WO2019190248A1 - 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents
화합물 및 이를 포함하는 유기 발광 소자 Download PDFInfo
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- WO2019190248A1 WO2019190248A1 PCT/KR2019/003676 KR2019003676W WO2019190248A1 WO 2019190248 A1 WO2019190248 A1 WO 2019190248A1 KR 2019003676 W KR2019003676 W KR 2019003676W WO 2019190248 A1 WO2019190248 A1 WO 2019190248A1
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- light emitting
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 97
- 239000000126 substance Substances 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000011368 organic material Substances 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000005264 aryl amine group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000002019 doping agent Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000010410 layer Substances 0.000 description 220
- -1 hole transport Substances 0.000 description 63
- 238000002347 injection Methods 0.000 description 55
- 239000007924 injection Substances 0.000 description 55
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- 230000005525 hole transport Effects 0.000 description 40
- 239000000463 material Substances 0.000 description 40
- 0 CC(C)c(c(-[n]1c2c3-c4ccccc4*c3ccc2c2c1cccc2)c1C(C)C)c(-c(cc2)ccc2F)c(-[n]2c3c(c(cccc4)c4[o]4)c4ccc3c3c2cccc3)c1-c(cc1)ccc1F Chemical compound CC(C)c(c(-[n]1c2c3-c4ccccc4*c3ccc2c2c1cccc2)c1C(C)C)c(-c(cc2)ccc2F)c(-[n]2c3c(c(cccc4)c4[o]4)c4ccc3c3c2cccc3)c1-c(cc1)ccc1F 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
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- 230000003111 delayed effect Effects 0.000 description 10
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- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
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- 239000007787 solid Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 230000008901 benefit Effects 0.000 description 8
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- PRWATGACIORDEL-UHFFFAOYSA-N 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=C(C#N)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C(N2C3=CC=CC=C3C3=CC=CC=C32)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C1C#N PRWATGACIORDEL-UHFFFAOYSA-N 0.000 description 7
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- 238000000151 deposition Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 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 6
- 238000001296 phosphorescence spectrum Methods 0.000 description 6
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- 125000004429 atom Chemical group 0.000 description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 5
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- 230000005281 excited state Effects 0.000 description 5
- 125000005241 heteroarylamino group Chemical group 0.000 description 5
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- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 5
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- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
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- 239000007983 Tris buffer Substances 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
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- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000003974 aralkylamines Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 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 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 2
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 2
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- UNTNRNUQVKDIPV-UHFFFAOYSA-N 3h-dithiazole Chemical group N1SSC=C1 UNTNRNUQVKDIPV-UHFFFAOYSA-N 0.000 description 2
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 2
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 2
- RSUUYNMJZPNCBL-JZMRLUECSA-N CC(/C(/[n]1c2ccc3[s]c(cccc4)c4c3c2c2c1cccc2)=C(/C(C)(C)[n]1c2ccccc2c2c1cccc2)\C([n]1c2ccc3[s]c4ccccc4c3c2c2c1cccc2)=C)F Chemical compound CC(/C(/[n]1c2ccc3[s]c(cccc4)c4c3c2c2c1cccc2)=C(/C(C)(C)[n]1c2ccccc2c2c1cccc2)\C([n]1c2ccc3[s]c4ccccc4c3c2c2c1cccc2)=C)F RSUUYNMJZPNCBL-JZMRLUECSA-N 0.000 description 2
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- VBAMVIBDBAKBOK-UHFFFAOYSA-N CC(C)(c(c(-[n]1c(ccc(C)c2)c2c2cc(C)ccc12)c(cc1-c(cc2)ccc2F)-c(cc2)ccc2F)c1-[n]1c2ccc(C)cc2c2c1ccc(C)c2)[n]1c2ccccc2c2c1cccc2 Chemical compound CC(C)(c(c(-[n]1c(ccc(C)c2)c2c2cc(C)ccc12)c(cc1-c(cc2)ccc2F)-c(cc2)ccc2F)c1-[n]1c2ccc(C)cc2c2c1ccc(C)c2)[n]1c2ccccc2c2c1cccc2 VBAMVIBDBAKBOK-UHFFFAOYSA-N 0.000 description 2
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- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 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
- 238000007670 refining Methods 0.000 description 1
- 230000000630 rising effect Effects 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
- KGFZGOVGODRJEE-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] 4-aminobenzenecarbothioate Chemical compound CCN(CC)CCSC(=O)C1=CC=C(N)C=C1 KGFZGOVGODRJEE-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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- RFWPGPDEXXGEOQ-UHFFFAOYSA-N tert-butyl(methyl)boron Chemical group C[B]C(C)(C)C RFWPGPDEXXGEOQ-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 125000005033 thiopyranyl group Chemical group 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 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
- 125000005580 triphenylene group Chemical group 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
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
Images
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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- 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
-
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Definitions
- the present specification relates to a compound and an organic light emitting device including the same.
- organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
- An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
- An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
- X is a direct bond; O; Or S,
- Y is NR; O; Or S,
- R1 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group,
- R and R2 to R4 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- R5 and R6 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
- a 1 or 2
- b 0 or 1
- c and e are each independently an integer of 0 to 4,
- d is an integer of 0 to 2
- f and g are each independently an integer of 0-5,
- an exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is It provides an organic light-emitting device comprising a compound according to one embodiment of the specification.
- the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
- the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and lifetime characteristics in the organic light emitting diode.
- the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron suppression, luminescence, hole suppression, electron transport or electron injection material.
- the compound according to the exemplary embodiment of the present invention has a structure having a high electron accepting ability, and excellent heat resistance to maintain an appropriate deposition temperature when fabricating an organic light emitting device.
- the sublimation temperature is high, high purity can be achieved by the sublimation refining method, and it does not cause contamination to the deposition apparatus or the organic light emitting device for deposition in manufacturing the organic light emitting device.
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
- FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
- An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
- the compound represented by Formula 1 is a delayed fluorescent compound.
- the number of excitons generated in the singlet and triplet is generated in the ratio of 25:75 (single term: triplet), and the fluorescence, phosphorescence, and thermal activation delayed fluorescence according to the emission form according to exciton movement It can be divided into luminescence.
- the excitons in the triplet excited state move to the ground state and emit light.
- the excitons in the singlet excited state are ground state ( The thermally activated delayed fluorescence emission is induced in the reverse interphase transition from the triplet excited state to the singlet excited state, and the singlet excited state This means that excitons move to the ground state and cause fluorescence.
- the thermally activated delayed fluorescence emission is distinguished from fluorescence in that the peak position of the emission spectrum is the same as the fluorescence but the decay time is long, and the peak position of the emission spectrum is the phosphorescence spectrum and S 1 -T although the decay time is long. It differs from phosphorescence in that it differs by one energy difference. In this case, S 1 is a singlet energy level, and T 1 is a triplet energy level.
- the difference ( ⁇ E ST ) between the singlet energy level and triplet energy level of the compound represented by Formula 1 is 0 eV or more and 0.3 eV or less, preferably Is 0 eV or more and 0.2 eV or less.
- the excitons generated in the triplet are converted into singlet by the reverse interphase transition (RISC). Since the exciton stays in the triplet is reduced by increasing the rate and speed of the movement, there is an advantage that the efficiency and life of the organic light emitting device is increased.
- the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted two or more substituents of the substituents exe
- a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
- adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted.
- two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as “adjacent” to each other.
- a substituent substituted for N in carbazole and a substituent of carbon 1 or carbon 8 of carbazole may be interpreted as “adjacent group”.
- examples of the halogen group include fluorine, chlorine, bromine or iodine.
- carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
- the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
- carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
- the silyl group may be represented by the formula of -SiR a R b R c , wherein R a , R b and R c are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
- Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group, but are not limited thereto. Do not.
- the boron group may be represented by the formula of -BR a R b , wherein R a and R b are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
- the boron group may include, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butyl methyl boron group, a diphenyl boron group, a phenyl boron group, and the like.
- the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
- alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
- the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C40. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
- Substituents comprising alkyl groups, alkoxy groups and other alkyl group moieties described herein include both straight and pulverized forms.
- the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
- the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
- the alkylamine group is not particularly limited in carbon number, but is preferably 1 to 40.
- Specific examples of the alkylamine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine Groups, diphenylamine groups, phenylnaphthylamine groups, ditolylamine groups, phenyltolylamine groups, triphenylamine groups and the like, but are not limited thereto.
- examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
- the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
- the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
- aryl amine group examples include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, and 2-methyl-biphenylamine.
- examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
- the heteroaryl group in the heteroarylamine group may be a monocyclic hetero ring group or may be a polycyclic hetero ring group.
- the heteroarylamine group including two or more heterocyclic groups may simultaneously include a monocyclic hetero ring group, a polycyclic hetero ring group, or a monocyclic hetero ring group and a polycyclic hetero ring group.
- the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.
- examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group.
- the aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group.
- the arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
- the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
- the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
- the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
- the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
- Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group).
- the present invention is not limited thereto.
- the heterocyclic group is a heterocyclic group including one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number is not particularly limited, but is preferably 1 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 1 to 30 carbon atoms.
- heterocyclic group examples include, for example, pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazole group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, deoxyyl group, triazinyl group, tetrazinyl group, qui Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acriridyl group, xanthenyl group
- the number of atoms constituting the ring of the heterocyclic group is 3 to 25. In another embodiment, the number of atoms constituting the ring of the heterocyclic group is 5 to 17.
