CN118265715A - Organic compound and organic electroluminescent device comprising the same - Google Patents
Organic compound and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- CN118265715A CN118265715A CN202280077056.XA CN202280077056A CN118265715A CN 118265715 A CN118265715 A CN 118265715A CN 202280077056 A CN202280077056 A CN 202280077056A CN 118265715 A CN118265715 A CN 118265715A
- Authority
- CN
- China
- Prior art keywords
- carbon atoms
- substituted
- unsubstituted
- compound
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 144
- 239000010410 layer Substances 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 92
- 239000000126 substance Substances 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 25
- 239000007924 injection Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 230000005525 hole transport Effects 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 93
- 238000003786 synthesis reaction Methods 0.000 description 93
- 238000002360 preparation method Methods 0.000 description 53
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 50
- 239000007858 starting material Substances 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- 238000000034 method Methods 0.000 description 35
- 239000002019 doping agent Substances 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 19
- 239000000463 material Substances 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 13
- 229910052796 boron Inorganic materials 0.000 description 13
- -1 2-butenyl (2-butenyl) Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 3
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 3
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 3
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 3
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 3
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 3
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 3
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 3
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 3
- JTWMOWRMSZZHDR-UHFFFAOYSA-N 7-(5-hydroxy-2-methylphenyl)-6-(2-methoxyphenyl)-4-methylpurino[7,8-a]imidazole-1,3-dione Chemical compound COC1=CC=CC=C1N(C(=CN12)C=3C(=CC=C(O)C=3)C)C2=NC2=C1C(=O)NC(=O)N2C JTWMOWRMSZZHDR-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 3
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 3
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 3
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 3
- 229940127007 Compound 39 Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 229940125961 compound 24 Drugs 0.000 description 3
- 229940125807 compound 37 Drugs 0.000 description 3
- 229940127113 compound 57 Drugs 0.000 description 3
- 229940125900 compound 59 Drugs 0.000 description 3
- 229940126179 compound 72 Drugs 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- CATUKADCLPCACU-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(4-phenylphenyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=C(C=2C=CC=CC=2)C=C1 CATUKADCLPCACU-UHFFFAOYSA-N 0.000 description 2
- MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- YMEKEHSRPZAOGO-UHFFFAOYSA-N boron triiodide Chemical compound IB(I)I YMEKEHSRPZAOGO-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QKBTTXJHJNXCOQ-UHFFFAOYSA-N dibenzofuran-4-amine Chemical compound O1C2=CC=CC=C2C2=C1C(N)=CC=C2 QKBTTXJHJNXCOQ-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- XMYLDITUFLHWLR-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43.C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 XMYLDITUFLHWLR-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- YWLXZCAOJYQMKY-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl.ClC1=CC=CC=C1Cl YWLXZCAOJYQMKY-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- YMRHXVOHLPIMNN-UHFFFAOYSA-N 1-n-(3-methylphenyl)-2-n,2-n-diphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YMRHXVOHLPIMNN-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- PNPLRTWSLDSFET-UHFFFAOYSA-N 2-naphthalen-1-yl-5-phenyl-1,3,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NN=C(C=2C3=CC=CC=C3C=CC=2)O1 PNPLRTWSLDSFET-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XXTPFCLFNHODHV-UHFFFAOYSA-N 9,10-dinaphthalen-2-yl-2-[4-(6-phenylcyclohexa-2,4-dien-1-yl)phenyl]anthracene Chemical compound C1=C(C=CC2=CC=CC=C12)C=1C2=CC=CC=C2C(=C2C=CC(=CC=12)C1=CC=C(C=C1)C1C(C=CC=C1)C1=CC=CC=C1)C1=CC2=CC=CC=C2C=C1 XXTPFCLFNHODHV-UHFFFAOYSA-N 0.000 description 1
- MAIALRIWXGBQRP-UHFFFAOYSA-N 9-naphthalen-1-yl-10-naphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 MAIALRIWXGBQRP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AWFDUOVDQHJMKG-UHFFFAOYSA-N N-(3-methylphenyl)-2-phenoxyaniline Chemical compound CC=1C=C(C=CC=1)NC1=C(C=CC=C1)OC1=CC=CC=C1 AWFDUOVDQHJMKG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 229910001573 adamantine Inorganic materials 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HTRXGEPDTFSKLI-UHFFFAOYSA-N butanoic acid;ethyl acetate Chemical compound CCCC(O)=O.CCOC(C)=O HTRXGEPDTFSKLI-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920003023 plastic 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
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007789 sealing 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
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a novel organic compound and an organic light emitting device including the same, and more particularly, to a novel organic compound exhibiting low driving voltage and high efficiency and improving lifetime, and an organic electroluminescent device including the same.
Description
Technical Field
The present invention relates to an organic compound and an organic electroluminescent device including the same.
Background
Compared with other flat panel display devices such as liquid crystal display devices (LCD), plasma Display Panels (PDP), and Field Emission Displays (FED), organic electroluminescent devices (OLED) have a simple structure, have various advantages in manufacturing processes, have high luminance and excellent viewing angle characteristics, and have a fast response speed and a low driving voltage, and thus are actively being developed and commercialized as light sources for flat panel displays such as wall-mounted Televisions (TV) or backlight, illumination, advertisement boards, and the like of the displays.
The organic electroluminescent device was originally an organic electroluminescent device (C.W.Tang, S.A.Vanslyke, applied Physics Letters, volume 51, page 913, 1987) reported by Tang (C.W.Tang) et al of Ikaman kodak, and the like, and its light emission principle is generally based on recombination of holes injected from an anode and electrons injected from a cathode to form excitons as electron-hole pairs upon application of a voltage, and conversion of the energy of the excitons to light was performed by transferring the energy of the excitons to a light emitting material.
More specifically, the organic electroluminescent device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and one or more organic layers between the two electrodes, in which case the organic electroluminescent device is laminated in the order of a hole injection layer (HIL, hole injection layer), a hole transport layer (HTL, hole transport layer), an emission layer (EML, LIGHT EMITTING LAYER), an electron transport layer (ETL, electron transport layer), or an electron injection layer (EIL, electron injection layer) from the anode, and further includes a hole transport auxiliary layer or a hole blocking layer (HBL, hole blocking layer) before and after the emission layer, respectively, in order to improve the efficiency of the emission layer.
The light emitting layer is composed of a host (host) and a dopant (dopant), and the dopant should preferably have high quantum efficiency, and the energy band gap of the host material is larger than that of the dopant material so as to induce energy transfer to the dopant.
