvent was removed under reduced pressure. The product was completely dissolved in CHCl 3 , washed with water, the solution was concentrated under reduced pressure by 50%, ethanol was added, and the crystals were dropped and filtered. Thereafter, the residue was purified using column chromatography. 237.27 g (yield 91%) of formula 1-a were obtained. [M + H] = 371
2) 화학식 1-b의 제조2) Preparation of Chemical Formula 1-b
화학식 1-a 237.27 g (1.0 eq)를 트라이에틸포스파이트 (P(OEt)3) 1L 에 녹여 환류하여 교반했다. 3시간 후 반응이 종료되면 진공 감압하여 50% 정도의 용매를 제거하고 식혀서 결정을 떨어트렸다. 여과 후 에틸 아세테이트에 완전히 녹인 후 물로 씻어주고 용액을 70% 정도 감압 농축하고 식혀서 결정을 떨어 트리고 여과했다. 화학식 1-b 166.62 g (수율 85 %)를 얻었다. [M+H]=307237.27 g (1.0 eq) of Chemical Formula 1-a was dissolved in 1 L of triethylphosphite (P (OEt) 3 ) and refluxed to stir. After 3 hours, when the reaction was completed, the resulting mixture was cooled under vacuum to remove about 50% of the solvent and cooled to drop crystals. After filtration, the solution was dissolved in ethyl acetate and washed with water. The solution was concentrated under reduced pressure at 70%, cooled, and dropped crystals. 166.62 g of formula 1-b (yield 85%) were obtained. [M + H] = 307
3) 화학식 1-c의 제조3) Preparation of Chemical Formula 1-c
화학식 1-b 166.62 g (1.0 eq), 1-브로모-2-클로로벤젠 124.04 g (1.2 eq), 구리 파우더(Copper powder) 67318 g (2.0 eq), K2CO3 150.44 g (2.0 eq)을 DMAC(디메아세트아마이드, Dimethylacetamide) 1L에 넣고 환류하여 교반했다. 반응이 종료되면 상온으로 식힌 뒤 구리 파우더를 먼저 여과하여 제거했다. 생성물 이 녹아 있는 용액을 감압하여 용매를 모두 제거해 준 뒤, CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 제거하고 이를 컬럼크로마토그래피를 이용하여 정제했다. 화학식 1-c 176.66 g (수율 78 %)을 얻었다. [M+H]=417166.62 g (1.0 eq) of Formula 1-b, 124.04 g (1.2 eq) of 1-bromo-2-chlorobenzene, Copper powder 67318 g (2.0 eq), 150.44 g (2.0 eq) K 2 CO 3 Was added to 1 L of DMAC (Diacetamide, Dimethylacetamide) and refluxed to stir. After the reaction was completed, after cooling to room temperature, the copper powder was first filtered off. After removing the solvent by depressurizing the solution in which the product was dissolved, completely dissolved in CHCl 3 , washed with water, and then depressurized to remove the solvent, which was then purified by column chromatography. 176.66 g (yield 78%) of formula 1-c were obtained. [M + H] = 417
4) 화학식 1A의 제조4) Preparation of Chemical Formula 1A
화학식 1-c 176.66 (1.0 eq) 에 Pd(dba)2 2.44 g (0.01 eq), PCy3 3.57 g (0.03 eq), K3PO4 180.23 g (2.00 eq)을 다이에틸아세트아마이드 (Dimethylacetamide) 1L에 넣고 환류하여 교반했다. 3시간 후 반응물을 물에 부어서 결정을 떨어트리고 여과했다. 여과한 고체를 에틸 아세테이트에 완전히 녹인 후 물로 씻어주고 생성물이 녹아있는 용액을 감압 농축하고 컬럼크로마토그래피를 이용하여 정제했다. 화학식 1A 117.81 g (수율 73 %)을 얻었다. [M]=3801.44 g (0.01 eq) of Pd (dba) 2 , 3.57 g (0.03 eq) of PCy 3 , 180.23 g (2.00 eq) of K 3 PO 4 were added to Diethylacetamide 1 L. To reflux and stirred. After 3 hours the reaction was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in ethyl acetate, washed with water, and the resulting solution was concentrated under reduced pressure and purified by column chromatography. 117.81 g (73% yield) of Formula 1A were obtained. [M] = 380
<제조예 2> 화학식 2A 의 제조Preparation Example 2 Preparation of Chemical Formula 2A
[화학식 2A][Formula 2A]
상기 제조예 1의 화학식 1A의 제조 방법에서 1-브로모-2-클로로벤젠 대신 1-브로모-2-클로로나프탈렌을 사용한 것을 제외 하고는 동일한 방법으로 화학식 2A를 제조했다.Formula 2A was prepared in the same manner as in Example 1, except that 1-bromo-2-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
<제조예 3> 화학식 3A 의 제조Preparation Example 3 Preparation of Chemical Formula 3A
[화학식 3A][Formula 3A]
상기 제조예 1의 화학식 1A의 제조 방법에서 1-브로모-2-클로로벤젠 대신 2-브로모-3-클로로나프탈렌을 사용한 것을 제외 하고는 동일한 방법으로 화학식 3A를 제조했다.Formula 3A was prepared in the same manner as in Example 1, except that 2-bromo-3-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
<제조예 4> 화학식 4A 의 제조Preparation Example 4 Preparation of Chemical Formula 4A
[화학식 4A][Formula 4A]