- heteroaryl group is aromatic
- the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above.
- the description of one aryl group may apply.
- the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.
- heteroaryl group a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl groups may be applied to the description of the aforementioned heterocyclic group.
- alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
- the description of the aryl group described above may be applied except that the arylene group is a divalent group.
- heteroarylene group is a divalent group.
- the meaning of combining with adjacent groups to form a ring means combining with adjacent groups with each other for a substituted or unsubstituted aliphatic hydrocarbon ring; Substituted or unsubstituted aromatic hydrocarbon rings; Substituted or unsubstituted aliphatic hetero ring; Substituted or unsubstituted aromatic hetero rings; Or to form a condensed ring thereof.
- the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
- examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like. There is, but is not limited to these.
- the aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms.
- examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, penalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaph Butylene, benzofluorene, spirofluorene and the like, but is not limited thereto.
- the aliphatic hetero ring means an aliphatic ring including at least one of heteroatoms.
- examples of aliphatic hetero rings include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepan, Azocaine, thiocaine and the like, but are not limited to these.
- the aromatic hetero ring means an aromatic ring including at least one of heteroatoms.
- aromatic hetero rings include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole , Thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, azine Cridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, di
- the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
- R1 is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms.
- R1 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.
- R1 is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms.
- R1 is a methyl group unsubstituted or substituted with a halogen group; An ethyl group unsubstituted or substituted with a halogen group; Isopropyl group unsubstituted or substituted with a carbazole group; T-butyl group unsubstituted or substituted with a carbazole group or a cyclohexane group substituted or unsubstituted.
- R and R2 to R4 are each independently, hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
- R and R2 to R4 are each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
- R and R2 to R4 are each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
- R and R2 to R4 are each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; Substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
- R and R2 to R4 are each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
- R is a substituted or unsubstituted phenyl group.
- the R2 to R4 are each independently, hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
- the R2 to R4 are each independently, hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with a halogen group; Substituted or unsubstituted isopropyl group or substituted or unsubstituted t-butyl group.
- R5 and R6 are each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
- R5 and R6 are each independently, hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted silyl group; Or a substituted or unsubstituted alkyl group.
- R5 and R6 are each independently, hydrogen; heavy hydrogen; Halogen group; An alkyl group substituted with a halogen group; Or cyano group.
- R5 and R6 are each independently, hydrogen; heavy hydrogen; Fluorine group; An alkyl group substituted with a fluorine group; Or cyano group.
- R5 and R6 is a cyano group.
- Formula 1 is represented by the following formula (2).
- Chemical Formula 1 is represented by the following Chemical Formula 3 or 4.
- Chemical Formula 1 is represented by the following Chemical Formula 5 or 6.
- Formula 1 is represented by the following formula (7) or (8).
- the compound of Formula 1 may be any one selected from the following compounds.
- a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
- the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
- the compound which has the intrinsic property of the introduced substituent can be synthesize
- the inventors of the present invention can realize the reduction of the driving voltage and the long life of the compound of Formula 1 having such a characteristic when applied to an organic light emitting device material, in particular, a hole injection layer, a hole transport layer, an electron blocking layer or a charge generation layer. It turned out that it was. In addition, it is easier to deposit than a material having a low molecular weight and high sublimation like F4TCNQ, and can form a stable interface with an electrode or an adjacent organic compound layer as compared with HAT-CN.
- the compound of formula 1 described above may be prepared using materials and reaction conditions known in the art.
- the organic light emitting device is an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, at least one of the organic layer It is characterized by including the compound.
- the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
- the organic material layer includes a light emitting layer
- the light emitting layer includes a dopant
- the dopant includes a compound according to an exemplary embodiment of the present specification.
- the light emitting material of the light emitting layer is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, wherein the light emitting layer is the delayed fluorescent material described above.
- the light emitting layer is the delayed fluorescent material described above.
- a dopant of the light emitting layer at least one of the singlet excitation energy and the excitation triplet energy has a higher value than the light emitting material of the delayed fluorescent material described above, has a hole transporting ability, an electron transporting ability, and has a long wavelength of light emission. It is possible to prevent oxidation and include an organic compound having a high glass transition temperature as a host.
- the organic material layer includes a light emitting layer, and the light emitting layer includes a host.
- the triplet energy level of the host is 2.5 eV or more, preferably 2.7 eV or more and 3.1 eV or less. If the triplet energy level of the host meets the above range, host exciton energy is efficiently transferred to the dopant, and the triplet / single excitons of the host or dopant and the surrounding hole (or electron) -polaron The exciton quenching by the interaction of is minimized. Accordingly, the lifespan of the light emitting diode device can be prevented from being degraded by electro-oxidation and photo-oxidation, and thus a long-life light emitting device can be realized.
- the organic material layer includes a host, and the host is at least one of the following structures, but is not limited thereto.
- the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present specification may further have a structure including at least one of a hole injection layer, a hole buffer layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer in addition to the light emitting layer as the organic layer. have.
- the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
- the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
- the organic light emitting device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
- the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1, that is, the compound represented by Chemical Formula 1.
- the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
- a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
- PVD physical vapor deposition
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon it can be prepared by depositing a material that can be used as a cathode thereon.
- the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
- the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
- an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
- the manufacturing method is not limited thereto.
- the first electrode is an anode
- the second electrode is a cathode
- the first electrode is a cathode and the second electrode is an anode.
- the organic light emitting diode may have a laminated structure as described below, but is not limited thereto.
- FIGS. 1 and 2 For example, the structure of an organic light emitting diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.
- FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound may be included in the hole transport layer.
- FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
- the compound may be included in the hole injection layer or hole transport layer.
- the anode 2 may be any one of an indium tin oxide (ITO), indium zinc oxide (IZO), or zinc oxide (ZnO) having a high work function as an electrode for injecting holes.
- ITO indium tin oxide
- IZO indium zinc oxide
- ZnO zinc oxide
- the anode 2 is a reflective electrode, the anode 2 is a reflective layer made of any one of aluminum (Al), silver (Ag), or nickel (Ni) under a layer made of any one of ITO, IZO, or ZnO. It may further include.
- the hole injection layer 5 may play a role of smoothly injecting holes from the anode 2 to the light emitting layer 7.
- the hole injection layer 5 may have a thickness of 1 to 150 nm.
- the thickness of the hole injection layer 5 is 1 nm or more, there is an advantage that the hole injection characteristics can be prevented from deteriorating.
- the hole injection layer 5 is too thick, the hole injection layer 5 is too thick to move the holes. There is an advantage that can be prevented from increasing the driving voltage to improve.
- As the hole injection layer material hole injection materials known in the art may be used.
- hole injection layer material CuPc (cupper phthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene), PANI (polyaniline) and NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine) Any one or more selected may be used, but is not limited thereto.
- the hole transport layer 6 may serve to facilitate the transport of holes.
- a hole transport material known in the art may be used.
- the hole transport layer 6 may include NPD (N, N-dinaphthyl-N, N'-diphenylbenzidine), TPD (N, N'-bis- (3-methylphenyl) -N, N'-bis- (phenyl)- benzidine), s-TAD and MTDATA (4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenyl-amino) -triphenylamine), but may be one or more selected from the group consisting of, but not limited to For example, as the hole transport layer material, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkaine derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino substituted chalcone derivatives,
- a hole buffer layer may be further provided between the hole injection layer and the hole transport layer.
- the hole buffer layer may comprise a hole injection or transport material known in the art.
- An electron blocking layer may be provided between the hole transport layer and the light emitting layer, and the compound of Formula 1 or a material known in the art may be used.
- a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.
- the electron transport layer 8 may serve to facilitate the transport of electrons. Materials known in the art such as Alq 3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq can be used.
- the electron transport layer 8 may have a thickness of about 1 nm to about 50 nm. In this case, when the thickness of the electron transport layer 8 is 1 nm or more, there is an advantage of preventing the electron transport characteristics from being lowered. When the thickness of the electron transport layer 8 is 50 nm or less, the thickness of the electron transport layer 8 is too thick to improve the movement of electrons. In order to prevent the driving voltage from rising, there is an advantage.
- the electron injection layer may play a role of smoothly injecting electrons.
- Alq 3 tris (8-hydroxyquinolino) aluminum
- PBD tris (8-hydroxyquinolino) aluminum
- TAZ tris (tris (8-hydroxyquinolino) aluminum
- spiro-PBD BAlq or SAlq
- Metal compounds include metal halides, and storage can be used, for example, can be used LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF 2, MgF 2, CaF 2, SrF 2, BaF 2 and RaF 2 and the like.
- the electron injection layer may have a thickness of about 1 nm to about 50 nm.
- the thickness of the electron injection layer is 1 nm or more, there is an advantage that the electron injection characteristics can be prevented from being lowered.
- the thickness of the electron injection layer is 50 nm or less, the thickness of the electron injection layer is too thick, and the driving voltage is increased to improve the movement of electrons. There is an advantage that can be prevented from being raised.
- the cathode 4 is an electron injection electrode, and may be made of magnesium (Mg), calcium (Ca), aluminum (Al), silver (Ag), or an alloy thereof having a low work function.
- the cathode 4 may be formed to a thickness thin enough to transmit light when the organic light emitting device is a front or double-sided light emitting structure, and may reflect light when the organic light emitting device is a rear light emitting structure. It can form thick enough.
- the light emitting layer 3 may include the compound of Formula 1.
- the light emitting layer 3 may be made of only the compound of Formula 1, but the compound of Formula 1 may be present in a mixed or doped state with other light emitting layer materials known in the art.
- the compound of Formula 1 may account for 100% of the light emitting layer, but may be doped with 0.1 to 50% by weight.
- the organic material layer may include two or more light emitting layers, and may include a charge generation layer including the compound of Formula 1 provided between the two light emitting layers.
- one of the light emitting layers emits blue light and the other emits yellow light, thereby manufacturing an organic light emitting device that emits white light.
- One or more organic material layers such as the above-described hole injection layer, hole buffer layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer, electron injection layer, between the light emitting layer and the anode or cathode, and between the light emitting layer and the charge generation layer May be included.
- the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
- Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
- the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
- the compound according to the present invention may also operate on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.
- the compound represented by Chemical Formula 1 may be prepared by introducing a phenyl boronic acid substituted in dibromodifluorobenzene substituted as follows in a Suzuki reaction and finally introducing a nitrogen compound through a SnAr reaction.
- the compounds of the embodiments were synthesized through the following procedure.
- an organic light emitting device is manufactured by including the compound represented by Chemical Formula 1 according to one embodiment of the present specification in a light emitting layer with a host material (m-CBP) having a triplet energy value of 2.9 eV. Was evaluated.
- m-CBP host material
- a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
- ITO indium tin oxide
- Fischer Co. product was used as a detergent
- distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
- ultrasonic washing was performed twice with distilled water for 10 minutes.
- ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
- the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
- Each thin film was deposited on the ITO transparent electrode thus prepared at a vacuum degree of 5 ⁇ 10 ⁇ 4 Pa by vacuum deposition.
- the following compound HAT-CN was thermally vacuum deposited to a thickness of 500 kPa on ITO to form a hole injection layer.
- the compound N-([1,1'-bisphenyl] -4-yl) -N- (4- (11-([1,1'-biphenyl] -4-yl) having a film thickness of 100 kPa on the hole transport layer ) -11H-benzo [a] carbazole-5-yl) phenyl)-[1,1'-biphenyl] -4-amine (EB1) (100 Pa) was vacuum deposited to form an electron blocking layer.
- the following m-CBP and the compound 4CzIPN were vacuum-deposited at a weight ratio of 70:30 on the electron blocking layer with a film thickness of 300 Pa to form a light emitting layer.
- Compound HB1 was vacuum deposited on the light emitting layer at a film thickness of 100 Pa to form a hole blocking layer.
- the following compound ET1 and compound LiQ were vacuum deposited on the hole blocking layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa.
- lithium fluoride (LiF) and aluminum were deposited sequentially to have a thickness of 12 kW to form a cathode.
- the deposition rate of the organic material was maintained at 0.4 ⁇ / sec to 0.7 ⁇ / sec, the lithium fluoride at the cathode was maintained at 0.3 ⁇ / sec, and the aluminum at 2 ⁇ / sec.
- the organic light emitting device was manufactured by maintaining the x10 -7 torr to 5 x 10 -6 torr.
- An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the compound of Table 1 instead of the compound 4CzIPN in Comparative Example 1.
- An organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using the following compound of T1 to T6 instead of compound 4CzIPN in Comparative Example 1.
- Comparative Example 2 Comparing the device of the present invention with the device of Comparative Example 7, it can be seen that the structure of the embodiments of the present invention improves both characteristics in terms of voltage and efficiency. It was confirmed that it is excellent and the color purity can be applied to the delayed fluorescent organic light emitting device.
- HOMO and LUMO energy levels were determined by dissolving the measured compound in 5mM and electrolyte in 0.1M concentration in dimethylformamide (dimethylformamide, DMF) and confirming the oxidation and reduction potentials through CV device measurements based on ferrocene compounds. .
- HOMO energy level of the compound and the LUMO energy level is a cyclic voltage comparing the oxidation and reduction potential of the dimethylformamide (DMF) solution in which the measured compound is dissolved at a concentration of 5 mM and the electrolyte is 0.1M. It was measured by cyclic voltammetry (CV). Specific measurement conditions are as follows.
- Measuring solution Dimethylformamide (DMF) solution in which the measuring compound was dissolved at a concentration of 5 mM and an electrolyte (KNO 3 , Aldrich) at a concentration of 0.1 M
- HOMO energy level (E (HOMO)) and LUMO energy level (E (LUMO)) were calculated through the following equation.
- V solvent is the energy level of the solvent
- E 1/2 (solvent) is the half wave level of the solvent
- E onset ex is the point where the oxidation starts
- E onset red is the point where the reduction begins.
- Triplet energy (T 1 ) was measured at cryogenic conditions using the characteristics of triplet excitons with long lifespan. Specifically, after dissolving the compound in toluene solvent to prepare a sample having a concentration of 10 -5 M, the sample is put in a quartz kit and cooled to 77K, and the 300 nm light source is irradiated to the sample for measuring phosphorescence while changing the wavelength Measure the spectrum. The spectrophotometer (FP-8600 spectrophotometer, JASCO Corporation) was used for the measurement of the spectrum.
- the vertical axis of the phosphorescence spectrum was phosphorescence intensity, and the horizontal axis was wavelength.
- a tangent line was drawn for the rise of the short wavelength side of the phosphorescence spectrum, and the wavelength value ( ⁇ edge1 (nm)) of the intersection point of the tangent line and the horizontal axis was obtained, and the wavelength value was substituted into the following equation 1 to calculate the triplet energy. .
- the tangent to the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. First, the maximum value of the shortest wavelength side of the maximum value of a spectrum is confirmed. At this time, the maximum point which has the peak intensity of 15% or less of the maximum peak intensity of a spectrum is not included in the maximum value of the shortest wavelength side mentioned above.
- the tangent line at each point on the spectral curve from the short wavelength side of the phosphorescence spectrum to the maximum value is considered. Of these tangent lines, the tangent line having the largest slope value (that is, the tangent line at the inflection point) is a tangent line to the rise of the short wavelength side of the phosphorescence spectrum.
- a 10 -5 M toluene solution of the compound to be measured was prepared, placed in a quartz cell, and the emission spectrum (vertical axis: light emission intensity, horizontal axis: wavelength) of the 300 nm light source of the sample was measured at room temperature (300 K).
- the tangent line was drawn about the rise of the short wavelength side of this emission spectrum, and the singlet energy was computed by substituting the wavelength value ((lambda edge2 (nm)) of the intersection of this tangent line and a horizontal axis in following conversion formula 2).
- the emission spectrum was measured by using a spectrophotometer (FP-8600 spectrophotometer) of JASCO.
- the tangent to the rise of the short wavelength side of the emission spectrum is drawn as follows. First, the maximum value of the shortest wavelength side of the maximum value of a spectrum is confirmed. The tangent line at each point on the spectral curve from the short wavelength side of the emission spectrum to the maximum value is considered. Of these tangent lines, the tangent line having the largest slope value (that is, the tangent line at the inflection point) is a tangent line to the rise of the short wavelength side of the emission spectrum. The maximum point which has the peak intensity of 15% or less of the maximum peak intensity of a spectrum is not included in the maximum value of the shortest wavelength side mentioned above.
- Compounds 1 to 9 used in the Examples of the present invention are all suitable as delayed fluorescent materials with ⁇ E ST of 0.3 eV or less.
- Compounds T1, T2, and T4 are not suitable as delayed fluorescent materials.
- 4CzIPN, T3, T5, and T6 correspond to delayed fluorescent materials with ⁇ E ST of 0.3 eV or less, but as shown in Table 1, compounds 1 to 9 have improved characteristics in terms of voltage and efficiency.
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Abstract
본 명세서는 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.
Description
본 발명은 2018년 03월 28일에 한국특허청에 제출된 한국 특허 출원 제10-2018-0036146의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.
본 명세서에는 신규한 화합물 및 이를 포함하는 유기 발광 소자가 기재된다.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.
[화학식 1]
화학식 1에 있어서,
X는 직접결합; O; 또는 S이고,
Y는 NR; O; 또는 S이고,
R1은 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 시클로알킬기이며,
R 및 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 할로겐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,
R5 및 R6은 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,
a는 1 또는 2이고,
b는 0 또는 1이고,
c 및 e는 각각 독립적으로, 0 내지 4의 정수이며,
d는 0 내지 2의 정수이며,
f 및 g는 각각 독립적으로, 0 내지 5의 정수이며,
a 및 c 내지 g가 각각 독립적으로 2 이상인 경우에는 괄호 안의 치환기는 서로 같거나 상이하다.
또한, 본 명세서의 일 실시상태는 제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 본 명세서의 일 실시상태에 따른 화합물을 포함하는 것을 특징으로 하는 유기 발광 소자를 제공한다.
본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및 수명 특성을 향상시킬 수 있다. 특히, 본 명세서에 기재된 화합물은 정공주입, 정공수송, 정공주입과 정공수송, 전자억제, 발광, 정공억제, 전자수송 또는 전자주입 재료로 사용될 수 있다.