Among the conventional substances used as Blue dopants, use of fluorescent molecules such as Perylene (Perylene), oxanaphthalenone (Coumarine), anthracene (ANTHRACENE), pyrene (Pyrene) and the like accounts for most of the specific gravity, and the Full width at half maximum (Full WIDTH HALF THE maximum) of the emission spectrum of the dopant is wide to 40nm level, so that it is difficult to realize Deep Blue (Deep Blue), and optical loss occurs even if a predetermined wavelength region is amplified by optical resonance in the front light emitting device.
In order to solve this problem, boron-based dopants having a narrow light emission spectrum of the device and high device efficiency have recently been increasingly in the trend of high efficiency and excellent color performance, but have too short lifetime, and thus, higher lifetime performance is required.
Prior art literature
Non-patent literature 1：Krebs,Frederik C.,et al."Synthesis,Structure,and Properties of 4,8,12-Trioxa-12c-phospha-4,8,12,12c-tetrahydrodibenzo[cd,mn]pyrene,aMolecular Pyroelectric."Journal of the American Chemical Society 119.6(1997)：1208-1216.
Disclosure of Invention
Technical problem
The purpose of the present invention is to provide a novel organic compound and an organic electroluminescent device comprising the same.
It is still another object of the present invention to provide a novel organic compound which can be used as a material for a light-emitting layer and has a lifetime improved as compared with conventional boron-based dopants while maintaining a low voltage and high efficiency.
Another object of the present invention is to provide an organic electroluminescent device as follows: the problem of lifetime reduction can be solved by using the above-mentioned organic compounds to maintain the excellent properties of boron-based dopants and by using host/dopant combinations suitable for the blue series of AM-OLEDs.
Technical proposal
In order to achieve the above object, the present invention provides a compound represented by the following chemical formula 1.
Chemical formula 1
Wherein,
N and m are the same or different from each other and are each independently an integer of 0 to 3,
X 1 is N or CR 3,
X 2 is selected from the group consisting of NR 4, O and S,
Y is B, and the Y is B,
Z 1 and Z 2 are identical or different from each other and are each independently selected from the group consisting of CR 5R6、NR7, O and S,
Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R 1 to R 7 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 2 to 60 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 24 carbon atoms, and an adjacent aryl group of 1 to 30 carbon atoms, wherein the substituted or unsubstituted aryl group is an oxygen atom, a substituted or unsubstituted silyl of 24 carbon atoms, a substituted or unsubstituted silyl of 2 to 30 carbon atoms, and an optionally substituted aryl group of 1 to 30 carbon atoms.
And, the present invention relates to an organic electroluminescent device comprising: a first electrode; a second electrode disposed opposite to the first electrode; one or more organic layers between the first electrode and the second electrode. The one or more organic layers include one or more compounds of the chemical formula 1.
In the present invention, "hydrogen" is hydrogen, protium, deuterium or tritium, unless otherwise specified.
In the present invention, "halogen" is fluorine, chlorine, bromine or iodine.
In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. For example, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl and the like can be used, but the present invention is not limited thereto.
In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. For example, vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl) and the like are possible, but not limited thereto.
In the present invention, "alkynyl group (alkynyl) means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms with one or more carbon-carbon triple bonds. For example, it may be an ethynyl group (ethynyl), a 2-propynyl group (2-propynyl), or the like, but is not limited thereto.
In the present invention, "alkylthio" means an alkyl group as described above bonded through a sulfur bond (-S-).
In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms which is a single ring or a combination of two or more rings. And may include a form of simple attachment (pendant) or condensation of two or more rings, specifically, naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, perylenyl,A group, a fluorenyl group, and the like, but is not limited thereto. The fluorenyl group may be substituted and may be bonded to an adjacent group to form a ring.
In the present invention, "heteroaryl" means a monovalent substituent derived from a mono-or multi-heterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this case, more than one carbon atom in the ring, preferably 1 to 3 carbon atoms are substituted with a heteroatom such as N, O, S or Se. Further, the aromatic compound may include a form in which two or more rings are simply attached or condensed, and may further include a form in which two or more rings are condensed with an aryl group. For example, the heteroaryl group may be a 6-membered monocyclic ring such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, etc., a polycyclic ring such as phenoxythienyl (phenoxathienyl), indolizinyl (indolizinyl), indolyl (indolyl), purinyl (purinyl), quinolinyl (quinolyl), benzothiazole (benzothiazole), carbazolyl (carbazolyl), etc., or a 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but is not limited thereto.
In the present invention, an "aryloxy group" is a monovalent substituent represented by RO-, and R represents an aryl group having 6 to 60 carbon atoms. For example, the aryloxy group may be a phenoxy group, a naphthoxy group, a diphenoxy group, or the like, but is not limited thereto.
In the present invention, the "alkyloxy group" is a monovalent substituent represented by R' O-which represents an alkyl group having 1 to 40 carbon atoms, and may include a straight chain (linear), branched (branched) or cyclic (cyclic) structure. For example, the alkoxy group may be methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, or the like, but is not limited thereto.
In the present invention, "alkoxy" may be straight, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, and preferably the number of carbon atoms is 1 to 20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but are not limited thereto.
In the present invention, "aralkyl" means aryl and alkyl groups forming an aryl-alkyl group as described above. Preferably, the aralkyl group includes a lower alkyl group. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl and naphthylmethyl. Binding to a residue is achieved by alkyl.
In the present invention, "arylamino group" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.
In the present invention, "alkylamino" means an amine substituted with an alkyl group having 1 to 30 carbon atoms.
In the present invention, "aralkylamino group" means an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.
In the present invention, "heteroarylamino" means an amino group substituted with an aryl group having 6 to 30 carbon atoms and a heterocyclic group.
In the present invention, "heteroarylalkyl" refers to an aryl-alkyl group substituted with a heterocycle.
In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bornyl (norboryl), adamantyl (adamantine), and the like.
In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and one or more carbon atoms in the ring, preferably 1 to 3 carbon atoms are substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl groups include, but are not limited to, morpholine, piperazine, and the like.
In the present invention, the "alkylsilyl group" is a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the "arylsilyl group" is a silyl group substituted with an aryl group having 6 to 60 carbon atoms.
In the present invention, "condensed ring" refers to a form of condensed aliphatic ring, condensed aromatic ring, condensed heteroalicyclic ring, condensed heteroaromatic ring, or a combination thereof.
In the present invention, "bonding to an adjacent group to form a ring" means bonding to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a condensed ring thereof.
In the present invention, examples of the "aromatic hydrocarbon ring" include phenyl, naphthyl, anthracenyl and the like, but are not limited thereto.
In the present invention, "aliphatic heterocyclic ring" means an aliphatic ring containing one or more hetero atoms.
In the present invention, the "aromatic heterocycle" means an aromatic ring containing one or more hetero atoms.
In the present invention, "boron element", "boron-based compound", "boron-based dopant" means boron (B) element having an atomic number of 5, a boron-containing compound or dopant.
In the present invention, "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted, that is, a position where a substituent can be substituted, and in the case of two or more substituents, two or more substituents may be the same or different. The substituent may be substituted with one or more substituents selected from the group consisting of cyano group, nitro group, halogen, hydroxyl group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 6 to 30 carbon atoms, aryl group having 5 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroaralkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms and heteroarylamino group having 2 to 24 carbon atoms, but is not limited to the above examples.
ADVANTAGEOUS EFFECTS OF INVENTION
Compared with the existing boron-based dopant, the organic compound can maintain low driving voltage and high efficiency, can improve service life, and can be used as a luminescent layer material.
Also, the excellent characteristics of the boron-based dopant can be maintained by using the above-described organic compound, and the problem of reduced lifetime of the organic electroluminescent device can be solved by a host/dopant combination of blue series suitable for AM-OLED.
Detailed Description
The compound of the present invention can be represented by the following chemical formula 1.
Chemical formula 1
Wherein,
N and m are the same or different from each other and are each independently an integer of 0 to 3,
X 1 is N or CR 3,
X 2 is selected from the group consisting of NR 4, O and S,
Y is B, and the Y is B,
Z 1 and Z 2 are identical or different from each other and are each independently selected from the group consisting of CR 5R6、NR7, O and S,
Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R 1 to R 7 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 2 to 60 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 24 carbon atoms, and an adjacent aryl group of 1 to 30 carbon atoms, wherein the substituted or unsubstituted aryl group is an oxygen atom, a substituted or unsubstituted silyl of 24 carbon atoms, a substituted or unsubstituted silyl of 2 to 30 carbon atoms, and an optionally substituted aryl group of 1 to 30 carbon atoms.
Embodiments of the invention
Hereinafter, embodiments of the present invention will be described in detail for easy implementation of the present invention by those of ordinary skill in the art to which the present invention pertains. However, the present invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
The organic compound of the present invention contains an aromatic hexagonal ring in a molecule, has a twisted structure having a non-planar structure, and in particular, contains a cycloalkyl group as a substituent, and is an organic compound that can improve the lifetime while maintaining a low driving voltage and high efficiency, as compared with a conventional boron-based dopant, and can be used as a light-emitting layer material.
Specifically, the compound of the present invention may be represented by the following chemical formula 1.
Chemical formula 1
Wherein,
N and m are the same or different from each other and are each independently an integer of 0 to 3,
X 1 is N or CR 3,
X 2 is selected from the group consisting of NR 4, O and S,
Y is B, and the Y is B,
Z 1 and Z 2 are identical or different from each other and are each independently selected from the group consisting of CR 5R6、NR7, O and S,
Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R 1 to R 7 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 2 to 60 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 24 carbon atoms, and an adjacent aryl group of 1 to 30 carbon atoms, wherein the substituted or unsubstituted aryl group is an oxygen atom, a substituted or unsubstituted silyl of 24 carbon atoms, a substituted or unsubstituted silyl of 2 to 30 carbon atoms, and an optionally substituted aryl group of 1 to 30 carbon atoms.
The compound represented by the above chemical formula 1 may be a compound represented by the following chemical formula 2.
Chemical formula 2
Wherein,
N, m, Y, X 1、X2、R1、R2、Z2 and ring A are the same as in chemical formula 1 above,
O is an integer of 1 to 10.
Specifically, the compound represented by the above chemical formula 1 may be a compound represented by the following chemical formula 5.
Chemical formula 5
Wherein,
N, m, Y, X 1、X2、R1、R2、Z2 and ring A are the same as in chemical formula 1 above,
O is an integer from 1 to 5.
Specifically, the compound represented by the above chemical formula 1 may be a compound represented by the following chemical formula 6.
Chemical formula 6
Wherein,
The n, m, Y, X 1、X2、R1、R2、Z2 and A rings are the same as in the above chemical formula 1.
The a ring may be selected from compounds represented by chemical formula 3 or chemical formula 4 below.
Chemical formula 3
Chemical formula 4
Wherein,
* In order to be a part of the bond,
P is an integer of 0 to 4,
Z 3 is selected from the group consisting of NR -11, O and S,
R 8 to R 11 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 2 to 60 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 24 carbon atoms, and substituted or unsubstituted aryl of 1 to 30 carbon atoms can be combined with each other to form an adjacent aryl group of 1 to 30 carbon atoms.
The compound represented by chemical formula 1 of the present invention may be represented by the following compound, but is not limited thereto.
The organic compound of the present invention can be effectively used as a material for forming a light-emitting layer. The light-emitting layer-forming material may contain a substance that is usually added when the organic compound is prepared in a form required for forming a light-emitting layer, and may contain a host substance, for example.
The material for forming the light-emitting layer may be a dopant material.
The present invention also relates to a material for forming a light-emitting layer, which contains the organic compound.
The material for forming a light-emitting layer may contain a substance which is usually added to prepare the organic compound into a form required for forming a light-emitting layer, and may contain a host substance, for example.
The present invention also relates to an organic electroluminescent device comprising an organic thin film layer formed of one or more layers including at least a light-emitting layer and laminated between a cathode and an anode,
The light-emitting layer contains a compound represented by the following chemical formula 1.
Chemical formula 1
Wherein,
N and m are the same or different from each other and are each independently an integer of 0 to 3,
X 1 is N or CR 3,
X 2 is selected from the group consisting of NR 4, O and S,
Y is B, and the Y is B,
Z 1 and Z 2 are identical or different from each other and are each independently selected from the group consisting of CR 5R6、NR7, O and S,
Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R 1 to R 7 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 2 to 60 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 24 carbon atoms, and an adjacent aryl group of 1 to 30 carbon atoms, wherein the substituted or unsubstituted aryl group is an oxygen atom, a substituted or unsubstituted silyl of 24 carbon atoms, a substituted or unsubstituted silyl of 2 to 30 carbon atoms, and an optionally substituted aryl group of 1 to 30 carbon atoms.
The organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked, and an electron blocking layer, a hole blocking layer, and the like may be stacked as needed.
Hereinafter, the organic electroluminescent device of the present invention is illustrated by way of example. However, the following illustrative contents do not limit the organic electroluminescent device of the present invention.
The organic electroluminescent device of the present invention may have a structure in which an anode (hole injection electrode), a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), and a cathode (electron injection electrode) are sequentially stacked, and preferably, an Electron Blocking Layer (EBL) may be further included between the anode and the emission layer, and an Electron Transport Layer (ETL), an Electron Injection Layer (EIL) may be further included between the cathode and the emission layer. And, a Hole Blocking Layer (HBL) may also be included between the cathode and the light emitting layer.
In the method for producing an organic electroluminescent device of the present invention, first, an anode is formed by applying an anode substance to a substrate surface by a usual method. In this case, the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, convenience and water repellency. As the anode material, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), or the like which is transparent and has excellent conductivity can be used.
Next, a hole injection layer is formed on the surface of the anode by vacuum thermal vapor deposition or spin coating of a hole injection layer material by a usual method. Examples of such hole injection layer materials are copper phthalocyanine (CuPc), 4',4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4',4" -tris (3-methylphenylamino) phenoxybenzene (m-MTDAPB), 4',4 "-tris (N-carbazolyl) triphenylamine (TCTA) as a starburst (starburst) amine, 4',4" -tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA), or IDE406 available from the light-emitting company (Idemitsu).
The hole transport layer is formed by vacuum thermal vapor deposition or spin coating of a hole transport layer substance on the surface of the hole injection layer by a usual method. In this case, examples of the hole transport layer substance are bis (N- (1-naphthyl-N-phenyl)) benzidine (. Alpha. -NPD), N '-bis (naphthalen-1-yl) -N, N' -biphenyl-benzidine (NPB), or N, N '-biphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD).
The light-emitting layer is formed by vacuum thermal vapor deposition or spin coating of a light-emitting layer substance on the surface of the hole transport layer by a usual method. The dopant that can be used together with the host in the light-emitting layer substance, preferably, the compound represented by the above chemical formula 1 of the present invention can be used.
Optionally, an electron blocking layer may also be formed between the hole transport layer and the light emitting layer.
An electron transport layer is formed by vacuum thermal vapor deposition or spin coating of an electron transport layer substance on the surface of the light-emitting layer by a usual method. In this case, the electron transport layer material to be used is not particularly limited, and preferably tris (8-hydroxyquinoline) aluminum (Alq 3) may be used.
Alternatively, the phenomenon of diffusing triplet excitons or holes into the electron transport layer may also be prevented by further forming a hole blocking layer between the light emitting layer and the electron transport layer and using phosphorescent dopants together in the light emitting layer.
The hole blocking layer can be formed by vacuum thermal vapor deposition or spin coating of a hole blocking layer substance using a general method, and the hole blocking layer substance is not particularly limited, and preferably (8-hydroxyquinoline) lithium (Liq), bis (8-hydroxy-2-methylquinoline) -biphenoxyaluminum (BAlq), bathocuproine (bathocuproine, BCP), lithium fluoride (LiF), and the like can be used.
An electron injection layer is formed by vacuum thermal vapor deposition or spin coating of an electron injection layer substance on the surface of the electron transport layer by a usual method. In this case, the electron injection layer material to be used may be lithium fluoride, (8-hydroxyquinoline) lithium, lithium oxide (Li 2 O), barium oxide (BaO), sodium chloride (NaCl), cesium fluoride (CsF), or the like.
The cathode is formed by vacuum deposition of a cathode material on the surface of the electron injection layer by a usual method.
In this case, the cathode material to be used may be lithium (Li), aluminum (Al), aluminum, lithium (al—li), calcium (Ca), magnesium (Mg), magnesium-indium (mg—in), magnesium-silver (mg—ag), or the like. In the case of the front-side light-emitting organic electroluminescent device, a transparent cathode capable of transmitting light may be formed using Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO).
The surface of the cathode may be covered with a cover layer forming substance to form a cover layer (CPL).
The synthesis method of the above-mentioned compound will be described below by way of representative examples. However, the method of synthesizing the compound of the present invention is not limited to the following exemplified method, and the compound of the present invention can be prepared by the following exemplified method and methods known in the art to which the present invention pertains.
Synthesis example 1: preparation of Compound 3
After 1.30g (2.00 mmol) of the starting material was dissolved in o-dichlorobenzene (o-Dichlorobenzene) (15 ml), 1.48g (4.00 mmol) of boron triiodide (Boron triiodide) was added under nitrogen atmosphere, and then the mixture was heated to 160℃at ordinary temperature and stirred for 12 hours. After the reaction solution was cooled to room temperature, the organic layer was extracted with ethyl acetate (ETHYL ACETATE) and water. After the solvent of the extracted organic layer was removed, it was purified by silica gel column chromatography (dichloromethane (DCM)/hexane (Hexane)). Then, the mixture was purified by recrystallization using a mixed solvent of methylene chloride/acetone (Acetone) to obtain 0.24g of the above compound 3 in a yield of 18.5%.
MS(MALDI-TOF)m/z:648[M]+
Synthesis example 2: preparation of Compound 4
0.24G of the above-mentioned compound 4 was obtained in the same manner as in Synthesis example 1 except that 1.52g of the starting material was used, in a yield of 15.6%.
MS(MALDI-TOF)m/z:768[M]+
Synthesis example 3: preparation of Compound 9
0.25G of the above-mentioned compound 9 was obtained in the same manner as in Synthesis example 1 in a yield of 17.1% except that 1.45g of the starting material was used.
MS(MALDI-TOF)m/z:730[M]+
Synthesis example 4: preparation of Compound 15
0.20G of the above-mentioned compound 15 was obtained in the same yield of 12.9% by the same method as in Synthesis example 1, except that 1.49g of the starting material was used.
MS(MALDI-TOF)m/z:750[M]+
Synthesis example 5: preparation of Compound 24
0.28G of the above-mentioned compound 24 was obtained in the same yield of 18.4% by the same method as in Synthesis example 1, except that 1.51g of the starting material was used.
MS(MALDI-TOF)m/z:762[M]+
Synthesis example 6: preparation of Compound 35
0.22G of the above-mentioned compound 35 was obtained in the same yield of 20.8% by the same method as in Synthesis example 1, except that 1.04g of the starting material was used.
MS(MALDI-TOF)m/z:526[M]+
Synthesis example 7: preparation of Compound 39
0.28G of the above-mentioned compound 39 was obtained in the same yield of 18.2% by the same method as in Synthesis example 1, except that 1.52g of the starting material was used.
MS(MALDI-TOF)m/z:746[M]+
Synthesis example 8: preparation of Compound 59
0.20G of the above-mentioned compound 59 was obtained in the same manner as in Synthesis example 1 except that 1.12g of the starting material was used, in a yield of 17.6%.
MS(MALDI-TOF)m/z:568[M]+
Synthesis example 9: preparation of Compound 65
0.28G of the above-mentioned compound 65 was obtained in the same yield of 18.6% by the same method as in Synthesis example 1, except that 1.48g of the starting material was used.
MS(MALDI-TOF)m/z:750[M]+
Synthesis example 10: preparation of Compound 72
0.25G of the above-mentioned compound 72 was obtained in the same manner as in Synthesis example 1 in a yield of 16.6% except that 1.49g of the starting material was used.
MS(MALDI-TOF)m/z:750[M]+
Synthesis example 11: preparation of Compound 75
0.26G of the above-mentioned compound 75 was obtained in the same manner as in Synthesis example 1 in a yield of 16.4% except that 1.57g of the starting material was used.
MS(MALDI-TOF)m/z:793[M]+
Synthesis example 12: preparation of Compound 92
0.27G of the above-mentioned compound 92 was obtained in the same manner as in Synthesis example 1 in a yield of 17.9% except that 1.4g of the starting material was used.
MS(MALDI-TOF)m/z:750[M]+
Synthesis example 13: preparation of Compound 101
0.28G of the above-mentioned compound 101 was obtained in the same yield of 18.6% by the same method as in Synthesis example 1, except that 1.49g of the starting material was used.
MS(MALDI-TOF)m/z:752[M]+
Synthesis example 14: preparation of Compound 108
0.28G of the above-mentioned compound 108 was obtained in the same yield of 18.7% by the same method as in Synthesis example 1, except that 1.48g of the starting material was used.
MS(MALDI-TOF)m/z:748[M]+
Synthesis example 15: preparation of Compound 125
0.26G of the above-mentioned compound 125 was obtained in the same yield as in Synthesis example 1 in 17.7% by using 1.45g of the starting material.
MS(MALDI-TOF)m/z:730[M]+
Synthesis example 16: preparation of Compound 127
0.34G of the above-mentioned compound 127 was obtained in the same yield as in Synthesis example 1 in 19.1% by using 1.76g of the starting material.
MS(MALDI-TOF)m/z:888[M]+
Synthesis example 17: preparation of Compound 150
0.29G of the above-mentioned compound 150 was obtained in the same yield of 17.7% by the same method as in Synthesis example 1, except that 1.62g of the starting material was used.
MS(MALDI-TOF)m/z:815[M]+
Synthesis example 18: preparation of Compound 161
0.24G of the above-mentioned compound 161 was obtained in the same yield of 17.6% by the same method as in Synthesis example 1, except that 1.35g of the starting material was used.
MS(MALDI-TOF)m/z:684[M]+
Synthesis example 19: preparation of Compound 7
0.27G of the above-mentioned compound 7 was obtained in the same manner as in Synthesis example 1 in a yield of 18.4% except that 1.45g of the starting material was used.
MS(MALDI-TOF)m/z:730[M]+
Synthesis example 20: preparation of Compound 66
0.28G of the above-mentioned compound 66 was obtained in the same manner as in Synthesis example 1 in a yield of 18.2% except that 1.52g of the starting material was used.
MS(MALDI-TOF)m/z:766[M]+
Synthesis example 21: preparation of Compound 19
0.21G of the above-mentioned compound 19 was obtained in the same manner as in Synthesis example 1 in a yield of 12.4% except that 1.68g of the starting material was used.
MS(MALDI-TOF)m/z:844[M]+
Synthesis example 22: preparation of Compound 69
0.24G of the above-mentioned compound 69 was obtained in the same manner as in Synthesis example 1 in 18.5% yield, except that 1.28g of the starting material was used.
MS(MALDI-TOF)m/z:648[M]+
Synthesis example 23: preparation of Compound 30
0.23G of the above-mentioned compound 30 was obtained in the same manner as in Synthesis example 1 in a yield of 12.8% except that 1.78g of the starting material was used.
MS(MALDI-TOF)m/z:899[M]+
Synthesis example 24: preparation of Compound 90
0.24G of the above-mentioned compound 90 was obtained in the same manner as in Synthesis example 1 in a yield of 14.2% except that 1.68g of the starting material was used.
MS(MALDI-TOF)m/z:848[M]+
Synthesis example 25: preparation of Compound 37
0.26G of the above-mentioned compound 37 was obtained in the same manner as in Synthesis example 1 in a yield of 17.2% except that 1.50g of the starting material was used.
MS(MALDI-TOF)m/z:758[M]+
Synthesis example 26: preparation of Compound 99
0.21G of the above-mentioned compound 99 was obtained in the same yield of 15.3% by the same method as in Synthesis example 1, except that 1.36g of the starting material was used.
MS(MALDI-TOF)m/z:688[M]+
Synthesis example 27: preparation of Compound 57
0.30G of the above-mentioned compound 57 was obtained in the same manner as in Synthesis example 1 in 18.8% yield, except that 1.58g of the starting material was used.
MS(MALDI-TOF)m/z:796[M]+
Synthesis example 28: preparation of Compound 103
0.18G of the above-mentioned compound 103 was obtained in the same yield of 13.3% by the same method as in Synthesis example 1, except that 1.34g of the starting material was used.
MS(MALDI-TOF)m/z:678[M]+
Synthesis example 29: preparation of Compound 140
0.16G of the above-mentioned compound 140 was obtained in the same yield of 12.6% by the same method as in Synthesis example 1, except that 1.25g of the starting material was used.
MS(MALDI-TOF)m/z:633[M]+
Synthesis example 30: preparation of Compound 163
0.24G of the above-mentioned compound 163 was obtained in the same yield of 14.5% by the same method as in Synthesis example 1 except that 1.64g of the starting material was used.
MS(MALDI-TOF)m/z:825[M]+
Synthesis example 31: preparation of Compound 78
19.33G (20.0 mmol) of the starting material and 3.80mL (40.0 mmol) of boron tribromide (Boron tribromide) were placed under nitrogen (N 2) in a 1000mL flask containing ortho-dichlorobenzene (ortho-Dichlorobenzene, 400 mL). Then, the temperature was raised to 80℃and stirred for 3 hours, and then the temperature was raised to 180℃and stirred for 12 hours. The end of the reaction was confirmed by thin film chromatography. The reaction solution was cooled to room temperature, then, water was added thereto, and the organic layer was extracted with ethyl acetate. The solvent of the organic layer was dried over magnesium sulfate (MgSO 4), filtered and concentrated before purification by silica gel column chromatography (dichloromethane (Dichloromethane)/hexane). Then, the purification was recrystallized using a mixed solvent of methylene chloride/acetone to obtain 4.18g of the above-mentioned compound 78 in a yield of 21.4%.
MS(MALDI-TOF)m/z:974[M]+
Synthesis example 32: preparation of Compound 13
4.85G of the above-mentioned compound 13 was obtained in the same yield of 25.8% by the same method as in Synthesis example 31, except that 18.65g of the starting material was used.
MS(MALDI-TOF)m/z:939[M]+
Synthesis example 33: preparation of Compound 32
3.52G of the above-mentioned compound 32 was obtained in the same yield of 18.6% by the same method as in Synthesis example 31, except that 18.73g of the starting material was used.
MS(MALDI-TOF)m/z:943[M]+
Synthesis example 34: preparation of Compound 51
4.88G of the above-mentioned compound 51 was obtained in the same yield as in Synthesis example 31 by using 19.29g of the starting material in the same manner as in 25.1%.
MS(MALDI-TOF)m/z:971[M]+
Synthesis example 35: preparation of Compound 138
2.91G of the above-mentioned compound 138 was obtained in the same yield of 19.9% by the same method as in Synthesis example 31, except that 14.44g of the starting material was used.
MS(MALDI-TOF)m/z:729[M]+
Synthesis example 36: preparation of Compound 165
2.62G of the above-mentioned compound 165 was obtained in the same yield of 18.9% by the same method as in Synthesis example 31, except that 13.72g of the starting material was used.
MS(MALDI-TOF)m/z:693[M]+
Synthesis example 37: preparation of Compound 45
3.55G of the above-mentioned compound 45 was obtained in the same yield of 17.2% by the same method as in Synthesis example 31, except that 20.49g of the starting material was used.
MS(MALDI-TOF)m/z:1031[M]+
Synthesis example 38: preparation of Compound 112
3.12G of the above-mentioned compound 112 was obtained in the same yield as in Synthesis example 31 by using 16.64g of the starting material in 18.6%.
MS(MALDI-TOF)m/z:839[M]+
Synthesis example 39: preparation of Compound 115
3.22G of the above-mentioned compound 115 was obtained in the same yield as in Synthesis example 31 by using 16.96g of the starting material in 18.8%.
MS(MALDI-TOF)m/z:855[M]+
Synthesis example 40: preparation of Compound 134
2.88G of the above-mentioned compound 134 was obtained in the same manner as in Synthesis example 31 in a yield of 16.8% except that 16.96g of the starting material was used.
MS(MALDI-TOF)m/z:855[M]+
Synthesis example 41: preparation of Compound 148
1.95G of the above-mentioned compound 148 was obtained in the same yield of 12.0% by the same method as in Synthesis example 31, except that 16.08g of the starting material was used.
MS(MALDI-TOF)m/z:811[M]+
Synthesis example 42: preparation of Compound 81
1.32G (2.00 mmol) of the starting material and 0.56g (2.00 mmol) of bis (4- (tert-butyl) phenyl) amine, 0.38g (4.00 mmol) of Sodium tert-butoxide, 0.03g (0.04 mmol) of tris (dibenzylideneacetone) dipalladium (0) (Tris (dibenzylideneacetone) dipalladium (0)), 0.03g (0.08 mmol) of 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (2-Dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl) are placed under nitrogen in 50ml of toluene. The temperature was then raised to 100℃and stirred for 4 hours. The end of the reaction was confirmed by thin film chromatography. The reaction solution was cooled to room temperature, then, water was added thereto, and the organic layer was extracted with dichloromethane. The solvent of the extracted organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by silica gel column chromatography (dichloromethane/hexane). Then, the purification was recrystallized using a mixed solvent of methylene chloride/acetone to obtain 1.24g of the above-mentioned compound 81 in a yield of 68.5%.
MS(MALDI-TOF)m/z:905[M]+
Synthesis example 43: preparation of Compound 83
1.16G of the above-mentioned compound 83 was obtained in the same yield of 59.5% by the same method as in Synthesis example 42, except that 1.45g of the starting material was used.
MS(MALDI-TOF)m/z:973[M]+
Synthesis example 44: preparation of Compound 84
1.31G of the above-mentioned compound 84 was obtained in the same yield of 66.2% by the same method as in Synthesis example 42, except that 1.49g of the starting material was used.
MS(MALDI-TOF)m/z:989[M]+
Synthesis example 45: preparation of Compound 87
1.32G of the above-mentioned compound 87 was obtained in the same manner as in Synthesis example 42 in a yield of 68.0% except that 1.45g of the starting material was used.
MS(MALDI-TOF)m/z:969[M]+
Synthesis example 46: preparation of Compound 26
1.01G of the above-mentioned compound 26 was obtained in the same manner as in Synthesis example 42 in a yield of 60.2% except that 1.41g of the starting material was used and 0.34g (2.00 mmol) of diphenylamine was used instead of 0.56g (2.00 mmol) of bis (4- (t-butyl) phenyl) amine.
MS(MALDI-TOF)m/z:835[M]+
Comparative example 1: preparation of Compound A
4.91G (10.0 mmol) of the starting material are dissolved in tert-butylbenzene (tert-Buthylbenzene) (50 ml) and cooled to 0 ℃. 7.9ml (20.0 mmol) of a 2.5M solution of N-butyllithium (N-BuLi) was added under nitrogen atmosphere (hexane solution (in hexane) and stirred at room temperature for 5 hours, then, after cooling the reaction to 0℃and adding 5.00g (20.0 mmol) of boron tribromide (Boron tribromide), stirred at room temperature for 6 hours, then, cooling the reaction to 0℃and adding 3.48ml (20 mmol) of N, N-diisopropylethylamine (N, N-Diisopropylethylamine) and stirred at a temperature of 60 to 70℃for 2 hours, the reaction solution was cooled to room temperature and then the organic layer was extracted with methylene chloride and water, after drying the solvent of the extracted organic layer with magnesium sulfate, filtered, concentrated the filtrate under reduced pressure and purified by silica gel column chromatography (methylene chloride/hexane), and then, recrystallized and purified using a methylene chloride/acetone mixed solvent to obtain 0.95g of the above comparative compound 1 in a yield of 22.6%.
MS(MALDI-TOF)m/z:420[M]+
Comparative example 2: preparation of Compound B
1.63G of the above-mentioned comparative compound 2 was obtained in the same manner as in comparative example 1 in a yield of 21.7% except that 8.20g of the starting material was used.
MS(MALDI-TOF)m/z:748[M]+
Comparative example 3: preparation of Compound C
2.78G of the above-mentioned comparative compound 3 was obtained in the same yield as in Synthesis example 30 in the same manner as in 23.6% except that 11.60g of the starting material was used.
MS(MALDI-TOF)m/z:587[M]+
Comparative example 4: preparation of Compound D
0.81G of the above-mentioned comparative compound 4 was obtained in the same manner as in Synthesis example 44 except that 0.91g of the starting material was used, in a yield of 68.8%.
MS(MALDI-TOF)m/z:587[M]+
Example 1: preparation of organic electroluminescent device
The substrate on which indium tin oxide (100 nm) as an anode of the organic electroluminescent device was laminated was aligned (Patterning) in such a manner as to distinguish a cathode region, an anode region, and an insulating layer through a photolithography (Photo-Lithograph) process, and then surface treatment was performed by ultraviolet Ozone (UV Ozone) treatment and O 2:N2 plasma for the purpose of increasing work-function (work-function) of the anode (indium tin oxide) and cleaning. HAT-CN with a thickness of 10nm was formed thereon as a Hole Injection Layer (HIL). Next, N4'-Tetra ([ 1,1' -biphenyl ] -4-yl) - [1,1'-biphenyl ] -4,4' -diamine (N4, N4'-Tetra ([ 1,1' -biphenyl ] -4-yl) - [1,1'-biphenyl ] -4,4' -diamine) having a thickness of 90nm was vacuum-deposited on the hole injection layer as a hole transport layer, and N-Phenyl-N- (4- (spiro [ benzo [ d, e ] anthracene-7,9'-fluorene ] -2' -yl) Phenyl) dibenzo [ b, d ] furan-4-amine (N-Phenyl-N- (4- (spiro [ benzod, e ] anthracene-7,9 '-fluorne ] -2' -yl) Phenyl) dibe nzo [ b, d ] furan-4-amine) having a thickness of 15nm was formed on the hole transport layer as an electron blocking layer. The electron blocking layer was vapor-deposited on top of the above-mentioned electron blocking layer, and a 25nm thick light-emitting layer was formed by doping 2% of compound 3 as a dopant while 9- (1-naphthyl) -10- (2-naphthyl) anthracene (9- (1-Naphtyl) -10- (2-Naphtyl) anthracene) was used as a host of the light-emitting layer.
25Nm of 2- (4- (9, 10-Di (naphthalen-2-yl) anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] imidazole (2- (4- (9, 10-Di (naphthalen-2-yl) ANTHRA CENE-2-yl) phenyl) -1-phenyl-1H-benzol [ d ] imidazole) and (8-hydroxyquinoline) lithium are evaporated on the substrate in a ratio of 1:1 to serve as an electron transport layer, a 1nm of electron injection layer is evaporated on the electron transport layer, and 100nm of aluminum is evaporated as a cathode. Then, a sealing cap (seal cap) containing an adsorbent (getter) as an Ultraviolet (UV) curable adhesive is joined to be able to protect the organic electroluminescent device from oxygen and moisture in the atmosphere, thereby preparing the organic electroluminescent device.
Examples 2 to 44: preparation of organic electroluminescent device
An organic electroluminescent device was produced by the same method as in example 1, except that compound 4, compound 9, compound 15, compound 24, compound 59, compound 72, compound 75, compound 65, compound 101, compound 108, compound 125, compound 127, compound 150, compound 161, compound 7, compound 66, compound 19, compound 30, compound 90, compound 57, compound 103, compound 140, compound 163, compound 35, compound 39, compound 37, compound 32, compound 78, compound 13, compound 51, compound 138, compound 165, compound 45, compound 112, compound 115, compound 134, compound 148, compound 83, compound 84, compound 87 and compound 26 were used instead of the above compound 3 as the dopant.
Comparative examples 5 to 8: preparation of organic electroluminescent device
An organic electroluminescent device was prepared by the same method as in example 1, except that compounds a to D (comparative examples 1 to 4) were used instead of the above-described compound 3 as a dopant.
Experimental example: analysis of characteristics of organic electroluminescent devices
The results of measuring the photoelectric characteristics by applying a current of 10mA/cm 2 to the organic electroluminescent devices prepared in examples 1 to 44 and comparative examples 5 to 8 and measuring the lifetime by constant current driving of 10mA/cm 2 are compared and shown in Table 1 below.
TABLE 1
Examples 1 to 44 of the present invention are compounds which share the features of the present invention and have a twisted structure other than a planar structure, and share the same structural features, and specifically, are characterized in that a substituent is condensed between N of a boron-based compound and a phenyl group to contain a cyclic compound to which a cycloalkyl group is bonded. In contrast, the compounds of comparative examples 1 to 4 did not condense substituents between N of the boron-based compound and phenyl group to form a ring compound, and there was a structural difference in the substituents including cycloalkyl group as phenyl group.
After organic electroluminescent devices including the compounds of the above comparative examples and synthesis examples were prepared, the structures of the driving voltages, external quantum efficiencies, and lifetime characteristics thereof were compared as shown in table 1 above. It was confirmed that the organic electroluminescent device showed a large difference in driving voltage, external quantum efficiency and lifetime characteristics according to the structural difference between the above compounds.
While the preferred embodiments of the present invention have been described in detail, the scope of the claims of the present invention is not limited thereto, and variations and modifications of the inventive concept defined by those skilled in the art to which the present invention pertains are also included in the scope of the claims of the present invention.
Industrial applicability
The present invention relates to an organic compound and an organic electroluminescent device including the same.
Claims (6)
1. A compound, characterized in that,
Represented by the following chemical formula 1,
Chemical formula 1
Wherein,
N and m are the same or different from each other and are each independently an integer of 0 to 3,
X 1 is N or CR 3,
X 2 is selected from the group consisting of NR 4, O and S,
Y is B, and the Y is B,
Z 1 and Z 2 are identical or different from each other and are each independently selected from the group consisting of CR 5R6、NR7, O and S,
Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
R 1 to R 7 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 2 to 60 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 24 carbon atoms, substituted or unsubstituted silyl of 24 carbon atoms, and substituted or unsubstituted aryl of 24 carbon atoms, and the like, and the substituted or unsubstituted aryl groups of 1 to 30 carbon atoms may be combined with each other to form an adjacent aryl group of the substituted or unsubstituted silyl of 1 to 30 carbon atoms.
2. A compound according to claim 1, wherein,
The compound represented by chemical formula 1 is a compound represented by chemical formula 2,
Chemical formula 2:
Wherein,
N, m, Y, X 1、X2、R1、R2、Z2 and ring a are defined in claim 1,
O is an integer of 1 to 10.
3. A compound according to claim 1, wherein,
The above-mentioned A ring is selected from compounds represented by the following chemical formula 3 or chemical formula 4,
Chemical formula 3:
Chemical formula 4:
Wherein,
* In order to be a part of the bond,
P is an integer of 0 to 4,
Z 3 is selected from the group consisting of NR- 11, O and S,
R 8 to R 11 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 2 to 60 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 24 carbon atoms, and substituted or unsubstituted aryl of 1 to 30 carbon atoms can be combined with each other to form an adjacent aryl group of 1 to 30 carbon atoms.
4. An organic electroluminescent device, characterized in that,
Comprising the following steps:
a first electrode;
A second electrode disposed opposite to the first electrode;
one or more organic layers between the first electrode and the second electrode,
The one or more organic layers comprising one or more compounds of claim 1.
5. The organic electroluminescent device as claimed in claim 4, wherein,
The organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
6. The organic electroluminescent device as claimed in claim 4, wherein,
The organic layer is a light-emitting layer.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020220003789A KR102654248B1 (en) | 2022-01-11 | 2022-01-11 | Organic compound and organic electroluminescent device comprising the same |
| KR10-2022-0003789 | 2022-01-11 | ||
| PCT/KR2022/021354 WO2023136508A1 (en) | 2022-01-11 | 2022-12-27 | Organic compound and organic electroluminescent device comprising same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN118265715A true CN118265715A (en) | 2024-06-28 |
Family
ID=87279399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280077056.XA Pending CN118265715A (en) | 2022-01-11 | 2022-12-27 | Organic compound and organic electroluminescent device comprising the same |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR102654248B1 (en) |
| CN (1) | CN118265715A (en) |
| WO (1) | WO2023136508A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024085404A1 (en) | 2022-10-20 | 2024-04-25 | (주) 엘지화학 | Thermoplastic resin composition, method for producing same, and molded article including same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107417715A (en) * | 2017-07-14 | 2017-12-01 | 瑞声科技（南京）有限公司 | A kind of electroluminescent organic material and its luminescent device |
| JP7260642B2 (en) * | 2018-11-19 | 2023-04-18 | エスエフシー カンパニー リミテッド | Novel boron compound and organic light-emitting device containing the same |
| KR102239995B1 (en) * | 2019-06-20 | 2021-04-14 | 에스에프씨주식회사 | Organic Compound for organic light emitting diode and an organic light emitting diode including the same |
| KR102352839B1 (en) * | 2020-01-06 | 2022-01-18 | 에스에프씨 주식회사 | Polycyclic aromatic compound and organoelectroluminescent device using the same |
| KR20210103988A (en) * | 2020-02-14 | 2021-08-24 | 에스에프씨 주식회사 | Polycyclic aromatic compound and organoelectroluminescent device using the same |
-
2022
- 2022-01-11 KR KR1020220003789A patent/KR102654248B1/en active IP Right Grant
- 2022-12-27 WO PCT/KR2022/021354 patent/WO2023136508A1/en active Application Filing
- 2022-12-27 CN CN202280077056.XA patent/CN118265715A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR20230108416A (en) | 2023-07-18 |
| WO2023136508A1 (en) | 2023-07-20 |
| KR102654248B1 (en) | 2024-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7026405B2 (en) | Organic compounds and organic electroluminescent devices containing them | |
| KR20200121228A (en) | An organic compound and an organic light emitting diode | |
| KR20200037732A (en) | An organic compound and an organic light emitting diode | |
| CN114149461B (en) | Organic compound and organic electroluminescent element comprising same | |
| US20220112221A1 (en) | Organic compound and organic electric field lightemitting device comprising same | |
| CN114181094B (en) | Organic compound and organic electroluminescent element comprising same | |
| CN113493475B (en) | Organic compound and organic electroluminescent element comprising same | |
| CN113527342B (en) | Organic compound and organic electroluminescent element comprising same | |
| CN110249030B (en) | Organic electroluminescent device | |
| CN115513400A (en) | Organic electroluminescent element | |
| CN111153811B (en) | Organic compound and organic electroluminescent element comprising same | |
| CN118265715A (en) | Organic compound and organic electroluminescent device comprising the same | |
| CN113666952B (en) | Organic compound and organic electroluminescent element comprising same | |
| KR102331271B1 (en) | Organic compound and organic electroluminescent device comprising the same | |
| KR20200097584A (en) | Organic compound and organic electroluminescent device comprising the same | |
| CN113880795B (en) | Organic compound and organic electroluminescent element comprising the same | |
| KR20210055873A (en) | An organic compound and an organic light emitting diode | |
| KR102654225B1 (en) | Organic compound and organic electroluminescent device comprising the same | |
| CN114573546B (en) | Organic compound and organic electroluminescent element comprising same | |
| KR102677026B1 (en) | Organic compound and organic electroluminescent device comprising the same | |
| KR102550442B1 (en) | Organic electroluminescent device | |
| KR102249719B1 (en) | An organic compound and an organic light emitting diode | |
| CN114133366A (en) | Organic compound and organic electroluminescent element comprising same | |
| KR20220150833A (en) | Organic compound and organoelectroluminescent device using the same | |
| KR20230007942A (en) | Organic compound and organoelectroluminescent device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |