CN108976132A - Compounds and organic luminescent device comprising it - Google Patents
Compounds and organic luminescent device comprising it Download PDFInfo
- Publication number
- CN108976132A CN108976132A CN201810550855.XA CN201810550855A CN108976132A CN 108976132 A CN108976132 A CN 108976132A CN 201810550855 A CN201810550855 A CN 201810550855A CN 108976132 A CN108976132 A CN 108976132A
- Authority
- CN
- China
- Prior art keywords
- compound
- unsubstituted
- substituted
- layer
- mentioned
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 73
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 48
- 238000002347 injection Methods 0.000 claims description 19
- 239000007924 injection Substances 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000005416 organic matter Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 230000003760 hair shine Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 abstract description 21
- 125000001424 substituent group Chemical group 0.000 abstract description 9
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 100
- 238000000034 method Methods 0.000 description 46
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 25
- 229940125904 compound 1 Drugs 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 21
- 239000000463 material Substances 0.000 description 18
- 238000004770 highest occupied molecular orbital Methods 0.000 description 11
- 150000002220 fluorenes Chemical group 0.000 description 10
- 238000001771 vacuum deposition Methods 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 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 7
- -1 Benzo fluorenyl Chemical group 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 125000005647 linker group Chemical group 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000003292 diminished effect Effects 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940125810 compound 20 Drugs 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910021389 graphene Inorganic materials 0.000 description 2
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical class C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SQISUZWPWJHTEP-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1.NC1=CC=CC=C1 SQISUZWPWJHTEP-UHFFFAOYSA-N 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- LVWNMZQGOVXREB-UHFFFAOYSA-N phenazine piperazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C12.N1CCNCC1 LVWNMZQGOVXREB-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- QPUMEZIFDXYGPG-UHFFFAOYSA-N piperazine 1H-pyrrole Chemical compound N1CCNCC1.N1C=CC=C1 QPUMEZIFDXYGPG-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to compounds and include its organic luminescent device, linker is arranged between the second position and arylamine of fluorenes in the compounds of an example of the invention, arylamine has the substituent group and phenyl substituent of the aryl with 2 or more, and the organic luminescent device comprising the compound of the present invention can realize low-voltage, high efficiency, long-life.
Description
Technical field
The present invention relates to compounds and include its organic luminescent device.
Background technique
In Organic Light Emitting Diode, the material as organic matter layer can be broadly dassified into luminescent material, sky according to function
Hole injection material, hole transporting material, electron transport materials, electron injection material etc..Also, above-mentioned luminescent material can according to point
Son amount is classified as macromolecule and low molecule, and the phosphor of the singlet excited state from electronics can be classified as according to luminescence mechanism
Material and the triplet excitation state from electronics phosphor material, luminescent material can be classified as according to illuminant colour blue, green,
Yellow and orange light emitting materials needed for red illuminating material and the better natural colour of embodiment.Also, in order to increase excitation purity, and
Increase luminous efficiency by energy transfer, main body/dopant class can be used as luminescent substance.If its principle is will be with main composition
The main body of luminescent layer is compared, and the dopant that band gap is small and luminous efficiency is outstanding is mixed in auxiliary layer on a small quantity, then in main body
The exciton of generation is conveyed to dopant, to issue high-efficient light.At this point, the wavelength of main body is moved to the wavelength band of dopant
It is dynamic, thus the light of required wavelength can be obtained according to the type of the dopant and main body utilized.
So far, as the substance for being used in this organic luminescent device, well-known there are many compounds, but are utilizing
So far it in the case where the organic luminescent device of well-known substance, due to high driving voltage, low efficiency and short life, holds
It is continuous to require to develop new material.Therefore, ongoing effort developed using the substance with outstanding characteristic with low voltage drive,
High brightness and the organic luminescent device of long-life.
Existing technical literature
Patent document
(patent document 1) KR published patent 10-2015-0086721
Summary of the invention
The present invention provides novel organic compound and preparation method thereof and organic hair comprising the novelty organic compound
Optical device.
But problem to be solved by this invention is not limited to problem described above, the technical field of the invention
Those of ordinary skill can be clearly understood that the other problems not described according to contents below.
First embodiment of the invention provides the compound indicated by following formula 1:
Chemical formula 1
In above-mentioned chemical formula 1,
L is substituted or unsubstituted C6-30Arlydene or substituted or unsubstituted C3-30Heteroarylidene,
AraAnd ArbIt is separately substituted or unsubstituted C6-30Aryl or substituted or unsubstituted C3-30's
Heteroaryl comprising nitrogen, wherein above-mentioned aryl and heteroaryl are not replaced by heavy hydrogen,
R、R'、R1And R2It is separately hydrogen, substituted or unsubstituted C1-30Alkyl, substituted or unsubstituted C6-30
Aryl or substituted or unsubstituted C3-30Heteroaryl,
R3For hydrogen or substituted or unsubstituted C1-30Alkyl,
The integer that l is 0 or 1 to 4, m are 0 or integer of 1 to 3, and the integer that n is 0 or 1 to 5, p is integer of 1 to 3, q 1
To 3 integer, the integer that p+q is 2 to 4.
It includes containing the compound of the present invention that the second aspect of the present invention, which is provided between first electrode and second electrode,
The organic luminescent device of organic matter layer.
The compound of an example of the invention is bonded arylamine in the second position of fluorenes, in the auxiliary that shines by linker
The higher LUMO for being easy shielding electronics can be maintained while layer deeper HOMO energy level easy to form.As a result, of the invention one
The compound of example be used in organic luminescent device, it can be achieved that organic luminescent device low-voltage and high efficiency.
Also, the compound of an example of the invention, arylamine have the substituent group connected by 2 or more aryl, can
Increase conjugation, when forming film, molecules align is outstanding, can inhibit by quick hole flow (hole mobility)
It roll-offs, thus can realize the long-life of organic luminescent device.
Also, the compound of an example of the invention, arylamine have the substituent group fixed by phenyl, maintain compound
HOMO energy level and lumo energy and high T1, exciton congregational rate in the luminescent layer that can maximize, can reach organic luminescent device
High efficiency.
Also, the substituent group that there is linker and arylamine between fluorenes and arylamine to be connected by 2 or more aryl, because
This improves Tg, prevents the recrystallization of film, the driving stability of organic luminescent device thus can be improved.