상기 제조예 1의 화학식 1A의 제조 방법에서 1-브로모-2-클로로벤젠 대신 2-브로모-1-클로로나프탈렌을 사용한 것을 제외 하고는 동일한 방법으로 화학식 4A를 제조했다.Formula 4A was prepared by the same method as the method of formula 1A of Preparation Example 1, except that 2-bromo-1-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
또한, 본 명세서는 상기 전술한 화합물을 포함하는 유기 전계 발광 소자를 제공한다. In addition, the present specification provides an organic electroluminescent device comprising the compound described above.
본 출원의 일 실시상태에 있어서, 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 유기물층 중 1 층 이상은 상기 화합물을 포함하는 것인 유기 전계 발광 소자를 제공한다. In one embodiment of the present application, the 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.
본 명세서에서 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 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 "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.
본 출원의 유기 전계 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 전계 발광 소자의 대표 적인 예로서, 유기 전계 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 전계 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic electroluminescent device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic EL device of the present invention, the organic EL device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic layers.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로환 화합물을 포함한다. In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기물층의 두께는 1Å 내지 1000Å이다 In an exemplary embodiment of the present application, the thickness of the organic material layer is 1 kPa to 1000 kPa.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로환 화합물을 호스트 물질로 포함한다. In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host material.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로환 화합물을 포함하고, 도펀트 화합물을 더 포함한다.In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound, and further includes a dopant compound.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로환 화합물과 도펀트 화합물을 100:1 내지 5:5 의 비율로 포함한다. In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound and the dopant compound in a ratio of 100: 1 to 5: 5.
본 출원의 일 실시상태에 있어서, 상기 도펀트 화합물은 하기 구조식들 중에서 선택될 수 있다. In one embodiment of the present application, the dopant compound may be selected from the following structural formulas.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함하고, 상기 정공주입층 또는 정공수송층은 상기 헤테로환 화합물을 포함한다. In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함하고, 상기 전자수송층 또는 전자주입층은 상기 헤테로환 화합물을 포함한다. In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 전자저지층 또는 정공저지층을 포함하고, 상기 전자저지층 또는 정공저지층은 상기 헤테로환 화합물을 포함한다. In an exemplary embodiment of the present application, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 유기 전계 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층 중 적어도 하나는 상기 헤테로환 화합물을 포함한다. In one embodiment of the present application, the organic electroluminescent device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound.
본 출원의 일 실시상태에 있어서, 상기 2층 이상의 유기물층은 전자수송층, 전자주입층, 전자 수송과 전자주입을 동시에 하는 층 및 정공저지층으로 이루어진 군에서 2 이상이 선택될 수 있다.In an exemplary embodiment of the present application, the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 전자수송층을 포함하고, 상기 2층 이상의 전자수송층 중 적어도 하나는 상기 헤테로환 화합물을 포함한다. 구체적으로 본 명세서의 일 실시상태에 있어서, 상기 화합물은 상기 2층 이상의 전자수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 전자수송층에 포함될 수 있다. In an exemplary embodiment of the present application, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound. Specifically, in one embodiment of the present specification, the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
또한, 본 출원의 일 실시상태에 있어서, 상기 화합물이 상기 각각의 2층 이상의 전자수송층에 포함되는 경우, 상기 헤테로환 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.In addition, in an exemplary embodiment of the present application, when the compound is included in each of the two or more electron transport layers, other materials except for the heterocyclic compound may be the same or different from each other.
