CN117295728A - Organic compound and organic electroluminescent device comprising the same - Google Patents
Organic compound and organic electroluminescent device comprising the same Download PDFInfo
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- CN117295728A CN117295728A CN202280034662.3A CN202280034662A CN117295728A CN 117295728 A CN117295728 A CN 117295728A CN 202280034662 A CN202280034662 A CN 202280034662A CN 117295728 A CN117295728 A CN 117295728A
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 215
- 239000010410 layer Substances 0.000 claims description 127
- 150000001875 compounds Chemical class 0.000 claims description 46
- 230000005525 hole transport Effects 0.000 claims description 45
- 239000000126 substance Substances 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 27
- 239000007924 injection Substances 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000005104 aryl silyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- -1 2-butenyl (2-butenyl) Chemical group 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 7
- 238000002207 thermal evaporation Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([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
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 108010021119 Trichosanthin Proteins 0.000 description 2
- HHHVVQDBJHQZNB-UHFFFAOYSA-N [SiH3]C1(CC=CC=C1)C=1C2=CC=C(C=3C=CC4=CC=C(C(C=1)=C4C=32)N)N Chemical compound [SiH3]C1(CC=CC=C1)C=1C2=CC=C(C=3C=CC4=CC=C(C(C=1)=C4C=32)N)N HHHVVQDBJHQZNB-UHFFFAOYSA-N 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001454 anthracenes Chemical class 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
- 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 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
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 229910052711 selenium Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 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 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
- ZLGVZKQXZYQJSM-UHFFFAOYSA-N 1,2-diphenylbenzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 ZLGVZKQXZYQJSM-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
- 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
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- CATUKADCLPCACU-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(4-phenylphenyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=C(C=2C=CC=CC=2)C=C1 CATUKADCLPCACU-UHFFFAOYSA-N 0.000 description 1
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AWFDUOVDQHJMKG-UHFFFAOYSA-N N-(3-methylphenyl)-2-phenoxyaniline Chemical compound CC=1C=C(C=CC=1)NC1=C(C=CC=C1)OC1=CC=CC=C1 AWFDUOVDQHJMKG-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- UYLGPDIVUOHYHU-UHFFFAOYSA-M [O-]C(C1=CC=CC=N1)=O.[Ir+3] Chemical compound [O-]C(C1=CC=CC=N1)=O.[Ir+3] UYLGPDIVUOHYHU-UHFFFAOYSA-M 0.000 description 1
- GBKYFASVJPZWLI-UHFFFAOYSA-N [Pt+2].N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 Chemical compound [Pt+2].N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 GBKYFASVJPZWLI-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 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 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011254 layer-forming composition Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Landscapes
- 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, remarkably improved device efficiency characteristics, and a lifetime.
Description
Technical Field
The present invention relates to an organic compound and an organic electroluminescent device including the same.
Background
Compared with other flat panel display devices such as a conventional Liquid Crystal Display (LCD), a plasma flat Panel Display (PDP), and a Field Emission Display (FED), the organic electroluminescent device has a simpler structure, and has various advantages in the manufacturing process, has excellent high brightness and viewing angle characteristics, has a fast response speed, and a low driving voltage, and thus is being actively developed for use as a light source for a flat panel display such as a wall-mounted Television (TV) or a backlight, illumination, and advertisement board of the display.
In an organic electroluminescent device, generally, when a voltage is applied, holes injected from an anode and electrons injected from a cathode are recombined to form excitons, i.e., electron-hole pairs, and energy of the excitons is converted into light by transfer to a light emitting material.
In order to improve the efficiency and stability of organic electroluminescent devices, c.w. tang et al by ishimann kodak et al report low-voltage driven organic electroluminescent devices (C.W.Tang, S.A.Vanslyke, applied Physics Letters, volume 51, page 913, 1987) in which a laminated organic film is disposed between two opposing electrodes, and since the report was published, studies on organic materials for organic electroluminescent devices having a multilayer film structure have been actively conducted.
In general, an organic electroluminescent device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and one or more organic layers between the two electrodes. At this time, the organic electroluminescent device is formed by stacking a hole injection layer (HIL, hole injection layer), a hole transport layer (HTL, hole transport layer), an emission layer (EML, light emitting layer), an electron transport layer (ETL, electron transport layer) or an electron injection layer (EIL, electron injection layer) in this order from the anode, and an electron blocking layer (EBL, electron blocking layer) or a hole blocking layer (HBL, hole blocking layer) may be added before and after the emission layer, respectively, in order to improve the efficiency of the emission layer.
The reason why the organic electroluminescent device is manufactured using such a multi-layered thin film structure is to stabilize the interface between the electrode and the organic material and to improve the luminous efficiency.
