CN115583911A - Organic compound and organic electroluminescent element comprising same - Google Patents
Organic compound and organic electroluminescent element comprising same Download PDFInfo
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- CN115583911A CN115583911A CN202210786784.XA CN202210786784A CN115583911A CN 115583911 A CN115583911 A CN 115583911A CN 202210786784 A CN202210786784 A CN 202210786784A CN 115583911 A CN115583911 A CN 115583911A
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 324
- 239000010410 layer Substances 0.000 claims description 130
- 150000001875 compounds Chemical class 0.000 claims description 82
- 239000000126 substance Substances 0.000 claims description 50
- 230000005525 hole transport Effects 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 238000002347 injection Methods 0.000 claims description 28
- 239000007924 injection Substances 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 26
- 125000001769 aryl amino group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 13
- -1 alkyl sulfide Chemical compound 0.000 claims description 12
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 12
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 3
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 79
- 238000003786 synthesis reaction Methods 0.000 description 78
- 238000002360 preparation method Methods 0.000 description 31
- 238000000746 purification Methods 0.000 description 25
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 229940126142 compound 16 Drugs 0.000 description 24
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- PCHYYOCUCGCSBU-UHFFFAOYSA-N 4-bromo-2-methylaniline Chemical compound CC1=CC(Br)=CC=C1N PCHYYOCUCGCSBU-UHFFFAOYSA-N 0.000 description 10
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000002207 thermal evaporation Methods 0.000 description 4
- YRPIGRRBBMFFBE-UHFFFAOYSA-N 1-(4-bromophenyl)naphthalene Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=CC=CC=C12 YRPIGRRBBMFFBE-UHFFFAOYSA-N 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- RIPZSADLUWTEFQ-UHFFFAOYSA-N 4-(4-bromophenyl)dibenzofuran Chemical compound C1=CC(Br)=CC=C1C1=CC=CC2=C1OC1=CC=CC=C21 RIPZSADLUWTEFQ-UHFFFAOYSA-N 0.000 description 3
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 2
- KETXQNLMOUVTQB-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethylporphyrin;platinum Chemical compound [Pt].C=1C(C(=C2CC)CC)=NC2=CC(C(=C2CC)CC)=NC2=CC(C(=C2CC)CC)=NC2=CC2=NC=1C(CC)=C2CC KETXQNLMOUVTQB-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- SAODOTSIOILVSO-UHFFFAOYSA-N 2-(4-bromophenyl)naphthalene Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=CC=C2)C2=C1 SAODOTSIOILVSO-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 2
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 229910052760 oxygen Inorganic materials 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
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- IDQUIFLAFFZYEX-UHFFFAOYSA-N (3-carbazol-9-ylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 IDQUIFLAFFZYEX-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-LOIXRAQWSA-N 1-bromo-2,3,5,6-tetradeuterio-4-(2,3,4,5,6-pentadeuteriophenyl)benzene Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1C1=C([2H])C([2H])=C(Br)C([2H])=C1[2H] PKJBWOWQJHHAHG-LOIXRAQWSA-N 0.000 description 1
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 1
- YMRHXVOHLPIMNN-UHFFFAOYSA-N 1-n-(3-methylphenyl)-2-n,2-n-diphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YMRHXVOHLPIMNN-UHFFFAOYSA-N 0.000 description 1
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- SVZMCEWNLVICKU-UHFFFAOYSA-N 2-bis(8-hydroxyquinolin-2-yl)alumanylquinolin-8-ol Chemical compound Oc1cccc2ccc(nc12)[Al](c1ccc2cccc(O)c2n1)c1ccc2cccc(O)c2n1 SVZMCEWNLVICKU-UHFFFAOYSA-N 0.000 description 1
- CRJISNQTZDMKQD-UHFFFAOYSA-N 2-bromodibenzofuran Chemical compound C1=CC=C2C3=CC(Br)=CC=C3OC2=C1 CRJISNQTZDMKQD-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VENKISSLGWHCOE-UHFFFAOYSA-N 4-bromo-2,3,5,6-tetramethylaniline Chemical compound CC1=C(C)C(Br)=C(C)C(C)=C1N VENKISSLGWHCOE-UHFFFAOYSA-N 0.000 description 1
- CXPJJDQQLXEYPM-UHFFFAOYSA-N 4-bromo-2,5-dimethylaniline Chemical compound CC1=CC(Br)=C(C)C=C1N CXPJJDQQLXEYPM-UHFFFAOYSA-N 0.000 description 1
- QGLAYJCJLHNIGJ-UHFFFAOYSA-N 4-bromo-2,6-dimethylaniline Chemical compound CC1=CC(Br)=CC(C)=C1N QGLAYJCJLHNIGJ-UHFFFAOYSA-N 0.000 description 1
- INMZDDDQLHKGPF-UHFFFAOYSA-N 4-bromo-2-chloroaniline Chemical compound NC1=CC=C(Br)C=C1Cl INMZDDDQLHKGPF-UHFFFAOYSA-N 0.000 description 1
- GZRMNMGWNKSANY-UHFFFAOYSA-N 4-bromo-2-fluoroaniline Chemical compound NC1=CC=C(Br)C=C1F GZRMNMGWNKSANY-UHFFFAOYSA-N 0.000 description 1
- MRHVSOBPZBXNEB-UHFFFAOYSA-N 4-bromo-2-tert-butylaniline Chemical compound CC(C)(C)C1=CC(Br)=CC=C1N MRHVSOBPZBXNEB-UHFFFAOYSA-N 0.000 description 1
- OGBPXDJLNYCSJH-UHFFFAOYSA-N 4-bromo-3,5-dimethylaniline Chemical compound CC1=CC(N)=CC(C)=C1Br OGBPXDJLNYCSJH-UHFFFAOYSA-N 0.000 description 1
- QLYHPNUFNZJXOQ-UHFFFAOYSA-N 4-bromo-3-chloroaniline Chemical compound NC1=CC=C(Br)C(Cl)=C1 QLYHPNUFNZJXOQ-UHFFFAOYSA-N 0.000 description 1
- MMEGELSFOYDPQW-UHFFFAOYSA-N 4-bromo-3-methylaniline Chemical compound CC1=CC(N)=CC=C1Br MMEGELSFOYDPQW-UHFFFAOYSA-N 0.000 description 1
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
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- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
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- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a novel organic compound and an organic light-emitting device including the same, and more particularly, to an organic electroluminescent device having a low driving voltage and remarkably improved luminous efficiency and life.