본 출원의 일 실시상태에 있어서, 상기 유기물층은 상기 헤테로환 화합물을 포함하는 유기물층 이외에 아릴아미노기, 카바졸릴기 또는 벤조카바졸릴기를 포함하는 화합물을 포함하는 정공주입층 또는 정공수송층을 더 포함한다. In an exemplary embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group or benzocarbazolyl group in addition to the organic material layer including the heterocyclic compound.
또 하나의 실시상태에 있어서, 유기 전계 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 전계 발광 소자일 수 있다. In another exemplary embodiment, the organic electroluminescent device may be an organic electroluminescent device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
또 하나의 실시상태에 있어서, 유기 전계 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 전계 발광 소자일 수 있다. In another exemplary embodiment, the organic electroluminescent device may be an organic electroluminescent device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
예컨대, 본 출원의 일 실시상태에 따른 유기 전계 발광 소자의 구조는 도 1 및 2에 예시되어 있다. For example, the structure of an organic EL device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)이 순차적으로 적층된 유기 전계 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 EL device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer (3).
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(3), 전자수송층(7) 및 음극(4)이 순차적으로 적층된 유기 전계 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서 상기 화합물은 상기 정공주입층(5), 정공 수송층(6), 발광층(3) 및 전자 수송층(7) 중 1층 이상에 포함될 수 있다. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. The structure of is illustrated. In such a structure, the compound may be included in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.
이와 같은 구조에 있어서, 상기 화합물은 상기 정공주입층, 정공수송층, 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. In such a structure, the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.
본 출원의 유기 전계 발광 소자는 유기물층 중 1층 이상이 본 출원의 화합물, 즉 상기 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.The organic EL device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.
상기 유기 전계 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic electroluminescent device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
본 출원의 유기 전계 발광 소자는 유기물층 중 1층 이상이 상기 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic EL device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Chemical Formula 1.
예컨대, 본 출원의 유기 전계 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(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, 정공 수송층, 발광층 및 전자 수송층을 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 전계 발광 소자를 만들 수 있다. For example, the organic EL device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic EL device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1의 화합물은 유기 전계 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic EL device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 전계 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to such a method, an organic electroluminescent device may be fabricated by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.
본 출원의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다. In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 실시상태에 있어서, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다. In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
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); ZnO: Al or SnO 2 : Combination of metals and oxides such as 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 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 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(porphyrin), 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 한정 되는 것은 아니다. The hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer. The compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 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. The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material 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 발광 물질로는 정공 수송층과 전자 수송층으로부터 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 light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport 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.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 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 화합물, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. 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 compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, and the like, but is not limited thereto.