보다 구체적으로, 본 발명의 일 실시상태에 따른 화합물은 전자 수용 능력이 높은 구조를 가지고 있으며, 내열성이 우수하여 유기 발광 소자 제작시 적절한 증착 온도를 유지할 수 있다. 또한, 승화 온도가 높아 승화 정제 방법으로 고순도화가 가능하며, 유기 발광 소자 제조시 증착용 성막 장치 또는 유기 발광 소자에 오염을 일으키지 않는다.
도 1은 기판(1), 양극(2), 발광층(3) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.
<부호의 설명>
1: 기판
2: 양극
3: 발광층
4: 음극
5: 정공주입층
6: 정공수송층
7: 발광층
8: 전자수송층
이하 본 명세서에 대하여 더욱 상세히 설명한다.
본 명세서의 일 실시상태는 상기 화학식 1로 표시되는 화합물을 제공한다.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 지연 형광 화합물이다.
일반적인 유기발광소자에서 일중항과 삼중항에서 생성되는 엑시톤의 수가 25:75(일중항: 삼중항)의 비율로 생성되며, 엑시톤 이동에 따른 발광 형태에 따라 형광 발광, 인광 발광 및 열활성화 지연형광 발광으로 나눌 수 있다. 상기 인광 발광의 경우 삼중항 여기 상태(excited state)의 엑시톤이 바닥 상태(ground state)로 이동하여 발광하는 것을 의미하고, 상기 형광 발광의 경우 일중항 여기 상태(excited state)의 엑시톤이 바닥 상태(ground state)로 이동하여 발광하게 되는 것을 의미하며, 상기 열활성화 지연형광 발광은 삼중항 여기 상태(excited state)로부터 일중항 여기 상태(excited state)로 역계간전이가 유도되고, 일중항 여기 상태의 엑시톤이 바닥 상태(Ground State)로 이동하여 형광 발광을 일으키는 것을 의미한다.
상기 열활성화 지연형광 발광은 발광스펙트럼의 피크 위치가 형광과 같지만 감쇠시간(decay time)이 길다는 점에서 형광 발광과 구분되며, 감쇠시간은 길지만 발광스펙트럼의 피크 위치가 인광 스펙트럼과 S1-T1 에너지의 차이만큼 다르다는 점에서 인광과 구별된다. 이때, S1은 일중항(singlet) 에너지 준위이며, T1는 삼중항(triplet) 에너지 준위이다.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물의 일중항(singlet) 에너지 준위와 삼중항(triplet) 에너지 준위의 차(△EST)는 0 eV 이상 0.3 eV 이하이고, 바람직하게는 0 eV 이상 0.2 eV 이하이다. 상기 화학식 1로 표시되는 화합물의 일중항(singlet) 에너지 준위와 삼중항(triplet) 에너지 준위의 차가 상기 범위를 만족하는 경우, 삼중항에서 생성된 엑시톤이 역계간전이(RISC)에 의해 일중항으로 이동하는 비율 및 속도가 증가하여 삼중항에 엑시톤이 머무는 시간이 줄어들게 되므로 유기발광소자의 효율 및 수명이 증가하는 이점이 있다.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 시클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 및 헤테로 고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오쏘(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한"기로 해석될 수 있다. 또는, 카바졸에서 N에 치환된 치환기와 카바졸의 1번 탄소 또는 8번 탄소의 치환기가 "인접한 기"로 해석될 수 있다.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 40의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.
본 명세서에 있어서, 실릴기는 -SiRaRbRc의 화학식으로 표시될 수 있고, 상기 Ra, Rb 및 Rc는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다.
본 명세서에 있어서, 붕소기는 -BRaRb의 화학식으로 표시될 수 있고, 상기 Ra 및 Rb는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 붕소기는 구체적으로 디메틸붕소기, 디에틸붕소기, t-부틸메틸붕소기, 디페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.
본 명세서에 기재된 알킬기, 알콕시기 및 그 외 알킬기 부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 40이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되지 않는다.
본 명세서에 있어서, 알킬아민기는 탄소수는 특별히 한정되지 않으나, 1 내지 40인 것이 바람직하다. 알킬아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 페닐나프틸아민기, 디톨릴아민기, 페닐톨릴아민기, 트리페닐아민기 등이 있으나, 이들에만 한정되는 것은 아니다.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 2 이상의 아릴기를 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식아릴기와 다환식 아릴기를 동시에 포함할 수 있다.
아릴 아민기의 구체적인 예로는 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 페닐 나프틸아민기, 디톨릴아민기, 페닐톨릴아민기 및 트리페닐아민기 등이 있으나, 이에 한정되는 것은 아니다.
본 명세서에 있어서, 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 치환 또는 비치환된 디헤테로아릴아민기, 또는 치환 또는 비치환된 트리헤테로아릴아민기가 있다. 상기 헤테로아릴아민기 중의 헤테로아릴기는 단환식 헤테로 고리기일 수 있고, 다환식 헤테로 고리기일 수 있다. 상기 2 이상의 헤테로 고리기를 포함하는 헤테로아릴아민기는 단환식 헤테로 고리기, 다환식 헤테로 고리기, 또는 단환식 헤테로 고리기와 다환식 헤테로 고리기를 동시에 포함할 수 있다.
본 명세서에 있어서, 아릴헤테로아릴아민기는 아릴기 및 헤테로 고리기로 치환된 아민기를 의미한다.
본 명세서에 있어서, 아릴포스핀기의 예로는 치환 또는 비치환된 모노아릴포스핀기, 치환 또는 비치환된 디아릴포스핀기, 또는 치환 또는 비치환된 트리아릴포스핀기가 있다. 상기 아릴포스핀기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴포스핀기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다.
상기 플루오레닐기가 치환되는 경우, , 등의 스피로플루오레닐기, (9,9-디메틸플루오레닐기), 및 (9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.
본 명세서에 있어서, 헤테로 고리기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 헤테로 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로 고리기의 탄소수는 1 내지 30이다. 헤테로 고리기의 예로는 예로는 피리딜기, 피롤기, 피리미딜기, 피리다지닐기, 퓨라닐기, 티오페닐기, 이미다졸기, 피라졸기, 옥사졸기, 이소옥사졸기, 티아졸기, 이소티아졸기, 트리아졸기, 옥사디아졸기, 티아디아졸기, 디티아졸기, 테트라졸기, 피라닐기, 티오피라닐기, 피라지닐기, 옥사지닐기, 티아지닐기, 디옥시닐기, 트리아지닐기, 테트라지닐기, 퀴놀리닐기, 이소퀴놀리닐기, 퀴놀릴기, 퀴나졸리닐기, 퀴녹살리닐기, 나프티리디닐기, 아크리딜기, 크산테닐기, 페난트리디닐기, 디아자나프탈레닐기, 트리아자인데닐기, 인돌기, 인돌리닐기, 인돌리지닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 벤조티아졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티오펜기, 벤조퓨라닐기, 디벤조티오페닐기, 디벤조퓨라닐기, 카바졸기, 벤조카바졸기, 디벤조카바졸기, 인돌로카바졸기, 인데노카바졸기, 페나지닐기, 이미다조피리딘기, 페녹사지닐기, 페난트리딘기, 페난트롤린(phenanthroline)기, 페노티아진(phenothiazine)기, 이미다조피리딘기, 이미다조페난트리딘기 등이 있으나, 이들에만 한정되는 것은 아니다.
본 명세서에 있어서, 헤테로 고리기의 고리를 구성하는 원자수는 3 내지 25이다. 또 하나의 실시상태에 있어서, 헤테로 고리기의 고리를 구성하는 원자수는 5 내지 17이다.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로 고리기에 관한 설명이 적용될 수 있다.
본 명세서에 있어서, 아릴옥시기, 아릴티옥시기, 아릴술폭시기, 아릴포스핀기, 아르알킬기, 아랄킬아민기, 아르알케닐기, 알킬아릴기, 아릴아민기, 아릴헤테로아릴아민기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.
본 명세서에 있어서, 알킬티옥시기, 알킬술폭시기, 아르알킬기, 아랄킬아민기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기에 관한 설명이 적용될 수 있다.
본 명세서에 있어서, 헤테로아릴기, 헤테로아릴아민기, 아릴헤테로아릴아민기 중 헤테로아릴기는 전술한 헤테로 고리기에 관한 설명이 적용될 수 있다.
본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기에 관한 설명이 적용될 수 있다.
본 명세서에 있어서, 아릴렌기는 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다.
본 명세서에 있어서, 헤테로아릴렌기는 2가기인 것을 제외하고는 전술한 헤테로 고리기에 관한 설명이 적용될 수 있다.
본 명세서에 있어서, 인접하는 기와 서로 결합하여 고리를 형성한다는 의미는 인접하는 기와 서로 결합하여 치환 또는 비치환된 지방족 탄화수소 고리; 치환 또는 비치환된 방향족 탄화수소 고리; 치환 또는 비치환된 지방족 헤테로 고리; 치환 또는 비치환된 방향족 헤테로 고리; 또는 이들의 축합고리를 형성하는 것을 의미한다.
본 명세서에 있어서, 지방족 탄화수소 고리란 방향족이 아닌 고리로서 탄소와 수소 원자로만 이루어진 고리를 의미한다. 구체적으로, 지방족 탄화수소 고리의 예로는 시클로프로판, 시클로부탄, 시클로부텐, 시클로펜탄, 시클로펜텐, 시클로헥산, 시클로헥센, 1,4-시클로헥사디엔, 시클로헵탄, 시클로헵텐, 시클로옥탄, 시클로옥텐 등이 있으나, 이들에만 한정되는 것은 아니다.
