CN116621842A - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
- Publication number
- CN116621842A CN116621842A CN202310478696.8A CN202310478696A CN116621842A CN 116621842 A CN116621842 A CN 116621842A CN 202310478696 A CN202310478696 A CN 202310478696A CN 116621842 A CN116621842 A CN 116621842A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- group
- chemical formula
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 239000000126 substance Substances 0.000 claims abstract description 95
- 239000012044 organic layer Substances 0.000 claims abstract description 37
- 239000010410 layer Substances 0.000 claims description 180
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000001624 naphthyl group Chemical group 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000004305 biphenyl Chemical group 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000010276 construction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 54
- 125000003118 aryl group Chemical group 0.000 description 51
- 238000002347 injection Methods 0.000 description 49
- 239000007924 injection Substances 0.000 description 49
- -1 triethylsilyl group Chemical group 0.000 description 48
- 230000015572 biosynthetic process Effects 0.000 description 45
- 238000003786 synthesis reaction Methods 0.000 description 45
- 125000000217 alkyl group Chemical group 0.000 description 37
- 230000005525 hole transport Effects 0.000 description 30
- 238000004519 manufacturing process Methods 0.000 description 29
- 125000001424 substituent group Chemical group 0.000 description 28
- 125000000623 heterocyclic group Chemical group 0.000 description 20
- 230000000903 blocking effect Effects 0.000 description 18
- 229940125904 compound 1 Drugs 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 239000002019 doping agent Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 12
- 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 10
- AMSJIGYDHCSSRE-UHFFFAOYSA-N 3,14-diazahexacyclo[11.11.0.02,10.04,9.015,24.016,21]tetracosa-1(24),2,4,6,8,10,12,14,16,18,20,22-dodecaene Chemical group C1=CC=C2C=CC3=C4C5=NC6=CC=CC=C6C5=CC=C4N=C3C2=C1 AMSJIGYDHCSSRE-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 8
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 6
- 229910001887 tin oxide Inorganic materials 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 5
- 125000006267 biphenyl group Chemical group 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 238000007740 vapor deposition Methods 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
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- LEHBLKHJWCNXKQ-UHFFFAOYSA-N 1-bromo-2-nitronaphthalene Chemical compound C1=CC=CC2=C(Br)C([N+](=O)[O-])=CC=C21 LEHBLKHJWCNXKQ-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DNBGKLNKPFOXLG-UHFFFAOYSA-N 2-bromo-9-phenylcarbazole Chemical compound BrC1=CC=2N(C3=CC=CC=C3C2C=C1)C1=CC=CC=C1.BrC1=CC=2N(C3=CC=CC=C3C2C=C1)C1=CC=CC=C1 DNBGKLNKPFOXLG-UHFFFAOYSA-N 0.000 description 3
- SOODLDGRGXOSTA-UHFFFAOYSA-N 2-bromo-9-phenylcarbazole Chemical compound C=1C(Br)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=C1 SOODLDGRGXOSTA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- VBQVHWHWZOUENI-UHFFFAOYSA-N 1-phenyl-2H-quinoline Chemical compound C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 VBQVHWHWZOUENI-UHFFFAOYSA-N 0.000 description 2
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 2
- KRQFZBUWIOZDMP-UHFFFAOYSA-N 2-bromo-3-nitronaphthalene Chemical compound C1=CC=C2C=C(Br)C([N+](=O)[O-])=CC2=C1 KRQFZBUWIOZDMP-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- PJRJXFPRMUZBHQ-UHFFFAOYSA-N [Ir].C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 Chemical compound [Ir].C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1.C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 PJRJXFPRMUZBHQ-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 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 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DYXNPKNQSCAHFG-UHFFFAOYSA-N 1-benzothiophene pyrimidine Chemical group N1=CN=CC=C1.S1C2=C(C=C1)C=CC=C2 DYXNPKNQSCAHFG-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 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
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- SBABEHDRJFHMEU-UHFFFAOYSA-N 2-bromo-1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(Br)C=CC2=C1 SBABEHDRJFHMEU-UHFFFAOYSA-N 0.000 description 1
- PYHCFFLUGHKAPZ-UHFFFAOYSA-N 2-bromo-9-naphthalen-2-ylcarbazole Chemical compound C12=CC=CC=C2C2=CC=C(Br)C=C2N1C1=CC=C(C=CC=C2)C2=C1 PYHCFFLUGHKAPZ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- XYKAAGZFDPVFTE-UHFFFAOYSA-N O1CCOCC1.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O Chemical compound O1CCOCC1.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O XYKAAGZFDPVFTE-UHFFFAOYSA-N 0.000 description 1
- 101150007013 PGH1 gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 101100065359 Zea mays ENO1 gene Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 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
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 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
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical group C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- SHNBXKOUKNSCSQ-UHFFFAOYSA-N iridium;1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 SHNBXKOUKNSCSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NTAYABHEVAQSJS-CDIPTNKSSA-N prostaglandin H1 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2CCCCCCC(O)=O NTAYABHEVAQSJS-CDIPTNKSSA-N 0.000 description 1
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 1
- 125000003226 pyrazolyl 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010345 tape casting Methods 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same. The compound of chemical formula 1 can be used as a material of an organic layer of an organic light emitting device, and the organic light emitting device using the same can improve efficiency, lifetime characteristics.
Description
The present application is a divisional application of application having a date of application of 2020, 1 month and 15, application number 202080002724.3, and title of the application "compound and organic light-emitting device comprising the same" (PCT/KR 2020/000736, date of entry into national stage 2020, 11 month and 12).
Technical Field
The present specification relates to a compound and an organic light emitting device including the same.
The present application claims priority from korean patent application No. 10-2019-0009968, filed to the korean patent office on 1 month 25 in 2019, the entire contents of which are included in the present specification.
Background
An organic light-emitting device is a light-emitting device using an organic semiconductor substance, and communication of holes and/or electrons between an electrode and the organic semiconductor substance is required. Organic light emitting devices can be broadly classified into the following two types according to the operation principle. The first is a light-emitting device in which an exciton (exiton) is formed in an organic layer by photons flowing into the device from an external light source, and the exciton is separated into an electron and a hole, and the electron and the hole are transferred to different electrodes to be used as a current source (voltage source). The second type is a light-emitting device in which a voltage or a current is applied to 2 or more electrodes, holes and/or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes, and the injected electrons and holes operate.
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state. Such an organic light emitting device is known to have characteristics of self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and the like.