In particular, in the case where a multilayer thin film is used as the material for the organic compound, there is a large difference in the movement speeds of holes and electrons depending on the characteristics thereof, and therefore it is necessary to use a hole transporting layer and an electron transporting layer containing an appropriate compound to efficiently transport holes and electrons to the light emitting layer and balance the densities of holes and electrons, so that the light emitting efficiency can be excellently improved.
As such, the characteristics of the organic compound components contained in each layer of the organic thin film layer have a significant influence not only on the driving voltage, light emitting efficiency, luminance, and lifetime of the device but also on the efficiency or lifetime of the finally produced display, and therefore, in the organic electroluminescent device, it is considered to be important to use a specific organic material suitable for a multilayer structure. Therefore, studies on the components contained in each of the organic thin film layers are actively being conducted.
Prior art literature
Patent literature
Patent document 1: KR 10-2014-0137572A 1
Patent document 2: KR 10-1663355B1
Disclosure of Invention
Technical problem
An object of the present invention is to provide an organic electroluminescent device comprising a novel organic compound, and thus having a low driving voltage and excellent device efficiency characteristics and lifetime characteristics.
Solution to the problem
In order to achieve the above object, the present invention relates to a compound represented by the following chemical formula 1:
chemical formula 1:
wherein,
n and m are integers from 0 to 4,
X 1 selected from the group consisting ofO、N(R 7 )、C(R 8 )(R 9 ) And S is selected from the group consisting of,
L 1 and L 2 And are 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 1 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 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 1 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,
Ar 1 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 1 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 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 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 2 to 20 carbon atoms,
R 1 to R 9 Are identical or different from one another and are each independently selected from the group consisting of hydrogen, deuterium, 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, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted In the group consisting of an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 2 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 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 1 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, can be combined with adjacent groups to form a substituted or unsubstituted ring,
R 1 to R 4 Can be combined with adjacent groups to form a substituted or unsubstituted ring.
And, the present invention relates to an organic electroluminescent device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic layers disposed between the first electrode and the second electrode, the one or more organic layers including a compound represented by chemical formula 1.
In the present invention, "hydrogen" means hydrogen, light hydrogen, deuterium or tritium unless otherwise specifically defined.
In the present invention, "halogen" means fluorine, chlorine, bromine or iodine.
In the present invention, "alkyl" refers to a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like, but are not limited thereto.
In the present invention, "alkenyl" refers to a monovalent substituent having more than one carbon-carbon double bond and derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but are not limited thereto.
In the present invention, "alkynyl" refers to a monovalent substituent having more than one carbon-carbon triple bond and derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms. Examples thereof include, but are not limited to, ethynyl (ethyl), 2-propynyl (2-propynyl), and the like.
In the present invention, "alkylthio" means an alkyl group as 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, which is a single ring or a combination of two or more rings. And, it may also include a form in which two or more rings are simply hung (pendant) or condensed with each other, specifically, naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, droyl, fluorenyl, and the like, but is not limited thereto. The above fluorenyl groups may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the present invention, "heteroaryl" refers to a monovalent substituent derived from a mono-or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with a heteroatom such as N, O, S or Se. And, it is also possible to include a form in which two or more rings are simply hung (pendant) or condensed with each other, and further, a form condensed with an aryl group. Examples of such heteroaryl groups include 6 membered monocyclic rings, such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; polycyclic rings such as phenoxythienyl (phenyloxathianyl), indolizinyl (indoziyl), indolyl (indolyl), purinyl (purinyl), quinolinyl (quinolyl), benzothiazole (benzothiazole), carbazolyl ring (carbazolyl); and 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.
In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R means an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, diphenoxy, and the like.
In the present invention, "alkyloxy" means a monovalent substituent represented by R 'O-and R' means an alkyl group having 1 to 40 carbon atoms, which may include a straight chain (linear), branched, or cyclic (cyclic) structure. Examples of the alkoxy group include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentyloxy and the like, but are not limited thereto.
In the present invention, "alkoxy" may be a straight, branched or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably has 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.
In the present invention, "aralkyl" refers to aryl-alkyl, wherein aryl and alkyl are as described above. Preferred aralkyl groups include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl, and naphthylmethyl. Through alkyl groups to the parent residue.
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 an aryl-alkyl group having 6 to 30 carbon atoms.
In the present invention, "heteroarylamino" 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 heterocyclic group.
In the present invention, "cycloalkyl" refers to monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl (norbornyl), adamantane (amantine), and the like.
In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl groups include, but are not limited to, morpholine, piperazine, and the like.
In the present invention, "alkylsilyl" refers to a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" refers to a silyl group substituted with an aryl group having 6 to 60 carbon atoms.
