CN109694365A - Compounds and organic luminescent device comprising it - Google Patents
Compounds and organic luminescent device comprising it Download PDFInfo
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- CN109694365A CN109694365A CN201811222653.9A CN201811222653A CN109694365A CN 109694365 A CN109694365 A CN 109694365A CN 201811222653 A CN201811222653 A CN 201811222653A CN 109694365 A CN109694365 A CN 109694365A
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- luminescent device
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 64
- 239000000126 substance Substances 0.000 claims description 59
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 23
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000005416 organic matter Substances 0.000 claims description 12
- 150000002220 fluorenes Chemical class 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims description 7
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 claims description 7
- 150000004826 dibenzofurans Chemical class 0.000 claims description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- 230000003760 hair shine Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 description 104
- 238000000034 method Methods 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 23
- 239000000463 material Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 150000004982 aromatic amines Chemical class 0.000 description 10
- 238000001771 vacuum deposition Methods 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- 229920000609 methyl cellulose Polymers 0.000 description 8
- 239000001923 methylcellulose Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- -1 benzo fluorenyl Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 150000002240 furans Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000005266 casting Methods 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000012790 confirmation Methods 0.000 description 4
- 229940035422 diphenylamine Drugs 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 3
- 206010011224 Cough Diseases 0.000 description 3
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940127271 compound 49 Drugs 0.000 description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation 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
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 229940126639 Compound 33 Drugs 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910021389 graphene Inorganic materials 0.000 description 2
- JQOAQUXIUNVRQW-UHFFFAOYSA-N hexane Chemical compound CCCCCC.CCCCCC JQOAQUXIUNVRQW-UHFFFAOYSA-N 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229930192474 thiophene Natural products 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
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 2
- QMFVLQXRHBTDSH-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C QMFVLQXRHBTDSH-UHFFFAOYSA-N 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- NFXZFMSTFIXHKO-UHFFFAOYSA-N BrC1=C(C=CC=C1)I.BrC1=C(C=CC=C1)I Chemical compound BrC1=C(C=CC=C1)I.BrC1=C(C=CC=C1)I NFXZFMSTFIXHKO-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
- 241001597008 Nomeidae Species 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 compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 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
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 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
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- 238000010276 construction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 1
- FQENSZQWKVWYPA-UHFFFAOYSA-N dibenzofuran-3-ylboronic acid Chemical compound C1=CC=C2C3=CC=C(B(O)O)C=C3OC2=C1 FQENSZQWKVWYPA-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 239000003205 fragrance Substances 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 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
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 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
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 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
- 239000004332 silver Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010409 thin film Substances 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
- 230000017260 vegetative to reproductive phase transition of meristem Effects 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
- 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
- C07C211/57—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—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 carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- 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
-
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Abstract
The present invention relates to compounds and comprising its organic luminescent device, the compounds of an example according to the present invention are suitable for organic luminescent device, it can be ensured that high efficiency, long-life, low driving voltage and the driving stability of organic luminescent device.
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 compounds and preparation method thereof and the organic luminescent device comprising it.
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,
A and B is each independently substituted or unsubstituted C6~30Aryl, substituted or unsubstituted C5~30Heteroaryl,
Or NAr1Ar2, at least one of A and B are NAr1Ar2, Ar1And Ar2It is each independently substituted or unsubstituted C6~30's
Aryl, substituted or unsubstituted C5~30Heteroaryl,
L1And L2It is each independently Direct Bonding, substituted or unsubstituted C6~30Arlydene or substituted or unsubstituted
C5~30Heteroarylidene.
It includes containing chemical combination of the invention that second embodiment of the present invention, which is provided between first electrode and second electrode,
The organic luminescent device of the organic matter layer of object.
The compound of an example according to the present invention includes to be connected to the terphenyl at ortho position (ortho) and be connected to above-mentioned
The aryl or arylamine at the ortho position (ortho) of terphenyl form the HOMO energy level for being readily injected into hole and conveying hole, simultaneously
The high lumo energy for being easy to block electronics can be formed.Thus be used in organic luminescent device, it can be achieved that organic luminescent device it is low
Voltage and higher efficiency.