본 명세서에 있어서, 방향족 탄화수소 고리란 탄소와 수소 원자로만 이루어진 방향족의 고리를 의미한다. 구체적으로, 방향족 탄화수소 고리의 예로는 벤젠, 나프탈렌, 안트라센, 페난트렌, 페릴렌, 플루오란텐, 트리페닐렌, 페날렌, 피렌, 테트라센, 크라이센, 펜타센, 플루오렌, 인덴, 아세나프틸렌, 벤조플루오렌, 스피로플루오렌 등이 있으나 이들에만 한정되는 것은 아니다.
본 명세서에 있어서, 지방족 헤테로 고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 구체적으로, 지방족 헤테로 고리의 예로는 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인 등이 있으나 이들에만 한정되는 것은 아니다. 본 명세서에 있어서, 방향족 헤테로 고리란 헤테로원자 중 1개 이상을 포함하는 방향족 고리를 의미한다. 구체적으로, 방향족 헤테로 고리의 예로는 피리딘, 피롤, 피리미딘, 피리다진, 퓨란, 티오펜, 이미다졸, 피라졸, 옥사졸, 이소옥사졸, 티아졸, 이소티아졸, 트리아졸, 옥사디아졸, 티아디아졸, 디티아졸, 테트라졸, 피란, 티오피란, 디아진, 옥사진, 티아진, 다이옥신, 트리아진, 테트라진, 이소퀴놀린, 퀴놀린, 퀴놀, 퀴나졸린, 퀴녹살린, 나프티리딘, 아크리딘, 페난트리딘, 디아자나프탈렌, 트리아자인덴, 인돌, 인돌리진, 벤조티아졸, 벤즈옥사졸, 벤즈이미다졸, 벤조티오펜, 벤조퓨란, 디벤조티오펜, 디벤조퓨란, 카바졸, 벤조카바졸, 디벤조카바졸, 페나진, 이미다조피리딘, 페녹사진, 페난트리딘, 인돌로카바졸, 인데노카바졸 등이 있으나, 이들에만 한정되는 것은 아니다.
본 명세서에 있어서, 상기 지방족 탄화수소 고리, 방향족 탄화수소 고리, 지방족 헤테로 고리 및 방향족 헤테로 고리는 단환 또는 다환일 수 있다.
본 명세서의 일 실시상태에 따르면, 상기 R1은 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 또는 치환 또는 비치환된 탄소수 3 내지 60의 시클로알킬기이다.
본 명세서의 일 실시상태에 따르면, 상기 R1는 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기이다.
본 명세서의 일 실시상태에 따르면, 상기 R1는 치환 또는 비치환된 탄소수 1 내지 15의 알킬기; 또는 치환 또는 비치환된 탄소수 3 내지 15의 시클로알킬기이다.
본 명세서의 일 실시상태에 따르면, 상기 R1는 할로겐기로 치환 또는 비치환된 메틸기; 할로겐기로 치환 또는 비치환된 에틸기; 카바졸기로 치환 또는 비치환된 이소프로필기; 카바졸기로 치환 또는 비치환된 t-부틸기 또는 치환 또는 비치환된 시클로헥산기이다.
본 명세서의 일 실시상태에 따르면, 상기 R 및 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.
본 명세서의 일 실시상태에 따르면, 상기 R 및 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.
본 명세서의 일 실시상태에 따르면, 상기 R 및 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.
본 명세서의 일 실시상태에 따르면, 상기 R 및 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 15의 알킬기; 치환 또는 비치환된 탄소수 6 내지 15의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 15의 헤테로고리기이다.
본 명세서의 일 실시상태에 따르면, 상기 R 및 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 15의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 15의 아릴기이다.
본 명세서의 일 실시상태에 따르면, 상기 R은 치환 또는 비치환된 페닐기이다.
본 명세서의 일 실시상태에 따르면, 상기 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 또는 치환 또는 비치환된 탄소수 1 내지 15의 알킬기이다.
본 명세서의 일 실시상태에 따르면, 상기 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 할로겐기로 치환 또는 비치환된 메틸기; 치환 또는 비치환된 이소프로필기 또는 치환 또는 비치환된 t-부틸기이다.
본 명세서의 일 실시상태에 따르면, 상기 R5 및 R6은 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.
본 명세서의 일 실시상태에 따르면, 상기 R5 및 R6은 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 또는 치환 또는 비치환된 알킬기이다.
본 명세서의 일 실시상태에 따르면, 상기 R5 및 R6은 각각 독립적으로, 수소; 중수소; 할로겐기; 할로겐기로 치환된 알킬기; 또는 시아노기이다.
본 명세서의 일 실시상태에 따르면, 상기 R5 및 R6은 각각 독립적으로, 수소; 중수소; 불소기; 불소기로 치환된 알킬기; 또는 시아노기이다.
본 명세서의 일 실시상태에 따르면, 상기 R5 및 R6은 시아노기이다.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2로 표시된다.
[화학식 2]
화학식 2에 있어서,
X, R1 내지 R3, R5, R6, a, c, d, f 및 g의 정의는 상기와 같다.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 3 또는 4로 표시된다.
[화학식 3]
[화학식 4]
화학식 3 및 4에 있어서,
X, Y, R1 내지 R6, a 및 c 내지 g의 정의는 상기와 같다.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 5 또는 6으로 표시된다.
[화학식 5]
[화학식 6]
화학식 5 및 6에 있어서,
X, Y, R1 내지 R6, a 및 c 내지 g의 정의는 상기와 같다.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 7 또는 8로 표시된다.
[화학식 7]
[화학식 8]
화학식 7 및 8에 있어서,
X, Y, R1 내지 R6, a 및 c 내지 g의 정의는 상기와 같다.
본 발명의 일 실시상태에 있어서, 상기 화학식 1의 화합물은 하기 화합물들 중에서 선택된 어느 하나일 수 있다.
본 발명에서는 상기와 같이 코어 구조에 다양한 치환기를 도입함으로써 다양한 에너지 밴드갭을 갖는 화합물을 합성할 수 있다. 통상 에너지 밴드갭이 큰 코어 구조에 치환기를 도입하여 에너지 밴드갭을 조절하는 것은 용이하나, 코어 구조가 에너지 밴드갭이 작은 경우에는 치환기를 도입하여 에너지 밴드갭을 크게 조절하기 어렵다. 또한, 본 발명에서는 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 화합물의 HOMO 및 LUMO 에너지 준위도 조절할 수 있다.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공주입층 물질, 정공수송용 물질, 발광층 물질 및 전자수송층 물질에 주로 사용되는 치환기를 상기 코어 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 합성할 수 있다.
따라서, 본 발명자들은 이와 같은특징을 갖는 화학식 1의 화합물은 유기 발광 소자용 재료, 특히 정공주입층, 정공수송층, 전자저지층 또는 전하생성층에 적용시, 구동 전압의 저전압화나 장수명화를 실현할 수 있다는 것을 밝혀내었다. 또한, F4TCNQ와 같이 분자량이 작고 승화성이 높은 재료에 비하여 증착이 용이하고, HAT-CN에 비하여 전극 또는 인접 유기물층과 안정적인 계면을 형성할 수 있다.
전술한 화학식 1의 화합물은 당기술분야에 알려져 있는 재료와 반응 조건을 이용하여 제조될 수 있다.
또한, 본 발명에 따른 유기 발광 소자는 제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것을 특징으로 한다.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하며, 상기 발광층은 도펀트를 포함하며, 상기 도펀트는 본 명세서의 일 실시상태에 따른 화합물을 포함한다.
본 명세서의 일 실시상태에 따르면, 상기 발광층의 발광 물질은 정공 수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 상기 발광층은 전술한 지연 형광 재료를 발광층의 도펀트로서 포함하고, 여기 홑겹항에너지 및 여기 삼중항 에너지의 적어도 어느 하나가 전술한 지연 형광 재료의 발광 재료보다 높은 값을 가지고, 정공 수송능, 전자 수송능을 가지며, 또한 발광의 장파장화를 방지하고, 높은 유리전이 온도를 가지는 유기 화합물을 호스트로서 포함할 수 있다.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 호스트를 포함한다.
본 명세서의 일 실시상태에 따르면, 호스트의 삼중항(triplet) 에너지 준위는 2.5 eV 이상이고, 바람직하게는 2.7 eV 이상 3.1 eV 이하일 수 있다. 상기 호스트의 삼중항(triplet) 에너지 준위가 상기 범위를 만족하는 경우, 호스트 엑시톤 에너지가 도펀트로 효율적으로 전달되고, 호스트 또는 도펀트의 삼중항/단일항 엑시톤과 주변의 정공(또는 전자)-폴라론의 상호작용에 의한 엑시톤 소광이 최소화된다. 이에 따라 전기-산화 및 광-산화에 의하여 발광다이오드 소자의 수명이 저하되는 방지할 수 있으므로, 장수명의 발광 소자를 구현할 수 있다.
또한, 본 명세서의 일 실시상태에 따르면 상기 유기물층은 호스트를 포함하며, 상기 호스트는 하기 구조들 중 적어도 하나이고, 이에 한정되지 않는다.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 명세서의 유기 발광 소자는 유기물층으로서 발광층 외에, 정공주입층, 정공버퍼층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층 중 적어도 한 층을 더 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.