상기 전자 수송 물질로는 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof 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 electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
상기 정공저지층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다. The hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
본 명세서에 따른 유기 전계 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electroluminescent device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 출원의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 출원의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present disclosure may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. Embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.
합성예Synthesis Example
<합성예 1> 화합물 1-9Synthesis Example 1 Compound 1-9
화학식 1A 10.0 g (1.0 eq), 2-(4-브로모페닐)-4,6-디페닐-1,3,5-트리아진 11.19 g (1.1 eq), K3PO4 11.15 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 1-9 15.54 g (수율 85 %)를 얻었다. [M]=687Formula 1A 10.0 g (1.0 eq), 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine 11.19 g (1.1 eq), K 3 PO 4 11.15 g (2.0 eq ) And 0.07 g (0.005 eq) of Pd (t-Bu 3 P) 2 were dissolved in 60 ml of xylene, refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 15.54 g (yield 85%) of compound 1-9. [M] = 687
<합성예 2> 화합물 1-17Synthesis Example 2 Compound 1-17
화학식 1A 10.0 g (1.0 eq), 2-클로로-4-페닐퀴나졸린 6.94 g (1.1 eq), K3PO4 11.15 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 1-17 12.60 g (수율 82 %)를 얻었다. [M+H]=58510.0 g (1.0 eq) of formula 1A, 6.94 g (1.1 eq) of 2-chloro-4-phenylquinazoline, 11.15 g (2.0 eq) of K 3 PO 4 , Pd (t-Bu 3 P) 2 0.07 g (0.005 eq ) Was dissolved in 60 ml of xylene, refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 12.60 g (yield 82%) of compound 1-17. [M + H] = 585
<합성예 3> 화합물 1-18Synthesis Example 3 Compound 1-18
화학식 1A 10.0 g (1.0 eq), 24-([1,1'-바이페닐]-4-일)-2-클로로퀴나졸린 9.14 g (1.1 eq), K3PO4 11.16 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 3 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 1-18 15.11 g (수율 87 %)를 얻었다. [M+H]=66110.0 g (1.0 eq) of Formula 1A, 9.14 g (1.1 eq) of 24-([1,1'-biphenyl] -4-yl) -2-chloroquinazoline, 11.16 g (2.0 eq) of K 3 PO 4 , 0.07 g (0.005 eq) of Pd (t-Bu 3 P) 2 was dissolved in 60 ml of xylene and refluxed to stir. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 15.11 g (87% yield) of compound 1-18. [M + H] = 661
<합성예 4> 화합물 1-19Synthesis Example 4 Compound 1-19
화학식 1A 10.0 g (1.0 eq), 2-클로로-4-(나프탈렌-2-일)퀴나졸린 8.39 g (1.1 eq), K3PO4 11.15 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 1-19 14.34g (수율 86 %)를 얻었다. [M]=634Formula 1A 10.0 g (1.0 eq), 2-chloro-4- (naphthalen-2-yl) quinazolin 8.39 g (1.1 eq), K 3 PO 4 11.15 g (2.0 eq), Pd (t-Bu 3 P) 2 0.07 g (0.005 eq) was dissolved in 60 ml of xylene, refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 14.34 g (yield 86%) of compound 1-19. [M] = 634
<합성예 5> 화합물 1-45Synthesis Example 5 Compound 1-45
화학식 1A 10.0 g (1.0 eq), 2-클로로-4-페닐벤조[4,5]티에노[3,2-d]피리미딘 8.39 g (1.1 eq), K3PO4 11.15 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 1-45 14.48 g (수율 86 %)를 얻었다. [M]=64010.0 g (1.0 eq) of Formula 1A, 8.39 g (1.1 eq) of 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine, 11.15 g (2.0 eq) of K 3 PO 4 0.07 g (0.005 eq) of Pd (t-Bu 3 P) 2 was dissolved in 60 ml of xylene and refluxed to stir. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 14.48 g (yield 86%) of compound 1-45. [M] = 640
<합성예 6> 화합물 4-9Synthesis Example 6 Compound 4-9
화학식 4A 10.0 g (1.0 eq), 2-(4-브로모페닐)-4,6-디페닐-1,3,5-트리아진 9.89 g (1.1 eq), K3PO4 11.15 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 4-9 13.83 g (수율 81 %)를 얻었다. [M]=73710.0 g (1.0 eq), 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine 9.89 g (1.1 eq), 11.15 g (2.0 eq) K 3 PO 4 ) And 0.07 g (0.005 eq) of Pd (t-Bu 3 P) 2 were dissolved in 60 ml of xylene, refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 13.83 g (yield 81%) of compound 4-9. [M] = 737