Also, terphenyl structure of the compound of the present invention because being connected to ortho position, can maintain high T1, be suitable for phosphorescence
, it can be achieved that high efficiency, the film of molecule is formed and interface arrangement is outstanding when device, increase hole flow (hole
Mobility), it can inhibit (roll-off) phenomenon of roll-offing, thus can realize high efficiency and the long-life of organic luminescent device.And
And terphenyl is combined with one or two arylamine, can be maintained high glass transition temperature (Tg), can be prevented the weight of film
Crystallization, thus can increase thermal stability, and can ensure that driving stability.
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. prompted in mentioned meaning intrinsic preparation and substance tolerance Shi Yiqi 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, fluorenes, phenanthryl base, triphenyl alkenyl, phenylakenyl,Base, fluorane thiophene first
Base, benzo fluorenyl, benzo triphenyl alkenyl, benzoThe aromatic ring of base, anthryl, stilbenyl, pyrenyl etc., " heteroaryl
Base " is as the C comprising at least one miscellaneous element5-30Aromatic ring, such as, it is meant that comprising from pyrrolinyl, pyrazinyl, pyrrole
Piperidinyl, indyl, isoindolyl, furyl, benzofuranyl, isobenzofuran-base, dibenzofuran group, aisaa benzothiophenyl,
Dibenzo thiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazyl, phenanthryl cry base, acridinyl, phenanthryl cough up quinoline base, thiophene
Base and by pyridine ring, pyridine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxanes
Ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan nucleus, thiphene ring, oxazole ring, oxadiazoles ring, benzoxazoles ring, thiazole
The fragrance that ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyranoid ring, dibenzofurans ring are formed
Race's heterocycle.
In the full text of description of the invention, " substitution " in term " substituted or unsubstituted " may imply that selected from by weight
Hydrogen, halogen, amino, itrile group, nitro or C1~C20Alkyl, C2~C20Alkenyl, C1~C20Alkoxy, C3~C20Cycloalkanes
Base, C3~C20Heterocyclylalkyl, C6~C30Aryl and C3~C30The group of one or more of group of heteroaryl composition take
Generation.Also, in description of the invention full text, identical appended drawing reference can have identical as long as no the special content referred to
The meaning.
First embodiment of the invention provides the compound indicated by following formula 1:
Chemical formula 1
In above-mentioned chemical formula 1,
A and B is each independently substituted or unsubstituted C6~30Aryl, substituted or unsubstituted C5~30Heteroaryl,
Or NAr1Ar2, at least one of A and B are NAr1Ar2, Ar1And Ar2It is each independently substituted or unsubstituted C6~30's
Aryl, substituted or unsubstituted C5~30Heteroaryl,
L1And L2It is each independently Direct Bonding, substituted or unsubstituted C6~30Arlydene or substituted or unsubstituted
C5~30Heteroarylidene.
Above-mentioned Ar1And Ar2It is connected and forms ring, or is possible to not form ring.
The compound of an example according to the present invention includes to be connected to the terphenyl at ortho position (ortho) and be connected to above-mentioned
The aryl or arylamine at the ortho position (ortho) of terphenyl form the HOMO energy level for being readily injected into hole and conveying hole, simultaneously
The high lumo energy for being easy to block electronics can be formed.Thus be used in organic luminescent device, it can be achieved that organic luminescent device it is low
Voltage and higher efficiency.
Also, terphenyl structure of the compound of the present invention because being connected to ortho position, can maintain high T1, be suitable for phosphorescence
, it can be achieved that high efficiency, the film of molecule is formed and interface arrangement is outstanding when device, increase hole flow (hole
Mobility), it can inhibit (roll-off) phenomenon of roll-offing, thus can realize high efficiency and the long-life of organic luminescent device.And
And terphenyl is combined with one or two arylamine, can be maintained high glass transition temperature (Tg), can be prevented the weight of film
Crystallization, thus can increase thermal stability, and can ensure that driving stability.
In an example of the invention, above-mentioned A and B be each independently phenyl, xenyl, naphthalene, terphenyl, fluorenes,
Dimethyl fluorene, diphenylfluorene, dibenzofurans, dibenzothiophenes, carbazole or their combination.These combinations may imply that benzene
The structure that the aryl of base, xenyl, naphthalene, terphenyl, fluorenes, dimethyl fluorene or diphenylfluorene etc. is connected.For example, there is phenyl
The structure etc. that structure, phenyl, fluorenes and the naphthalene that structure, phenyl and the fluorenes being connected with naphthalene are connected are connected, is not limited to
This, and may imply that the structure that 2 or more aryl are connected.
In an example of the invention, above-mentioned L1And L2Be each independently phenyl, xenyl, naphthalene, terphenyl, fluorenes,
Dimethyl fluorene, diphenylfluorene or their combination.
An example according to the present invention, above compound can be indicated by following formula 2 or chemical formula 3.
In above-mentioned chemical formula 2 or chemical formula 3,
Ar3、Ar4、Ar5And Ar6It is each independently substituted or unsubstituted C6~30Aryl or substituted or unsubstituted
C5~30Heteroaryl,
X is CR1R2、NR3, O or S, R1、R2And R3It is each independently hydrogen, heavy hydrogen, substituted or unsubstituted C1~24Alkane
Base, substituted or unsubstituted C6~30Aryl or substituted or unsubstituted C5~30Heteroaryl.
Above-mentioned Ar3And Ar4Or Ar5And Ar6It can be connected each independently and form ring or be possible to not form ring.
In an example of the invention, above-mentioned Ar3、Ar4、Ar5And Ar6Can be each independently phenyl, xenyl, naphthalene,
Terphenyl, fluorenes, dimethyl fluorene, diphenylfluorene, dibenzofurans, dibenzothiophenes, carbazole or their combination.
In an example of the invention, above-mentioned Ar3And Ar4Can be identical, Ar5And Ar6It can be identical.Or Ar3、Ar4、Ar5And
Ar6It can be identical.Or Ar3It can be with Ar5It is identical, Ar4It can be with Ar6It is identical.
In an example of the invention, by above-mentioned chemical formula 3 indicate the case where compound can be formed be suitable for shining it is auxiliary
The HOMO energy level of layer is helped, in this case, it can be achieved that the low-voltage of organic luminescent device, high efficiency and long-life.
Also, in above-mentioned chemical formula 2, there is Ar3With Ar5Identical and Ar4With Ar6When identical symmetrical structure, it can be formed
It is suitable for the HOMO energy level of hole transporting layer, this feelings see down low-voltage, high efficiency and longevity, it can be achieved that organic luminescent device
Life.At this point, there is Ar in above-mentioned chemical formula 23With Ar5Identical and Ar4With Ar6Identical symmetrical structure, Ar3And Ar5Include two
In the case where benzofuran, can more it improve the service life.
An example according to the present invention, above compound can be indicated by following formula 4.
Chemical formula 4
The compound indicated by above-mentioned chemical formula 4 connects arylamine and hexichol at the ortho position of terphenyl (ortho) respectively
And furans, this compound can more improve the life characteristic of organic luminescent device.
An example according to the present invention, the compound indicated by above-mentioned chemical formula 2 can be according to the works such as following formula 1
Sequence is synthesized:
Reaction equation 1
An example according to the present invention, the compound indicated by above-mentioned chemical formula 3 can be according to the works such as following formulas 2
Sequence is synthesized:
Reaction equation 2
In an example of the invention, the compound indicated by above-mentioned chemical formula 1 to chemical formula 4 can be disclosed below
Compound, it is possible to not limited to this:
According to an embodiment of the present invention, the compound indicated by above-mentioned chemical formula 1 to 4 can be in following compound
It is any.Following compound can more effectively realize the long-life of device.
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 the organic of 1 layer or more containing the compounds of this invention between first electrode and second electrode
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 being not limited except as.Also, the compound of the present invention formed organic matter layer when, can be used alone or with it is well known
Organic luminescent compounds are used together.
Above-mentioned organic luminescent device can be between first electrode (anode, anode) and second electrode (cathode, cathode)
Including 1 layer or more of hole injection layer (HIL), hole transporting layer (HTL), luminescent layer (EML), electron supplying layer (ETL), electronics
The organic matter layer of implanted layer (EIL) etc..
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, can be used alone or with it is well known
Compound is used together the compound of the present invention.Also, the hole transporting layer 300 of an example of the invention can be 1 layer or more,
It can together include the hole transporting layer only formed by well known substance.Also, an example according to the present invention, it is defeated in above-mentioned hole
Luminous auxiliary layer can be formed by sending on layer 300.In the present invention, luminous auxiliary layer refer to be formed in hole transporting layer and luminescent layer it
Between layer, according to the quantity of hole transporting layer, also referred to as the second hole transporting layer or third hole transporting layer etc..Above-mentioned hair
The compound of the present invention can be used in light auxiliary layer, as described above, can be used alone the compound of the present invention or with well known chemical combination
Object is used together.
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
Layer overburden luminescent layer substance, thus can form luminescent layer 400.In the feelings for forming luminescent layer by above-mentioned vacuum deposition method
Under condition, sedimentary condition is different due to the compound used, but typically it will be preferred to, in the almost phase of the formation with hole injection layer
It is selected in same condition and range.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 can be enumerated or triazole derivative, phenanthryl cough up quinoline derivant or Japanese Unexamined Patent Publication 11-
Documented hole inhibits material etc. in 329734 (A1), typically, can be used Balq (bis- (8- hydroxy-2-methylquinolines)-
Aluminium biphenyl phenates), phenanthryl cough up quinoline (phenanthrolines) class compound (such as BCP of general purpose display (UDC) company
(Basso 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 1 layer or 2 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, it is likely that being not limited except as.
Hereinafter, embodiment through the invention carries out more specific description, the scope of the present invention is not limited to the present embodiment.
Embodiment
Preparation example 1: the synthesis of main core (main core) 1
It is following to synthesize main core 1 (main core 1) for synthesising target compound.
In round-bottomed flask, by 1,2- phenylene hypoboric acid (1,2-phenylenediboronic acid) 100.0g
Bromo- 2- iodobenzene (1-bromo-2-iodobenzene) 341.3g (1206.64mmol, 2eq) of (603.32mmol, 1eq), 1-, Pd
(PPh3)434.85g (30.17mmol, 0.05eq), K3PO4256.13g (1206.64mmol, 2eq) is dissolved in the evil of Isosorbide-5-Nitrae-two
Alkane (1,4-dioxan) 1000ml, H2After O 200mL, return stirring.After 2 hours, pass through thin-layered chromatography (TLC)
Confirmation reaction terminates, and extracts organic layer with methylcellulose (MC).After being filtered under diminished pressure to the substance of extraction, with MC and just
Hexane (Hexane) recrystallization, obtains 1 220g of main core (yield (yield)=94.0%, white solid (White solid)).
Preparation example 2: the synthesis of main core (main core) 2
For synthesising target compound, it regard the main core 1 obtained in above-mentioned preparation example 1 as initial substance, use is a variety of
Reagent (Reagent) (dibenzo [b, p] furans -4- ylboronic acid (dibenzo [b, d] furan-4-ylboronic acid), two
Benzo [b, p] furans -3- ylboronic acid (dibenzo [b, d] furan-3-ylboronic acid), dibenzo [b, p] furans -2-
Ylboronic acid (dibenzo [b, d] furan-2-ylboronic acid)), by suzuki reaction (Suzuki reaction), into
The synthesis of row main core 2.
In round-bottomed flask, by 1 50.0g of main core (128.8mmol, 1eq), dibenzo [b, p] furans -4- ylboronic acid
(dibenzo [b, d] furan-4-ylboronic acid) 24.6g (115.94mmol, 0.9eq), Pd (PPh3)4 7.44g
(6.44mmol, 0.05eq), K3PO454.7g (257.6mmol, 2eq) be dissolved in Isosorbide-5-Nitrae-dioxanes (Isosorbide-5-Nitrae-dioxane) 500mL,
H2After O 100mL, return stirring.After 1 hour, terminated by thin-layered chromatography (TLC) confirmation reaction, with methyl fibre
It ties up plain (MC) and extracts organic layer.After being filtered under diminished pressure to the substance of extraction, column purification is carried out, with MC and n-hexane
(Hexane) it recrystallizes, obtains main core 2-1 51.74g (yield (yield)=84.5%, white solid (White solid)).
Using different reagents (Reagent), main core 2-2,2-3 such as flowering structure is obtained.
Compound synthesis
Compound 1
In round-bottomed flask, by main core 2-1 10.0g (21.01mmol, 1eq), diphenylamines (diphenylamine)
3.56g (21.01mmol, 1.0eq), Pd2(dba)30.38g (0.42mmol, 0.02eq), tri-tert-butylphosphine (Tri-tert-
Butylphosphine) 0.2g (0.84mmol, 0.04eq), NaOtBu 4.04g (42.02mmol, 2eq) are dissolved in toluene
(Toluene) after 100mL, return stirring.After 5 hours, is terminated by thin-layered chromatography (TLC) confirmation reaction, used
Methylcellulose (MC) extracts organic layer.Column purification and recrystallization are carried out to the substance of extraction, 1 10.9g of compound is obtained and (receives
Rate (yield)=91.7%, white solid (White solid)).
Compound 2 to 16
Using method identical with the synthesis of above compound 1, main core 2-1 is used as initial substance, uses following table 1
Substance replace diphenylamines (diphenylamine), thus synthesize compound 2 to 16.
Table 1
Compound 17 to 32
Using method identical with the synthesis of above compound 1, used in main core 2-2 and following table 2 as initial substance
The substance of record replaces main core 2-1, thus synthesizes compound 17 to 32.
Table 2
Compound 33 to 48
Using method identical with the synthesis of above compound 1, main core 2-3 and following table 3 are used as initial substance
Substance replaces main core 2-1, thus synthesizes compound 33 to 48.
Table 3
Compound 49
In round-bottomed flask, 1 10.0g of main core (25.77mmol, 1eq), diphenylamines (dip henylamine) 9.16g
(54.12mmol, 2.1eq), Pd2(dba)30.47g (0.52mmol, 0.02eq), tri-tert-butylphosphine (Tri-tert-
Butylphosphine) 0.25mL (1.03mmol, 0.04eq), NaOtBu 4.95g (51.53mmol, 2eq) are dissolved in toluene
(Toluene) after, return stirring.After 2 hours, terminated by thin-layered chromatography (TLC) confirmation reaction, with methyl fibre
It ties up plain (MC) and extracts organic layer.Column purification and recrystallization are carried out to the substance of extraction, obtain 49 11.6g (yield of compound
(yield)=80.0%, white solid (White solid)).
Compound 50 to 56
Using method identical with the synthesis of above compound 49, main core 1 is used as initial substance, uses following table 4
Substance replace diphenylamines (diphenylamine), thus synthesize compound 50 to 56.
Table 4
Liquid chromatography-mass spectrometry (the LC-MS:Liquid chromat ography mass of above compound 1 to 56
Spectrometry) and1H NMR (CDCl3,300Mz) is shown in following table 5 and table 6.
Table 5
Table 6
The preparation of organic luminescent device
Embodiment 1: it is used as and shines auxiliary layer (the second hole transporting layer)
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 layer's
DNTPD、HATCN be filmed, as the first hole transporting layer willNPB be filmed, as second sky
Cave transfer layer willCompound 1 be filmed after, as above-mentioned luminescent layer doping 3% BH01:BD01, withIt is filmed.It then, will as electron supplying layerET01:Liq (1:1) be filmed after, will's
LiF、Aluminium (Al) be filmed, and the device is sealed (Encapsulation) in glove box, thus
It is prepared for organic luminescent device.
Embodiment 2 is to embodiment 48
Using method same as Example 1, it is prepared for being made using compound 2 to compound 48 instead of compound 1
The organic luminescent device of film.
Comparative example 1 is to comparative example 4 and comparative example 9 to 12
Using method same as Example 1, compound is replaced using following Ref.1 to Ref.4 and Ref.9 to Ref.12
1 is prepared for organic luminescent device.
Embodiment 49: it is used as the first hole transporting layer
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 layer's
DNTPD、HATCN be filmed, as the first hole transporting layer willCompound 49 be filmed, as
Two hole transporting layers willDN TPD be filmed after, as above-mentioned luminescent layer doping 3% BH01:BD01, with 2It is filmed.It then, will as electron supplying layerET01:Liq (1:1) be filmed after, will's
LiF、Aluminium (Al) be filmed, and the device is sealed (Encapsulation) in glove box, thus
It is prepared for organic luminescent device.
Embodiment 50 is to embodiment 56
Using method identical with embodiment 49, it is prepared for replacing compound 49 to carry out using compound 50 to compound 56
The organic luminescent device of film.
Comparative example 5 is to comparative example 8 and comparative example 13 to 16
Using method identical with embodiment 49, chemical combination is replaced using following Ref.5 to Ref.8 and Ref.13 to Ref.16
Object 49 is prepared for organic luminescent device.
The performance evaluation of organic luminescent device
Applied using 2400 source measuring unit of Keithley (2400 source measureme nt unit of Kiethley)
Voltage injects electronics and hole, is surveyed using Konica Minolta (Konica Minolta) spectroradiometer (CS-2000)
Thus under atmospheric conditions brightness when shining surely is measured for applying alive current density and brightness, to have rated
The performance of the organic luminescent device of Examples and Comparative Examples, and the results are shown in table 7 and table 8.
Table 7
As shown in Table 7 above, the embodiment of the present invention is compared with comparative example 1 to 4, comparative example 9 to 12, it is seen that organic light emission
The result that the efficiency of device and service life rise.
More specifically, being connected to the contraposition (Para) of terphenyl or the comparative example of meta position (Meta) with arylamine or aryl
1 to 4 compares, and the arylamine or aryl of embodiment 1 to 48 are connected to the ortho position (Ortho) of terphenyl, has high T1 value, thin
Film is formed and interface arrangement is outstanding, is had quick hole flow (hole mobility).Also, by dibenzofurans
The characteristic of more long-life is presented as the embodiment 1 to 16 of binding site for 4th position.
Table 8
| Op.V | mA/cm2 | Cd/A | lm/w | CIEx | CIEy | LT95 | |
| Embodiment 49 | 3.913 | 10 | 7.41 | 6.62 | 0.139 | 0.111 | 160 |
| Embodiment 50 | 3.910 | 10 | 7.39 | 6.60 | 0.140 | 0.110 | 162 |
| Embodiment 51 | 3.913 | 10 | 7.52 | 6.62 | 0.139 | 0.111 | 160 |
| Embodiment 52 | 3.910 | 10 | 7.38 | 6.60 | 0.140 | 0.110 | 162 |
| Embodiment 53 | 3.913 | 10 | 7.41 | 6.62 | 0.139 | 0.111 | 180 |
| Embodiment 54 | 3.910 | 10 | 7.39 | 6.60 | 0.140 | 0.110 | 210 |
| Embodiment 55 | 3.913 | 10 | 7.52 | 6.62 | 0.139 | 0.111 | 170 |
| Embodiment 56 | 3.910 | 10 | 7.38 | 6.60 | 0.140 | 0.110 | 170 |
| Comparative example 5 | 4.201 | 10 | 6.02 | 5.26 | 0.141 | 0.110 | 90 |
| Comparative example 6 | 4.222 | 10 | 6.40 | 5.38 | 0.141 | 0.110 | 95 |
| Comparative example 7 | 4.471 | 10 | 6.29 | 5.48 | 0.141 | 0.111 | 100 |
| Comparative example 8 | 4.106 | 10 | 6.11 | 5.19 | 0.141 | 0.112 | 85 |
| Comparative example 13 | 4.111 | 10 | 6.16 | 5.88 | 0.141 | 0.110 | 100 |
| Comparative example 14 | 4.271 | 10 | 6.55 | 5.55 | 0.141 | 0.110 | 110 |
| Comparative example 15 | 4.335 | 10 | 6.51 | 5.55 | 0.141 | 0.111 | 90 |
| Comparative example 16 | 4.296 | 10 | 6.19 | 5.67 | 0.141 | 0.112 | 80 |
As shown in Table 8 above, the embodiment of the present invention 49 to 56, can be true compared with comparative example 5 to 8, comparative example 13 to 16
Recognize that efficiency and service life rise as a result, can simultaneously confirm that physical property upper in all respects is outstanding.
More specifically, being incorporated in three with arylamine or aryl when two ends of terphenyl have symmetrical structure
The contraposition (Para) of xenyl or the comparative example of meta position (Meta) are compared, the arylamine or aryl of the embodiment of the present invention 49 to 56
It is connected to the ortho position (Ortho) of terphenyl, can be confirmed with high efficiency, the characteristic of long-life.Also, it can confirm in terphenyl
Base has the long-life characteristics of the embodiment 53,54 of 2 dibenzofuran groups especially outstanding.
Also, compared with comparative example 5 to 8, comparative example 13 to 16, arylamine or aryl are connected to the ortho position of terphenyl
(Ortho) embodiment 49 to 56 has high T1 value, and film is formed and interface arrangement is outstanding, has quick hole flow
(hole mobility), it is thus upper outstanding in terms of all physical property, and confirm the structure for being suitable for hole transporting layer.
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 (13)
1. a kind of compound, which is characterized in that indicated by following formula 1:
Chemical formula 1
In the chemical formula 1,
A and B is each independently substituted or unsubstituted C6~30Aryl, substituted or unsubstituted C5~30Heteroaryl or
NAr1Ar2, at least one of A and B are NAr1Ar2, Ar1And Ar2It is each independently substituted or unsubstituted C6~30Aryl,
Substituted or unsubstituted C5~30Heteroaryl,
L1And L2It is each independently Direct Bonding, substituted or unsubstituted C6~30Arlydene or substituted or unsubstituted
C5~30Heteroarylidene.
2. compound according to claim 1, which is characterized in that the A and B is each independently phenyl, xenyl, naphthalene
Base, terphenyl, fluorenes, dimethyl fluorene, diphenylfluorene, dibenzofurans, dibenzothiophenes, carbazole or their combination.
3. compound according to claim 1, which is characterized in that the compound is by 3 table of following formula 2 or chemical formula
Show:
In the chemical formula 2 or chemical formula 3,
Ar3、Ar4、Ar5And Ar6It is each independently substituted or unsubstituted C6~30Aryl or substituted or unsubstituted C5~30
Heteroaryl,
X is CR1R2、NR3, O or S, R1、R2And R3It is each independently hydrogen, heavy hydrogen, substituted or unsubstituted C1~24Alkyl, take
Generation or unsubstituted C6~30Aryl or substituted or unsubstituted C5~30Heteroaryl.
4. compound according to claim 1 or 3, which is characterized in that the L1And L2It is each independently phenyl, biphenyl
Base, naphthalene, terphenyl, fluorenes, dimethyl fluorene, diphenylfluorene or their combination.
5. compound according to claim 3, which is characterized in that the Ar3、Ar4、Ar5And Ar6It is each independently benzene
Base, xenyl, naphthalene, terphenyl, fluorenes, dimethyl fluorene, diphenylfluorene, dibenzofurans, dibenzothiophenes, carbazole or they
Combination.
6. compound according to claim 3, which is characterized in that the Ar3For with Ar5Identical aryl, Ar4For with Ar6
Identical aryl.
7. compound according to claim 3, which is characterized in that the Ar3With Ar5It is identical, Ar4With Ar6It is identical, Ar3And
Ar5For dibenzofurans.
8. compound according to claim 3, which is characterized in that the compound is indicated by following formula 4:
Chemical formula 4
9. compound according to claim 1, which is characterized in that the compound is one of following compound,
10. a kind of organic luminescent device, which is characterized in that include containing claim 1 between first electrode and second electrode
To the organic matter layer of compound described in any one of 7.
11. organic luminescent device according to claim 10, which is characterized in that the organic matter layer be hole injection layer,
1 layer or more in hole transporting layer and luminous auxiliary layer.
12. organic luminescent device according to claim 11, which is characterized in that the organic matter layer is hole transporting layer.
13. organic luminescent device according to claim 11, which is characterized in that the organic matter layer is the auxiliary layer that shines.
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| KR10-2017-0136775 | 2017-10-20 | ||
| KR1020170136775A KR20190044395A (en) | 2017-10-20 | 2017-10-20 | Novel compound and organic electroluminescent divice including the same |
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