Description
Technical Field
The present invention relates to an organic compound and an organic electroluminescent element including the organic compound.
Background
Organic electroluminescent devices (OLEDs) have a simple structure, various advantages in manufacturing processes, high luminance and excellent viewing angle characteristics, a high response speed, and a low driving voltage, compared to other flat panel display devices such as conventional Liquid Crystal Displays (LCDs), plasma Display Panels (PDPs), and Field Emission Displays (FEDs), and have been actively developed and commercialized to be used as light sources for flat panel displays such as wall-mounted televisions and displays, backlights for lighting, and billboards.
As for the organic electroluminescent element, the original organic EL element was reported by down (c.w.tang) et al of eastman kodak company, (c.w.tang, s.a.vansylke, applied Physics Letters, vol. 51, page 913, 1987), the light emission principle of which is generally based on that, when a voltage is Applied, holes injected from an anode and electrons injected from a cathode recombine to form excitons, i.e., electron-hole pairs, by transferring the energy of the excitons to a light emitting material to convert into light.
More specifically, the organic electroluminescent element has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode) and one or more organic layers between the two electrodes. In this case, the organic electroluminescent element may further include a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a light emitting layer (EML), an Electron Transport Layer (ETL), or an Electron Injection Layer (EIL) in this order from the anode, and a hole transport auxiliary layer or a Hole Blocking Layer (HBL) may be further included in front of and behind the light emitting layer, respectively, in order to improve the efficiency of the light emitting layer.
Materials used as an organic layer in an organic electronic element may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron injection material, and the like, according to functions.
Lifetime and efficiency are the biggest problems of organic electroluminescent elements, and as displays become larger, these efficiency and lifetime problems must be solved. Efficiency, lifetime, driving voltage, and the like are correlated with each other, and when efficiency is improved, driving voltage is relatively lowered, and as driving voltage is lowered, crystallization of an organic substance due to Joule heat (Joule heating) generated during driving is reduced, and as a result, lifetime tends to be increased.
However, simply improving the above organic layer cannot maximize efficiency. This is because, when the energy levels and T1 values between the respective organic layers, intrinsic properties of the substance (mobility, interfacial properties, etc.), and the like are optimally combined, both long life and high efficiency can be achieved.
In recent years, in order to solve the problem of light emission in the hole transport layer, an emission assistance layer must be present between the hole transport layer and the light emitting layer, and different emission assistance layers must be developed for each of the light emitting layers (red (R), green (G), and blue (B)).
Generally, electrons (electrons) are transferred from the electron transport layer to the light emitting layer, holes (holes) are transferred from the hole transport layer to the light emitting layer, and excitons (exitons) are generated by recombination (recombination).
However, as for the substance used for the hole transport layer, since it is required to have a low HOMO value, most of them have a low T1 value, and thus, excitons (exitons) generated in the light emitting layer are transferred to the hole transport layer, resulting in charge imbalance (charge imbalance) in the light emitting layer, which results in light emission at the hole transport layer interface.
When light is emitted at the interface of the hole transport layer, there occurs a problem that the color purity and efficiency of the organic electronic device are lowered and the lifetime is shortened. Therefore, development of a light emission assisting layer having a high T1 value and a HOMO level between the HOMO level of the hole transport layer and the HOMO level of the light emitting layer is urgently required.
Documents of the prior art
Patent literature
(non-patent document 1) Krebs, fredrik.c et al (Krebs, frederik C., et al), "Synthesis, structure and Properties of a Molecular thermoelectric substance, 4,8,12-Trioxa-12C-phospha-4,8,12,12c-tetrahydrodibenzo [ cd, mn ] pyrene, (Synthesis, structure, and Properties of 4,8,12-Trioxa-12C-phospha-4,8,12,12c-tetrahydrodibenzo [ cd, mn ] pyrene, a Molecular pyroelectricity ], american Chemical Society (Journal of the Chemical Society), 119.6 (1997): pages 1208-1216.
Disclosure of Invention
Problems to be solved by the invention
An object of the present invention is to provide a novel organic compound and an organic electroluminescent element including the same.
Another object of the present invention is to provide an organic electroluminescent element which exhibits excellent hole transport characteristics and reduces accumulation of holes at an interface of a light emitting layer by reducing a difference in HOMO level between a hole transport layer and the light emitting layer, adjusting hole injection characteristics, thereby allowing a low driving voltage and significantly improving light emitting efficiency and life characteristics.
Means for solving the problems
In order to accomplish the above objects of the present invention, there is provided a compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein the content of the first and second substances,
n is an integer of 0 to 4,
L 1 and L 2 The same or different from each other, each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted alkenylene group having 3 to 10 carbon atomsA cycloalkenyl group, a substituted or unsubstituted heteroalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heteroalkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,
Ar 1 and Ar 2 The same or different from each other, each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,
R 1 selected from the group consisting of a hydrogen group, a cyano group, a nitro group, a halogen group, a hydroxyl group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 1 to 30 carbon atomsA group of radicals, and (b) a group of radicals,
R 2 to R 5 Is selected from the group consisting of a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
r other than the above substituents 2 To R 5 The same or different from each other, each independently selected from the group consisting of a hydrogen group, a cyano group, a nitro group, a halogen group, a hydroxyl group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted arylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, and a substituted silyl group or unsubstituted aryloxy group which may be bonded to each other,
l above 1 、L 2 And R 1 To R 5 Are the same or different from each other, and are each independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atomsA cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaralmino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyloxy group having 1 to 30 carbon atoms and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, which may be bonded to each other adjacent to each other to form a substituted or unsubstituted ring.
Further, the present invention relates to an organic electroluminescence element including: a first electrode; a second electrode opposed to the first electrode; and one or more organic layers interposed between the first electrode and the second electrode. Wherein the one or more organic layers include the compound represented by chemical formula 1.
In the present invention, unless otherwise specifically limited, "hydrogen" is hydrogen, protium, deuterium, or tritium.
In the present invention, "halo" is fluoro, chloro, bromo or iodo.
In the present invention, "alkyl group" means a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.
In the present invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), and 2-butenyl (2-butenyl).
In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms with one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl (ethyl) and 2-propynyl (2-propyl).
In the present invention, "alkylthio" refers to an alkyl group described above bonded through a sulfur bond (-S-).