Materials used as an organic layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material, such as a hole injecting material, a hole transporting material, an electron inhibiting substance, an electron transporting material, an electron injecting material, and the like, according to functions. Depending on the emission color, the luminescent materials are blue, green, red luminescent materials and yellow and orange luminescent materials which are required to achieve a better natural color.
In addition, for the purpose of increasing color purity and increasing luminous efficiency by energy transfer, a host/dopant system may be used as a light-emitting material. The principle is that when a dopant having a smaller band gap and excellent light emission efficiency than a host mainly constituting the light emitting layer is mixed in a small amount in the light emitting layer, excitons generated in the host are transferred to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength range of the dopant, light of a desired wavelength can be obtained according to the kind of the dopant to be used.
In order to fully develop the excellent characteristics of the organic light-emitting device, materials constituting the organic layer in the device, for example, hole injection materials, hole transport materials, light-emitting materials, electron-suppressing materials, electron transport materials, electron injection materials, and the like are stable and effective materials, and therefore development of new materials is continuously demanded.
Disclosure of Invention
Technical problem
The specification describes compounds and organic light emitting devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
ar is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R1 to R5 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with each other with adjacent groups to form a substituted or unsubstituted ring,
r1 is an integer of 0 to 6,
r2 to r4 are each integers of 0 to 4,
r5 is an integer of 0 to 2,
when r1 to r5 are 2 or more, structures in parentheses of 2 or more are the same or different from each other,
n and m are each 0 or 1,
n+m＝1，
when n is 1, X1 is a direct bond,
when m is 1, X2 is a direct bond.
Another embodiment provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound.
Effects of the invention
The compound represented by chemical formula 1 of the present invention may be used as a material of an organic layer of an organic light emitting device.
An organic light emitting device including the compound represented by chemical formula 1 according to an embodiment of the present specification can improve efficiency.
An organic light emitting device including the compound represented by chemical formula 1 according to an embodiment of the present specification can improve lifetime characteristics.
Drawings
Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.
Fig. 2 illustrates an organic light emitting device according to another embodiment of the present specification.
Fig. 3 illustrates an organic light emitting device according to another embodiment of the present specification.
[ description of the symbols ]
1: substrate board
2: anode
3: light-emitting layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: light-emitting layer
8: electron transport layer
9: electron blocking layer
10: electron transport and injection layers
Detailed Description
The present specification will be described in detail below.
The present specification provides a compound represented by the above chemical formula 1.
An organic light emitting device including the compound represented by chemical formula 1 according to an embodiment of the present specification can improve efficiency.
An organic light emitting device including the compound represented by chemical formula 1 according to an embodiment of the present specification can improve lifetime characteristics.
The compound represented by chemical formula 1 of the present application is composed of a quinoxaline unit functioning as an electron acceptor and a benzoindolocarbazole unit functioning as an electron donor. Since two units having completely different properties are directly combined, charge is exchanged in the inside of the molecule, and thus the band gap becomes small.
In addition, the benzoindolocarbazole unit contains a naphthalene ring, and thus the triplet energy is reduced, with the result that both the singlet energy and the triplet energy are small, facilitating energy transfer to the red dopant, and thus being suitable for use as a host of a red light emitting layer.
In particular, by locating the triplet-stabilized naphthalene ring at a ring beside the nitrogen to which the quinoxaline is attached, the movement of internal charges between the quinoxaline and the benzoindolocarbazole is made more stable. In addition, two nitrogens inside the benzoindolocarbazole unit are located at para positions (para) to each other, and thus the electron-pushing effect is maximized, and at this time, the HOMO (highest occupied molecular orbital ) energy level becomes high, holes are prevented from being trapped by the dopant, and thus hole transport ability becomes excellent.
In addition, based on the quinoxaline unit, the Ar unit and the carbazole unit condensed with the ring are substituted at the ortho position (ortho), face to face due to structural obstruction, and the structure is more stabilized by pi-pi interaction between them, so that the characteristic of long service life is exhibited.
In the present specification, when a certain component is referred to as "comprising" or "including" a certain component, unless otherwise specified, it is intended that the component may be further included, rather than excluded
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where the other member exists between the two members.
In the present specification, examples of the substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium (-D), halogen group, nitrile group, nitro group, hydroxyl group, silyl group, boron group, alkoxy group, alkyl group, cycloalkyl group, aryl group, and heterocyclic group, or substituted with a substituent in which 2 or more substituents out of the above exemplified substituents are linked, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the silyl group may be represented by the chemical formula of —siyaybyc, and the above Ya, yb, and Yc may each be hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group may be represented by the formula of-bydyye, and the above Yd and Ye may each be oxygen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 1 0 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, and the like. .
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2. Phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 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 and the like are possible, but not limited thereto.
The alkyl group, the alkoxy group, and the substituent containing an alkyl moiety other than them described in the present specification are all included in a straight chain or branched form.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 20 carbon atoms. According to one embodiment, the aryl group has 6 to 30 carbon atoms. The aryl group may be a monocyclic aryl group such as phenyl, biphenyl, terphenyl, or tetrabiphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, and the like,Perylene groups,A group, a fluorenyl group, a triphenylene group, and the like, but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.
In the case where the fluorenyl group is substituted, it may be thatAn isospirofluorenyl group;(9, 9-dimethylfluorenyl), and +.>(9, 9-diphenylfluorenyl) and the like. However, the present invention is not limited thereto.
In the present specification, the heterocyclic group is a ring group containing 1 or more heteroatoms in N, O, P, S, si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolinyl, pyridazinyl, barking, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, indenocarzolyl, indolocarbazolyl, and the like.
In this specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group can be applied thereto.
According to an embodiment of the present specification, the above chemical formula 1 may be represented by any one of the following chemical formulas 2 to 7.
[ chemical formula 2]
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
In the above-mentioned chemical formulas 2 to 7,
ar, R1 to R5 and R1 to R5 are as defined in chemical formula 1.
According to an embodiment of the present description, ar is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to an embodiment of the present specification, ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
According to an embodiment of the present specification, ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to an embodiment of the present disclosure, ar is substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted fluorenyl group; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothienyl; or a heterocyclic group comprising a substituted or unsubstituted bicyclic ring of N, O or S.
According to an embodiment of the present specification, ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzo groupAn oxazolyl group, or a substituted or unsubstituted benzothiazolyl group.
According to one embodiment of the present disclosure Ar is phenyl substituted or unsubstituted with alkyl or aryl, naphthyl substituted or unsubstituted with alkyl or aryl, biphenyl substituted or unsubstituted with alkyl or aryl, terphenyl substituted or unsubstituted with alkyl or aryl, carbazolyl substituted or unsubstituted with alkyl or aryl, fluorenyl substituted or unsubstituted with alkyl or aryl, dibenzobarking moiety substituted or unsubstituted with alkyl or aryl, dibenzothiophene substituted or unsubstituted with alkyl or aryl, benzo substituted or unsubstituted with alkyl or arylOxazolyl, or benzothiazolyl substituted or unsubstituted with alkyl or aryl.
According to an embodiment of the present specification, ar is phenyl, naphthyl, biphenyl, terphenyl, carbazolyl substituted or unsubstituted with phenyl, fluorenyl substituted or unsubstituted with methyl, dibenzofuranyl, dibenzothiophenyl, or benzothiazolyl.
According to an embodiment of the present specification, ar is phenyl, naphthyl, biphenyl, terphenyl, carbazolyl substituted or unsubstituted with phenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or benzothiazolyl.
According to an embodiment of the present specification, ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzobarking group, or a substituted or unsubstituted dibenzothiophene group.
According to an embodiment of the present specification, ar is phenyl, naphthyl, biphenyl, dimethylfluorenyl, carbazolyl substituted or unsubstituted with phenyl, dibenzofuranyl, or dibenzothiophenyl.
According to one embodiment of the present description Ar is phenyl, naphthyl, biphenyl, dimethylfluorenyl, carbazolyl, dibenzofuranyl.
According to an embodiment of the present specification, ar may be represented by any one of the following structures.
In the above-described structure, the first and second heat exchangers,
b1 to B13 are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
b1 is an integer of 0 to 5,
b2 is an integer of 0 to 9,
b3 is an integer of 0 to 13,
b4 to b7 are each integers from 0 to 7,
b8 is an integer of 0 to 8,
b9 is an integer of 0 to 4,
b10 is an integer of 0 to 7,
when b1 to b10 are 2 or more, structures in parentheses of 2 or more are the same or different from each other.
According to an embodiment of the present specification, ar may be represented by any one of the following structures.
In the above structure, the broken line indicates the bonding position.
According to an embodiment of the present specification, ar may be represented by any one of the following structures.
In the above structure, the broken line indicates the bonding position.
According to an embodiment of the present specification, B1 to B10 are hydrogen.
According to an embodiment of the present specification, B11 to B13 are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, B11 to B13 are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
According to an embodiment of the present specification, B11 to B13 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to one embodiment of the present description, B11 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
According to one embodiment of the present description, B11 is a substituted or unsubstituted phenyl group.
According to one embodiment of the present description, B11 is phenyl.
According to an embodiment of the present specification, B12 and B13 are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
According to an embodiment of the present description, B12 and B13 are methyl groups.
According to an embodiment of the present description, b1 to b10 are 0 or 1.
According to an embodiment of the present description, b1 to b10 are 0.
According to an embodiment of the present specification, R1 to R5 are the same as or different from each other, each independently is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or may be combined with each other with an adjacent group to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or are combined with each other with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.
According to an embodiment of the present specification, R1 to R5 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or are combined with each other with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.
According to an embodiment of the present specification, R1 to R5 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group, or are combined with each other with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.
According to an embodiment of the present specification, R1 to R5 are the same or different from each other, each is independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group, or are combined with each other with adjacent groups to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted benzofurane ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indene ring.
According to an embodiment of the present specification, R1 to R5 are the same or different from each other, each is independently hydrogen, deuterium, or phenyl, or are combined with each other with an adjacent group to form a benzene ring, a benzofuran ring, a benzothiophene ring, or an indene ring substituted or unsubstituted with methyl.
According to an embodiment of the present description, R1 to R5 are hydrogen.
According to an embodiment of the present description, R1, R4 and R5 are hydrogen.
According to one embodiment of the present specification, R2 and R3 are hydrogen, deuterium, or phenyl, or a plurality of R2 or a plurality of R3 are combined with each other to form a benzene ring, a benzobarking ring, a benzothiophene ring, or an indene ring substituted with methyl.
According to an embodiment of the present disclosure, R2 and R3 are hydrogen, deuterium, or phenyl, or a plurality of R2 or a plurality of R3 are combined with each other to form a benzene ring, a benzofuran ring, a benzothiophene ring, or an indene ring substituted with methyl.
According to an embodiment of the present disclosure, R1 to R5 may combine with each other with an adjacent group to form a substituted or unsubstituted ring.
In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on the atom substituted by the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the benzene ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the cycloalkyl or aryl group as exemplified above, except for the 2-valent group. Specifically, the description of the aryl group is applicable to the aromatic hydrocarbon ring except that the aromatic hydrocarbon ring is 2-valent, and the description of the cycloalkyl group is applicable to the aliphatic hydrocarbon ring except that the aromatic hydrocarbon ring is 2-valent.
The heterocyclic ring may be 2-valent, and the above description of the heterocyclic group may be applied.
According to an embodiment of the present specification, a plurality of R1, a plurality of R2, a plurality of R3, or a plurality of R4 may be bonded to each other to form a substituted or unsubstituted ring, and R2 and R3 may be bonded to each other to form a substituted or unsubstituted ring.
According to an embodiment of the present specification, when R1 to R5 each independently combine with an adjacent group to form a substituted or unsubstituted ring, any one of the following structures may be formed.
In the above-described structure, the first and second heat exchangers,
a1 to a24 are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl,
a1 to a11 are each integers of 0 to 4,
a12 is an integer of 0 to 6,
* Indicating the position of substitution.
According to an embodiment of the present specification, A1 to a12 are hydrogen.
According to an embodiment of the present specification, a13 to a24 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
According to an embodiment of the present description, a20 and a21 are each independently substituted or unsubstituted alkyl.
According to one embodiment of the present description, a20 and a21 are methyl groups.
According to an embodiment of the present description, r1 is an integer from 0 to 6.
According to an embodiment of the present description, r1 is an integer from 0 to 1.
According to an embodiment of the present specification, r2 to r4 are each integers of 0 to 4.
According to an embodiment of the present specification, r2 to r4 are each integers of 0 to 1.
According to an embodiment of the present description, r5 is an integer from 0 to 2.
According to an embodiment of the present description, r5 is an integer from 0 to 1.
According to an embodiment of the present specification, R2 or R3 may be combined with each other to form a substituted or unsubstituted ring independently from each other.
According to an embodiment of the present specification, R2 or R3 may be combined with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring independently of each other.
According to an embodiment of the present specification, R2 or R3 may be combined with each other to form any one ring of the following structure independently. In the following structures, A1 to A4, a20, a21, and A1 to A4 are the same as defined above.
According to an embodiment of the present disclosure, R2 and R3 are hydrogen, deuterium, or phenyl, orR2 or +.>R3 are bonded to each other to form any one of the following structures.
In the above-described structure, the first and second heat exchangers,indicating the position of the bond with N.
According to an embodiment of the present disclosure, R2 and R3 are hydrogen, deuterium, or phenyl, orR2 or +.>R3 are bonded to each other to form any one of the following structures. />
In the above-described structure, the first and second heat exchangers,indicating the position of the bond with N.
According to one embodiment of the present description, R2 and R3 are hydrogen, deuterium, or phenyl, or a plurality of R2 or a plurality of R3 are bonded to each other to integrally form a naphthalene, dibenzofuran, or dibenzothiophene ring.
According to one embodiment of the present description, R2 and R3 are hydrogen, or a plurality of R2 or a plurality of R3 are bonded to each other to integrally form a naphthalene or dibenzofuran ring.
According to an embodiment of the present description, X1 is a direct bond when n and m are each 0 or 1, n+m=1, n is 1, and X2 is a direct bond when m is 1.
According to one embodiment of the present disclosure, when n is 0, X1 is not present because it is not bonded.
According to one embodiment of the present disclosure, when m is 0, X2 is not present because it is not bonded.
According to an embodiment of the present specification, the above chemical formula 1 may be represented by any one of the following compounds.
The compound represented by chemical formula 1 in the present specification can produce a core structure as shown in the following reaction formula. Substituents may be combined by methods known in the art, and the kinds, positions and number of substituents may be changed according to techniques known in the art.
< reaction >
In the above reaction formula, ar, X1, X2, R1 to R5, R1 to R5, m and n are as defined in chemical formula 1, and X are each independently a halogen group.
In this specification, by introducing a plurality of substituents into the core structure as described above, a compound having a plurality of energy gaps can be synthesized. In addition, in this specification, by introducing a plurality of substituents into the core structure of the structure described above, HOMO and LUMO energy levels of the compound can also be adjusted.
In addition, an organic light emitting device according to the present specification, characterized by comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound.
The organic light-emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light-emitting device, except that 1 or more organic layers are formed using the compound represented by chemical formula 1.
In the case of manufacturing an organic light-emitting device in which an organic layer containing the compound represented by the above-described compound 1 is formed, the organic layer may be formed not only by a vacuum vapor deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including 1 or more layers of a hole transporting layer, a hole injecting layer, an electron blocking layer, a layer that performs hole transport and hole injection simultaneously, an electron transporting layer, an electron injecting layer, a hole blocking layer, and a layer that performs electron transport and electron injection simultaneously as organic layers. However, the structure of the organic light emitting device of the present specification is not limited thereto, and may include a smaller or larger number of organic layers.
In the organic light emitting device of the present specification, the organic layer may include a hole transporting layer or a hole injecting layer, and the hole transporting layer or the hole injecting layer may include a compound represented by chemical formula 1.
In another organic light emitting device of the present specification, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by chemical formula 1.
In another organic light emitting device of the present specification, the organic layer includes a light emitting layer, and the light emitting layer may include a compound represented by chemical formula 1.
According to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound as a host of the light-emitting layer.
In one embodiment of the present specification, the light emitting layer may include the compound represented by chemical formula 1 as a host of the light emitting layer, and may further include a dopant. At this time, the content of the above dopant may be contained in an amount of 1 to 60 parts by weight, preferably 1 to 20 parts by weight, more preferably 1 to 10 parts by weight, based on 100 parts by weight of the body.
In this case, as the dopant, (4, 6-F) 2 ppy) 2 Examples of the fluorescent substance include phosphorescent substances such as Irpic, and fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymer, PPV-based polymer, anthracene-based compound, pyrene-based compound, and boron-based compound, but are not limited thereto.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.
For example, the above-described organic light emitting device may have a laminated structure as described below, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(5) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(7) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(8) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(9) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(10) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(11) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(12) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(13) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(14) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
The structure of the organic light emitting device of the present specification may have a structure as shown in fig. 1 to 3, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described light-emitting layer 3.
Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described light-emitting layer 7.
Fig. 3 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light emitting layer 7, an electron transport and injection layer 10, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described light-emitting layer 7.
For example, the organic light emitting device according to the present specification may be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical vapor deposition) method such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that performs electron injection and electron transport simultaneously, or the like, but the organic layer is not limited to this and may have a single layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer printing, using a plurality of polymer materials.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc Oxide, steel Tin Oxide (ITO), and zinc Oxide (IZO, indium Zinc Oxide); znO: al or SnO 2 : a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathode is an electron-injecting electricityIn general, a cathode material is preferably a material having a small work function in order to facilitate injection of electrons into an organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, steel, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that functions to smoothly inject holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can favorably inject holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the deterioration of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the movement of holes can be prevented.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring them to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples thereof include an arylamine-based organic substance, a conductive polymer, and a block copolymer having both conjugated and unconjugated portions, but are not limited thereto.
An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may use materials known in the art.
The light-emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The above-mentioned luminescenceThe substance is a substance capable of receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; l 0-hydroxybenzoquinoline-metal compound; benzo (E) benzo (E Azole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light-emitting layer may contain the compound represented by chemical formula 1 of the present application, and specifically, may contain the compound represented by chemical formula 1 of the present application as a host. Specifically, the compound represented by chemical formula 1 of the present application can be used as a phosphorescent substance that emits red light when used as a host of a light-emitting layer.
In the case where the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonide, bis (1-phenylisoquinoline) iridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq may be used 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but are not limited thereto.
The light emitting layer may further include a compound represented by chemical formula 8 below. Specifically, the light-emitting layer may include a compound represented by chemical formula 8 as an additional host. At this time, the compound represented by chemical formula 1 may be contained in an amount of 10 to 70 parts by weight, preferably 20 to 50 parts by weight, based on 100 parts by weight of the entire body.
[ chemical formula 8]
In the above-mentioned chemical formula 8,
R a and R is b Are identical or different from one another and are each independently of one another a substituted or unsubstituted aryl radical or a substituted or unsubstituted heteroaryl radical,
R c and R is d Are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; a nitro group; an amino group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms selected from any one or more of N, O and S,
r and s are each an integer of 0 to 7, and R is 2 or more c When s is 2 or more, R is the same as or different from each other d The same as or different from each other.
According to one embodiment of the present specification, R c And R is d Are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; a nitro group; an amino group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms; substituted or unsubstituted alkenyl having 2 to 30 carbon atoms; substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; or a heteroaryl group having 2 to 30 carbon atoms selected from any one or more of substituted or unsubstituted N, O and S.
According to one embodiment of the present specification, R c And R is d Is hydrogen.
According to one embodiment of the present specification, R a And R is b Are identical or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
According to one embodiment of the present specification, R a And R is b Each otherThe same or different, each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
According to one embodiment of the present specification, R a And R is b Each of which is the same or different from the other and is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted benzothiazolyl group.
According to one embodiment of the present specification, R a And R is b Each of which is the same or different from the other and is independently an alkyl-or aryl-substituted or unsubstituted phenyl group, an alkyl-or aryl-substituted or unsubstituted biphenyl group, an alkyl-or aryl-substituted or unsubstituted terphenyl group, an alkyl-or aryl-substituted or unsubstituted naphthyl group, an alkyl-or aryl-substituted or unsubstituted fluorenyl group, an alkyl-or aryl-substituted or unsubstituted dibenzofuranyl group, or an alkyl-or aryl-substituted or unsubstituted dibenzothiophenyl group.
According to one embodiment of the present specification, R a And R is b Are identical to or different from one another and are each independently phenyl which is substituted or unsubstituted by methyl, phenyl or naphthyl; biphenyl substituted or unsubstituted with methyl, phenyl or naphthyl; terphenyl substituted or unsubstituted with methyl, phenyl or naphthyl; naphthyl substituted or unsubstituted with methyl, phenyl or naphthyl; fluorenyl substituted or unsubstituted with methyl, phenyl, or naphthyl; dibenzofuranyl substituted or unsubstituted with methyl, phenyl or naphthyl; or dibenzothienyl substituted or unsubstituted with methyl, phenyl or naphthyl. According to one embodiment of the present specification, R a And R is b Each of which is the same or different from the other and is independently phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dibenzothiophenyl substituted or unsubstituted with phenyl or naphthyl.
According to one embodiment of the present specification, R a And R is b Each may be represented by any one of the following structures.
In the above-described structure, the first and second heat exchangers,
c1 to C13 are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
c1 is an integer of 0 to 5,
c2 is an integer of 0 to 9,
c3 is an integer of 0 to 13,
c4 to c7 are each integers from 0 to 7,
c8 is an integer of 0 to 8,
c9 is an integer of 0 to 4,
c10 is an integer of 0 to 7,
when c1 to c10 are 2 or more, structures in parentheses of 2 or more are the same or different from each other.
According to an embodiment of the present description, C1 to CI0 are hydrogen.
According to an embodiment of the present specification, C11 to C13 are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, C11 to C13 are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
According to an embodiment of the present specification, C11 to C13 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to one embodiment of the present disclosure, C11 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
According to one embodiment of the present description, C11 is a substituted or unsubstituted phenyl group.
According to an embodiment of the present description, C11 is phenyl.
According to an embodiment of the present specification, C12 and C13 are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
According to an embodiment of the present description, C12 and C13 are methyl.
According to one embodiment of the present specification, R a And R is b Each may be represented by any one of the following structures.
The definitions of C1 to C3, C5 to C7, C10, C12, C13, C1 to C3, C5 to C7 and C10 described above are the same as those described above.
According to an embodiment of the present description, r and s are each integers from 0 to 7.
According to an embodiment of the present description, r and s are each 0 or 1.
According to an embodiment of the present specification, the above chemical formula 8 may be represented by any one of the following compounds.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of hole transport characteristics can be prevented, and when the thickness of the electron transport layer is 50nm or less, there is an advantage that the increase of driving voltage for improving the movement of electrons can be prevented.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dioxane, diphenoquinone, thiopyran dioxide, and,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as the hole injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto. />
The organic light emitting device according to the present application may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the application
In the following, examples are given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. Embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
Synthesis example
PREPARATION EXAMPLE 1 Synthesis of intermediate A
1) Synthesis of intermediate A-1
In a three-necked flask, 2-bromo-9-phenyl-9H-carbazole (2-bromoo-9-phenyl-9H-carbazole) (20.0 g,62.1 mmol), bis (pinacolato) diboron (bis (pinacolato) diboron) (18.9 g,74.5 mmol), tris (dibenzylideneacetone) dipalladium (0) (Tris (dibenzylideneacetone) dipalladium (0)) (Pd (dba) was charged 2 ) (0.7 g,1.2 mmol) and tricyclohexylphosphine (PCy) 3 )(07g,2.5 mmol), potassium acetate (potassium acetate) (KOAc) (12.2 g,124.1 mmol), 300ml of 1, 4-di-1The alkane (1, 4-dioxane) was stirred under reflux for 12 hours under argon. At the end of the reaction, after cooling to room temperature, the reaction solution was transferred to a separating funnel, water (200 mL) was added thereto, and extraction was performed with ethyl acetate. The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography to obtain intermediate A-1 (17.2 g). (yield 75%, MS: [ M+H)] + ＝369)
2) Synthesis of intermediate A-2