Detailed description of the invention
Fig. 1 shows the schematic diagrams of the organic luminescent device of an example of the invention.
The explanation of appended drawing reference
100: substrate
200: hole injection layer
300: hole transporting layer
400: luminescent layer
500: electron supplying layer
600: electron injecting layer
1000: anode
2000: cathode
Specific embodiment
Hereinafter, referring to attached drawing, the example and embodiment that the present invention will be described in detail, so that the technical field of the invention is general
Logical technical staff can be easy to implement.
But the present invention can by it is a variety of it is different in the form of realize, and be not limited to example and embodiment described herein.
Also, the part unrelated with explanation is omitted, in the specification, for similar in the figure in order to clearly state the present invention
Part, be labelled with similar appended drawing reference.
In the full text of description of the invention, when a component is located at another component "upper", not only include component with
The case where another component is in contact, include thes case where there is other component between the two parts.
In the full text of description of the invention, when one structural element of a part " comprising ", unless there are especially opposite
It records, then means to may also include other structures element, rather than exclude other structures element.In the full text of description of the invention
The term " about " that uses, " substantial " etc. when prompting intrinsic preparation and substance tolerance in mentioned meaning with its numerical value or
Meaning close to its numerical value uses, and is undeservedly utilized with the infringer for preventing against one's conscience and is referred to help to understand the present invention
The disclosure of accurate or absolute numerical value.Term "~() step " used in the full text of description of the invention or "~
Step " do not mean that " for~the step of ".
In the full text of description of the invention, " their combination " contained in the performance of Markush (Markush) form this
One term means one or more of the group that documented multiple structural elements form in the performance by Markush form
Mixing or combination, it is meant that including selected from one or more of the group that is made of above-mentioned multiple structural elements.
In the full text of description of the invention, " A and/or B " this record means " A or B or A and B ".
In the full text of description of the invention, term " aryl " means comprising C6-30Aromatic cyclic hydrocarbon group, for example, benzene
Base, benzyl, naphthalene, xenyl, terphenyl, fluorenyl, phenanthryl, triphenyl alkenyl, phenylakenyl,Base, fluorane thenyl,
Benzo fluorenyl, benzo triphenyl alkenyl, benzoThe aromatic ring of base, anthryl, stilbenyl, pyrenyl etc., " heteroaryl "
As the C comprising at least one miscellaneous element3-30Aromatic ring, such as, it is meant that comprising from pyrrolinyl, pyrazinyl, pyridine
Base, indyl, isoindolyl, furyl, benzofuranyl, isobenzofuran-base, dibenzofuran group, aisaa benzothiophenyl, two
Aisaa benzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazyl, luxuriant and rich with fragrance cry base, acridinyl, phenanthroline, thienyl and by
Pyridine ring, pyridine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxanes ring, piperazine
Phenazine ring, morpholine ring, piperazine ring, carbazole ring, furan nucleus, thiphene ring, oxazole ring, oxadiazoles ring, benzoxazoles ring, thiazole ring, thiophene
The aromatic series that diazonium ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyranoid ring, dibenzofurans ring are formed is miscellaneous
Ring group.
In the full text of description of the invention, may imply that can be by selecting free halogen, amino, nitrile for term " substituted or unsubstituted "
Base, nitro or C1~C20Alkyl, C2~C20Alkenyl, C1~C20Alkoxy, C3~C20Naphthenic base, C3~C20Heterocycle
Alkyl, C6~C30Aryl and C3~C30Heteroaryl composition one or more of group base it is substituted or unsubstituted.Also, this
In description of the invention full text, identical appended drawing reference can have equivalent as long as no the special content referred to.
In the full text of description of the invention, in term " fluorenes ", the hydrogen with the 9th bond with carbon may include by substituted or unsubstituted
C1-20Alkyl, substituted or unsubstituted C5-30Aryl or substituted or unsubstituted C3-30Heteroaryl replace feelings
Condition.
First embodiment of the invention provides the compound indicated by following formula 1:
Chemical formula 1
In above-mentioned chemical formula 1,
L is substituted or unsubstituted C6-30Arlydene or substituted or unsubstituted C3-30Heteroarylidene,
AraAnd ArbIt is separately substituted or unsubstituted C6-30Aryl or substituted or unsubstituted C3-30's
Heteroaryl comprising nitrogen, wherein above-mentioned aryl and heteroaryl are not replaced by heavy hydrogen,
R、R'、R1And R2It is separately hydrogen, substituted or unsubstituted C1-30Alkyl, substituted or unsubstituted C6-30
Aryl or substituted or unsubstituted C3-30Heteroaryl,
R3For hydrogen or substituted or unsubstituted C1-30Alkyl,
The integer that l is 0 or 1 to 4, m are 0 or integer of 1 to 3, and the integer that n is 0 or 1 to 5, p is integer of 1 to 3, q 1
To 3 integer, the integer that p+q is 2 to 4.
The compound of the above-mentioned chemical formula 1 of an example of the invention is bonded aryl in the second position of fluorenes by linker
Amine, 1 substituent group that above-mentioned arylamine has 1 substituent group with 2 or more aryl and fixed by phenyl.
The above compound of an example of the invention is bonded arylamine in the second position of fluorenes, is being shone by linker
The higher LUMO for being easy shielding electronics can be maintained while auxiliary layer deeper HOMO energy level easy to form.It is of the invention as a result,
An example compound be used in organic luminescent device, it can be achieved that organic luminescent device low-voltage and high efficiency.
Also, the compound of an example of the invention, arylamine have the substituent group connected by 2 or more aryl, can
Increase conjugation, when forming film, molecules align is outstanding, can inhibit by quick hole flow (hole mobility)
It roll-offs, thus can realize the long-life of organic luminescent device.
Also, the compound of an example of the invention, arylamine have the substituent group fixed by phenyl, maintain compound
HOMO energy level and lumo energy and high T1, exciton congregational rate in the luminescent layer that can maximize, can reach organic luminescent device
High efficiency.
Also, the substituent group that there is linker and arylamine between fluorenes and arylamine to be connected by 2 or more aryl, because
This improves Tg, prevents the recrystallization of film, the driving stability of organic luminescent device thus can be improved.