일 예에 따르면, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 노말 구조(normal type)의 유기 발광 소자일 수 있다. 다른 예에 따르면, 상기 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 상기 화학식 1의 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공주입층, 정공수송층, 발광층 및 전자수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.
또한, 상기 화학식 1의 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다.
또 하나의 실시상태에 있어서, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.
상기 유기 발광 소자는 예컨대 하기와 같은 적층 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.
(1) 양극/정공수송층/발광층/음극
(2) 양극/정공주입층/정공수송층/발광층/음극
(3) 양극/정공주입층/정공버퍼층/정공수송층/발광층/음극
(4) 양극/정공수송층/발광층/전자수송층/음극
(5) 양극/정공수송층/발광층/전자수송층/전자주입층/음극
(6) 양극/정공주입층/정공수송층/발광층/전자수송층/음극
(7) 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극
(8) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층//음극
(9) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/전자주입층 /음극
(10) 양극/ 정공수송층/전자저지층/발광층/전자수송층/ 음극
(11) 양극/ 정공수송층/전자저지층/발광층/전자수송층/전자주입층 /음극
(12) 양극/정공주입층/정공수송층/전자저지층/발광층/전자수송층/음극
(13) 양극/정공주입층/정공수송층/전자저지층/발광층/전자수송층/전자주입 층/음극
(14) 양극/정공수송층/발광층/정공저지층/전자수송층/음극
(15) 양극/정공수송층/발광층/ 정공저지층/전자수송층/전자주입층/음극
(16) 양극/정공주입층/정공수송층/발광층/ 정공저지층/전자수송층/음극
(17) 양극/정공주입층/정공수송층/발광층/ 정공저지층/전자수송층/전자주입 층/음극
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공수송층에 포함될 수 있다.
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 상기 정공주입층 또는 정공수송층에 포함될 수 있다.
양극(2)은 정공을 주입하는 전극으로 일함수가 높은 ITO(Indium Tin Oxide), IZO(Indium Zinc Oxide) 또는 ZnO(Zinc Oxide) 중 어느 하나일 수 있다. 또한, 상기 양극(2)이 반사 전극일 경우에 양극(2)은 ITO, IZO 또는 ZnO 중 어느 하나로 이루어진 층 하부에 알루미늄(Al), 은(Ag) 또는 니켈(Ni) 중 어느 하나로 이루어 진 반사층을 더 포함할 수 있다.
정공주입층(5)은 양극(2)으로부터 발광층(7)으로 정공의 주입을 원활하게 하는 역할을 할 수 있다. 정공주입층(5)의 두께는 1 내지 150nm일 수 있다. 여기서, 상기 정공주입층(5)의 두께가 1nm 이상이면, 정공주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 150nm 이하이면, 정공주입층(5)의 두께가 너무 두꺼워 정공의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다. 그외 정공주입층 재료로는 당기술분야에 알려져 있는 정공주입 재료를 사용할 수 있다. 예컨대, 정공주입층 재료로서 CuPc(cupper phthalocyanine), PEDOT(poly(3,4)-ethylenedioxythiophene), PANI(polyaniline) 및 NPD(N,N-dinaphthyl-N,N'-diphenyl benzidine)로 이루어진 군에서 선택된 어느 하나 이상이 사용될 수 있으나, 이에 한정되는 것은 아니다.
정공수송층(6)은 정공의 수송을 원활하게 하는 역할을 할 수 있다. 정공수송층 재료로는 당기술분야에 알려져 있는 정공수송 재료를 사용할 수 있다. 예컨대, 정공수송층(6)은 NPD(N,N-dinaphthyl-N,N'-diphenylbenzidine), TPD(N,N'-bis-(3-methylphenyl)-N,N'-bis-(phenyl)-benzidine), s-TAD 및 MTDATA(4,4',4"- Tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine)로 이루어진 군에서 선택된 어느 하나 이상으로 이루 어질 수 있으나 이에 한정되지 않는다. 예컨대 정공수송층 재료로서 트라이아졸 유도체, 옥사다이아졸 유도체, 이미다졸 유도체, 폴리아릴알케인 유도체, 피라졸린 유도체 및 피라졸론 유도체, 페닐렌다이아민 유도체, 아릴아민 유도체, 아미노 치환 칼콘 유도체, 옥사졸 유도체, 스타이릴안트라센 유도체, 플루오렌온 유도체, 하이드라존 유도체, 스틸벤 유도체, 실라제인 유도체, 폴리실레인계, 아닐린계 공중합체, 도전성 고분자 올리고머(특히 싸이오펜 올리고머) 등을 들 수 있다.
정공주입층과 정공수송층 사이에 추가로 정공버퍼층이 구비될 수 있다. 정공버퍼층은 당 기술분야에 알려져 있는 정공주입 또는 수송 재료를 포함될 수 있다.
정공수송층과 발광층 사이에 전자저지층이 구비될 수 있으며, 상기 화학식 1의 화합물 또는 당기술분야에 알려져 있는 재료가 사용될 수 있다.
전자수송층과 발광층 사이에 정공저지층이 구비될 수 있으며, 당기술분야에 알려져 있는 재료가 사용될 수 있다.
전자수송층(8)은 전자의 수송을 원활하게 하는 역할을 할 수 있다. Alq3(tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq와 같은 당기술분야에 알려진 재료가 사용될 수 있다. 상기 전자수송층(8)의 두께는 1 내지 50nm일 수 있다. 여기서, 상기 전자수송층(8)의 두께가 1nm 이상이면, 전자수송 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면, 전자수송층(8)의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.
상기 전자주입층은 전자의 주입을 원활하게 하는 역할을 할 수 있다. Alq3(tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro-PBD, BAlq 또는 SAlq과 같은 당기술분야에 알려져 있는 유기물이나 착체 또는 금속화합물로 이루어질 수 있다. 금속화합물로는 금속 할로겐화물이 사용될 수 있으며, 예컨대 LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2 및 RaF2 등이 사용될 수 있다. 상기 전자주입층의 두께는 1 내지 50nm일 수 있다. 여기서, 상기 전자주입층의 두께가 1nm 이상이면, 전자주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면, 전자주입층의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.
상기 음극(4)은 전자주입 전극으로, 일함수가 낮은 마그네슘(Mg), 칼슘(Ca), 알루미늄(Al), 은(Ag) 또는 이들의 합금으로 이루어질 수 있다. 여기서, 음극(4)은 유기전계발광소자가 전면 또는 양면발광구조일 경우, 빛을 투과할 수 있을 정도로 얇은 두께로 형성할 수 있으며, 유기전계발광소자가 배면발광구조일 경우, 빛을 반사시킬 수 있을 정도로 두껍게 형성할 수 있다.
본 명세서의 일 실시상태에 따른 발광층(3)은 상기 화학식 1의 화합물을 포함할 수 있다. 이 경우, 발광층(3)은 상기 화학식 1의 화합물만으로 이루어질 수도 있으나, 상기 화학식 1의 화합물은 당기술분야에 알려져 있는 다른 발광층 재료에 혼합 또는 도핑된 상태로 존재할 수 있다. 상기 화학식 1의 화합물은 발광층의 100%를 차지할 수도 있으나, 0.1 내지 50 중량%로 도핑될 수도 있다.
또 하나의 실시상태에 따르면 상기 유기물층은 2층 이상의 발광층을 포함하고, 상기 2층의 발광층 사이에 구비된 상기 화학식 1의 화합물을 포함하는 전하생성층(charge generation layer)을 포함할 수 있다. 이 때, 상기 발광층 중 하나는 청색을 발광하고, 다른 하나는 노란색 발광을 하도록 함으로써 백색 발광을 하는 유기 발광 소자를 제작할 수 있다. 상기 발광층과 양극 또는 음극 사이, 상기 발광층과 전하생성층 사이에는 전술한 정공주입층, 정공버퍼층, 정공수송층, 전자저지층, 정공저지층, 전자수송층, 전자주입층과 같은 1층 이상의 유기물층이 더 포함될 수 있다.
상기 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.
본 발명에 따른 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기 발광 소자에 적용되는 것과 유사한 원리로 작용할 수 있다.
상기 화학식 1의 화합물의 제조방법 및 이들을 이용한 유기 발광 소자의 제조는 이하의 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.
<제조예>
상기 화학식 1로 표시되는 화합물은 하기와 같이 치환된 다이브로모다이플루오로벤젠에 치환된 페닐 보로닉액시드를 스즈키 반응으로 도입하고 SnAr 반응을 통해 최종적으로 함질소 화합물을 도입하여 제조할 수 있다. 하기 과정을 통하여 구체예 상의 화합물들을 합성하였다.
제조예 1-1: 화합물 1-A의 합성
(4-시아노페닐)보로닉액시드 30g(100mmol), 1,3-다이브로모-4,6-다이플루오로-2,5-다이메틸벤젠 50mmol, 테트라하이드로퓨란 200mL 및 물 100mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(600mmol) 및 테트라키스트라이페닐포스핀팔라듐(1mmol)을 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액에서 유기층을 추출한 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 1-A (31g)을 얻었다(수율 90%).