In the present invention, "fused ring" refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
In the present invention, "form a ring in combination with an adjacent group" means form a substituted or unsubstituted aliphatic hydrocarbon ring in combination with an adjacent group; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; or their fused rings.
In the present invention, examples of the "aromatic hydrocarbon ring" include phenyl, naphthyl, anthracenyl, and the like, but are not limited thereto.
In the present invention, "aliphatic heterocyclic ring" means an aliphatic ring containing one or more hetero atoms.
In the present invention, "aromatic heterocycle" means an aromatic ring containing one or more hetero atoms.
In the present invention, "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not particularly limited as long as it is a position where a hydrogen atom is substituted, that is, a position where a substituent can be substituted, and when two or more substituents are substituted, two or more substituents may be the same or different from each other. The above substituent may be substituted with one or more substituents selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxy, 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 6 to 30 carbon atoms, aryl having 5 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroarylalkyl 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, heteroarylamino 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 examples.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention provides a novel organic compound which has excellent interface characteristics with an adjacent layer and can have excellent chemical stability when used as an organic electroluminescent device material.
Also, the present invention can provide an organic electroluminescent device comprising the above novel organic compound, and thus having a low driving voltage and excellent device efficiency characteristics and lifetime characteristics.
Detailed Description
The present invention relates to a compound represented by the following chemical formula 1.
Chemical formula 1:
wherein,
n and m are integers from 0 to 4,
X 1 selected from the group consisting of O, N (R) 7 )、C(R 8 )(R 9 ) And S is selected from the group consisting of,
L 1 and L 2 Are identical or different from one another and are each independently selected from the group consisting of single bonds, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 1 to 30 carbon atoms, substituted or unsubstituted alkylene groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 10 carbon atoms, substituted or unsubstituted arylene groups havingAn alkenylene group of 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkenylene group of 3 to 10 carbon atoms, a substituted or unsubstituted heteroalkylene group of 1 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group of 2 to 10 carbon atoms, a substituted or unsubstituted heteroalkenylene group of 2 to 10 carbon atoms and a substituted or unsubstituted heterocycloalkenylene group of 2 to 10 carbon atoms,
Ar 1 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 1 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 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 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 2 to 20 carbon atoms,
R 1 to R 9 And are each independently selected from the group consisting of hydrogen, deuterium, 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, 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 1 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl having 2 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 atoms, substituted or unsubstituted aralkylamino having 7 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 1 to 24 carbon atoms A group, 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, capable of forming a substituted or unsubstituted ring in combination with the adjacent groups,
R 1 to R 4 Can be combined with adjacent groups to form a substituted or unsubstituted ring.
Embodiments of the invention
Embodiments of the present invention are described in detail below to enable those of ordinary skill in the art to practice them easily. This invention may, however, be embodied in many different forms and is not limited to the embodiments described herein.
The novel organic compound of the present invention has excellent interface characteristics with an adjacent layer, and can have excellent chemical stability, particularly has a HOMO level contributing to hole transport, and thus can be used as a hole transport auxiliary layer material for an organic electroluminescent device having excellent hole transport characteristics for a light emitting layer.
Specifically, the compound represented by the following chemical formula 1 is shown below:
chemical formula 1:
wherein,
n and m are integers from 0 to 4,
X 1 selected from the group consisting of O, N (R) 7 )、C(R 8 )(R 9 ) And S is selected from the group consisting of,
L 1 and L 2 Are identical or different from one another and are each independently selected from the group consisting of single bonds, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 1 to 30 carbon atoms, substituted or unsubstituted alkylene groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 10 carbon atoms, substituted or unsubstituted arylene groups having 2 to 10 carbon atomsAn alkenyl group of atoms, a substituted or unsubstituted cycloalkenyl group of 3 to 10 carbon atoms, a substituted or unsubstituted heteroalkylene group of 1 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group of 2 to 10 carbon atoms, a substituted or unsubstituted heteroalkenylene group of 2 to 10 carbon atoms and a substituted or unsubstituted heterocycloalkenylene group of 2 to 10 carbon atoms,
Ar 1 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 1 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 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 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 2 to 20 carbon atoms,
R 1 To R 9 And are each independently selected from the group consisting of hydrogen, deuterium, 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, 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 1 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl having 2 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 atoms, substituted or unsubstituted aralkylamino having 7 to 30 carbon atoms, substituted or unsubstituted arylamino having 1 to 24 carbon atoms, and substituted or unsubstituted heteroaryl having 1 to 24 carbon atomsOr an 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, capable of forming a substituted or unsubstituted ring in combination with the adjacent groups,
R 1 To R 4 Can be combined with adjacent groups to form a substituted or unsubstituted ring.