In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms bonded to a single ring or two or more rings. And may include two or more ring side-linked (pendant) or fused forms, specifically, naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, perylene, and the like,
A phenyl group, a fluorenyl group, and the like, but are not limited thereto. The above-mentioned fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the present invention, "heteroaryl" means a monovalent substituent derived from a mono-or poly-heterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this case, more than one carbon, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom such as N, O, S or Se. Also, more than two rings may be included in a pendant or fused form to each other, and also in a fused form with an aryl group. Examples of such heteroaryl groups include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl, polycyclic rings such as phenylthienyl (phenoxathienyl), indolizinyl (indolizinyl), indolyl (indolinyl), purinyl (purinyl), quinolinyl (quinolyl), benzothiazole (benzothiazolyl) and carbazolyl (carbazolyl), and 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl and 2-pyrimidinyl.
In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and R is an aryl group having 6 to 60 carbon atoms. Examples of the aryloxy group include, but are not limited to, a phenoxy group, a naphthoxy group, and a diphenoxy group.
In the present invention, the "alkyloxy group" is a monovalent substituent represented by R 'O-, wherein R' represents an alkyl group having 1 to 40 carbon atoms, and may have a linear (linear), branched (branched) or cyclic (cyclic) structure. Examples of the alkyloxy group include, but are not limited to, methoxy group, ethoxy group, n-propoxy group, 1-propoxy group, tert-butoxy group, n-butoxy group, and pentyloxy group.
In the present invention, "alkoxy" may be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, and is preferably 1 to 20. Specifically, there may be mentioned methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxy), isopropoxy (i-propyloxy), n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but not limited thereto.
In the present invention, "aralkyl group" means an aryl group as well as an aryl-alkyl group in which an alkyl group is a group as described above. Preferred aralkyl groups include lower alkyl groups. Non-limiting examples of preferred aralkyl groups include benzyl, 2-phenylethyl, and naphthylmethyl. The bond to the parent residue is through the alkyl group.
In the present invention, "arylamino" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.
In the present invention, "alkylamino" refers to an amine substituted with an alkyl group having 1 to 30 carbon atoms.
In the present invention, "aralkylamino" refers to an amine substituted with aryl-alkyl having 6 to 30 carbon atoms.
In the present invention, "heteroarylamino group" refers to an amino group substituted with an aryl group having 6 to 30 carbon atoms and a heterocyclic group.
In the present invention, "heteroaralkyl" refers to an aryl-alkyl group substituted with a heterocyclyl group.
In the present invention, "cycloalkyl group" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl (norbonyl), and adamantane (adamantine).
In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, in which one or more carbons, preferably 1 to 3 carbons, are substituted with a heteroatom such as N, O, S or Se. Examples of such a heterocycloalkyl group include, but are not limited to, morpholine and piperazine.
In the present invention, "alkylsilyl group" means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl group" means a silyl group substituted with an aryl group having 6 to 60 carbon atoms.
In the present invention, "fused ring" means a form of fused aliphatic ring, fused aromatic ring, fused heteroaliphatic ring, fused heteroaromatic ring, or a combination thereof.
In the present invention, "form a ring by bonding to an adjacent group" means that a substituted or unsubstituted aliphatic hydrocarbon ring is formed by bonding to an adjacent group; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; or a fused ring thereof.
In the present invention, examples of the "aromatic hydrocarbon ring" include, but are not limited to, phenyl, naphthyl, anthryl and the like.
In the present invention, "aliphatic heterocyclic ring" means an aliphatic ring containing one or more heteroatoms.
In the present invention, "aromatic heterocycle" refers to an aromatic ring containing one or more heteroatoms.
In the present invention, "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the position of the substituent can be substituted, and when two or more substituents are substituted, the two or more substituents are the same as or different from each other. The above-mentioned substituent may be substituted with one or more substituents selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 24 carbon atoms, heteroalkyl having 2 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroaralkyl having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, alkylamino having 1 to 30 carbon atoms, arylamino having 6 to 30 carbon atoms, aralkylamino having 6 to 30 carbon atoms, heteroaralmino having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms, and substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, but is not limited to the above-mentioned examples.
Effects of the invention
The present invention relates to a novel organic compound used as a material for an organic electroluminescent element having the following effects: namely, excellent hole transport characteristics can be exhibited, and by reducing the HOMO level difference between the hole transport layer and the light emitting layer, hole injection characteristics are adjusted, and accumulation of holes at the interface of the light emitting layer is reduced, thereby allowing a low driving voltage and allowing luminous efficiency and life characteristics to be significantly improved.
Detailed Description
Hereinafter, examples of the present invention will be described in detail so that those skilled in the art to which the present invention pertains can easily carry out the present invention. However, the present invention may be embodied in various different forms and is not limited to the embodiments described in the present specification.
The novel organic compound according to the present invention can exhibit high glass transition temperature and thermal stability, particularly has HOMO level where holes are easily transported, and thus can be used as a hole transport assist layer material for an organic electroluminescent element excellent in hole transport characteristics to a light-emitting layer.
Specifically, the compound represented by the following chemical formula 1 is as follows:
[ chemical formula 1]
Wherein the content of the first and second substances,
n is an integer of 0 to 4,
L 1 and L 2 The same or different from each other, each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heteroalkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,
Ar 1 and Ar 2 The same or different from each other, each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,
R 1 selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, and mixtures thereofA substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyloxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,
R 2 to R 5 Any one or more of which is selected from the group consisting of a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
r other than the above substituents 2 To R 5 The same or different from each other, each is independently selected from the group consisting of a hydrogen group, a cyano group, a nitro group, a halogen group, a hydroxyl group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylamino group having 6 to 30 carbon atomsAn aralkylamino group, a substituted or unsubstituted heteroaralmino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyloxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to each other with an adjacent group to form a substituted or unsubstituted ring,
l above 1 、L 2 And R 1 To R 5 The substituents of (a) are the same or different from each other, and each is independently selected from the group consisting of a hydrogen, cyano group, nitro group, halogen group, hydroxyl group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted arylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 6 to 30 carbon atoms, and a substituted silyl group or unsubstituted aryloxy group having 1 to 30 carbon atoms and being capable of bonding to each other, and a substituted silyl group being bonded to each other.