In a three-necked flask, intermediate A-1 (17.0 g,46.0 mmol), 1-bromo-2-nitronaphthalene (1-bromoo-2-nitronaphthalene) (12.8 g,50.6 mmol) was dissolved in 255ml of Tetrahydrofuran (THF), and potassium carbonate (potassium carbonate) (K) 2 CO 3 ) (25.5 g,184.1 mmol) dissolved in 85ml H 2 O was added. To this was added tetrakis (triphenylphosphine) palladium (0) (tetrakis (triphenylphosphine) paladium (0)) (Pd (PPh) 3 ) 4 ) (2.7 g,2.3 mmol) was stirred under reflux for 8 hours under argon. At the end of the reaction, after cooling to room temperature, the reaction solution was transferred to a separating funnel and extracted with ethyl acetate (ethyl acetate). The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography to obtain intermediate A-2 (12.0 g). (yield 63%, MS [ M+H ]] + ＝414)
3) Synthesis of intermediate A
In a two-necked flask, intermediate A-2 (12.0 g,29.0 mmol), triphenylphosphine (PPh) 3 )(60g,43.4 mmol), 120ml o-dichlorobenzene (o-DCB) and stirring under reflux for 24 hours. At the end of the reaction, cooling to room temperature, distilling off the solvent under reduced pressure, and using CH 2 Cl 2 And (5) extracting. The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography to obtain intermediate a (8.9 g). (yield 69%, MS [ M+H ]] + ＝382)
PREPARATION EXAMPLE 2 Synthesis of intermediate B
In production example 1, intermediate B was produced by the same production method as that of intermediate a except that 1-bromo-2-nitronaphthalene (1-bromoo-2-nitronaphthalene) was used instead of 2-bromo-3-nitronaphthalene (2-bromoo-3-nitronaphthalene). (MS [ M+H)] + ＝382)
PREPARATION EXAMPLE 3 Synthesis of intermediate C
In production example 1, intermediate C was produced by the same production method as that of intermediate a except that 1-bromo-2-nitronaphthalene (1-bromoo-2-nitronaphthalene) was used instead of 2-bromo-1-nitronaphthalene (2-bromoo-1-nitronaphthalene). (MS [ M+H) ] + ＝382)
PREPARATION EXAMPLE 4 Synthesis of intermediate D
In production example 1, intermediate D was produced by the same production method as intermediate a except that 2-bromo-9-phenyl-9H-carbazole (2-bromoo-9-phenyl-9H-carbazole) was used instead of 2-bromo-9- (naphthalen-2-yl) -9H-carbazole (2-bromoo-9- (naphthalen-2-y 1) -9H-carbazole). (MS [ M+H)] + ＝423)
PREPARATION EXAMPLE 5 Synthesis of intermediate E
In production example 1, intermediate E was produced by the same production method as that of intermediate a except that 2-bromo-9-phenyl-9H-carbazole (2-bromo-9-phenyl-9H-carbazole) was used instead of 4-bromo-9-phenyl-9H-carbazole (4-bromo-9-phenyl-9H-carbazole). (MS [ M+H)] + ＝382)
PREPARATION EXAMPLE 6 Synthesis of intermediate F
In production example 1, intermediate F was produced by the same production method as that of intermediate a except that 2-bromo-9-phenyl-9H-carbazole (2-bromo-9-phenyl-9H-carbazole) was used instead of 4-bromo-9-phenyl-9H-carbazole (4-bromo-9-phenyl-9H-carbazole) and 1-bromo-2-nitronaphthalene (1-bromo-2-nitronaphthalene) was used instead of 2-bromo-3-nitronaphthalene (2-bromo-3-nitronaphthalene). (MS [ m+h ] +=382)
PREPARATION EXAMPLE 7 Synthesis of intermediate G
In production example 1, intermediate G was produced by the same production method as that of intermediate a except that 2-bromo-9-phenyl-9H-carbazole (2-bromo-9-phenyl-9H-carbazole) was used instead of 4-bromo-9-phenyl-9H-carbazole (4-bromo-9-phenyl-9H-carbazole) and 1-bromo-2-nitronaphthalene (1-bromo-2-nitronaphthalene) was used instead of 2-bromo-1-nitronaphthalene (2-bromo-1-nitronaphthalene). (MS [ M+H) ] + ＝382)
PREPARATION EXAMPLE 8 Synthesis of intermediate H
In production example 1, 2-bromo-9-phenyl-9H-carbazole (2-bromoo-9-phenyl-9H-carbazole) was changed to 4-bromo-9- (dibenzo [ b, d)]Furan-3-yl) -9H-carbazole (4-bromoo-9- (dibenzo [ b, d)]Furan-3-yl) -9H-carbazole, intermediate H was produced by the same production method as that of intermediate A except that 1-bromo-2-nitronaphthalene (1-bromoo-2-nitronaphthalene) was used instead of 2-bromo-3-nitronaphthalene (2-bromoo-3-nitronaphthalene). (MS [ M+H)] + ＝472)
Synthesis example 1 Synthesis of Compound 1
In a three-necked flask, intermediate A (10.0 g,26.1 mmol) and intermediate a (6.9 g,28.8 mmol) were dissolved in 300ml of toluene (tolene), and sodium tert-butoxide (NaOtBu) (3.8 g,39.2 mmol) and bis (tri-tert-butylphosphine) palladium (0) (bis (tri-tert-butylphosphine) palladium (0)) (Pd (P-tBu) 3 ) 2 ) (0.3 g,0.5 mmol) was followed by stirring under reflux of argon for 6 hours. At the end of the reaction, cooling to normal temperature, adding H 2 O, the reaction solution was transferred to a separatory funnel and extracted. The extract was treated with MgSO 4 After drying and concentration, the sample was purified by silica gel column chromatography and then purified by sublimation, whereby 5.7g of compound 1 was obtained. (yield 37%, MS [ M+H ] ] + ＝586)
Synthesis example 2 Synthesis of Compound 2
In synthesis example 1, compound 2 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate b. (MS [ M+H)] + ＝636)
Synthesis example 3 Synthesis of Compound 3
In synthesis example 1, compound 3 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate c. (MS [ M+H)] + ＝676)
Synthesis example 4 Synthesis of Compound 4
In synthesis example 1, compound 4 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate B. (MS [ M+H)] + ＝586)
Synthesis example 5 Synthesis of Compound 5
In synthesis example 1, compound 5 was produced by the same production method as that of compound 1 except that intermediate a was changed to intermediate B and intermediate a was changed to intermediate d. (MS [ M+H)] + ＝662)
Synthesis example 6 Synthesis of Compound 6
In synthesis example 1, compound 6 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate C.
(MS[M+H] + ＝586)
Synthesis example 7 Synthesis of Compound 7
In synthesis example 1, compound 7 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate D.
(MS[M+H] + ＝636)
Synthesis example 8 Synthesis of Compound 8
In synthesis example 1, compound 8 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate E. (MS [ M+H)] + ＝586)
Synthesis example 9 Synthesis of Compound 9
In synthesis example 1, compound 9 was produced by the same production method as that of compound 1 except that intermediate a was changed to intermediate E and intermediate a was changed to intermediate E. (MS [ M+H)] + ＝702)
Synthesis example 10 Synthesis of Compound 10
In synthesis example 1, compound 10 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate F.
(MS[M+H] + ＝586)
Synthesis example 11 Synthesis of Compound 11
In synthesis example 1, compound 11 was produced by the same production method as that of compound 1 except that intermediate a was changed to intermediate F and intermediate a was changed to intermediate F. (MS [ M+H)] + ＝675)
Synthesis example 12 Synthesis of Compound 12
In synthesis example 1, compound 12 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate G.
(MS[M+H] + ＝586)
Synthesis example 13 Synthesis of Compound 13
In synthesis example 1, compound 13 was produced by the same production method as that of compound 1 except that intermediate a was used as intermediate H.
(MS[M+H] + ＝676)
Experimental example
Comparative example 1-1
ITO (Tin Oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, the washing was repeated twice with distilled water for 10 minutes to perform ultrasonic treatmentWashing with waves. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following HI-A and hexanitrile hexaazatriphenylene (HAT-CN) were respectively usedSequentially performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, as a hole transport layer, HT-A as described below is used +.>After vacuum evaporation, the following EB-A was used as an electron blocking layer>Is subjected to thermal vacuum evaporation. Next, as the light-emitting layer, the host RH-A described below and 2wt% (based on 100 parts by weight of the host) of dopant RD were added +.>Vacuum evaporation was performed on the thickness of (c). Next, as an electron transporting and injecting layer, ET-A and Liq described below were added in a ratio of 1:1 +.>Is subjected to thermal vacuum evaporation, and then Liq is added with +.>Vacuum evaporation was performed on the thickness of (c).
On the electron transport and injection layer, the electron transport and injection layers are sequentially arranged in a ratio of 10:1Magnesium and silver toIs made of aluminum +.>And vapor deposition is performed to form a cathode, thereby manufacturing an organic light-emitting device.
Experimental examples 1-1 to 1-13 and comparative examples 1-2 to 1-8
Organic light-emitting devices of examples 1-1 to 1-13 and comparative examples 1-2 to 1-8 were produced in the same manner as in comparative example 1-1 except that the above comparative example 1-1 was modified as shown in Table 1 to replace RH-A.
The current was applied to the organic light emitting devices fabricated in the above-mentioned experimental examples 1-1 to 1-13 and comparative examples 1-1 to 1-8, and the voltage, efficiency, and lifetime were measured, and the results are shown in table 1 below. At this time, the voltage and the efficiency were 10mA/cm applied 2 LT, measured by current density of (a) 97 Expressed in current density of 20mA/cm 2 The time when the lower initial brightness was reduced to 97%.
TABLE 1
The compound represented by chemical formula 1 of the present invention is composed of a quinoxaline unit functioning as an electron acceptor and a benzoindolocarbazole unit functioning as an electron donor. Since two units having completely different properties are directly bonded, charge is exchanged inside the molecule, and thus the band gap becomes small. In addition, the benzoindolocarbazole unit contains a naphthalene ring, and thus the triplet energy becomes low, with the result that both the singlet energy and the triplet energy are small to facilitate energy transfer to the red dopant, and thus are suitable for application as a host of a red light emitting layer.
In the case of using an indolocarbazole unit instead of benzoindolocarbazole as an electron donor, as in RH-D, the triplet energy cannot be sufficiently reduced, and energy transfer to the red dopant cannot be smoothly performed, and as a result, voltage, efficiency, and lifetime all show poor results.
In particular, the structure of chemical formula 1 stabilizes the movement of internal charges between quinoxaline and benzoindolocarbazole by locating the triplet-stabilized naphthalene ring at a ring beside the nitrogen to which the quinoxaline is attached. As a result, the characteristic of long life is exhibited as compared with the case of RH-F having a naphthalene ring on the side farther from the quinoxaline unit.
In addition, two nitrogens inside the benzoindolocarbazole unit are located at para positions (para) to each other, and thus the electron-donating effect is maximized, thereby exhibiting a characteristic of high HOMO (highest occupied molecular orbital ) energy level. As a result, the benzoindolocarbazole structure of chemical formula 1 of the present invention prevents holes from being trapped by the dopant when compared with RH-B in which a sulfur atom having a lower electron donor capability than a nitrogen atom is located at the same position or RH-E and RH-G in which a sulfur atom is located at a meta position (meta) of non-para (para), and thus hole transport capability becomes excellent, and device characteristics become excellent.
In addition, when the electron donor property is adjusted by applying a condensed ring structure, the stability of the substance becomes higher when compared with the RH-a in which carbazole is used as a substituent to adjust the electron donor property.
In the present invention, chemical formula 1 has a characteristic of being face to face with each other by substituting an Ar unit and a carbazole unit condensed with a ring at an ortho position (ortho) with each other based on a quinoxaline unit, and thus the structure is more stabilized by pi-pi interaction between the two, thereby exhibiting a characteristic of long life. This can be seen by comparing with RH-C using a benzothiophene pyrimidine unit as an electron acceptor structure, or RH-H using a quinazoline unit as an electron acceptor structure.
Therefore, when the compound having the structure of chemical formula 1 is applied as a red light emitting layer host of an organic electroluminescent device in comparison with the results of comparative examples 1-1 to 1-8, which apply similar structures, an optimal device exhibiting low voltage, high efficiency, and long life characteristics can be obtained.
Experimental examples 2-1 to 2-7 and comparative examples 2-2 to 2-3
Organic light-emitting devices of examples 2-1 to 2-14 and comparative examples 2-1 to 2-3 were produced in the same manner as in comparative example 1-1 except that a mixture of 2 host compounds as shown in table 2 was used instead of RH-a in comparative example 1-1. In this case, when a mixture of 2 compounds is used as the main component, the weight ratio between the main components is shown in brackets.
TABLE 2
As shown in table 2, when the compound of chemical formula 1 is mixed with a compound having a biscarbazole structure such as PGH1 or PGH2 as a host, injection of holes into the light emitting layer is smooth, the voltage is reduced, the position of the light emission due to the hole meeting the electrons in the device is widened while moving in the direction of the electron transporting layer in the light emitting layer, and the lifetime of the device is increased. This effect according to the balanced change of holes and electrons may occur together with the efficiency reduction of the device, but the compound of chemical formula 1 exhibits low-voltage, long-life device characteristics while minimizing such efficiency reduction. In particular, when compared with comparative examples 2-1 to 2-3, it was found that this effect was more remarkably exhibited in the compound having the structure of chemical formula 1.
Claims (8)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein in the chemical formula 1 described above, a compound having the formula,
ar is phenyl, naphthyl, biphenyl, carbazolyl, or fluorenyl substituted or unsubstituted by methyl,
r1, R4 and R5 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, or cyano,
r2 and R3 are the same or different from each other and are each independently hydrogen or deuterium, or a plurality of R2 are bonded to each other to form a benzofuran ring,
r1 is an integer of 0 to 6,
r2 to r4 are each integers of 0 to 4,
r5 is an integer of 0 to 2,
when r1 to r5 are 2 or more, structures in parentheses of 2 or more are the same or different from each other,
m is 1 and n is 0,
x2 is a direct bond, and
x1 is absent as unbound.
2. The compound of claim 1, wherein Ar of chemical formula 1 is represented by any one of the following structures:
in the case of the construction described above, in which the first and second support members are arranged,
b1, B2, B5, B8 and B10 are each independently hydrogen,
b12 and B13 are methyl groups,
b1 is an integer of 0 to 5,
b2 is an integer of 0 to 9,
b5 is an integer of 0 to 7,
b8 is an integer of 0 to 8,
b10 is an integer of 0 to 7,
when b1, b2, b5, b8 and b10 are 2 or more, the structures in brackets of 2 or more are the same as each other.
3. The compound of claim 1, wherein the chemical formula 1 is selected from the following compounds:
4. an organic light emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound represented by chemical formula 1 of any one of claims 1 to 3.
5. The organic light-emitting device according to claim 4, wherein the organic layer comprises a light-emitting layer including the compound represented by chemical formula 1.
6. The organic light-emitting device according to claim 4, wherein the organic layer comprises a light-emitting layer including the compound represented by chemical formula 1 as a host of the light-emitting layer.
7. The organic light-emitting device according to claim 6, wherein the light-emitting layer further comprises a compound represented by the following chemical formula 8 as an additional host,
wherein the compound represented by chemical formula 1 is 20 to 50 parts by weight based on 100 parts by weight of the entire main body:
chemical formula 8
In the chemical formula 8 described above, the chemical formula,
R a and R is b Are identical or different from one another and are each independently of one another phenyl, biphenyl, naphthyl or dibenzobarking radical which is substituted or unsubstituted by naphthyl,
R c and R is d Are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; cyano group; a nitro group; or an amino group,
r and s are each integers of 0 to 7, rc is the same or different from each other when r is 2 or more, and Rd is the same or different from each other when s is 2 or more.
8. The organic light-emitting device according to claim 7, wherein the chemical formula 8 is represented by any one of the following compounds:
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20190009968 | 2019-01-25 | ||
| KR10-2019-0009968 | 2019-01-25 | ||
| CN202080002724.3A CN112204030B (en) | 2019-01-25 | 2020-01-15 | Compound and organic light emitting device comprising the same |
| PCT/KR2020/000736 WO2020153653A1 (en) | 2019-01-25 | 2020-01-15 | Compound and organic light-emitting diode comprising same |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080002724.3A Division CN112204030B (en) | 2019-01-25 | 2020-01-15 | Compound and organic light emitting device comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116621842A true CN116621842A (en) | 2023-08-22 |
Family
ID=71736357
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310478696.8A Pending CN116621842A (en) | 2019-01-25 | 2020-01-15 | Compound and organic light emitting device comprising the same |
| CN202080002724.3A Active CN112204030B (en) | 2019-01-25 | 2020-01-15 | Compound and organic light emitting device comprising the same |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080002724.3A Active CN112204030B (en) | 2019-01-25 | 2020-01-15 | Compound and organic light emitting device comprising the same |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR102338205B1 (en) |
| CN (2) | CN116621842A (en) |
| WO (1) | WO2020153653A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117343061A (en) * | 2022-06-24 | 2024-01-05 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device and electronic device |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150108330A (en) * | 2014-03-17 | 2015-09-25 | 롬엔드하스전자재료코리아유한회사 | Electron buffering material and organic electroluminescent device comprising the same |
| KR20170010715A (en) * | 2015-07-20 | 2017-02-01 | 롬엔드하스전자재료코리아유한회사 | Luminescent Material for Delayed Fluorescence and Organic Electroluminescent Device Comprising the Same |
| KR102479135B1 (en) * | 2016-04-18 | 2022-12-21 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials and organic electroluminescent device comprising the same |
| US10840458B2 (en) * | 2016-05-25 | 2020-11-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2018021737A1 (en) * | 2016-07-29 | 2018-02-01 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
| KR102018685B1 (en) * | 2016-07-29 | 2019-09-04 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR102152194B1 (en) * | 2016-08-18 | 2020-09-04 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| US10944060B2 (en) * | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR20200046339A (en) * | 2018-10-24 | 2020-05-07 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20200049635A (en) * | 2018-10-31 | 2020-05-08 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| CN110862381B (en) | 2019-12-04 | 2021-03-19 | 宁波卢米蓝新材料有限公司 | Organic electroluminescent compound and preparation method and application thereof |
-
2020
- 2020-01-15 CN CN202310478696.8A patent/CN116621842A/en active Pending
- 2020-01-15 WO PCT/KR2020/000736 patent/WO2020153653A1/en active Application Filing
- 2020-01-15 CN CN202080002724.3A patent/CN112204030B/en active Active
- 2020-01-15 KR KR1020200005339A patent/KR102338205B1/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| KR102338205B1 (en) | 2021-12-10 |
| WO2020153653A1 (en) | 2020-07-30 |
| KR20200092874A (en) | 2020-08-04 |
| CN112204030A (en) | 2021-01-08 |
| CN112204030B (en) | 2023-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112585145B (en) | Polycyclic compound and organic light emitting device including the same | |
| EP3767694B1 (en) | Organic light-emitting device | |
| CN111936479B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN112218861B (en) | Polycyclic compound and organic light-emitting element including the same | |
| CN113906582B (en) | Organic light emitting device | |
| CN111527081A (en) | Polycyclic compound and organic light emitting diode comprising same | |
| CN113056471B (en) | Compound and organic light-emitting diode comprising same | |
| CN113994497B (en) | Organic light emitting device | |
| CN113056468B (en) | Compound and organic light emitting device comprising the same | |
| CN116057039B (en) | Compound and organic light emitting device comprising the same | |
| CN112204030B (en) | Compound and organic light emitting device comprising the same | |
| CN113056463B (en) | Compound and organic light emitting device comprising the same | |
| CN114364660B (en) | Compound and organic light emitting device comprising the same | |
| CN113015733B (en) | Compound and organic light emitting device comprising the same | |
| CN112868111B (en) | Organic light emitting device | |
| CN112912365B (en) | Polycyclic compound and organic light emitting device including the same | |
| CN113950480B (en) | Compound and organic light emitting device comprising the same | |
| CN112088161B (en) | Polycyclic compound and organic light emitting diode including the same | |
| CN116761794A (en) | Compound and organic light emitting device comprising the same | |
| CN117561234A (en) | Compound and organic light emitting device comprising the same | |
| CN116783185A (en) | Compound and organic light emitting device comprising the same | |
| CN118614161A (en) | Organic light emitting device | |
| CN118285172A (en) | Organic light emitting device | |
| CN118511676A (en) | Organic light emitting device | |
| CN117616024A (en) | Compound and organic light emitting device comprising 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 |