In an example of the invention, above-mentioned AraAnd/or ArbIt can be substituted or unsubstituted C6-30Aryl or
C3-30The heteroaryl comprising nitrogen, but above-mentioned aryl and heteroaryl are not replaced by heavy hydrogen.For being replaced by heavy hydrogen, work is synthesized
Sequence is complicated, is possible to be difficult to obtain high-purity compound needed for hole transporting layer in this case.This is possible to organic
The service life of luminescent device brings deleterious effect.
In an example of the invention, the above-mentioned heteroaryl comprising nitrogen is not limited to this, but can for example illustrate pyridine, pyrrole
Piperazine, triazine or quinoline.
Also, in an example of the invention, above compound can be indicated by following formula 2.
Chemical formula 2
In above-mentioned chemical formula 2, o be 1 to 4 integer.
When as linker L have more than one phenylene when, luminous auxiliary layer can deeper HOMO energy easy to form
Grade, and the higher lumo energy for being easy shielding electronics can be maintained.
Also, an example according to the present invention, in above-mentioned chemical formula 1 or chemical formula 2, above-mentioned R and R` are separately
It can be substituted or unsubstituted C6-30Aryl or substituted or unsubstituted C3-30Heteroaryl.In this case, it can tie up
Deeper HOMO is held, molecules align is outstanding, can form higher Tg.Thus efficiency and the service life of organic luminescent device can be improved.
Also, an example according to the present invention, in above-mentioned chemical formula 1 or chemical formula 2, R and R` be separately hydrogen,
Substituted or unsubstituted C1-30Alkyl, substituted or unsubstituted C6-30Aryl or substituted or unsubstituted C3-30Heteroaryl
Base, above-mentioned AraAnd ArbIt separately can be substituted or unsubstituted C6-30Aryl.If AraAnd ArbTo replace or not taking
The C in generation6-30Aryl, then can maintain deeper HOMO energy level, low-voltage and high efficiency effect can be more excellent.On more specifically,
State AraAnd ArbIt can be phenyl.
An example according to the present invention, above compound can be indicated by following formula 3.
Chemical formula 3
In above-mentioned chemical formula 3,
R4And R5It is separately hydrogen, substituted or unsubstituted C1-24Alkyl, substituted or unsubstituted C6-24Virtue
Base or substituted or unsubstituted C3-24Heteroaryl,
The integer that o is 1 to 4.
An example according to the present invention, above-mentioned-(Ara)p-(Arb)qIt can be by any of the following Expression 1-1 to 1-6 chemistry
Formula indicates.
In above-mentioned formula 1-1 into 1-6,
Ar1To Ar4It separately can be substituted or unsubstituted C6-30Aryl or substituted or unsubstituted
C3-30The heteroaryl comprising nitrogen, wherein above-mentioned aryl and heteroaryl are not replaced by heavy hydrogen.Also, according to the present invention one is real
Example, in above-mentioned formula 1-1 into 1-6, Ar1To Ar4It can be phenyl.
Also, the second position of fluorenes is set as link position by an example according to the present invention, is had and is used as hole transporting layer
Appropriate deeper HOMO, maintains the balance appropriate of exciton forming region in luminescent layer, may achieve the low electricity of organic luminescent device
Pressure and high efficiency.
In an example of the invention, the compound indicated by above-mentioned chemical formula 1 can be specifically following compound, have
It may be not limited to this:
The compound of 1 above-mentioned to the 210th has stable Tg, and thermal stability is outstanding, when driving element, prevents weight
Crystallization, is effectively improved the service life.
Second embodiment of the present invention provides the organic luminescent device of the compound comprising being indicated by above-mentioned chemical formula 1.
Above-mentioned organic luminescent device can include having for one layer or more containing the compounds of this invention between first electrode and second electrode
Machine nitride layer.
In an example of the invention, above-mentioned organic matter layer can be hole injection layer, hole transporting layer and the auxiliary that shines
Layer, it is likely that not limited to this, also, when the compound of the present invention forms organic matter layer can be used alone or with well knownization
Object is closed to be used together.
In an example of the invention, above-mentioned organic luminescent device may include containing the chemical combination indicated by above-mentioned chemical formula 1
The organic matter layer of object is as the auxiliary layer that shines, it is likely that not limited to this.Also, the compound indicated by above-mentioned chemical formula 1
It can be specific specific compound as described above.
Above-mentioned organic luminescent device can include one layer or more of hole between anode (anode) and cathode (cathode)
Implanted layer (HIL), hole transporting layer (HTL), luminescent layer (EML), electron supplying layer (ETL), electron injecting layer (EIL) etc. have
Machine nitride layer.
For example, above-mentioned organic luminescent device can be prepared according to structure documented in Fig. 1.Organic luminescent device can
To it is lower and on stack gradually anode (hole injecting electrode 1000)/200/ hole transporting layer of hole injection layer, 300/ luminescent layer 400/
500/ electron injecting layer of electron supplying layer, 600/ cathode (electron injection electrode 2000).
In Fig. 1, the substrate for organic luminescent device is can be used in substrate 100, in particular, can be steady for mechanical strength, heat
Qualitative, transparent, surface smoothness, ease of handling and the outstanding transparent glass substrate or flexible plastic base of waterproofness
Plate.
Hole injecting electrode 1000 is used as the anode for being injected with the hole of machine luminescent device.In order to which hole can be injected,
It, can be by tin indium oxide (ITO), indium zinc oxide (IZO), graphene (graphene) etc using the substance with low work function
Transparent material formed.
By vacuum deposition method, spin-coating method, casting, LB (Langmuir-Blodgett) method etc. come in above-mentioned anode electricity
Pole overburden hole injection layer substance, thus can form hole injection layer 200.Sky is being formed by above-mentioned vacuum deposition method
In the case where the implanted layer of cave, the compound of material of the sedimentary condition because being used as hole injection layer 200, needed for hole injection layer
Structure and thermal characteristics etc. and it is different, but usually can 50-500 DEG C depositing temperature, 10-8To 10-3The vacuum degree of torr (support),
0.01 toDeposition velocity,It is suitably selected in 5 μm of layer thickness range.