<합성예 7> 화합물 4-17Synthesis Example 7 Compound 4-17
화학식 4A 10.0 g (1.0 eq), 2-클로로-4-페닐퀴나졸린 6.13 g (1.1 eq), K3PO4 11.15 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 4-17 11.50 g (수율 78 %)를 얻었다. [M+H]=63510.0 g (1.0 eq), 6.13 g (1.1 eq) of 2-chloro-4-phenylquinazoline, 11.15 g (2.0 eq) of K 3 PO 4 , Pd (t-Bu 3 P) 2 0.07 g (0.005 eq ) Was dissolved in 60 ml of xylene, refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 11.50 g (yield 78%) of compound 4-17. [M + H] = 635
<합성예 8> 화합물 4-19Synthesis Example 8 Compound 4-19
화학식 4A 10.0 g (1.0 eq), 2-클로로-4-(나프탈렌-2-일)퀴나졸린 7.41 g (1.1 eq), K3PO4 11.15 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 4-19 12.88 g (수율 81 %)를 얻었다. [M+H]=68510.0 g (1.0 eq), 2-chloro-4- (naphthalen-2-yl) quinazoline 7.41 g (1.1 eq), K 3 PO 4 11.15 g (2.0 eq), Pd (t-Bu 3 P) 2 0.07 g (0.005 eq) was dissolved in 60 ml of xylene, refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 12.88 g of a compound 4-19 (yield 81%). [M + H] = 685
<합성예 9> 화합물 4-45Synthesis Example 9 Compound 4-45
화학식 4A 10.0 g (1.0 eq), 2-클로로-4-페닐벤조[4,5]티에노[3,2-d]피리미딘 8.39 g (1.1 eq), K3PO4 11.15 g (2.0 eq), Pd(t-Bu3P)2 0.07 g (0.005 eq) 를 자일렌(Xylene) 60 ml 에 녹여 환류하여 교반했다. 1 시간 후 반응이 종료되면 감압하여 용매를 제거했다. 이 후 CHCl3에 완전히 녹여 물로 씻어주고 다시 감압하여 용매를 50% 정도 제거했다. 다시 환류 상태에서 에틸 아세테이트를 넣어주며 결정을 떨어트려 식힌 후 여과했다. 이를 컬럼크로마토그래피하여 화합물 4-45 12.99 g (수율 81 %)를 얻었다. [M]=69010.0 g (1.0 eq) of Formula 4A, 8.39 g (1.1 eq) of 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine, 11.15 g (2.0 eq) of K 3 PO 4 0.07 g (0.005 eq) of Pd (t-Bu 3 P) 2 was dissolved in 60 ml of xylene and refluxed to stir. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3 , washed with water, and removed under reduced pressure by about 50%. Ethyl acetate was added again at reflux, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to give 12.99 g of compound 4-45 (yield 81%). [M] = 690
<실시예 1><Example 1>
ITO(인듐 주석 산화물)가 1,000Å 두께로 박막 코팅된 유리 기판(corning 7059 glass)을, 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며, 증류수는 Millipore Co. 제품의 필터(Filter)로 2차 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜, 아세톤, 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다. A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
이렇게 준비된 ITO 투명 전극 위에 헥사니트릴 헥사아자트리페닐렌(hexanitrile hexaazatriphenylene, HAT-CN)를 50Å의 두께로 열 진공 증착하여 정공 주입층을 형성하였다. 그 위에 정공을 수송하는 HT1(700Å)을 진공 증착하고 연이어 HT2(200 Å) 증착하였다. 발광층에는 호스트로 화합물 1-9와 도펀트 Dp-7 화합물을 300Å의 두께로 진공 증착하였다. 호스트와 도판트의 합계량에 대해 도판트는 3중량%의 양을 사용하였다. 그 다음에 E1 화합물(300Å)을 전자주입 및 수송층으로 순차적으로 열진공 증착하였다. 상기 전자 수송층 위에 순차적으로 12Å 두께의 리튬 플루오라이드(LiF)와 2,000Å 두께의 알루미늄을 증착하여 음극을 형성하여, 유기 전계 발광 소자를 제조하였다. 상기의 과정에서 유기물의 증착속도는 1 Å/sec를 유지하였고, LiF는 0.2 Å/sec, 알루미늄은 3Å/sec 내지 7Å/sec의 증착속도를 유지하였다.Hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer. HT1 (700 mW) carrying holes thereon was vacuum deposited and subsequently HT2 (200 mW) was deposited. Compound 1-9 and dopant Dp-7 compound were vacuum deposited to a light emitting layer to a thickness of 300 kPa as a host. The dopant was used in an amount of 3% by weight based on the total amount of the host and the dopant. Subsequently, E1 compound (300 kPa) was thermally vacuum deposited sequentially to the electron injection and transport layer. An organic electroluminescent device was manufactured by depositing lithium fluoride (LiF) having a thickness of 12 kW and aluminum having a thickness of 2,000 kW sequentially on the electron transport layer to form a cathode. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, LiF was 0.2 Å / sec, and the aluminum was maintained at a deposition rate of 3 Å / sec to 7 Å / sec.
<실시예 2><Example 2>
상기 실시예 1에서 화합물 1-9 대신 화합물 1-17을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-17 was used instead of Compound 1-9 in Example 1.
<실시예 3><Example 3>
상기 실시예 1에서 화합물 1-9 대신 화합물 1-18을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다,An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-18 was used instead of Compound 1-9 in Example 1,
<실시예 4><Example 4>
상기 실시예 1에서 화합물 1-9 대신 화합물 1-19를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-19 was used instead of Compound 1-9 in Example 1.