MS[M+H]+ = 345
제조예 1-2: 화합물 1-B의 합성
(4-시아노페닐)보로닉액시드 30g(100mmol), (2,6-다이브로모-3,5-다이플루오로-1,4-페닐렌)다이사이클로헥세인 50mmol, 테트라하이드로퓨란 200mL 및 물 100mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(600mmol) 및 테트라키스트라이페닐포스핀팔라듐(1mmol)을 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액에서 유기층을 추출한 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 1-B (42.3g)을 얻었다(수율 88%).
MS[M+H]+ = 481
제조예 1-3: 화합물 1-C의 합성
(4-시아노페닐)보로닉액시드 30g(100mmol), 2,4-다이브로모-3-사이클로헥실-1,5-다이플루오로벤젠 50mmol, 테트라하이드로퓨란 200mL 및 물 100mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(600mmol) 및 테트라키스트라이페닐포스핀팔라듐(1mmol)을 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액에서 유기층을 추출한 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 1-C (34.7g)을 얻었다(수율 87%).
MS[M+H]+ = 399
제조예 1-4: 화합물 1-D의 합성
(4-시아노페닐)보로닉액시드 30g(100mmol), 1,3-다이브로모-4,6-다이플루오로-2,5-다이아이소프로필벤젠 50mmol, 테트라하이드로퓨란 200mL 및 물 100mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(600mmol) 및 테트라키스트라이페닐포스핀팔라듐(1mmol)을 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액에서 유기층을 추출한 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 1-D (35.6g)을 얻었다(수율 89%).
MS[M+H]+ = 401
제조예 1-5: 화합물 1-E의 합성
(4-시아노페닐)보로닉액시드 30g(100mmol), 1,3-다이브로모-2,5-다이-터트-뷰틸-4,6-다이플루오로벤젠 50mmol, 테트라하이드로퓨란 200mL 및 물 100mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(600mmol) 및 테트라키스트라이페닐포스핀팔라듐(1mmol)을 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액에서 유기층을 추출한 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 1-E (38.6g)을 얻었다(수율 90%).
MS[M+H]+ = 429
제조예 1-6: 화합물 1-F의 합성
(4-시아노페닐)보로닉액시드 30g(100mmol), 1,3-다이브로모-2,5-다이플루오로-4,6-다이아이소프로필벤젠 50mmol, 테트라하이드로퓨란 200mL 및 물 100mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(600mmol) 및 테트라키스트라이페닐포스핀팔라듐(1mmol)을 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액에서 유기층을 추출한 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 1-F (34.8g)을 얻었다(수율 87%).
MS[M+H]+ = 401
제조예 2-1: 화합물 1 의 합성
1-A 18.7 g(54.3 mmol), 9H-카바졸 109 mmol 및 디메틸포름아미드(DMF) 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 1 (28.8 g)을 얻었다(수율 83%).
MS[M+H]+ = 639
제조예 2-2: 화합물 2 의 합성
1-B 26.1 g(54.3 mmol), 9H-카바졸 109 mmol 및 디엠에프 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 2 (33.7 g)을 얻었다(수율 80%).
MS[M+H]+ = 775
제조예 2-3: 화합물 3 의 합성
1-B 26.1 g(54.3 mmol), 3,6-다이-터트-뷰틸-9H-카바졸 109 mmol 및 디엠에프 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 3 (42.3 g)을 얻었다(수율 78%).
MS[M+H]+ = 999
제조예 2-4: 화합물 4 의 합성
1-C 21.6 g(54.3 mmol), 9H-카바졸 109 mmol 및 디엠에프 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 4 (28.2 g)을 얻었다(수율 75%).
MS[M+H]+ = 693
제조예 2-5: 화합물 5 의 합성
1-D 21.7 g(54.3 mmol), 3,6-다이-터트-뷰틸-9H-카바졸 109 mmol 및 디엠에프 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 5 (38.4 g)을 얻었다(수율 77%).
MS[M+H]+ = 919
제조예 2-6: 화합물 6 의 합성
1-D 21.7 g(54.3 mmol), 5H-벤조퓨로[3,2-c]카바졸 109 mmol 및 디엠에프 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 6 (34.7 g)을 얻었다(수율 73%).
MS[M+H]+ = 875
제조예 2-7: 화합물 7 의 합성
1-D 21.7 g(54.3 mmol), 5-페닐-5,12-다이하이드로인돌로[3,2-a]카바졸 109 mmol 및 디엠에프 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 7 (42.3 g)을 얻었다(수율 76%).
MS[M+H]+ = 1028
제조예 2-8: 화합물 8 의 합성
1-E 23.3 g(54.3 mmol), 10H-페노사이아진 109 mmol 및 디엠에프 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 동안 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 8 (31.6 g)을 얻었다(수율 74%).
MS[M+H]+ = 787
제조예 2-9: 화합물 9 의 합성
1-F 21.7 g(54.3 mmol), 9H-카바졸 109 mmol 및 디엠에프 150mL를 혼합하고 60℃로 가열하였다. 포타슘카보네이트(271.5 mmol)를 첨가하여 리플럭스 상태로 3시간 교반하였다. 반응 후 실온으로 되돌린 반응 용액을 물에 역침전하여 고체를 얻은 후, 클로로포름과 헥산으로 2회 재결정을 실시하여, 화합물 9 (30.2 g)을 얻었다(수율 80%).
MS[M+H]+ = 695
상기 화합물 1 내지 9 이외에도, 상기 제조예와 동일한 반응을 이용하여 치환기 종류를 다양하게 도입하여 기타 화학식 1로 표시되는 화합물을 합성할 수 있다.
<비교예 1>
본 실시예에 있어서, 본 명세서의 일 실시상태에 따른 화학식 1로 표시되는 화합물을 삼중항 에너지 값이 2.9eV인 호스트 재료(m-CBP)와 함께 발광층에 포함하여 유기 발광 소자를 제조하고, 특성을 평가하였다.
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다. 이렇게 준비된 ITO 투명 전극 위에 각 박막을 진공 증착법으로 진공도 5×10-4 ㎩로 적층하였다. 먼저, ITO 상에 하기 화합물 HAT-CN을 500Å의 두께로 열 진공 증착하여 정공 주입층을 형성하였다.
상기 정공 주입층 위에 정공을 수송하는 물질인 하기 화합물 4-4'-비스[N-(1-나프틸)-N-페닐아미노]비페닐(NPB)(300Å)를 진공 증착하여 정공 수송층을 형성하였다.
상기 정공 수송층 위에 막 두께 100Å으로 하기 화합물 N-([1,1'-비스페닐]-4-yl)-N-(4-(11-([1,1'-비페닐]-4-yl)-11H-벤조[a]카바졸-5-yl)페닐)-[1,1'-비페닐]-4-아민(EB1)(100Å)를 진공 증착하여 전자 저지층을 형성하였다.
이어서, 상기 전자 저지층 위에 막 두께 300Å으로 아래와 같은 m-CBP와 화합물 4CzIPN을 70:30의 중량비로 진공 증착하여 발광층을 형성하였다.
상기 발광층 위에 막 두께 100Å으로 화합물 HB1을 진공 증착하여 정공 저지층을 형성하였다.
상기 정공 저지층 위에 하기 화합물 ET1과 화합물 LiQ(Lithium Quinolate)를 1:1의 중량비로 진공 증착하여 300Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 12Å두께로 리튬플로라이드(LiF)와 2,000Å 두께로 알루미늄을 순차적으로 증착하여 음극을 형성하였다.
상기의 과정에서 유기물의 증착속도는 0.4 Å/sec 내지 0.7 Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 torr 내지 5×10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.
<실험예 1 내지 9>
상기 비교예 1에서 화합물 4CzIPN 대신 하기 표 1의 화합물을 사용한 것을 제외하고는 비교예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.
<비교예 2 내지 7>
상기 비교예 1에서 화합물 4CzIPN 대신 하기 T1 내지 T6의 화합물을 사용한 것을 제외하고는 비교예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.
실험예 1 내지 9, 비교예 1 내지 7에 의해 제작된 유기 발광 소자에 전류를 인가하였을 때, 하기 [표 1]의 결과를 얻었다.
구분 | 화합물(발광층) | 전압(V@10mA/cm2) | 효율(cd/A@10mA/cm2) | 색좌표(x,y) |
비교예 1 | 4CzIPN | 4.5 | 13 | (0.32, 0.62) |
실험예 1 | 1 | 4.0 | 20 | (0.31, 0.63) |
실험예 2 | 2 | 4.1 | 19 | (0.33, 0.62) |
실험예 3 | 3 | 4.0 | 19 | (0.32, 0.62) |
실험예 4 | 4 | 4.1 | 20 | (0.32, 0.66) |
실험예 5 | 5 | 4.1 | 21 | (0.31, 0.67) |
실험예 6 | 6 | 4.0 | 19 | (0.32, 0.68) |
실험예 7 | 7 | 4.0 | 21 | (0.32, 0.67) |
실험예 8 | 8 | 4.1 | 20 | (0.31, 0.68) |
실험예 9 | 9 | 3.9 | 20 | (0.32, 0.66) |
비교예 2 | T1 | 4.6 | 3 | (0.13, 0.23) |
비교예 3 | T2 | 4.4 | 4 | (0.15, 0.38) |
비교예 4 | T3 | 4.4 | 8 | (0.17, 0.49) |
비교예 5 | T4 | 4.6 | 3 | (0.23, 0.27) |
비교예 6 | T5 | 4.2 | 11 | (0.27, 0.59) |
비교예 7 | T6 | 4.2 | 12 | (0.28, 0.58) |
상기 표 1에서 보는 바와 같이, 상기 화학식 1의 구조를 코어로 하는 화합물을 사용한 실험예 1 내지 9의 소자는 모두 4CzIPN을 사용한 소자보다 전압이 낮고, 효율이 올라가는 결과를 얻었다.또한, 비교예 2 내지 비교예 7의 소자와 본원 실시예를 비교해보면 본원 실시예들의 구조가 전압, 효율 면에서 특성이 모두 향상됨을 알 수 있었다.상기 표 1의 결과와 같이, 본 발명에 따른 화합물은 발광 능력이 우수하고 색순도가 높아 지연형광 유기 발광 소자에 적용 가능함을 확인할 수 있었다.