The compound represented by the above chemical formula 1 may be a compound represented by the following chemical formula 2 to chemical formula 6:
[ chemical formula 2]
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
Wherein the content of the first and second substances,
n、R 1 、L 1 、L 2 、Ar 1 and Ar 2 As defined in chemical formula 1, is used,
R 5 to R 12 The same or different from each other, each is independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms, substituted or unsubstituted heteroaralkyl having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino having 1 to 30 carbon atoms, substituted or unsubstituted arylamino having 6 to 30 carbon atomsA substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaralmino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyloxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to each other to form a substituted or unsubstituted ring,
however, in the above chemical formula 2, R 5 When being methyl and phenyl, ar 2 Excluding substituted or unsubstituted naphthyl, in the above chemical formula 4, R 7 And R 8 When it is methyl, ar 2 Not including substituted or unsubstituted naphthyl groups,
r is as defined above 5 To R 12 The substituents are the same or different from each other, and each is independently selected from the group consisting of a hydrogen, cyano, nitro, halogen, hydroxyl, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms and a substituted silyl group, which is bonded to 6 to 30 carbon atoms, and a substituted aryloxy group, which is capable of forming a substituted or unsubstituted aryloxy group, and a substituted silyl group, which is bonded to 30 alkyl group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atom number of 1 to 30, and a substituted silyl groupAnd (4) a ring.
L above 1 And L 2 The same or different from each other, each independently selected from the group consisting of a single bond, and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In the above chemical formula 2, R 5 When being methyl and phenyl, ar 2 Is phenyl, R in the above chemical formula 4 7 And R 8 When it is methyl, ar 2 Is phenyl, but is not limited to the above examples.
Ar above 1 And Ar 2 The same or different from each other, and each is independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
The compound represented by chemical formula 1 according to the present invention is selected from the group consisting of, but not limited to:
the compound of chemical formula 1 of the present invention may be usefully used as a hole transport auxiliary layer material.
Since the compound of the present invention is used as a material for a hole transport assist layer in an organic light emitting element, a substituent capable of increasing HOMO and finely adjusting it is contained in the above compound to adjust hole mobility to be optimal according to electron mobility injected into a light emitting layer.
Because of these characteristics, when the above organic compound is used as a material for an organic light-emitting element, it can exhibit the same or excellent characteristics in most of element characteristics such as light-emitting efficiency, lifetime, and the like.
The present invention provides an organic electroluminescent element comprising the compound represented by the above chemical formula 1.
The organic compound of the present invention can be usefully used as a material for a hole transport assist layer.
Further, the present invention provides an organic electroluminescence element in which at least a light emitting layer is included between a cathode and an anode, and an organic thin film layer composed of one or more layers is laminated, the organic thin film layer being a hole transporting layer and/or a hole transporting auxiliary layer between a first electrode and the light emitting layer.
The hole transport layer and/or the hole transport auxiliary layer are compounds represented by chemical formula 1.
The hole transport assist layer reduces the HOMO level difference between the hole transport layer and the light emitting layer to control the hole injection property, thereby reducing hole accumulation at the interface between the hole transport assist layer and the light emitting layer and reducing quenching phenomenon (quenching) in which excitons disappear at the interface due to polarons (polarons). Therefore, a thermalization phenomenon of the element is reduced and the element is stabilized, thereby improving efficiency and life.
The organic electroluminescent element may have a structure of an anode, a hole injection layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, and an electron transport auxiliary layer may be further stacked as necessary.
Hereinafter, an organic electroluminescent device of the present invention will be described by way of example. However, the contents of the following examples do not limit the organic electroluminescent element of the present invention.
The organic electroluminescent element of the present invention may have a structure in which an anode (hole injection electrode), a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a hole transport auxiliary layer, an emission layer (EML), and a cathode (electron injection electrode) are sequentially stacked, and preferably, may further include a hole transport auxiliary layer between the anode and the emission layer, and an Electron Transport Layer (ETL), an Electron Injection Layer (EIL) between the cathode and the emission layer. And, an electron transport auxiliary layer may be further included between the cathode and the light emitting layer.
As a method for manufacturing an organic electroluminescent element according to the present invention, an anode is first formed by coating an anode substance on a substrate surface in a conventional manner. In this case, the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and water resistance. As the anode material, transparent and highly conductive Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), or the like can be used.
Next, a Hole Injection Layer (HIL) material is vacuum-thermally evaporated or spin-coated on the surface of the anode in a conventional manner to form a hole injection layer. Examples of such a hole injection layer material include copper phthalocyanine (CuPc), 4,4',4 ″ -tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4',4 ″ -tris (3-methylphenylamino) phenoxybenzene (m-MTDAPB), 4,4',4 ″ -tris (N-carbazolyl) triphenylamine (TCTA) as a starburst (starburst) type amine, 4,4',4 ″ -tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA), and IDE406 available from yohimshing (idetsu).
And forming a hole transport layer on the surface of the hole injection layer by vacuum thermal evaporation or spin coating of a hole transport layer substance by a conventional method. As the hole transport layer material, a commonly used hole transport layer substance can be used.
The compound represented by chemical formula 1 of the present invention is vacuum-thermally evaporated or spin-coated on the surface of the hole transport layer to form a hole transport auxiliary layer. As described above, the compound of the present invention can be used as a hole transport assist layer substance, and a hole transport assist layer can also be formed using a commonly used hole transport assist layer material.
A light-emitting layer (EML) material is formed on the surface of the hole transport auxiliary layer by vacuum thermal evaporation or spin coating in a conventional manner. In this case, as a light-emitting substance, among light-emitting substances used, tris (8-hydroxyquinolyl) aluminum (Alq 3) or the like can be used for green, alq3, 4,4' -N, N ' -dicarbazole-biphenyl (4,4 ' -N, N ' -dicarbazole-biphenol, CBP), poly (N-vinylcarbazole), PVK, 9,10-bis (naphthalene-2-yl) anthracene (9,10-di (naphthalene-2-yl) anthracene, ADN), 4,4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene (1,3,5-tris (N-phenylbenzimidazole-2-yl) benzene (TPBI), 3-tert-butyl-9,10-di (naphthalen-2-yl) anthracene (3-tert-butyl-9,10-di (naphth-2-yl) anthrylene, TBADN), E3, distyrylarylene (DSA), or a mixture of two or more thereof, but is not limited thereto.
As the Dopant (Dopant) which can be used together with the light-emitting host in the light-emitting layer material, IDE102 and IDE105 available from the light-emitting product (Idemitsu) can be used, and as the phosphorescent Dopant (Dopant) (IDE) tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3), bis [ (4,6-difluorophenyl) pyridyl-N, C-2' ] picolinoyl iridium (III) (FIrpic) (reference [ Chihaya Adachi et al, appl.phys.lett.,2001, 79, 3082-3084 ]), platinum (II) octaethylporphyrin (PtOEP), TBE002 (cobber) and the like can be used.