<실시예 5>Example 5
상기 실시예 1에서 화합물 1-9 대신 화합물 1-45를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자유기 전계 발광 소자유기 전계 발광 소자기 실시예 1에서 화합물 1-9 대신 화합물 4-9를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device organic electroluminescent device organic electroluminescent device group A compound instead of compound 1-9 in Example 1, except that compound 1-45 was used instead of compound 1-9 in Example 1 An organic electroluminescent device was manufactured in the same manner as in Example 1, except that 4-9 was used.
<실시예 7><Example 7>
상기 실시예 1에서 화합물 1-9 대신 화합물 4-17을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-17 was used instead of Compound 1-9 in Example 1.
<실시예 8><Example 8>
상기 실시예 1에서 화합물 1-9 대신 화합물 4-19을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-19 was used instead of Compound 1-9 in Example 1.
<실시예 9>Example 9
상기 실시예 1에서 화합물 1-9 대신 화합물 4-45를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-45 was used instead of Compound 1-9 in Example 1.
<비교예 1>Comparative Example 1
상기 실시예 1에서 화합물 1-9 대신 H-1을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 전계 소자를 제작하였다. An organic light emitting diode device was manufactured according to the same method as Example 1 except for using H-1 instead of compound 1-9 in Example 1.
<비교예 2>Comparative Example 2
상기 실시예 1에서 화합물 1-9 대신 H-2를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that H-2 was used instead of Compound 1-9 in Example 1.
<비교예 3>Comparative Example 3
상기 실시예 1에서 화합물 1-9 대신 H-3을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that H-3 was used instead of Compound 1-9 in Example 1.
상기 실시예 1 내지 9과 비교예 1 내지 3에 의해 제작된 유기 전계 발광 소자의 결과를 표 1에 나타냈다. 전압, 효율, 발광색은 5000nit 휘도에서의 데이터이다. 수명은 처음 광전류 값을 100%로 보고 이에 대한 98%일때의 시간을 표시했다.Table 1 shows the results of the organic electroluminescent devices produced according to Examples 1 to 9 and Comparative Examples 1 to 3. Voltage, efficiency and emission color are data at 5000 nit luminance. The lifetime was initially measured at 100% and the time at 98%.
| 구분division | 물질matter | 구동전압(V)Driving voltage (V) | 효율(cd/A)Efficiency (cd / A) | 수명 T98(hr)Lifespan T98 (hr) | 발광색Luminous color |
| 실시예 1Example 1 | 화합물 1-9Compound 1-9 | 4.04.0 | 32.232.2 | 2727 | 적색Red |
| 실시예 2Example 2 | 화합물 1-17Compound 1-17 | 4.34.3 | 28.728.7 | 5353 | 적색Red |
| 실시예 3Example 3 | 화합물 1-18Compound 1-18 | 4.34.3 | 29.029.0 | 4848 | 적색Red |
| 실시예 4Example 4 | 화합물 1-19Compound 1-19 | 4.34.3 | 29.529.5 | 5151 | 적색Red |
| 실시예 5Example 5 | 화합물 1-45Compound 1-45 | 4.24.2 | 31.431.4 | 3737 | 적색Red |
| 실시예 6Example 6 | 화합물 4-9Compound 4-9 | 3.93.9 | 32.832.8 | 3333 | 적색Red |
| 실시예 7Example 7 | 화합물 4-17Compound 4-17 | 4.24.2 | 29.629.6 | 5555 | 적색Red |
| 실시예 8Example 8 | 화합물 4-19Compound 4-19 | 4.24.2 | 31.031.0 | 6262 | 적색Red |
| 실시예 9Example 9 | 화합물 4-45Compound 4-45 | 4.14.1 | 31.931.9 | 4040 | 적색Red |
| 비교예 1Comparative Example 1 | H-1H-1 | 4.44.4 | 26.926.9 | 3737 | 적색Red |
| 비교예 2Comparative Example 2 | H-2H-2 | 4.14.1 | 30.230.2 | 1515 | 적색Red |
| 비교예 3Comparative Example 3 | H-3H-3 | 4.24.2 | 28.128.1 | 2323 | 적색Red |