<실시예 2>
HOMO 및 LUMO 에너지 준위는 측정 화합물을 5mM, 전해질을 0.1M 농도로 다이메틸폼아마이드(dimethylformamide, DMF)에 용해시키고 CV기기 측정을 통해 산화, 환원 전위를 확인하여 페로센 화합물을 기준으로 비교하여 확인하였다.
HOMO 에너지 준위의 측정
화합물의 HOMO 에너지 준위와 상기 LUMO 에너지 준위는 측정 화합물이 5mM 농도, 전해질이 0.1M 농도로 용해된 다이메틸폼아마이드(dimethylformamide, DMF) 용액의 산화, 환원 전위를 페로센 화합물을 기준으로 비교하는 순환 전압 전류법(cyclic voltammetry; CV)으로 측정하였다. 구체적인 측정 조건은 다음과 같다.
CV 기기: Ivium Tech사의 Iviumstat
측정 용액: 측정 화합물이 5mM의 농도 및 전해질(KNO3, Aldrich 사)이 0.1M의 농도로 용해된 다이메틸폼아마이드(DMF) 용액
작업 전극(Working Electrode): 카본 전극
기준 전극(Reference Electorde): Al/AgCl 전극
상대 전극(Counter Electrode): 백금 전극
측정 온도: 25℃
Scan rate: 50mV/S
HOMO 에너지 준위(E(HOMO)) 및 LUMO 에너지 준위(E(LUMO))는 하기의 식을 통하여 계산하였다.
E(HOMO)=[Vsolvent-(Eonset ox-E1/2(solvent))eV
E(LUMO)=[Vsolvent-(Eonset red-E1/2(solvent))eV
상기 식에 있어서, Vsolvent는 용매의 에너지 준위이고, E1/2(solvent)는 용매의 반파 준위이고, Eonset ex는 산화가 시작되는 지점이고, Eonset red는 환원이 시작되는 지점이다.
삼중항 에너지의 측정
삼중항 에너지(T1)는 수명이 긴 삼중항 엑시톤의 특성을 이용해 극저온 상태에서 측정하였다. 구체적으로, 화합물을 톨루엔 용매에 용해하여 10-5M의 농도의 시료를 제조한 후, 상기 시료를 석영 키트에 담아 77K로 냉각시키고, 300nm 광원을 인광 측정용 시료에 조사하여 파장을 변경하면서 인광 스펙트럼을 측정한다. 스펙트럼의 측정에는 분광광도계(FP-8600 spectrophotometer, JASCO사)를 이용하였다.
인광 스펙트럼의 세로축은 인광 강도로, 가로축은 파장으로 하였다. 인광 스펙트럼의 단파장측의 상승에 대해 접선을 긋고, 그 접선과 가로축의 교점의 파장값(λedge1(nm))을 구한 후, 이 파장값을 하기 환산식 1에 대입하여 삼중항 에너지를 산출하였다.
환산식 (F1):T1(eV) = 1239.85/λedge1
인광 스펙트럼의 단파장측의 상승에 대한 접선은 이하와 같이 긋는다. 우선, 스펙트럼의 극대값 중 가장 단파장측의 극대값을 확인한다. 이 때, 스펙트럼의 극대 피크 강도의 15% 이하의 피크 강도를 갖는 극대점은, 상기 서술한 가장 단파장측의 극대값에는 포함시키지 않는다. 인광 스펙트럼의 단파장측으로부터 상기 극대값까지의 스펙트럼 곡선 상의 각 점에 있어서의 접선을 생각한다. 이 접선 중 기울기 값이 제일 큰 접선(즉, 변곡점에 있어서의 접선)을 당해 인광 스펙트럼의 단파장측의 상승에 대한 접선으로 한다.
일중항 에너지의 측정
일중항 에너지(S1)는 다음의 방법으로 측정하였다.
측정 대상이 되는 화합물의 10-5M 톨루엔 용액을 조제하여 석영 셀에 넣고, 상온(300K)에서 시료의 300nm 광원의 발광 스펙트럼(세로축:발광 강도, 가로축:파장)을 측정하였다. 이 발광 스펙트럼의 단파장측의 상승에 대해 접선을 긋고, 그 접선과 가로축의 교점의 파장값(λedge2(㎚))을 하기 환산식 2에 대입하여 일중항 에너지를 산출하였다. 상기 발광 스펙트럼은 JASCO사의 분광 광도계(FP-8600 spectrophotometer)를 이용하여 측정하였다.
환산식 2:S1(eV) = 1239.85/λedge2
발광 스펙트럼의 단파장측의 상승에 대한 접선은 이하와 같이 긋는다. 우선, 스펙트럼의 극대값 중 가장 단파장측의 극대값을 확인한다. 발광 스펙트럼의 단파장측으로부터 상기 극대값까지의 스펙트럼 곡선 상의 각 점에 있어서의 접선을 생각한다. 이 접선 중 기울기 값이 제일 큰 접선(즉, 변곡점에 있어서의 접선)을 당해 발광 스펙트럼의 단파장측의 상승에 대한 접선으로 한다. 스펙트럼의 극대 피크 강도의 15% 이하의 피크 강도를 갖는 극대점은, 상기 서술한 가장 단파장측의 극대값에는 포함시키지 않는다.
화합물 | S1(eV) | T1(eV) | HOMO(eV) | LUMO(eV) | △EST(eV) |
1 | 2.43 | 2.37 | 5.70 | 2.91 | 0.06 |
2 | 2.45 | 2.38 | 5.75 | 2.92 | 0.07 |
3 | 2.44 | 2.38 | 5.76 | 2.90 | 0.06 |
4 | 2.44 | 2.39 | 5.72 | 2.92 | 0.05 |
5 | 2.43 | 2.38 | 5.75 | 2.91 | 0.05 |
6 | 2.43 | 2.37 | 5.70 | 2.90 | 0.06 |
7 | 2.45 | 2.39 | 5.71 | 2.92 | 0.06 |
8 | 2.44 | 2.40 | 5.73 | 2.93 | 0.04 |
9 | 2.43 | 2.39 | 5.72 | 2.91 | 0.04 |
T1 | 2.84 | 2.45 | 6.11 | 2.90 | 0.39 |
T2 | 2.77 | 2.41 | 6.06 | 2.91 | 0.36 |
T3 | 2.61 | 2.39 | 5.40 | 2.90 | 0.22 |
T4 | 2.84 | 2.43 | 6.02 | 2.89 | 0.41 |
T5 | 2.63 | 2.39 | 5.41 | 2.88 | 0.24 |
T6 | 2.64 | 2.40 | 5.44 | 2.87 | 0.24 |
4CzIPN | 2.44 | 2.39 | 5.55 | 2.88 | 0.05 |
본원 실시예들에 사용된 화합물 1 내지 9는 모두 △EST가 0.3eV 이하로 지연 형광 물질로 적합한 것을 알 수 있다.비교예로 사용된 화합물 T1, T2 및 T4의 경우 지연 형광 물질로 적합하지 않은 것을 확인할 수 있었고, 4CzIPN, T3, T5 및 T6는 △EST가 0.3eV 이하로 지연 형광 물질에 해당하나, 표 1 에서 살펴본 바와 같이 화합물 1 내지 9가 전압, 효율 면에서 특성이 모두 향상됨을 알 수 있었다.이상을 통해 본 발명의 바람직한 실험예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.
Claims (9)
- 하기 화학식 1 로 표시되는 화합물:[화학식 1]화학식 1에 있어서,X는 직접결합; O; 또는 S이고,Y는 NR; O; 또는 S이고,R1은 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 시클로알킬기이며,R 및 R2 내지 R4는 각각 독립적으로, 수소; 중수소; 할로겐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,R5 및 R6은 각각 독립적으로, 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴아민기; 치환 또는 비치환된 알킬아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이며,a는 1 또는 2이고,b는 0 또는 1이고,c 및 e는 각각 독립적으로, 0 내지 4의 정수이며,d는 0 내지 2의 정수이며,f 및 g는 각각 독립적으로, 0 내지 5의 정수이며,a 및 c 내지 g가 각각 독립적으로 2 이상인 경우에는 괄호 안의 치환기는 서로 같거나 상이하다.
- 제1 전극, 제2 전극, 및 상기 제1 전극과 제2 전극 사이에 배치된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 청구항 1 내지 6 중 어느 하나의 항에 따른 화합물을 포함하는 것을 특징으로 하는 유기 발광 소자.
- 청구항 7에 있어서,상기 유기물층은 도펀트를 갖는 발광층을 포함하며,상기 도펀트는 상기 화합물인 것을 특징으로 하는 유기 발광 소자.
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