An Electron Transport Layer (ETL) material is vacuum-thermally evaporated or spin-coated on the surface of the light-emitting layer by a conventional method to form the ETL. At this time, the electron transport layer material used is not particularly limited, and tris (8-hydroxyquinoline) aluminum (Alq 3) can be preferably used.
Alternatively, a Hole Blocking Layer (HBL) is further formed between the light emitting layer and the electron transport layer, and a phosphorescent Dopant (Dopant) is used in the light emitting layer, so that a phenomenon in which triplet excitons or holes are diffused into the electron transport layer can be prevented.
The formation of the hole blocking layer can be carried out by vacuum thermal evaporation or spin coating of a hole blocking layer material by a conventional method, and the hole blocking layer material is not particularly limited, but lithium (8-hydroxyquinolyl) lithium (Liq), bis (8-hydroxy-2-methylquinolyl) -diphenoxyaluminum (BAlq), bathocuproine (BCP), lithium fluoride (LiF), and the like can be preferably used.
An Electron Injection Layer (EIL) material is vacuum-thermally evaporated or spin-coated on the surface of the electron transport layer by a conventional method to form an electron injection layer. In this case, liF, liq, li or the like may be used as the electron injection layer material 2 O, baO, naCl, csF and the like.
The cathode is formed by vacuum thermal deposition of a cathode material on the surface of the electron injection layer by a conventional method.
In this case, examples of the cathode material to be used include lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Also, the front light emitting organic electroluminescent element may use Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO) to form a transparent cathode capable of transmitting light.
A coating layer (CPL) can be formed on the surface of the cathode using the coating layer-forming composition.
Hereinafter, the synthesis method of the above compound will be explained by representative examples. However, the synthetic method of the compound of the present invention is not limited to the following exemplified method, and the compound of the present invention can be prepared by the following exemplified method and methods known in the art.
Synthesis example of intermediate
1. Synthesis example of intermediate 1
Under a stream of nitrogen, 4-bromo-2-methylaniline (20.0g, 107.5mmol), (3- (9H-carbazol-9-yl) phenyl) boronic acid (32.4g, 112.9mmol), and K were added to a 1000mL round-bottomed flask 2 CO 3 (29.7g,215.0mmol)、Pd(PPh 3 ) 4 (2.48g, 2.15mmol), toluene (300 mL), ethanol (100 mL) and water (100 mL) and refluxed with stirring. After the reaction was completed, the organic layer was extracted with toluene and water. With MgSO 4 The extracted organic layer was treated to remove residual water and concentrated under reduced pressure, followed by purification by silica gel column chromatography (silicagel column) to prepare 28.1g of intermediate 1 (yield: 75%).
2. Synthesis example of intermediate 2
By synthesizing and purifying according to the production method of intermediate 1 except for using 4-bromo-2-fluoroaniline (20.4 g,107.5 mmol) instead of 4-bromo-2-methylaniline, 27.3g of intermediate 2 was produced (yield: 72%).
3. Synthesis example of intermediate 3
Synthesized and purified by the preparation method of intermediate 1 except for using 4-bromo-2- (tert-butyl) aniline (24.5g, 107.5mmol) instead of 4-bromo-2-methylaniline, to prepare 29.8g of intermediate 3 (yield: 71%).
4. Synthesis example of intermediate 4
By synthesizing and purifying according to the preparation method of intermediate 1 except for using 4-bromo-2,6-dimethylaniline (21.5g, 107.5mmol) instead of 4-bromo-2-methylaniline, 29.6g of intermediate 4 was prepared (yield: 76%).
5. Synthesis example of intermediate 5
28.1g of intermediate 5 (yield: 72%) was synthesized and purified by the preparation method of intermediate 1 except that 4-bromo-2,5-dimethylaniline (21.5g, 107.5mmol) was used instead of 4-bromo-2-methylaniline.
6. Synthesis example of intermediate 6
Synthesized and purified by the preparation method of intermediate 1 except for using 4-bromo-2,3,5,6-tetramethylaniline (24.5g, 107.5mmol) instead of 4-bromo-2-methylaniline, to prepare 29.4g of intermediate 6 (yield: 70%).
7. Synthesis example of intermediate 7
1) Synthesis of intermediate 7-1
139.3g of intermediate 7-1 (yield: 78%) was prepared by synthesizing and purifying according to the preparation method of intermediate 1 except that 4-bromo-2-chloroaniline (100.0 g,484.3 mmol) was used instead of 4-bromo-2-methylaniline.
2) Synthesis of intermediate 7
To a 500mL round-bottomed flask were added the intermediate 7-1 (20.0 g, 54.22mmol), phenylboronic acid (7.27g, 59.64mmol), K under a nitrogen stream 3 PO 4 (23.0g,108.4mmol)、Pd(OAc) 2 (0.24g, 1.08mmol), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (phos) (0.89g, 2.17mmol), toluene (300 mL) and water (30 mL) and refluxed with stirring. After the reaction was completed, the organic layer was extracted with toluene and water. With MgSO 4 The extracted organic layer was treated to remove residual water, concentrated under reduced pressure, and purified by silica gel column chromatography (silica gel column) to prepare 17.4g of intermediate 7 (yield: 78%).
8. Synthesis example of intermediate 8
Synthesized and purified according to the preparation method of intermediate 7 except for using 1-naphthalene boronic acid (10.3g, 59.64mmol) instead of phenylboronic acid, 18.7g of intermediate 8 was prepared (yield 75%).
9. Synthesis example of intermediate 9
Synthesized and purified according to the preparation method of intermediate 7 except for using 2-naphthalene boronic acid (10.3g, 59.64mmol) instead of phenylboronic acid, 19.2g of intermediate 9 was prepared (yield 77%).
10. Synthesis example of intermediate 10
Synthesized and purified according to the preparation method of intermediate 7 except for using 9-phenanthreneboronic acid (13.2g, 59.64mmol) instead of phenylboronic acid, to prepare 20.5g of intermediate 10 (yield 74%).
11. Synthesis example of intermediate 11
19.3g of intermediate 11 (yield 71%) was synthesized and purified according to the preparation method of intermediate 7 except that 4-dibenzofuranboronic acid (12.6 g, 59.64mmol) was used instead of phenylboronic acid.
12. Synthesis example of intermediate 12
20.2g of intermediate 12 was prepared (yield 72%) by synthesizing and purifying according to the preparation method of intermediate 7 except that 2-dibenzothiopheneboronic acid (13.6 g, 18.08mmol) was used instead of phenylboronic acid.
13. Synthesis example of intermediate 13
28.8g of intermediate 13 (yield: 77%) was prepared by synthesizing and purifying the intermediate 1 except that 4-bromo-3-methylaniline (20.0 g,107.5 mmol) was used instead of 4-bromo-2-methylaniline.
14. Synthesis example of intermediate 14
By synthesizing and purifying according to the preparation method of intermediate 1 except for using 4-bromo-3,5-dimethylaniline (21.5g, 107.5mmol) instead of 4-bromo-2-methylaniline, 27.7g of intermediate 14 was prepared (yield: 71%).
15. Synthesis example of intermediate 15
1) Synthesis of intermediate 15-1
130.4g of intermediate 15-1 (yield: 73%) was prepared by synthesizing and purifying according to the preparation method of intermediate 1 except that 4-bromo-3-chloroaniline (100.0 g,484.3 mmol) was used instead of 4-bromo-2-methylaniline.
2) Synthesis of intermediate 15
Synthesis and purification were carried out in accordance with the preparation method of intermediate 7 except that intermediate 15-1 (20.0 g, 54.22mmol) was used instead of intermediate 7-1, to prepare 16.7g of intermediate 15 (yield: 75%).
16. Synthesis example of intermediate 16
Synthesis and purification by the method for preparation of intermediate 8, except that intermediate 15-1 (20.0 g, 54.22mmol) was used instead of intermediate 7-1, produced 17.7g of intermediate 16 (yield: 71%).
17. Synthesis example of intermediate 17
Synthesis and purification by the preparation method of intermediate 9 were carried out except for using intermediate 15-1 (20.0 g, 54.22mmol) instead of intermediate 7-1, to prepare 17.5g of intermediate 17 (yield: 70%).
The compound belonging to the intermediate may be, but is not limited to:
synthesis example of Final Compound
1. Synthesis example of Compound 16
To a 500mL round-bottomed flask, under a nitrogen stream, were added intermediate 1 (10.0g, 28.70mmol), 4-bromo-1,1' -biphenyl (14.7g, 63.14mmol), sodium t-butoxide (t-BuONa) (11.0g, 114.8mmol), pd 2 (dba) 3 (1.05g, 1.15mmol), sphos (0.94g, 2.30mmol) and toluene (200 mL), followed by refluxing with stirring. After completion of the reaction, the organic layer was extracted with toluene and water. The extract was MgSO 4 Residual water was removed, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain 12.2g of compound 16 (yield: 65%).
MS[M+H]+＝653.29
2. Synthesis example of Compound 48
14.3g of Compound 48 was obtained (yield: 60%) by synthesizing and purifying compound 16 except for using intermediate 2 (10.0 g, 28.38mmol) and 4- (4-bromophenyl) dibenzofuran (20.2 g, 62.43mmol).
MS[M+H]+＝837.28
3. Synthesis example of Compound 220
Synthesis and purification by the method for preparing Compound 16 except for using intermediate 3 (10.0g, 25.61mmol) and 1- (4-bromophenyl) naphthalene (16.0g, 56.33mmol) gave 11.6g of Compound 220 (yield: 57%).
MS[M+H]+＝795.36
4. Synthesis example of Compound 116
Synthesis and purification by the method for preparing Compound 16 except for using intermediate 4 (10.0g, 27.59mmol) and 4-bromo-1,1' -biphenyl (14.15g, 60.69mmol) gave 11.2g of Compound 116 (yield: 61%).
MS[M+H]+＝667.31
5. Synthesis example of Compound 150
Synthesis and purification by the method for producing Compound 16 were carried out except for using intermediate 5 (10.0g, 27.59mmol) and 5' -bromo-1,1 ':3',1 "-terphenyl (18.8g, 60.69mmol) to obtain 12.4g of Compound 150 (yield: 55%).
MS[M+H]+＝819.35
6. Synthesis example of Compound 178
Synthesis and purification by the preparation method of Compound 16 except for using intermediate 6 (10.0 g, 25.61mmol) and 9-bromophenanthrene (14.5 g, 56.33mmol) gave 11.0g of Compound 178 (yield: 58%).
MS[M+H]+＝743.33
7. Synthesis example of Compound 266
Synthesis and purification by the preparation method of Compound 16 except for using intermediate 7 (10.0 g, 24.36mmol) and 4-bromo-1,1' -biphenyl (12.5 g, 53.59mmol) gave 10.8g of Compound 266 (yield: 62%).
MS[M+H]+＝715.31
8. Synthesis example of Compound 400
Synthesis and purification by the preparation method of Compound 16 except for using intermediate 8 (10.0 g, 21.71mmol) and 2-bromodibenzofuran (11.80g, 47.77mmol) gave 9.0g of Compound 400 (yield: 52%).
MS[M+H]+＝793.27
9. Synthesis example of Compound 392
Synthesis and purification by the method for the preparation of Compound 16 except for using intermediate 9 (10.0g, 21.71mmol) and 3-bromo-1,1' -biphenyl (11.10g, 47.77mmol) gave 8.97g of Compound 392 (yield: 54%).
MS[M+H]+＝765.32
10. Synthesis example of Compound 376
Synthesis and purification by the preparation method of Compound 16 were carried out except for using intermediate 10 (10.0 g, 19.58mmol) and bromobenzene (6.76g, 43.08mmol) to obtain 7.14g of Compound 376 (yield: 55%).
MS[M+H]+＝663.26
11. Synthesis example of Compound 466
Synthesis and purification by the method for preparation of Compound 16 except for using intermediate 11 (10.0g, 19.98mmol) and 4-bromo-1,1' -biphenyl (10.2g, 43.95mmol) gave 9.33g of Compound 466 (yield: 58%).
MS[M+H]+＝805.30
12. Synthesis example of Compound 492
Synthesis and purification by the preparation method of Compound 16 except for using intermediate 12 (10.0g, 19.36mmol) and 2-bromo-1,1' -biphenyl (9.93g, 42.58mmol) gave 7.63g of Compound 492 (yield: 48%).
MS[M+H]+＝821.28
13. Synthesis example of Compound 70
Synthesis and purification by the method for preparation of Compound 16 except for using intermediate 13 (10.0g, 28.70mmol) and 2- (4-bromophenyl) naphthalene (17.88g, 63.14mmol) gave 12.32g of Compound 70 (yield: 57%).
MS[M+H]+＝753.33
14. Synthesis example of Compound 170
Synthesis and purification by the preparation method of Compound 16 were carried out except for using intermediate 14 (10.0 g, 27.59mmol) and 1- (4-bromophenyl) naphthalene (17.19g, 60.69mmol), to obtain 10.59g of Compound 170 (yield: 51%).
MS[M+H]+＝767.34
15. Synthesis example of Compound 316
Synthesis and purification by the preparation method of Compound 16 except for using intermediate 15 (10.0 g, 24.36mmol) and 4-bromo-1,1' -biphenyl (12.5 g, 53.59mmol) gave 10.45g of Compound 316 (yield: 60%).
MS[M+H]+＝715.30
16. Synthesis example of Compound 121
1) Synthesis example of Compound 121-1
To a 500mL round bottom flask, under a stream of nitrogen, were added intermediate 4 (10.0g, 27.59mmol), 4-bromo-1,1' -biphenyl (6.43g, 27.59mmol), t-BuONa (5.30g, 55.18mmol), pd 2 (dba) 3 (0.51g, 0.55mmol), sphos (0.45g, 1.10mmol) and toluene (200 mL), followed by refluxing with stirring. After completion of the reaction, the organic layer was extracted with toluene and water. The extract was MgSO 4 The residual water was removed, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain 10.1g of compound 121-1 (yield: 71%).
2) Synthesis example of Compound 121
Synthesis and purification were carried out by the method for preparing Compound 16 except for using compound 121-1 (10.0 g, 19.43mmol) and 4- (4-bromophenyl) dibenzofuran (6.91g, 21.37mmol), to give 8.53g of Compound 121 (yield: 58%).
MS[M+H]+＝757.31
17. Synthesis example of Compound 271
1) Synthesis example of Compound 271-1
Synthesis and purification by the method for producing compound 121-1 except for using intermediate 7 (10.0g, 24.36mmol) and 4-bromo-1,1' -biphenyl (5.68g, 24.36mmol) gave 10.0g of compound 271-1 (yield: 73%).
2) Synthesis example of Compound 271
Synthesis and purification were carried out by the method for preparation of Compound 16 except for using 271-1 (10.0 g, 17.77mmol) and 4- (4-bromophenyl) dibenzofuran (6.32g, 19.55mmol) to obtain 7.44g of Compound 271 (yield: 52%).
MS[M+H]+＝805.32
18. Synthesis example of Compound 448
1) Synthesis example of Compound 448-1
Synthesis and purification by the method for producing compound 121-1 except for using intermediate 16 (10.0g, 21.71mmol) and 4-bromo-1,1' -biphenyl (5.06g, 21.71mmol) gave 10.11g of compound 448-1 (yield: 76%).
2) Synthesis example of Compound 448
Synthesis and purification by the method for preparing Compound 16 were carried out except for using compound 448-1 (10.0 g, 16.32mmol) and 2- (4-bromophenyl) naphthalene (5.08g, 17.95mmol), to obtain 6.38g of compound 448 (yield: 48%).
MS[M+H]+＝815.32
19. Synthesis example of Compound 444
1) Synthesis example of Compound 444-1
Synthesis and purification by the preparation method of Compound 121-1 were carried out except for using intermediate 17 (10.0g, 21.71mmol) and 4-bromo-1,1' -biphenyl (5.06g, 21.71mmol), to obtain 9.98g of Compound 444-1 (yield: 75%).
2) Synthesis example of Compound 444
Synthesis and purification by the preparation method of Compound 16 were carried out except for using compound 444-1 (10.0 g, 16.32mmol) and 1- (4-bromophenyl) naphthalene (5.08g, 17.95mmol), to obtain 5.99g of Compound 444 (yield: 45%).
MS[M+H]+＝815.32
20. Synthesis example of Compound 274
Synthesis and purification by the method for preparing Compound 16 except for using intermediate 7 (10.0g, 24.36mmol) and 4-bromo-1,1' -biphenyl-d 9 (12.98g, 53.59mmol) gave 9.46g of Compound 274 (yield: 53%).
MS[M+H]+＝733.42
Example 1: preparation of organic electroluminescent element
An anode was formed on the substrate on which the reflective layer was formed using ITO, and N was used 2 Plasma or Ultraviolet (UV) -ozone surface-treats the anode. Then, HAT-CN was vapor-deposited on the anode to a thickness of 10nm to form a Hole Injection Layer (HIL). Then, N4, N4, N4', N4' -tetrakis ([ 1,1' -biphenyl) having a thickness of 110nm was vapor-deposited on the HIL layer]-4-yl) - [1,1' -biphenyl]-4,4' -diamine to form a Hole Transport Layer (HTL).
A compound 16 was vacuum-evaporated in a thickness of 15nm on top of the hole transport layer to form a hole transport auxiliary layer. As the light emitting layer (EML), 9,10-bis (2-naphthyl) Anthracene (ADN) capable of forming a blue light emitting layer (EML) was deposited on the hole transporting assist layer in a thickness of 25nm, and about 3 wt% of N1, N6-tetrakis (4- (1-silyl) phenyl) pyrene-1,6-diamine was doped therein as a dopant.
The method comprises the following steps of 1:1 an anthracene derivative and LiQ were mixed and evaporated on an emission layer (EML) at a thickness of 30nm to form an Electron Transport Layer (ETL). Then, liQ was evaporated on the Electron Transport Layer (ETL) at a thickness of 1nm to form an Electron Injection Layer (EIL). Thereafter, evaporation was performed on the Electron Injection Layer (EIL) at a thickness of 15nm to give a 9: a mixture of magnesium (Mg) and silver (Ag) was mixed at a ratio of 1 to form a cathode. N4, N4' -bis [4- [ bis (3-methylphenyl) amino ] was vapor-deposited on the cathode in a thickness of 60nm]Phenyl radical]-N4, N4 '-diphenyl- [1,1' -biphenyl]-4,4' -diamine (DNTPD) to form a capping layer (capping layer). Then, a sealing cap (sealcap) containing a moisture absorbent is bonded to the capping layer by an ultraviolet-curable adhesive, thereby preventing the organic electroluminescent element from being protected from O in the atmosphere 2 Or the influence of moisture. In this way, an organic electroluminescent element was manufactured.
Examples 2 to 20: preparation of organic electroluminescent element
An organic electroluminescent element was produced in the same manner as in example 1, except that the compounds 48, 220, 116, 150, 178, 266, 400, 392, 376, 466, 492, 70, 170, 316, 121, 271, 448, 444, and 274 synthesized in synthesis examples 2 to 20 were used, respectively, instead of the compound 16 used in the hole transport assist layer in example 1.
Comparative examples 1 to 6: preparation of organic electroluminescent element
An organic electroluminescent element was produced in the same manner as in example 1, except that the following compounds a to F were used instead of the compound 16 used in the hole transport assist layer in example 1.
[ Compound A ]
[ Compound B ]
[ Compound C ]
[ Compound D ]
[ Compound E ]
[ Compound F ]
[ Experimental example 1: device Performance analysis
The organic electroluminescent elements produced in examples and comparative examples were each controlled at 10mA/cm 2 Was analyzed for electro-optical characteristics at a constant current of 20mA/cm 2 The lifetime was measured under the driving conditions of (1), and the results thereof are shown in table 1 below. As shown in table 1 below, it was confirmed that the organic electroluminescent elements including the compounds of examples 1 to 20 were reduced in driving voltage and improved in efficiency and lifetime, as compared to the organic electroluminescent elements including the compounds of comparative examples 1 to 6.
[ Table 1]
From the experimental results of table 1, it was confirmed that when the compound of the present invention was used as a hole transport assist layer of an organic electroluminescent element, the organic electroluminescent element had a low driving voltage and exhibited excellent element efficiency characteristics and long life characteristics, as compared to comparative examples.
As described above, the present invention is not limited to the embodiments disclosed herein, and it is apparent that those skilled in the art can make various modifications within the scope of the technical idea of the present invention. Further, although the effect based on the features of the present invention is not explicitly described in the description of the embodiments of the present invention, it should be recognized that a predictable effect can be achieved based on the features of the present invention.
Claims (7)
1. A compound represented by the following chemical formula 1, wherein,
[ chemical formula 1]
Wherein, the first and the second end of the pipe are connected with each other,
n is an integer of 0 to 4,
L 1 and L 2 The same or different from each other, each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms, a substituted or unsubstituted heteroalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heteroalkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,
Ar 1 and Ar 2 The same or different from each other, each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having a heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having a heteroaryl group,A substituted or unsubstituted heterocycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,
R 1 selected from the group consisting of a hydrogen group, a cyano group, a nitro group, a halogen group, a hydroxyl group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,
R 2 to R 5 Any one or more of which is selected from the group consisting of a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
r other than said substituent 2 To R 5 The same or different from each other, each is independently selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, and a pharmaceutically acceptable salt thereof,A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaralmino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and being capable of bonding to each other adjacent groups to form a substituted or unsubstituted ring,
said L 1 、L 2 And R 1 To R 5 The substituents are the same or different from each other, and each is independently selected from the group consisting of a hydrogen group, a cyano group, a nitro group, a halogen group, a hydroxyl group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 6 to 30 carbon atoms, and a substituted silyl group having 6 to 30 carbon atomsSubstituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, and capable of bonding to each other adjacent groups to form a substituted or unsubstituted ring.
2. The compound of claim 1, wherein,
the compound represented by chemical formula 1 is a compound represented by the following chemical formula 2 to 6,
[ chemical formula 2]
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
Wherein the content of the first and second substances,
n、R 1 、L 1 、L 2 、Ar 1 and Ar 2 As defined in claim 1, the first and second,
R 5 to R 12 The same or different from each other, and are respectively and independently selected from hydrogen, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkyl sulfide with 1 to 4 carbon atomsA group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, which are adjacent to each other and which may form a ring structure,
however, in the chemical formula 2, R 5 When being methyl and phenyl, ar 2 Excluding substituted or unsubstituted naphthyl, in the chemical formula 4, R 7 And R 8 When it is methyl, ar 2 A substituted or unsubstituted naphthyl group is not included,
the R is 5 To R 12 The substituents of (b) are the same as or different from each other, and each is independently selected from the group consisting of a hydrogen group, a cyano group, a nitro group, a halogen group, a hydroxyl group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group, and the likeSubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can be bonded to each other with adjacent groups to form a substituted or unsubstituted ring.
3. The compound according to claim 1, wherein,
said L 1 And L 2 The same or different from each other, each independently selected from the group consisting of a single bond, and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
4. The compound of claim 1, wherein,
ar is 1 And Ar 2 The same or different from each other, and each is independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
5. An organic electroluminescent element, wherein,
the method comprises the following steps:
a first electrode for forming a first electrode layer on a substrate,
a second electrode opposite to the first electrode, an
One or more organic layers interposed between the first electrode and the second electrode;
at least one of the one or more organic layers comprises the compound of claim 1.
6. The organic electroluminescent element according to claim 5, wherein,
the organic layer includes a material selected from the group consisting of a hole injection layer, a hole transport auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer.
7. The organic electroluminescent element according to claim 5, wherein,
the organic layer is a hole transport auxiliary layer.
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| KR1020220078604A KR20230007942A (en) | 2021-07-05 | 2022-06-28 | Organic compound and organoelectroluminescent device using the same |
| KR10-2022-0078604 | 2022-06-28 |
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| KR20200088704A (en) * | 2019-01-15 | 2020-07-23 | 머티어리얼사이언스 주식회사 | Organic compound and organic electroluminescent device comprising the same |
| CN113563253A (en) * | 2020-04-28 | 2021-10-29 | 江苏三月科技股份有限公司 | Organic compound with triarylamine as core and application thereof |
| CN113563316A (en) * | 2020-04-28 | 2021-10-29 | 江苏三月科技股份有限公司 | Aromatic amine derivative and application thereof |
| WO2022108222A1 (en) * | 2020-11-20 | 2022-05-27 | 단국대학교 천안캠퍼스 산학협력단 | Organic light-emitting material and device which comprise dibenzo derivative |
| CN114634493A (en) * | 2020-12-16 | 2022-06-17 | 三星显示有限公司 | Organic electroluminescent device and amine compound for organic electroluminescent device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20200088704A (en) * | 2019-01-15 | 2020-07-23 | 머티어리얼사이언스 주식회사 | Organic compound and organic electroluminescent device comprising the same |
| CN113563253A (en) * | 2020-04-28 | 2021-10-29 | 江苏三月科技股份有限公司 | Organic compound with triarylamine as core and application thereof |
| CN113563316A (en) * | 2020-04-28 | 2021-10-29 | 江苏三月科技股份有限公司 | Aromatic amine derivative and application thereof |
| WO2022108222A1 (en) * | 2020-11-20 | 2022-05-27 | 단국대학교 천안캠퍼스 산학협력단 | Organic light-emitting material and device which comprise dibenzo derivative |
| CN114634493A (en) * | 2020-12-16 | 2022-06-17 | 三星显示有限公司 | Organic electroluminescent device and amine compound for organic electroluminescent device |
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