상기 표 1의 결과로부터 알 수 있듯이, 본 발명의 화합물을 사용한 유기 전계 발광 소자는 구동 전압을 낮추면서 발광효율이 개선되었고 모두 적색의 발광을 나타냈다. 비교예 물질인 H-1 보다 효율 측면에서 최고 80% 이상의 개선효과를 보였고, 전체적으로 구동전압의 장점이 있었다. 비교예 2, 비교예 3 은 구동전압의 장점이 있어 보이기도 했지만 수명이 실시예 5 대비 절반 이하 수준이고, 비교예1은 수명이 유사성이 보이나 구동전압, 효율 측면에서 큰 장점이 있어 보이지 않았다. 그렇기에 본 발명의 화합물은 유기 전계 발광 소자에서 높은 효율, 낮은 구동전압 그리고 장수명의 장점이 있다고 판단 할 수 있다. As can be seen from the results of Table 1, the organic electroluminescent device using the compound of the present invention improved the luminous efficiency while lowering the driving voltage and all showed red light emission. It showed up to 80% more improvement in efficiency than H-1, a comparative material, and had the advantage of driving voltage as a whole. Although Comparative Example 2 and Comparative Example 3 seemed to have the advantages of the driving voltage, the lifespan is less than half the level of Example 5, Comparative Example 1 is similar in life but did not seem to have a great advantage in terms of driving voltage and efficiency. Therefore, the compound of the present invention can be judged to have the advantages of high efficiency, low driving voltage and long life in the organic EL device.
Claims (11)
- 하기 화학식 1로 표시되는 헤테로환 화합물:Heterocyclic compound represented by the formula (1):[화학식 1][Formula 1]
상기 화학식 1에 있어서, In Chemical Formula 1,Ar은 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로고리기; 또는 치환 또는 비치환된 아릴아민기이고, Ar is a substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted arylamine group,L은 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이며, L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,R1 내지 R15는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고, R1 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,R1 내지 R4 중 인접하는 2이상의 기가 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.Two or more adjacent groups of R1 to R4 may combine with each other to form a substituted or unsubstituted ring. - 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2 내지 4 중 어느 하나로 표시되는 것인 헤테로환 화합물:The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 2 to 4 below:[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 2 내지 4에 있어서, 상기 Ar, L 및 R1 내지 R15의 정의는 화학식 1과 같고, In Formulas 2 to 4, Ar, L and R1 to R15 are the same as defined in Formula 1,Ra 내지 Rl 은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다. Ra to Rl are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group. - 청구항 1에 있어서, 상기 L은 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 나프탈렌기; 치환 또는 비치환된 2가의 트리아진기; 치환 또는 비치환된 2가의 피리미딘기; 치환 또는 비치환된 2가의 피리딘기; 치환 또는 비치환된 2가의 퀴놀린기; 치환 또는 비치환된 2가의 퀴나졸린기; 치환 또는 비치환된 2가의 벤조퀴나졸린기; 치환 또는 비치환된 2가의 퀴놀살린기; 치환 또는 비치환된 2가의 피리도피리미딘기; 치환 또는 비치환된 2가의 피리도피라진기; 치환 또는 비치환된 2가의 프테리딘기; 치환 또는 비치환된 2가의 피라지노피라진기; 치환 또는 비치환된 2가의 벤조퓨로피리미딘기; 치환 또는 비치환된 2가의 벤조티에노피미딘기; 또는 치환 또는 비치환된 2가의 디메틸 인데노 피리미딘기인 헤테로환 화합물.The method according to claim 1, wherein L is a direct bond; Substituted or unsubstituted phenylene group; Substituted or unsubstituted naphthalene group; A substituted or unsubstituted divalent triazine group; A substituted or unsubstituted divalent pyrimidine group; A substituted or unsubstituted divalent pyridine group; Substituted or unsubstituted divalent quinoline group; A substituted or unsubstituted divalent quinazoline group; A substituted or unsubstituted divalent benzoquinazolin group; A substituted or unsubstituted divalent quinolsaline group; A substituted or unsubstituted divalent pyridopyrimidine group; A substituted or unsubstituted divalent pyridopyrazine group; Substituted or unsubstituted divalent pteridine group; A substituted or unsubstituted divalent pyrazinopyrazine group; A substituted or unsubstituted divalent benzopuropyrimidine group; A substituted or unsubstituted divalent benzothienopimidine group; Or a heterocyclic compound which is a substituted or unsubstituted divalent dimethyl indeno pyrimidine group.