The compound represented by the above chemical formula 1 may be a compound represented by the following chemical formulas 2 to 7:
chemical formula 2:
chemical formula 3:
chemical formula 4:
chemical formula 5:
chemical formula 6:
chemical formula 7:
wherein,
n、m、L 1 、L 2 、Ar 1 、X 1 、R 1 to R 6 As defined in chemical formula 1 above.
Above L 1 And L 2 Are identical or different from one another and can each independently be a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
The above X may be O or S.
Ar as described above 1 May be selected from the group consisting of the following chemical formulas 8 to 12:
chemical formula 8:
chemical formula 9:
chemical formula 10:
chemical formula 11:
chemical formula 12:
wherein,
* In order to bond the portions together,
o is an integer of 0 to 5,
p is an integer of 0 to 7,
q is an integer of 0 to 6,
r, s, t and u are each otherIdentical or different and are each independently an integer from 0 to 4, X 2 Selected from O, N (R) 17 )、C(R 18 )(R 19 ) And S is selected from the group consisting of,
R 10 to R 19 And are each independently selected from the group consisting of hydrogen, deuterium, 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, 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 1 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl having 2 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 atoms, substituted or unsubstituted aralkylamino having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 1 to 24 carbon atoms, substituted or unsubstituted aryl having 1 to 30 carbon atoms, and substituted or unsubstituted silyl having 1 to 30 carbon atoms can be bonded to adjacent groups of the substituted or unsubstituted aryl having 1 to 30 carbon atoms.
The compound represented by chemical formula 1 of the present invention may be selected from the group consisting of, but not limited to:
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the compound of the above chemical formula 1 of the present invention is effective as a hole transport auxiliary layer material.
When the above-described organic compound is used as a material for an organic electroluminescent device, it may exhibit equivalent or excellent characteristics in most device characteristics such as luminous efficiency, lifetime, and the like.
The present invention provides an organic electroluminescent device comprising the compound represented by the above chemical formula 1.
The organic compound of the present invention is effective as a hole transport auxiliary layer material.
In the organic electroluminescent device according to the present invention, an organic thin film layer composed of one or more layers including at least a light-emitting layer is laminated between a cathode and an anode, and the organic thin film layer is a hole transport layer and/or a hole transport auxiliary layer between the first electrode and the light-emitting layer.
The hole transport layer and/or the hole transport auxiliary layer is a compound represented by the above chemical formula 1.
The hole transport auxiliary layer adjusts hole injection characteristics by reducing a HOMO level difference between the hole transport layer and the light emitting layer, thereby reducing accumulation of holes at an interface between the hole transport auxiliary layer and the light emitting layer, and reducing quenching phenomenon (quenching) of exciton annihilation at the interface due to polarons (polarons). Thereby, deterioration of the device can be reduced and the device can be stabilized, thereby improving efficiency and lifetime.
The organic electroluminescent device may have a structure in which 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 are stacked, and if necessary, the electron transport auxiliary layer may be stacked.
The organic electroluminescent device of the present invention is illustrated below. However, the following exemplary contents do not limit the organic electroluminescent device of the present invention.
The organic electroluminescent device 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, the hole transport auxiliary layer may be further included between the anode and the emission layer, and the Electron Transport Layer (ETL) and the Electron Injection Layer (EIL) may be further included between the cathode and the emission layer. Further, an electron transport auxiliary layer may be included between the cathode and the light-emitting layer.
In the method of manufacturing an organic electroluminescent device of the present invention, first, an anode is formed by coating an anode material on a surface of a substrate by a conventional method. In this case, the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handleability, and water repellency. As the anode material, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) which is transparent and has excellent conductivity can be used 2 ) And zinc oxide (ZnO), and the like.
Then, a Hole Injection Layer (HIL) material is vacuum-thermally deposited or spin-coated on the surface of the above anode by a conventional method to form the hole injection layer. Such hole injection layer materials may include copper phthalocyanine (CuPc), 4',4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4',4" -tris (3-methylphenylamino) phenoxybenzene (m-MTDAPB), 4',4 "-tris (N-carbazolyl) triphenylamine (TCTA) belonging to the starburst (starburst) amine family, 4',4" -tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA), or IDE406 available from the japan light-emitting (Idemitsu) company.
The hole transport layer is formed by vacuum thermal deposition or spin coating of a hole transport layer material on the surface of the hole injection layer by a conventional method. The hole transport layer material may be a conventional hole transport layer material.
The hole transport auxiliary layer may be formed by vacuum thermal deposition or spin coating of the compound represented by the above chemical formula 1 of the present invention on the surface of the above hole transport layer. As described above, in the above-described hole transport auxiliary layer, the compound of the present invention may be used as a hole transport auxiliary layer material, and a hole transport auxiliary layer may be formed using a usual hole transport auxiliary layer material.