Then, by vacuum deposition method, spin-coating method, casting, LB method etc. come in above-mentioned 200 overburden of hole injection layer
Thus hole transporting layer substance can form hole transporting layer 300.Hole transporting layer is being formed by above-mentioned vacuum deposition method
In the case of, sedimentary condition is different due to the compound used, but typically it will be preferred to, the formation with hole injection layer almost
It is selected in identical condition and range.
The compound of the present invention can be used in above-mentioned hole transporting layer 300, as described above, the chemical combination of the invention that can be used alone
Object is used together well known compound.Also, an example according to the present invention, hole transporting layer 300 can be one layer with
On, it can together include the hole transporting layer only formed by well known substance.
Also, an example according to the present invention can form luminous auxiliary layer on above-mentioned hole transporting layer 300.Above-mentioned hair
The compound of the present invention can be used in light auxiliary layer, and can be used together the multiple compounds indicated by above-mentioned chemical formula 1.Also,
One closes well known compound using the compound of the present invention, can form luminous auxiliary layer.
By the methods of vacuum deposition method, spin-coating method, casting, LB method, in above-mentioned hole transporting layer 300 or the auxiliary that shines
Thus depositing light emitting layer substance on layer can form luminescent layer 400.By above-mentioned vacuum deposition method to form luminescent layer the case where
Under, sedimentary condition is different due to the compound used, but typically it will be preferred to, almost the same with the formation of hole injection layer
Condition and range in selected.Also, well known compound can be used as main body or dopant by above-mentioned emitting layer material.
Also, in the case where being used together in luminescent layer with phosphorescent dopants, triplet exciton or hole in order to prevent
The phenomenon that spreading to electron supplying layer can also be laminated hole by vacuum deposition method or spin-coating method and inhibit material (HBL).At this time may be used
The hole inhibiting substances used are not particularly limited, but selection in the well known substance of material can be inhibited any from hole is used as
Substance utilizes.For example, oxadiazole derivatives or triazole derivative, phenanthroline derivative or Japanese Unexamined Patent Publication 11- can be enumerated
Documented hole inhibits material etc. in 329734 (A1), typically, can be used Balq (bis- (8- hydroxy-2-methylquinolines)-
Aluminium biphenyl phenates), phenanthroline (phe nanthrolines) class compound (such as BCP (Basso of general purpose display (UDC) company
Coupoline)) etc..
It is formed with electron supplying layer 500 on 400 top of luminescent layer as formed above, at this point, above-mentioned electron supplying layer can lead to
The methods of vacuum deposition method, spin-coating method, casting are crossed to be formed.Also, the sedimentary condition of above-mentioned electron supplying layer is because using
Compound and it is different, but typically it will be preferred to, selected in the condition and range almost the same with the formation of hole injection layer.
Later, electron injecting layer 600 can be formed in above-mentioned 500 overburden electron injecting layer substance of electron supplying layer,
At this point, above-mentioned electron supplying layer can form conventional electron injection by the method for vacuum deposition method, spin-coating method, casting etc.
Layer substance.
Hole injection layer 200, hole transporting layer 300, luminescent layer 400, the electron supplying layer 500 of above-mentioned organic luminescent device
The compound of the present invention or following substance can be used, alternatively, the compound of the present invention and well known substance can be used together.
The yin for injecting electronics is formed on electron injecting layer 600 by the method for vacuum deposition method or sputtering method etc.
Pole 2000.As cathode, various metals can be used.Concrete example has the substance of aluminium, gold, silver etc..
Organic luminescent device of the invention can not only use anode, hole injection layer, hole transporting layer, luminescent layer, electricity
Sub- transfer layer, electron injecting layer, cathode construction organic luminescent device, the knot of the organic luminescent device of various structures also can be used
Structure can also form the middle layer of one or two layers as needed.
As described above, the thickness of each organic matter layer formed according to the present invention can be adjusted according to required degree
Section, it is preferable that be specially 10 to 1000nm, more specifically 20 to 150nm.
Also, the organic matter layer in the present invention, comprising the compound indicated by above-mentioned chemical formula 1 can be by organic matter layer
Thickness is adjusted to molecular unit, thus has the advantages that surface is uniform and morphological stability is prominent.
It is applicable that first embodiment of the invention recorded for the organic luminescent compounds of present embodiment
Content, but can be not limited to this.
Hereinafter, embodiment through the invention carries out more specific description, the scope of the present invention is not limited to the present embodiment.
Embodiment
Intermediate synthesis
In order to synthesize purpose compound, by as above reacting, intermediate compound I M has been synthesized.
Synthesis example 1: intermediate (IM1) synthesis
In round-bottomed flask, by (9,9- dimethyl -9H- fluorenes -2- base) boric acid ((9,9-dimethyl-9H-fluoren-
2-yl) boronic acid) bromo- 4- iodobenzene (1-bromo-4-iodobenzene) 10.0g of 8.5g, 1- be dissolved in 1,4- bis- evil
Alkane (Isosorbide-5-Nitrae-dioxan) 200ml, is put into K2CO3(2M) 50ml and Pd (PPh3)4After 1.3g, return stirring is carried out.Using thin
Layer chromatography (TLC) confirms reaction, and after adding water, reaction was completed.Organic layer is extracted using methylcellulose (MC),
And after being filtered under diminished pressure, column purification is carried out to obtain the IM1-1 of 8.27g (yield 67%).
In round-bottomed flask, by above-mentioned IM1-1 8.0g, aniline (aniline) 2.4g, t-BuONa3.3g, Pd2(dba)3
0.85g、(t-Bu)3P 1.0ml is dissolved in after toluene 110ml, carries out return stirring.Using thin-layered chromatography (TLC) come really
Recognize reaction, and after adding water, reaction was completed.Organic layer is extracted using methylcellulose (MC), and carries out being filtered under diminished pressure it
Afterwards, column purification and recrystallization are carried out to obtain the IM1 of 6.04g (yield 73%).
Synthesis example 2 to 4: intermediate (IM2 to IM4) synthesis
Using method identical with above-mentioned intermediate IM1, as shown in the following Table 1, using different initial substances, synthesize
Mesosome IM2 to IM4.
Table 1
Compound synthesis
The synthesis of compound 1
In round-bottomed flask, by IM1 3.0g, 4- bromo- 1,1':4', 1 "-terphenyl (4-bromo-1,1':4', 1 "-
terphenyl)2.5g、t-BuONa 1.2g、Pd2(dba)3 0.3g、(t-Bu)3P 0.3ml is dissolved in after the toluene of 60ml,
Carry out return stirring.Reaction is confirmed using thin-layered chromatography (TLC), and after adding water, reaction was completed.Utilize Methyl cellulose
Plain (MC) extracts organic layer, and after being filtered under diminished pressure, carries out column purification and recrystallization to obtain 3.34g (yield
70%) compound 1.
The synthesis of compound 2
Using method identical with compound 1, using bromo- 1,1':4', 1 ": 4 ", 1 " '-quaterphenyl of 4- (4-bromo-1,
1':4', 1 ": 4 ", 1 " '-quaterphenyl) replace the bromo- 1,1':4' of 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 2 has been synthesized.
The synthesis of compound 3
Using method identical with compound 1, IM1 is replaced using IM2, has synthesized compound 3.
The synthesis of compound 4
Using method identical with compound 1, using IM2 and 4- bromo- 1,1':3', 1 "-terphenyl (4-bromo-1,1':
3', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 4 has been synthesized.
The synthesis of compound 5
Using method identical with compound 1, using IM2 and 4- bromo- 1,1':2', 1 "-terphenyl (4-bromo-1,1':
2', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 5 has been synthesized.
The synthesis of compound 6
Using method identical with compound 1, bromo- 1,1'- biphenyl (4-bromo-1, the 1'- of IM3 and 4- is utilized
Biphenyl) IM1 and 4- bromo- 1,1':4' is replaced, 1 "-the terphenyl (- terphenyl of 4-bromo-1,1':4', 1 "), synthesis
Compound 6.
The synthesis of compound 7
Using method identical with compound 1, IM1 is replaced using IM3, has synthesized compound 7.
The synthesis of compound 8
Using method identical with compound 1, using IM3 and 4- bromo- 1,1':3', 1 "-terphenyl (4-bromo-1,1':
3', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 8 has been synthesized.
The synthesis of compound 9
Using method identical with compound 1, using IM3 and 4- bromo- 1,1':2', 1 "-terphenyl (4-bromo-1,1':
2', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 9 has been synthesized.
The synthesis of compound 10
Using method identical with compound 1, using IM3 and 3- bromo- 1,1':4', 1 "-terphenyl (3-bromo-1,1':
4', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 10 has been synthesized.
The synthesis of compound 11
Using method identical with compound 1, using IM3 and 3- bromo- 1,1':3', 1 "-terphenyl (3-bromo-1,1':
3', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 11 has been synthesized.
The synthesis of compound 12
Using method identical with compound 1, using IM3 and 3- bromo- 1,1':2', 1 "-terphenyl (3-bromo-1,1':
2', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 12 has been synthesized.
The synthesis of compound 13
Using method identical with compound 1, using IM3 and 2- bromo- 1,1':4', 1 "-terphenyl (2-bromo-1,1':
4', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 13 has been synthesized.
The synthesis of compound 14
Using method identical with compound 1, using IM3 and 2- bromo- 1,1':3', 1 "-terphenyl (2-bromo-1,1':
3', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 14 has been synthesized.
The synthesis of compound 15
Using method identical with compound 1, using IM3 and 2- bromo- 1,1':2', 1 "-terphenyl (2-bromo-1,1':
2', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-bromo-1,1':4', 1 "-
Terphenyl), compound 15 has been synthesized.
The synthesis of compound 16
Using method identical with compound 1, bromo- 1,1'- biphenyl (4-bromo-1, the 1'- of IM4 and 4- is utilized
Biphenyl) IM1 and 4- bromo- 1,1':4' is replaced, 1 "-the terphenyl (- terphenyl of 4-bromo-1,1':4', 1 "), synthesis
Compound 16.
The synthesis of compound 17
Using method identical with compound 1, bromo- 1,1'- biphenyl (3-bromo-1, the 1'- of IM4 and 3- is utilized
Biphenyl) IM1 and 4- bromo- 1,1':4' is replaced, 1 "-the terphenyl (- terphenyl of 4-bromo-1,1':4', 1 "), synthesis
Compound 17.
The synthesis of compound 18
Using method identical with compound 1, bromo- 1,1'- biphenyl (2-bromo-1, the 1'- of IM4 and 2- is utilized
Biphenyl) IM1 and 4- bromo- 1,1':4' is replaced, 1 "-the terphenyl (- terphenyl of 4-bromo-1,1':4', 1 "), synthesis
Compound 18.
The synthesis of compound 19
Using method identical with compound 1, the bromo- 5'- phenyl -1,1':3' of IM3 and 4-, 1 "-terphenyl (4- are utilized
Bromo-5'-phenyl-1,1':3', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-
- the terphenyl of bromo-1,1':4', 1 "), synthesize compound 19.
The synthesis of compound 20
Using method identical with compound 1, the bromo- 5'- phenyl -1,1':3' of IM3 and 2-, 1 "-terphenyl (2- are utilized
Bromo-5'-phenyl-1,1':3', 1 "-terphenyl) replace the bromo- 1,1':4' of IM1 and 4-, 1 "-terphenyl (4-
- the terphenyl of bromo-1,1':4', 1 "), synthesize compound 20.
As above the specific chemical formula of the compound 1 to 20 synthesized is shown in following table 2.
Table 2
Organic luminescent device manufacture
Embodiment 1
By distilled water ultrasonic wave toThickness by tin indium oxide (ITO) be applied as the glass substrate of film into
Row washing.If distillation water washing terminates, ultrasonic washing is carried out using the solvent of isopropanol, acetone, methanol etc., and carry out
After drying, it is transferred to plasma cleaner, after then being cleaned aforesaid substrate 5 minutes using oxygen plasma, is being aoxidized
Indium tinbase plate top utilizes thermal vacuum depositor (thermal evaporator), will as hole injection layerHI01
It is filmed, it willHATCN be filmed, as hole transporting layer willBPA be filmed, it is auxiliary as shining
Help layer willCompound 1 be filmed after, as above-mentioned luminescent layer doping 3% BH01:BD01, with Into
Row film.It then, will as electron supplying layerET01:Liq (1:1) be filmed after, willLiF,Aluminium (Al) be filmed, and by the device sealing (Encapsulation) in glove box, to be prepared for
Machine luminescent device.