- 청구항 1에 있어서, 상기 Ar은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디메틸플루오레닐기; 치환 또는 비치환된 비스비페닐아민기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 피리미딘기; 치환 또는 비치환된 퀴나졸린기; 치환 또는 비치환된 벤조퀴나졸린기; 치환 또는 비치환된 프탈라진기; 치환 또는 비치환된 이소퀴놀린기;; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 피리도 인돌기; 치환 또는 비치환된 벤조퓨로피리미딘기; 치환 또는 비치환된 벤조티에노피미딘기; 치환 또는 비치환된 플루오란텐기; 치환 또는 비치환된 아세나프토피라진기; 또는 치환 또는 비치환된 아세나프토퀴녹살린기인 헤테로환 화합물.The method of claim 1, wherein Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzoquinazolin group; Substituted or unsubstituted phthalazine group; Substituted or unsubstituted isoquinoline group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted pyrido indole group; Substituted or unsubstituted benzofurypyrimidine group; Substituted or unsubstituted benzothienopimidine group; Substituted or unsubstituted fluoranthene group; Substituted or unsubstituted acenaphtopyrazine group; Or a heterocyclic compound which is a substituted or unsubstituted acenaphthoquinoxaline group.
- 청구항 1에 있어서, 상기 R5 내지 R15는 수소 또는 중수소인 것인 헤테로환 화합물.The heterocyclic compound of claim 1, wherein R 5 to R 15 are hydrogen or deuterium.
- 청구항 1에 있어서, 상기 화학식 1은 하기 구조식들 중에서 선택되는 것인 헤테로환 화합물:The heterocyclic compound according to claim 1, wherein Formula 1 is selected from the following structural formulas:
- 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 유기물층 중 적어도 하나는 청구항 1 내지 6 중 어느 한 항에 따른 헤테로환 화합물을 포함하는 것인 유기 전계 발광 소자.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 comprises a heterocyclic compound according to any one of claims 1 to 6. Phosphorescent organic electroluminescent device.
- 청구항 7에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로환 화합물을 포함하는 것인 유기 전계 발광 소자.The organic electroluminescent device according to claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
- 청구항 7에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 헤테로환 화합물을 호스트 물질로 포함하는 것인 유기 전계 발광 소자.The organic electroluminescent device according to claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host material.
- 청구항 7에 있어서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함하고, 상기 정공주입층 또는 정공수송층은 상기 헤테로환 화합물을 포함하는 것인 유기 전계 발광 소자.The organic electroluminescent device according to claim 7, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.
- 청구항 7에 있어서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함하고, 상기 전자수송층 또는 전자주입층은 상기 헤테로환 화합물을 포함하는 것인 유기 전계 발광소자.The organic electroluminescent device according to claim 7, wherein the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6355289B1 (en) * | 2017-12-01 | 2018-07-11 | 株式会社奥本研究所 | Organic electroluminescence device |
| WO2019039414A1 (en) * | 2017-08-21 | 2019-02-28 | 出光興産株式会社 | Organic electroluminescence element and electronic device |
| US10249832B1 (en) | 2017-12-06 | 2019-04-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
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| US10593889B1 (en) | 2018-09-26 | 2020-03-17 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
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| KR102427493B1 (en) * | 2017-11-14 | 2022-08-01 | 덕산네오룩스 주식회사 | Organic electronic element comprising compound for organic electronic element and electronic device thereof |
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| JP6355289B1 (en) * | 2017-12-01 | 2018-07-11 | 株式会社奥本研究所 | Organic electroluminescence device |
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| US11557730B2 (en) | 2017-12-06 | 2023-01-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US11569449B2 (en) | 2017-12-06 | 2023-01-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| WO2019111971A1 (en) * | 2017-12-06 | 2019-06-13 | 出光興産株式会社 | Organic electroluminescent element and novel compound |
| US10249832B1 (en) | 2017-12-06 | 2019-04-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10593889B1 (en) | 2018-09-26 | 2020-03-17 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101879121B1 (en) | 2018-07-18 |
| JP6825192B2 (en) | 2021-02-03 |
| KR20170094767A (en) | 2017-08-21 |
| CN108602836B (en) | 2020-12-25 |
| JP2019506399A (en) | 2019-03-07 |
| CN108602836A (en) | 2018-09-28 |
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