The light emitting layer is formed by vacuum thermal deposition or spin coating of a light emitting layer (EML) material on the surface of the above hole transport auxiliary layer by a conventional method. At this time, in the case where a light-emitting material alone or a light-emitting host material among the light-emitting layer materials used is green, tris (8-hydroxyquinoline) aluminum (Alq 3 ) Etc., in the case of blue, alq may be used 3 CBP (4, 4'-N, N' -dicarbazole-biphen yl, 4'-N, N' -dicarbazole-biphenyl), PVK (poly (N-vinylcarbazole), poly (N-vinylcarbazole)), ADN (9, 10-di (naphthalen-2-yl) anthracene), TCTA, TPBI (1, 3,5-tris (N-phenylbenzozinamidazole-2-yl) benzene,1,3, 5-tris (N-phenylbenzoimidazol-2-yl) benzene), TBADN (3-tert-butyl-9, 10-di (napth2-yl) anthracene), E3, 3-tert-butyl-9,10-di (naphthalen-2-yl) anthracene, DSA (distyryl) arylene, or mixtures thereof.
As dopants (Dopant) which can be used together with the light-emitting host in the light-emitting layer material, IDE102, IDE105, which are commercially available from japan light-emitting (Idemitsu) corporation, and as phosphorescent dopants (Dopant), tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3), bis [ (4, 6-difluorophenyl) pyridinyl-N, C-2' ] picolinic acid iridium (III) (FIrpic) (reference [ Chihaya Adachi et al., appl. Phys. Lett.,2001,79,3082-3084 ]), octaethylporphyrin platinum (II) (PtOEP), TBE002 (Corbion corporation), and the like can be used.
The electron transport layer is formed by vacuum thermal deposition or spin coating of an Electron Transport Layer (ETL) material on the surface of the above light emitting layer by a conventional method. In this case, the electron transport layer material to be used is not particularly limited, and tris (8-hydroxyquinoline) aluminum (Alq 3 )。
Alternatively, by further forming a Hole Blocking Layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent Dopant (Dopant) in the light emitting layer, triplet excitons or holes may be prevented from diffusing into the electron transport layer.
The hole blocking layer may be formed by vacuum thermal deposition and spin coating by a conventional method, and the hole blocking layer material is not particularly limited, and preferably (8-hydroxyquinoline) lithium (Liq), bis (8-hydroxy-2-methylquinoline) -biphenoxyaluminum (BAlq), bathocuproine (BCP), liF, and the like may be used.
The electron injection layer is formed by vacuum thermal deposition or spin-coating an Electron Injection Layer (EIL) material on the surface of the electron transport layer by a conventional method. At this time, the electron injection layer material used may be LiF, liq, li 2 O, baO, naCl, csF, etc.
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, the cathode material used may be lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or the like. Also, in the case of a top emission organic electroluminescent device, indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO) may be used to form a transparent cathode through which light can pass.
A coating layer (CPL) may be formed on the surface of the cathode using the coating layer-forming composition.
The synthetic methods of the above compounds are described below by way of representative examples. However, the synthetic method of the compound of the present invention is not limited to the methods exemplified below, and the compound of the present invention can be prepared by the methods exemplified below and methods well known in the art.
Synthesis example
Synthesis of intermediate group C
Into a round bottom flask were placed, under a stream of nitrogen, reactant A (28.7 g,100 mmol), reactant B (18.9 g,110 mmol), pd (PPh 3 ) 4 (2.31g，2.0mmol)、K 2 CO 3 (27.6 g,200 mmol), toluene (150 mL), water (80 mL) and ethanol (50 mL) were then stirred at 100deg.C to effect a reaction. After the reaction was completed, the organic layer was separated, moisture was removed, filtered, and then purified by a silica gel column (silica gel column) and recrystallization to prepare intermediate group C.
The results are shown in Table 1 below.
TABLE 1
Synthesis of intermediate F group
Into a round bottom flask was placed reactant D (17.2 g,110 mmol), reactant E (29.7 g,100 mmol), pd (PPh) under a nitrogen flow 3 ) 4 (2.31g，2.0mmol)、K 2 CO 3 (27.6 g,200 mmol), toluene (150 mL), water (80 mL), ethanol (50 mL) and then stirred at 100deg.C to effect a reaction. After the completion of the reaction, the organic layer was separated, water was removed, filtered, and then purified by a silica gel column (silica gel column) and recrystallization to prepare intermediate group F.
The results are shown in Table 2 below.