Embodiment 2 is to embodiment 20
Using method same as Example 1, preparation is replaced compound 1 using compound 2 to 20 and is film-made organic
Luminescent device.
Comparative example 1 to 9
Using method same as Example 1, preparation replaces compound using the Ref.1 of following table 4 to Ref.9 respectively
1 and be film-made organic luminescent device.
Table 4
The performance evaluation of organic luminescent device
Apply electricity using 2400 source measuring unit of Keithley (Kiethley 2400source measurement unit)
Pressure is measured to inject electronics and hole using Konica Minolta (Konica Minolta) spectroradiometer (CS-2000)
Thus under atmospheric conditions brightness when shining is measured for applying alive current density and brightness, to have rated reality
The performance of the organic luminescent device of example and comparative example is applied, and the results are shown in table 5.
Table 5
| Op.V | mA/cm2 | Cd/A | QE (%) | CIEx | CIEy | LT95 | |
| Embodiment 1 | 3.96 | 10 | 7.22 | 6.14 | 0.140 | 0.109 | 115 |
| Embodiment 2 | 3.95 | 10 | 7.25 | 6.10 | 0.140 | 0.110 | 112 |
| Embodiment 3 | 3.94 | 10 | 7.29 | 6.19 | 0.141 | 0.110 | 115 |
| Embodiment 4 | 3.95 | 10 | 7.25 | 6.12 | 0.140 | 0.110 | 110 |
| Embodiment 5 | 3.94 | 10 | 7.27 | 6.15 | 0.141 | 0.110 | 115 |
| Embodiment 6 | 3.91 | 10 | 7.34 | 6.23 | 0.140 | 0.110 | 142 |
| Embodiment 7 | 3.89 | 10 | 7.45 | 6.33 | 0.140 | 0.110 | 156 |
| Embodiment 8 | 3.90 | 10 | 7.53 | 6.40 | 0.140 | 0.111 | 162 |
| Embodiment 9 | 3.89 | 10 | 7.50 | 6.42 | 0.139 | 0.111 | 166 |
| Embodiment 10 | 3.92 | 10 | 7.60 | 6.49 | 0.141 | 0.110 | 162 |
| Embodiment 11 | 3.93 | 10 | 7.62 | 6.50 | 0.140 | 0.110 | 169 |
| Embodiment 12 | 3.92 | 10 | 7.59 | 6.50 | 0.140 | 0.110 | 160 |
| Embodiment 13 | 3.89 | 10 | 7.49 | 6.35 | 0.140 | 0.110 | 165 |
| Embodiment 14 | 3.90 | 10 | 7.52 | 6.43 | 0.139 | 0.111 | 169 |
| Embodiment 15 | 3.89 | 10 | 7.50 | 6.40 | 0.141 | 0.110 | 170 |
| Embodiment 16 | 3.91 | 10 | 7.37 | 6.25 | 0.140 | 0.110 | 147 |
| Embodiment 17 | 3.93 | 10 | 7.40 | 6.27 | 0.140 | 0.110 | 150 |
| Embodiment 18 | 3.90 | 10 | 7.37 | 6.23 | 0.141 | 0.110 | 152 |
| Embodiment 19 | 3.94 | 10 | 7.41 | 6.29 | 0.140 | 0.110 | 165 |
| Embodiment 20 | 3.95 | 10 | 7.43 | 6.30 | 0.140 | 0.109 | 160 |
| Comparative example 1 | 4.40 | 10 | 6.45 | 5.60 | 0.14 | 0.111 | 13 |
| Comparative example 2 | 4.20 | 10 | 6.77 | 4.06 | 0.143 | 0.113 | 55 |
| Comparative example 3 | 4.22 | 10 | 6.90 | 4.04 | 0.141 | 0.113 | 18 |
| Comparative example 4 | 4.10 | 10 | 7.10 | 5.28 | 0.141 | 0.112 | 60 |
| Comparative example 5 | 4.13 | 10 | 7.00 | 4.10 | 0.141 | 0.111 | 85 |
| Comparative example 6 | 4.18 | 10 | 6.95 | 5.64 | 0.142 | 0.112 | 76 |
| Comparative example 7 | 4.05 | 10 | 7.05 | 4.23 | 0.141 | 0.113 | 105 |
| Comparative example 8 | 4.11 | 10 | 7.06 | 6.00 | 0.140 | 0.115 | 97 |
| Comparative example 9 | 4.30 | 10 | 7.00 | 5.97 | 0.140 | 0.112 | 81 |
As shown in Table 5 above, the embodiment of the present invention is confirmed compared with comparative example 1 to comparative example 8, driving voltage
Low, physical property is outstanding from the point of view of efficiency and service life improve etc. in all aspects.
More specifically, between fluorenes and arylamine do not have linker comparative example 1 and 2 and the embodiment of the present invention into
Row compare, the embodiment of the present invention between fluorenes and arylamine have linker, luminous auxiliary layer can be easy to form deeper
HOMO energy level, and the higher LUMO for being easy shielding electronics can be maintained, thus compared with comparative example 1 and 2, low-voltage and height is presented
Efficiency.
Also, compared with the aryl of arylamine all has the comparative example 3 and 4 of phenyl or aminomethyl phenyl, implementation of the invention
Side of the example in 2 aryl substituents of arylamine imports 2 or more aryl, can increase the conjugation of compound, film and
Molecules align is outstanding, has compared with comparative example 3 and 4 faster hole flows, and the long-life is presented by inhibiting to roll-off.
Also, it is taken with 2 aryl of comparative example 5, arylamine that one in 2 aryl substituents of arylamine is naphthalene
Dai Ji is that the comparative example 6 and 7 of xenyl is compared, and in the embodiment of the present invention, the side of arylamine is fixed by phenyl, maintains to hold
The easily lumo energy of shielding electronics, forms higher T1, so that exciton congregational rate in luminescent layer is maximized, high efficiency is presented.
Also, compared with arylamine has the comparative example 8 of dibenzofurans, the embodiment of the present invention, which does not include to have, to be played
The heteroatomic heterocycle such as O, S of electron donor effect, can maintain deeper HOMO energy level, and low-voltage and efficiently is thus presented
Rate.
Also, with using the 3rd position of fluorenes, compared with the comparative example 9 of link position, the embodiment of the present invention has conduct
The appropriate deep HOMO of hole transporting layer, maintains the balance appropriate of exciton forming region in luminescent layer, thus present low-voltage and
High efficiency.
The explanation of aforementioned present invention is for illustrative, and general technical staff of the technical field of the invention can manage
Solution can be easily deformed in other specific ways in the case where not changing technical idea or essential feature of the invention.Therefore,
It should be understood that various embodiments described above be in all respects it is illustrative, without being restrictive.For example, being said with single type
Bright each structural element is implemented dispersiblely, and equally, illustrating also can be in a manner of combination for multiple structural elements of dispersion
Implement.
Range Representation, rather than above-mentioned detailed description, patent is claimed by appended patented invention in the scope of the present invention
The meaning and range and the mode for having altered or deforming as derived from its equivalents for inventing claimed range should be by
It is construed to be included within the scope of the present invention.
Claims (10)
1. a kind of compound, which is characterized in that indicated by following formula 1:
Chemical formula 1
In above-mentioned chemical formula 1,
L is substituted or unsubstituted C6-30Arlydene or substituted or unsubstituted C3-30Heteroarylidene,
AraAnd ArbIt is separately substituted or unsubstituted C6-30Aryl or substituted or unsubstituted C3-30Include nitrogen
Heteroaryl, wherein the aryl and heteroaryl are not replaced by heavy hydrogen,
R、R'、R1And R2It is separately hydrogen, substituted or unsubstituted C1-30Alkyl, substituted or unsubstituted C6-30Virtue
Base or substituted or unsubstituted C3-30Heteroaryl,
R3For hydrogen or substituted or unsubstituted C1-30Alkyl,
The integer that l is 0 or 1 to 4, m are 0 or integer of 1 to 3, and the integer that n is 0 or 1 to 5, p is integer of 1 to 3, and q is 1 to 3
Integer, p+q be 2 to 4 integer.
2. compound according to claim 1, which is characterized in that above compound is indicated by following formula 2:
Chemical formula 2
In above-mentioned chemical formula 2,
The integer that o is 1 to 4.
3. compound according to claim 1 or 2, which is characterized in that above-mentioned R and R` is separately to replace or do not take
The C in generation6-30Aryl or substituted or unsubstituted C3-30Heteroaryl.
4. compound according to claim 1, which is characterized in that above compound is indicated by following formula 3:
Chemical formula 3
In above-mentioned chemical formula 3,
R4And R5It is separately hydrogen, substituted or unsubstituted C1-24Alkyl, substituted or unsubstituted C6-24Aryl or
Substituted or unsubstituted C3-24Heteroaryl,
The integer that o is 1 to 4.
5. compound according to claim 1, which is characterized in that above-mentioned-(Ara)p-(Arb)qBy the following Expression 1-1 into 1-6
A chemical formula indicate:
In above-mentioned formula 1-1 into 1-6,
Ar1To Ar4It is separately substituted or unsubstituted C6-30Aryl or substituted or unsubstituted C3-30Include nitrogen
Heteroaryl, wherein the aryl and heteroaryl are not replaced by heavy hydrogen.
6. compound according to claim 5, which is characterized in that above-mentioned Ar1To Ar4For phenyl.
7. compound according to claim 1, which is characterized in that above compound is one in following compound:
8. a kind of organic luminescent device, which is characterized in that between first electrode and second electrode include containing claim 1 to
The organic matter layer of compound described in any one of 7.
9. organic luminescent device according to claim 8, which is characterized in that above-mentioned organic matter layer is hole injection layer, sky
1 layer or more in cave transfer layer and luminous auxiliary layer.
10. organic luminescent device according to claim 8, which is characterized in that above-mentioned organic matter layer is the auxiliary layer that shines.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2017-0067673 | 2017-05-31 | ||
| KR1020170067673A KR102519794B1 (en) | 2017-05-31 | 2017-05-31 | Novel compound and organic electroluminescent divice including the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108976132A true CN108976132A (en) | 2018-12-11 |
Family
ID=64542847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810550855.XA Pending CN108976132A (en) | 2017-05-31 | 2018-05-31 | Compounds and organic luminescent device comprising it |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102519794B1 (en) |
| CN (1) | CN108976132A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112601732A (en) * | 2018-10-15 | 2021-04-02 | 株式会社Lg化学 | Novel compound and organic light emitting device comprising same |
| CN113039173A (en) * | 2019-03-13 | 2021-06-25 | 株式会社Lg化学 | Novel compound and organic light emitting device using the same |
| WO2021200876A1 (en) * | 2020-03-31 | 2021-10-07 | 出光興産株式会社 | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| WO2023221231A1 (en) * | 2022-05-20 | 2023-11-23 | 石家庄诚志永华显示材料有限公司 | Aromatic amine compound containing quaterphenyl structure and organic electroluminescent device comprising same |
| WO2024066916A1 (en) * | 2022-09-29 | 2024-04-04 | 石家庄诚志永华显示材料有限公司 | Aromatic amine compound comprising quaterphenyl structure and organic electroluminescent device comprising same |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7406486B2 (en) * | 2018-06-25 | 2023-12-27 | 保土谷化学工業株式会社 | Compounds with triarylamine structure and organic electroluminescent devices |
| WO2020080799A1 (en) * | 2018-10-15 | 2020-04-23 | 주식회사 엘지화학 | Novel compound and organic light emitting diode comprising same |
| JP2022037253A (en) * | 2018-11-07 | 2022-03-09 | 出光興産株式会社 | Compound and organic electroluminescent element employing the same |
| KR20240013118A (en) | 2021-05-28 | 2024-01-30 | 이데미쓰 고산 가부시키가이샤 | Compounds, materials for organic electroluminescent devices, organic electroluminescent devices, and electronic devices |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103403125A (en) * | 2011-01-17 | 2013-11-20 | 株式会社Lg化学 | Novel compound and organic light-emitting device comprising same |
| US20140027747A1 (en) * | 2011-04-01 | 2014-01-30 | Duksan High Metal Co., Ltd. | Compound, organic electronic element using same, and electronic device using the latter |
| US20150171335A1 (en) * | 2013-12-12 | 2015-06-18 | Samsung Display Co., Ltd. | Organic light-emitting device |
| WO2016099204A2 (en) * | 2014-12-18 | 2016-06-23 | 주식회사 동진쎄미켐 | Novel compound and organic light emitting element comprising same |
| US20170125690A1 (en) * | 2015-10-30 | 2017-05-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US20170125678A1 (en) * | 2015-10-30 | 2017-05-04 | Nanjing Topto Materials Co., Ltd. | Novel organic compound, material comprising the same for organic electroluminescence devices, and organic electroluminescence device comprising the material |
| CN106699634A (en) * | 2016-11-10 | 2017-05-24 | 长春海谱润斯科技有限公司 | Aromatic amine derivative, and preparation method and application thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102177213B1 (en) | 2014-01-20 | 2020-11-11 | 삼성디스플레이 주식회사 | Organic light-emitting devices |
| KR102441556B1 (en) * | 2015-09-11 | 2022-09-08 | 삼성디스플레이 주식회사 | Compound and Organic light emitting device comprising same |
-
2017
- 2017-05-31 KR KR1020170067673A patent/KR102519794B1/en active IP Right Grant
-
2018
- 2018-05-31 CN CN201810550855.XA patent/CN108976132A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103403125A (en) * | 2011-01-17 | 2013-11-20 | 株式会社Lg化学 | Novel compound and organic light-emitting device comprising same |
| US20140027747A1 (en) * | 2011-04-01 | 2014-01-30 | Duksan High Metal Co., Ltd. | Compound, organic electronic element using same, and electronic device using the latter |
| US20150171335A1 (en) * | 2013-12-12 | 2015-06-18 | Samsung Display Co., Ltd. | Organic light-emitting device |
| WO2016099204A2 (en) * | 2014-12-18 | 2016-06-23 | 주식회사 동진쎄미켐 | Novel compound and organic light emitting element comprising same |
| US20170125690A1 (en) * | 2015-10-30 | 2017-05-04 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US20170125678A1 (en) * | 2015-10-30 | 2017-05-04 | Nanjing Topto Materials Co., Ltd. | Novel organic compound, material comprising the same for organic electroluminescence devices, and organic electroluminescence device comprising the material |
| CN106699634A (en) * | 2016-11-10 | 2017-05-24 | 长春海谱润斯科技有限公司 | Aromatic amine derivative, and preparation method and application thereof |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112601732A (en) * | 2018-10-15 | 2021-04-02 | 株式会社Lg化学 | Novel compound and organic light emitting device comprising same |
| CN112601732B (en) * | 2018-10-15 | 2023-04-21 | 株式会社Lg化学 | Novel compound and organic light emitting device comprising the same |
| CN113039173A (en) * | 2019-03-13 | 2021-06-25 | 株式会社Lg化学 | Novel compound and organic light emitting device using the same |
| CN113039173B (en) * | 2019-03-13 | 2023-11-14 | 株式会社Lg化学 | Compound and organic light emitting device using the same |
| WO2021200876A1 (en) * | 2020-03-31 | 2021-10-07 | 出光興産株式会社 | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| JPWO2021200876A1 (en) * | 2020-03-31 | 2021-10-07 | ||
| CN114206826A (en) * | 2020-03-31 | 2022-03-18 | 出光兴产株式会社 | Compound, material for organic electroluminescent element, and electronic device |
| JP7177966B2 (en) | 2020-03-31 | 2022-11-24 | 出光興産株式会社 | Compounds, materials for organic electroluminescence devices, organic electroluminescence devices and electronic devices |
| US11678569B2 (en) | 2020-03-31 | 2023-06-13 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| WO2023221231A1 (en) * | 2022-05-20 | 2023-11-23 | 石家庄诚志永华显示材料有限公司 | Aromatic amine compound containing quaterphenyl structure and organic electroluminescent device comprising same |
| WO2024066916A1 (en) * | 2022-09-29 | 2024-04-04 | 石家庄诚志永华显示材料有限公司 | Aromatic amine compound comprising quaterphenyl structure and organic electroluminescent device comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180131091A (en) | 2018-12-10 |
| KR102519794B1 (en) | 2023-04-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108976132A (en) | Compounds and organic luminescent device comprising it | |
| CN109485577A (en) | Compounds and organic luminescent device comprising it | |
| CN109096124A (en) | Compounds and organic luminescent device comprising it | |
| CN108774141A (en) | Compounds and organic luminescent device comprising it | |
| CN110698448B (en) | Novel compound and organic light emitting device comprising the same | |
| CN107915648A (en) | Compounds and the organic luminescent device for including it | |
| CN109553597A (en) | Compounds and organic luminescent device comprising it | |
| CN110642819B (en) | Novel compound and organic light emitting device comprising the same | |
| CN109206327A (en) | Compounds and organic luminescent device comprising it | |
| CN109988134A (en) | Compounds and organic luminescent device comprising it | |
| CN108276326A (en) | Compounds and organic luminescent device comprising it | |
| CN107963973A (en) | Compounds and the organic luminescent device for including it | |
| TW201817707A (en) | Novel compound and organic electroluminescent device including the same | |
| KR20190007892A (en) | Novel compound and organic electroluminescent divice including the same | |
| CN108689913A (en) | Compounds and organic luminescent device comprising it | |
| KR20190003329A (en) | Novel compound and organic electroluminescent divice including the same | |
| CN109206324A (en) | Compounds and organic luminescent device comprising it | |
| CN109896965A (en) | Compounds and organic luminescent device comprising it | |
| CN109206325A (en) | Compounds and organic luminescent device comprising it | |
| CN109206326A (en) | Compounds and organic luminescent device comprising it | |
| CN111936481B (en) | Novel compound and organic light emitting device comprising the same | |
| CN112041314A (en) | Novel compound and organic light emitting device comprising the same | |
| CN109694365A (en) | Compounds and organic luminescent device comprising it | |
| KR20200134694A (en) | Novel compound and organic electroluminescent divice including the same | |
| CN112745231B (en) | Novel compound and organic light-emitting element comprising same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |