CN113039173B - Compound and organic light emitting device using the same - Google Patents
Compound and organic light emitting device using the same Download PDFInfo
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- CN113039173B CN113039173B CN202080006175.7A CN202080006175A CN113039173B CN 113039173 B CN113039173 B CN 113039173B CN 202080006175 A CN202080006175 A CN 202080006175A CN 113039173 B CN113039173 B CN 113039173B
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- 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
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 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
- 230000005283 ground state Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
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- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- 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
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- 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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- 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
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- 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
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
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Abstract
The present application provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
The present application claims priority based on korean patent application No. 10-2019-0028864, 3/13/2019, the entire contents of the disclosure of which are incorporated as part of the present specification.
The present application relates to novel compounds and organic light emitting devices comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
[ Prior Art literature ]
[ patent literature ]
(patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present application relates to novel compounds and organic light emitting devices comprising the same.
Solution to the problem
The present application provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 and L 2 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracyl, triphenylenyl, pyrenyl, and,A group, a naphthacene group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzonaphthacene furanyl group or a benzonaphthacene thiophenyl group,
wherein Ar is as described above 1 And Ar is a group 2 Unsubstituted or each independently selected from C 1-20 Alkyl and C 6-20 More than 1 substituent group in the aryl group is substituted,
Ar 3 is a substituted or unsubstituted biphenyl group.
In addition, the present application provides an organic light emitting device, wherein comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the application
The compound represented by the above chemical formula 1 can be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, low driving voltage, and/or improvement of lifetime characteristics can be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6.
Detailed Description
In the following, the application will be described in more detail in order to aid understanding thereof.
(definition of terms)
In the present description of the application,and->Represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio group [ ]Alkylthio) is described; arylthio (/ -> Aryl thio xy); alkylsulfonyl [ ]Alkylsulfoxy); arylsulfonyl (+)>Aryl sulfoxy); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent containing 1 or more of N, O and 1 or more of the heteroaryl groups of S atoms is substituted or unsubstituted, or a substituent linked with 2 or more of the above-exemplified substituents is substituted or unsubstituted. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present application is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity (aromaticity). According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, perylenyl,A base, etc., but is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Azolyl, thiadiazolyl, and phenoneThiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group are the same as those exemplified for the aryl groups described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heteroaryl group. In this specification, alkenyl groups in aralkenyl groups are the same as those exemplified for the alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heteroaryl group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied thereto. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of heteroaryl groups can be applied thereto.
(Compound)
In another aspect, the present application provides a compound represented by the above chemical formula 1.
Specifically, the compound represented by the above chemical formula 1 is Ar 3 Amine compounds in which a substituent is bonded to an N atom through a biphenyl-1, 4-diyl linking group (ortho-biphenyl linking group). At this time, ar is as described above 3 The substituent is preferably a monocyclic substituent structure in which 2 or more phenyl groups are bonded to each other as a substituted or unsubstituted biphenyl group. Therefore, the above compound may exhibit an improved hole transporting ability and improved thermal stability as compared with a compound having a monocyclic substituent structure in which the above-described linking group is not present or in which 2 or more phenyl groups are not present. Thus, the organic light emitting device using the above compound can exhibit characteristics of high efficiency, low driving voltage, long life, and the like.
In the above chemical formula 1, preferably, L 1 And L 2 Each independently is a single bond, phenylene, biphenyldiyl, or naphthylene.
More preferably L 1 And L 2 Is a single bond or 1, 4-phenylene.
Preferably Ar 1 And Ar is a group 2 Is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, carbazolyl, dibenzofuranyl, dibenzothienyl, benzonaphthofuranyl or benzonaphthothienyl, wherein Ar is as defined above 1 And Ar is a group 2 Unsubstituted or C 6-20 Aryl substitution.
More preferably Ar 1 And Ar is a group 2 Each independently is any one selected from the following groups:
of the above-mentioned groups, the group,
r is hydrogen or phenyl.
At this time, ar 1 And Ar is a group 2 May be identical to each other. Preferably Ar 1 And Ar is a group 2 All of which are phenyl groups, are excluded because the glass transition temperature (Tg) of the above-mentioned compound may become low.
In addition, ar 1 And Ar is a group 2 May be different from each other.
Preferably Ar 3 Biphenyl which is unsubstituted or substituted by phenyl, biphenyl or terphenyl.
More preferably Ar 3 Is biphenyl, terphenyl or tetrabiphenyl.
Most preferably Ar 3 Is any one selected from the following groups:
preferably, the above compound is represented by any one of the following chemical formulas 1-1 to 1-3: [ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
In the above chemical formulas 1-1 to 1-3,
for Ar 1 And Ar is a group 2 The description of (a) is the same as that of the above chemical formula 1,
ph means a phenyl group, and the like,
n is 0 or 1, and the number of the N is not limited,
m is 0, 1 or 2.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
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on the other hand, as an example, the compound represented by the above chemical formula 1 can be produced by the production method shown in the following reaction formula 1. The above-described production method can be more specifically described in the production example described later.
[ reaction type 1]
In the above reaction formula 1, the description of each substituent is the same as the above definition. The step 1-1 is a step of introducing a bromine group into the starting material S-1 to produce an intermediate compound I-1, and the step 1-2 is a step of introducing a substituent Ar at a position substituted with bromine by a Suzuki-coupling reaction 3 The step of producing the intermediate compound I-2 is preferably performed in the presence of a palladium catalyst and a base, and the step 1-3 is a reaction of introducing a substituent into the intermediate compound I-2 as a secondary amine to produce the compound represented by the above chemical formula 1 as a tertiary amine compound, preferably performed in the presence of a palladium catalyst. Such a manufacturing method can be more concretely described in a manufacturing example described later.
(organic light-emitting device)
In another aspect, the present application provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present application provides an organic light emitting device, including: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present application may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present application may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer including the compound represented by chemical formula 1.
The organic layer of the organic light-emitting device of the present application may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting device of the present application may have a structure including, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller or larger number of organic layers.
The organic light-emitting device according to the present application may have a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present application may be an organic light emitting device having a reverse structure (inverted type) in which the first electrode is a cathode and the second electrode is an anode, and the cathode, 1 or more organic layers, and the anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present application is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above chemical formula 1 may be contained in the above hole transport layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above chemical formula 1 may be contained in the above hole injection layer, hole transport layer, or electron suppression layer.
The organic light emitting device according to the present application may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present application may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, a substance having a large mobility to the holes is preferable. As the hole transporting substance, the compound represented by the above chemical formula 1 is used, or an arylamine-based organic substance, a conductive polymer, a block copolymer in which a conjugated moiety and a non-conjugated moiety are simultaneously present, or the like may be used, but the present application is not limited thereto.
The electron suppression layer refers to the following layer: the hole transport layer is preferably formed on the light emitting layer, and the hole transport layer is preferably provided so as to be in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility and preventing excessive migration of electrons to increase the probability of hole-electron bonding. The electron blocking layer contains an electron blocking material, and as an example of such an electron blocking material, a compound represented by the above chemical formula 1, an arylamine-based organic compound, or the like may be used, but the present application is not limited thereto.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compoundThe method comprises the steps of carrying out a first treatment on the surface of the Benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
As described above, the light emitting layer may include a host material and a dopant material. The host material may further contain an aromatic condensed ring derivative, a heterocyclic compound, or the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present application is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The hole blocking layer refers to the following layer: which is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and which improves holes by adjusting electron mobility and preventing excessive migration of holesThe probability of binding between electrons, thereby serving to improve the efficiency of the organic light emitting device. The hole blocking layer contains a hole blocking substance, and as an example of such a hole blocking substance, triazine derivatives, triazole derivatives, triazine derivatives, and the like can be used,The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto.
The electron injection and transport layer is a layer which injects electrons from an electrode and transports the received electrons to a light emitting layer and functions as both an electron transport layer and an electron injection layer, and is formed on the light emitting layer or the hole blocking layer. Such an electron injection and transport substance is a substance that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer, and is suitable for a substance having a large mobility of electrons. As specific examples of the electron injecting and transporting substance, there are Al complexes of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) with (c), organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, and the like. Or can be mixed with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->The compounds are used together with diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present application may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are given by way of illustration of the present application, and the scope of the present application is not limited thereto.
Production example 1: production of Compound 1
Step 1-1: production of N- (biphenyl-4-yl) -5-bromobiphenyl-2-amine
The compound N- ([ 1,1 '-biphenyl ] -4-yl) - [1,1' -biphenyl ] -2-amine (100.0 g,311.52 mmol) and NBS (55.46 g,310.52 mmol) were completely dissolved in 600mL of DMF in a 1000mL round bottom flask under nitrogen atmosphere and stirred at room temperature for 5 hours. The material obtained by filtration (filter) was recrystallized from 850mL of ethyl acetate to thereby produce the title compound (89.91 g, yield 72%).
MS[M+H] + ＝400
Step 1-2: production of Compound A-1
After the compound N- (biphenyl-4-yl) -5-bromobiphenyl-2-amine (15.0 g,37.50 mmol) and the compound b1 (7.43 g,37.50 mmol) produced in step 1-1 above were completely dissolved in 300mL of Tetrahydrofuran (THF) in a 500mL round-bottomed flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (150 mL) was added, tetrakis (triphenylphosphine) palladium (1.30 g,1.13 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 320mL of ethyl acetate, whereby Compound A-1 (12.47 g, yield 70%) was produced.
MS[M+H] + ＝474
Step 1-3: production of Compound 1
After complete dissolution of compound a-1 (9.72 g,20.56 mmol) and compound a1 (6.50 g,19.58 mmol) in 280mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.82 g,29.37 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.20 g,0.39 mmol) was added and heated for 3 hours. After the temperature was lowered to room temperature and the base (base) was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give compound 1 (7.44 g, yield: 52%).
MS[M+H] + ＝726
Production example 2: production of Compound 2
Compound a-2 was produced by the same method as in production example 1 above, except that compound b2 was used instead of compound b1 in production example 1 above.
Then, after complete dissolution of compound a-2 (9.69 g,20.48 mmol) and compound a2 (5.50 g,19.50 mmol) in 290mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.22 g,43.95 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.15 g,0.29 mmol) was added and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate to give Compound 2 (8.24 g, yield: 62%).
MS[M+H] + ＝676
Production example 3: production of Compound 3
Compound A-3 was produced by the same method as in production example 1 above, except that in production example 1, compound b3 was used instead of compound b 1.
Then, after compound a-3 (7.93 g,16.76 mmol) and compound a3 (4.50 g,15.96 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.30 g,23.94 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.16 g,0.32 mmol) was added, and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate to give Compound 3 (6.36 g, yield: 59%).
MS[M+H] + ＝676
Production example 4: production of Compound 4
In production example 1, a compound B-1 was produced by the same method as in production example 1 except that the compound B4 was used instead of the compound B1.
Then, after compound B-1 (12.24 g,22.30 mmol) and compound a4 (6.50 g,21.24 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.06 g,31.86 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.22 g,0.42 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 280mL of ethyl acetate to give Compound 4 (10.07 g, yield: 61%).
MS[M+H] + ＝776
Production example 5: production of Compound 5
Compound B-2 was produced by the same method as in production example 1 above, except that compound B5 was used instead of compound B1 in production example 1 above.
Then, after compound B-2 (15.23 g,27.74 mmol) and compound a5 (6.50 g,26.42 mmol) were completely dissolved in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.81 g,39.63 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.27 g,0.53 mmol) was added, and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 210mL of ethyl acetate to give Compound 5 (9.74 g, yield: 51%).
MS[M+H] + ＝716
Production example 6: production of Compound 6
Compound B-3 was produced by the same method as in production example 1 above except that compound B6 was used instead of compound B1 in production example 1 above.
Then, after compound B-3 (12.10 g,22.04 mmol) and compound a6 (5.50 g,20.99 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.03 g,31.49 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.42 mmol) was added, and then heated and stirred for 35 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give Compound 6 (9.74 g, yield: 51%).
MS[M+H] + ＝732
Production example 7: production of Compound 7
In production example 1, a compound C-1 was produced by the same method as in production example 1 except that the compound b7 was used instead of the compound b 1.
Then, after compound C-1 (14.64 g,26.66 mmol) and compound a7 (6.50 g,25.39 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.66 g,38.09 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.26 g,0.51 mmol) was added, and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give Compound 7 (6.88 g, yield: 37%).
MS[M+H] + ＝726
Production example 8: production of Compound 8
Compound C-2 was produced by the same method as in production example 1 above except that in production example 1, compound b8 was used instead of compound b 1.
Then, after compound C-2 (12.17 g,22.16 mmol) and compound a8 (6.50 g,21.10 mmol) were completely dissolved in 250mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.04 g,31.66 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.22 g,0.42 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give Compound 8 (11.55 g, yield: 70%).
MS[M+H] + ＝778
Production example 9: production of Compound 9
Compound D-1 was produced by the same method as in production example 1 above, except that compound b9 was used instead of compound b1 in production example 1 above.
Then, after compound D-1 (16.60 g,27.13 mmol) and compound a9 (7.50 g,26.60 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.83 g,39.89 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,0.27 mmol) was added, and then heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of tetrahydrofuran to give Compound 9 (13.27 g, yield: 61%).
MS[M+H] + ＝778
Production example 10: production of Compound 10
Compound D-2 was produced by the same method as in production example 1 above, except that compound b10 was used instead of compound b1 in production example 1 above.
Then, after compound D-2 (11.21 g,17.93 mmol) and compound a10 (5.50 g,17.08 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.46 g,25.62 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.17 g,0.34 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate, whereby compound 10 (8.87 g, yield: 60%) was produced.
MS[M+H] + ＝868
Example 1: fabrication of organic light emitting devices
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, the washing was repeated twice with distilled water for 10 minutes with ultrasonic wavesAnd (5) washing. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. Further, after the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine
On the ITO transparent electrode as an anode thus prepared, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio)And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, a compound represented by the following formula HT1 is added>Vacuum evaporation is performed to form a hole transport layer. Next, on the hole transport layer, the film thickness is +.>The compound 1 produced in production example 1 was vacuum-evaporated to form an electron-inhibiting layer.
Then, on the electron suppression layer, the film thickness is set to beA compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, the film thickness is set toA compound represented by the following chemical formula HB1 was vacuum-evaporated to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to form ∈ ->Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>To the thickness of aluminumAnd vapor deposition is performed to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 ～5×10 -6 The support is thus fabricated into an organic light emitting device.
Examples 2 to 10
An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of the compound of manufacturing example 1.
Comparative examples 1 to 4
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compound described in table 1 below was used instead of the compound of manufacturing example 1. Compounds of EB1, EB2, EB3 and EB4 used in table 1 below are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
TABLE 1
As shown in table 1 above, the organic light emitting device using the compound of the present application as an electron suppression layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light emitting device.
Specifically, it was found that in examples 1 to 10, the organic light-emitting device using an amine-based substance in which "N atom" and "substituted or unsubstituted biphenyl group" are linked with biphenyl-1, 4-diyl group as an electron-inhibiting layer exhibited characteristics of low voltage, high efficiency, and long lifetime as compared with the organic light-emitting device of comparative example 1 using compound EB1 having a fluorenyl group as one of the amino substituents, comparative example 2 using compound EB2 in which a fluoro group is linked to biphenyl-1, 4-diyl group, comparative example 4 using compound EB4 in which biphenyl-1, 4-diyl group is not substituted, and comparative example 3 using compound EB3 in which phenyl group is linked to biphenyl-1, 4-diyl group.
[ description of the symbols ]
1: substrate 2: anode
3: hole transport layer 4: light-emitting layer
5: electron injection and transport layer 6: cathode electrode
7: hole injection layer 8: electron suppression layer
9: a hole blocking layer.
Claims (6)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
L 1 is a phenylene group, and is preferably a phenylene group,
Ar 1 is a phenyl group, and is a phenyl group,
L 2 is a single bond, or a phenylene group,
Ar 2 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracyl, triphenylenyl, pyrenyl, and,A group, a naphthacene group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzonaphthacene furanyl group or a benzonaphthacene thiophenyl group,
Ar 3 is any one selected from the following groups:
2. the compound of claim 1, wherein L 2 Is a single bond.
3. The compound of claim 1, wherein Ar 2 Is any one selected from the following groups:
of the above-mentioned groups, the group,
r is hydrogen.
4. A compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-3:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
In the chemical formulas 1-1 to 1-3,
Ar 1 and Ar is a group 2 As defined in claim 1,
ph means a phenyl group, and the like,
n is 1, and the number of the n is 1,
m is 0.
5. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
6. an organic light emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 5.
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