TABLE 2
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Synthesis of intermediate group G
Synthesis of intermediate group G
Into a round bottom flask was placed intermediate C (33.4 g,100 mmol), 4-bromobiphenyl (4-bromobiphenyl, 25.6g,110 mmol), pd under nitrogen flow 2 (dba) 3 (1.83 g,2.0 mmol), t-Buona (19.2 g,200 mmol), SPhos (1.64 g,4.0 mmol) and toluene (480 mL) were stirred at 100deg.C to effect a reaction. After the reaction was completed, it was precipitated in methanol, and the precipitate was filtered, followed by purification by silica gel column (silica gel column) and recrystallization to prepare intermediate group G.
The results are shown in Table 3 below.
TABLE 3 Table 3
Synthesis of Compound H group
Into a round bottom flask was placed intermediate G (4.86G, 10 mmol), intermediate E (or F) (11 mmol), pd under a nitrogen flow 2 (dba) 3 (0.183 g,0.2 mmol), t-Buona (1.92 g,20 mmol), SPhos (0.164 g,0.4 mmol) and toluene (60 mL) were then stirred at 100℃to effect a reaction. After the reaction was completed, the mixture was put into methanol for precipitation, and the precipitate was filtered, and then purified by a silica gel column (silica gel column) and recrystallization to prepare compound H group.
The results are shown in Table 4 below.
TABLE 4 Table 4
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Synthesis of intermediate group J
Into a round bottom flask was placed intermediate C (33.4 g,100 mmol), intermediate F (36.2 g,110 mmol), pd under a nitrogen flow 2 (dba) 3 (1.83 g,2.0 mmol), t-Buona (19.2 g,200 mmol), SPhos (1.64 g,4.0 mmol) and toluene (560 mL) were then stirred at 100deg.C to effect a reaction. After the reaction was completed, it was precipitated in methanol, and the precipitate was filtered, followed by purification by silica gel column (silica gel column) and recrystallization to prepare intermediate group J.
The results are shown in Table 5 below.
TABLE 5
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Synthesis of Compound L group
Into a round bottom flask was placed reactant K (11 mmol), intermediate J (10 mmol), pd under a nitrogen flow 2 (dba) 3 (0.183 g,0.2 mmol), t-Buona (1.92 g,20 mmol), SPhos (0.164 g,0.4 mmol) and toluene (60 mL) were then stirred at 100℃to effect a reaction. After the reaction was completed, the mixture was put into methanol for precipitation, and the precipitate was filtered, and then purified by a silica gel column (silica gel column) and recrystallization to prepare compound L group.
The results are shown in Table 6 below.
TABLE 6
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Synthesis of intermediate N group
Into a round bottom flask were placed reactant D (17.2 g,110 mmol), reactant M (100 mmol), pd (PPh) under a nitrogen flow 3 ) 4 (2.31g，2.0mmol)、K 2 CO 3 (27.6 g,200 mmol), toluene (150 mL), water (80 mL) and ethanol (50 mL) were then stirred at 100deg.C to effect a reaction. After the reaction was completed, the organic layer was separated, water was removed, filtered, and then purified by a silica gel column (silica gel column) and recrystallization to prepare intermediate N group.
The results are shown in Table 7 below.
TABLE 7
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Synthesis of Compound O group
Into a round bottom flask was placed intermediate G (4.86G, 10 mmol), intermediate M (or N) (11 mmol), pd under a nitrogen flow 2 (dba) 3 (0.183 g,0.2 mmol), t-Buona (1.92 g,20 mmol), SPhos (0.164 g,0.4 mmol) and toluene (60 mL) were then stirred at 100℃to effect a reaction. After the reaction was completed, the mixture was put into methanol for precipitation, and the precipitate was filtered, and then purified by a silica gel column (silica gel column) and recrystallization to prepare compound O group.
The results are shown in Table 8 below.
TABLE 8
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Synthesis of intermediate P group
Under nitrogen flow into a round bottom flaskPut intermediate C (33.4 g,100 mmol), intermediate M (or N) (110 mmol), pd 2 (dba) 3 (1.83 g,2.0 mmol), t-Buona (19.2 g,200 mmol), SPhos (1.64 g,4.0 mmol) and toluene (560 mL) were then stirred at 100deg.C to effect a reaction. After the reaction was completed, it was precipitated in methanol, and the precipitate was filtered, followed by purification by silica gel column (silica gel column) and recrystallization to prepare intermediate group P.
The results are shown in Table 9 below.
TABLE 9
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Synthesis of Compound Q group
Into a round bottom flask were placed reactant K (11 mmol), intermediate P (10 mmol), pd under a nitrogen flow 2 (dba) 3 (0.183 g,0.2 mmol), t-Buona (1.92 g,20 mmol), SPhos (0.164 g,0.4 mmol) and toluene (60 mL) were then stirred at 100℃to effect a reaction. After the reaction was completed, the mixture was put into methanol for precipitation, and the precipitate was filtered, and then purified by a silica gel column (silica gel column) and recrystallization to prepare compound Q group.
The results are shown in Table 10 below.
Table 10
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Example 1: preparation of organic electroluminescent device 1
An anode is formed with ITO on a substrate on which a reflective layer is formed, and the surface is treated with N2 plasma or UV-ozone. HAT-CN was deposited to a thickness of 10nm above this as a Hole Injection Layer (HIL). Next, N4 '-tetrakis ([ 1,1' -biphenyl ] -4-yl) - [1,1 '-biphenyl ] -4,4' -diamine was deposited to a thickness of 110nm to form a Hole Transport Layer (HTL).
A hole transport auxiliary layer was formed by vacuum depositing the compound 1-97 to a thickness of 15nm on top of the above hole transport layer, 9,10-Bis (2-naphthyl) Anthracene (ADN) capable of forming blue EML (blue EML) was deposited to a thickness of 25nm as an emission layer (EML) on top of the above hole transport auxiliary layer, and about 3wt% of N1, N6-tetrakis (4- (1-silyl) phenyl) pyrene-1, 6-diamine as a dopant (dopant) was doped.
Above this will be the same as 1:1 mass ratio of the anthracene derivative and LiQ was deposited to a thickness of 30nm as an Electron Transport Layer (ETL), and above that, liQ was deposited to a thickness of 1nm as an Electron Injection Layer (EIL). Then, the process will be repeated at 9:1 mass ratio of magnesium and silver (Ag) as a cathode, and depositing N4, N4' -bis [4- [ bis (3-methylphenyl) amino ] on the cathode to a thickness of 15nm ]Phenyl group]-N4, N4 '-diphenyl- [1,1' -biphenyl]4,4' -diamine (DNTPD) was deposited to a thickness of 60nm as a capping layer. Protection of organic electroluminescent devices from atmospheric O by applying a moisture absorbent containing seal cap thereto using UV curable adhesive 2 Or the influence of moisture, thereby producing an organic electroluminescent device.
Examples 2 to 37
An organic electroluminescent device was prepared in the same manner as in example 1, except that the compounds listed in table 11 below were used as hole transport auxiliary layers instead of the compounds 1 to 97 in example 1 described above.
Comparative examples 1 to 4
An organic electroluminescent device was prepared in the same manner as in example 1, except that compounds a to D were used as hole transport auxiliary layers instead of the compounds 1 to 97 in example 1 described above.
Compound a:
compound B:
compound C:
compound D:
experimental example 1: device performance analysis
For the organic electroluminescent devices prepared in the above examples and comparative examples, the concentration was set at 10mA/cm 2 The electro-optic characteristics of the device were analyzed under constant current conditions and at 20mA/cm 2 The lifetime of the device is measured under the driving conditions.
The experimental results are shown in table 11 below.
TABLE 11
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From the experimental results of table 11 described above, it was confirmed that in the case of using the compound of the present invention as a hole transport auxiliary layer material for an organic electroluminescent device, the driving voltage was low, and excellent device efficiency characteristics and long life characteristics were exhibited, as compared with comparative examples.
Example 38: preparation of organic electroluminescent device 2
Forming an anode with ITO on a substrate with a reflective layer formed thereon, and using N 2 Plasma or UV-ozone treatment of the surface. HAT-CN was deposited to a thickness of 10nm above this as a Hole Injection Layer (HIL). Next, N4, N4, N4', N4' -tetrakis ([ 1,1' -biphenyl)]-4-yl) - [1,1' -biphenyl]-4,4' -diamine deposited to a thickness of 110nm to form a Hole Transport Layer (HTL).
A hole transport auxiliary layer was formed by vacuum depositing the compound 2-25 to a thickness of 15nm on top of the above hole transport layer, and 9,10-Bis (2-naphthyl) Anthracene (ADN) capable of forming blue EML was deposited to a thickness of 25nm as an emission layer (EML) on top of the above hole transport auxiliary layer, and about 3wt% of N1, N6-tetrakis (4- (1-silyl) phenyl) pyrene-1, 6-diamine as a dopant was doped.
Above this will be the same as 1:1 mass ratio of the anthracene derivative and LiQ was deposited to a thickness of 30nm as an Electron Transport Layer (ETL), and above that, liQ was deposited to a thickness of 1nm as an Electron Injection Layer (EIL). Then, the process will be repeated at 9:1 mass ratio of magnesium and silver (Ag) as a cathode, and depositing N4, N4' -bis [4- [ bis (3-methylphenyl) amino ] on the cathode to a thickness of 15nm ]Phenyl group]-N4, N4 '-diphenyl- [1,1' -biphenyl]4,4' -diamine (DNTPD) was deposited to a thickness of 60nm as a capping layer. Protection of organic electroluminescent devices from atmospheric O by applying a moisture absorbent containing seal cap thereto using UV curable adhesive 2 Or the influence of moisture, thereby producing an organic electroluminescent device.
Examples 39 to 57
An organic electroluminescent device was produced in the same manner as in example 38, except that the compounds listed in table 12 below were used as a hole transport auxiliary layer instead of the compounds 2 to 25 in example 38 described above.
Comparative examples 5 to 8
An organic electroluminescent device was produced in the same manner as in example 38, except that compounds E to H were used as the hole transport auxiliary layer instead of the compounds 2 to 25 in example 38 described above.
Compound E:
compound F:
compound G:
compound H:
experimental example 2: device performance analysis
For the organic electroluminescent devices prepared in the above examples and comparative examples, the concentration was set at 10mA/cm 2 The electro-optic characteristics of the device were analyzed under constant current conditions and at 20mA/cm 2 The lifetime of the device is measured under the driving conditions.
The experimental results are shown in table 12 below.
Table 12
From the experimental results of table 12 described above, it was confirmed that in the case of using the compound of the present invention as a hole transport auxiliary layer material for an organic electroluminescent device, the driving voltage was low, and excellent device efficiency characteristics and long life characteristics were exhibited, as compared with comparative examples. Although the preferred embodiment of the present invention has been described in detail hereinabove, the scope of the present invention is not limited thereto, and various changes and modifications may be made by those skilled in the art using the basic concepts of the present invention as defined in the scope of the present invention.
Industrial applicability
The present invention relates to an organic compound and an organic electroluminescent device including the same.
Claims (8)
1. A compound represented by the following chemical formula 1, characterized in that,
chemical formula 1:
wherein,
n and m are integers from 0 to 4,
X 1 selected from the group consisting of O, N (R) 7 )、C(R 8 )(R 9 ) And S is selected from the group consisting of,
L 1 and L 2 And are 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 1 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 1 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 1 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms, and a substituted or unsubstituted heterocycloalkenylene group having 2 to 10 carbon atoms,
Ar 1 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 1 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 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 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 2 to 20 carbon atoms,
R 1 to R 9 Are identical or different from one another and are each independently selected from the group consisting of hydrogen, deuterium, 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 alkyl having 2 to 30 carbon atomsAlkenyl of a child, 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 1 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl having 2 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 atoms, substituted or unsubstituted aralkylamino having 7 to 30 carbon atoms, substituted or unsubstituted heteroarylamino having 1 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, capable of bonding with adjacent groups to form a substituted or unsubstituted ring,
R 1 To R 4 Can be combined with adjacent groups to form a substituted or unsubstituted ring.
2. A compound according to claim 1, wherein,
the compounds represented by the above chemical formula 1 are represented by the following chemical formulas 2 to 7:
chemical formula 2:
chemical formula 3:
chemical formula 4:
chemical formula 5:
chemical formula 6:
chemical formula 7:
wherein,
n、m、L 1 、L 2 、Ar 1 、X 1 、R 1 to R 6 As defined in claim 1.
3. The compound according to claim 1, wherein L 1 And L 2 Are identical or different from one another and are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
4. The compound of claim 1, wherein X is O or S.
5. A compound according to claim 1, wherein,
ar as described above 1 Selected from the group consisting of the following chemical formulas 8 to 12:
chemical formula 8:
chemical formula 9:
chemical formula 10:
chemical formula 11:
chemical formula 12:
wherein,
* In order to bond the portions together,
o is an integer of 0 to 5,
p is an integer of 0 to 7,
q is an integer of 0 to 6,
r, s, t and u are the same or different from each other and are each independently an integer of 0 to 4,
X 2 selected from O, N (R) 17 )、C(R 18 )(R 19 ) And S is selected from the group consisting of,
R 10 To R 19 Are identical or different from one another and are each independently selected from the group consisting of hydrogen, deuterium, 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, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 1 to 30 carbon atomsA heteroaryl group of 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group of 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group of 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group of 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group of 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group of 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group of 1 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 30 carbon atoms and a substituted or unsubstituted aryloxy group of 6 to 30 carbon atoms can be combined with adjacent groups to form a substituted or unsubstituted ring.
6. An organic electroluminescent device is provided, which comprises a substrate,
comprising the following steps:
a first electrode;
a second electrode disposed opposite to the first electrode; and
more than one organic layer arranged between the first electrode and the second electrode,
in the above-mentioned organic electroluminescent device, a light emitting layer,
at least one of the one or more organic layers comprises the compound of claim 1.
7. The organic electroluminescent device according to claim 6, wherein the organic layer is 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.
8. The organic electroluminescent device of claim 6, wherein the organic layer is a hole transport auxiliary layer.
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