CN112218861B - Polycyclic compound and organic light-emitting element including the same - Google Patents
Polycyclic compound and organic light-emitting element including the same Download PDFInfo
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- CN112218861B CN112218861B CN201980037279.1A CN201980037279A CN112218861B CN 112218861 B CN112218861 B CN 112218861B CN 201980037279 A CN201980037279 A CN 201980037279A CN 112218861 B CN112218861 B CN 112218861B
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- -1 Polycyclic compound Chemical class 0.000 title description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 135
- 239000000126 substance Substances 0.000 claims abstract description 89
- 239000010410 layer Substances 0.000 claims description 221
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 238000002347 injection Methods 0.000 claims description 57
- 239000007924 injection Substances 0.000 claims description 57
- 239000012044 organic layer Substances 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
- 230000005525 hole transport Effects 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 48
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 38
- 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 38
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- 238000004519 manufacturing process Methods 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 230000000903 blocking effect Effects 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 26
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 229910052805 deuterium Inorganic materials 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 238000007740 vapor deposition Methods 0.000 description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
- 230000003111 delayed effect Effects 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- PRWATGACIORDEL-UHFFFAOYSA-N 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=C(C#N)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C(N2C3=CC=CC=C3C3=CC=CC=C32)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C1C#N PRWATGACIORDEL-UHFFFAOYSA-N 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
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- 238000010992 reflux Methods 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- 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 6
- HNACKJNPFWWEKI-UHFFFAOYSA-N 3,6-dimethyl-9h-carbazole Chemical compound C1=C(C)C=C2C3=CC(C)=CC=C3NC2=C1 HNACKJNPFWWEKI-UHFFFAOYSA-N 0.000 description 6
- ROEOVWIEALGNLM-UHFFFAOYSA-N 5h-benzo[b]carbazole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4NC3=CC2=C1 ROEOVWIEALGNLM-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JRWCYAOEUILTDX-UHFFFAOYSA-N 5-bromo-4,6-dichloro-2-fluorobenzene-1,3-dicarbonitrile Chemical compound BrC=1C(=C(C(=C(C#N)C1Cl)F)C#N)Cl JRWCYAOEUILTDX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- AUPCUNJLSROPKA-UHFFFAOYSA-N 2-bromo-4,6-dichloro-5-fluorobenzene-1,3-dicarbonitrile Chemical compound BrC1=C(C#N)C(=C(C(=C1C#N)Cl)F)Cl AUPCUNJLSROPKA-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003220 pyrenes Chemical class 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 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 3
- 238000001771 vacuum deposition Methods 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
- FIPZWVLCZIYEMW-UHFFFAOYSA-N (4-cyanophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(C#N)C=C1 FIPZWVLCZIYEMW-UHFFFAOYSA-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
- 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
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- 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
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- PCMKGEAHIZDRFL-UHFFFAOYSA-N 3,6-diphenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C(NC=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=C1 PCMKGEAHIZDRFL-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- WLKLBMLIJRMZJS-UHFFFAOYSA-N 6-(3,4,5,16,17,18-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2,4,6,8,10,12,14,16-nonaen-6-yl)hexanenitrile Chemical compound C1(=NN=NC=2C3=NN=NC=C3C3=CC=CC=C3C1=2)CCCCCC#N WLKLBMLIJRMZJS-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-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
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
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- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
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- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
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- 239000001301 oxygen Substances 0.000 description 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
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- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
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- 125000005504 styryl group Chemical group 0.000 description 2
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 1
- MNJYZNVROSZZQC-UHFFFAOYSA-N (4-tert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=C(B(O)O)C=C1 MNJYZNVROSZZQC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
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Abstract
The present specification provides a compound represented by chemical formula 1 and an organic light emitting element including the same.
Description
Technical Field
The present application claims priority from korean patent application No. 10-2018-0125957, filed to the korean patent office on 10/22 of 2018, the entire contents of which are incorporated herein.
The present specification relates to a polycyclic compound and an organic light-emitting element including the same.
Background
The organic light emitting element has a structure in which an organic thin film is arranged between 2 electrodes. If a voltage is applied to the organic light emitting element having such a structure, electrons and holes injected from 2 electrodes are combined in the organic thin film to be paired, quenched, and emitted. The organic thin film may be formed of a single layer or a plurality of layers as required.
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 element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. In order to improve efficiency and stability of the organic light-emitting element, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light-emitting element, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode, electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition again to the ground state.
There is a continuing need to develop new materials for organic light emitting elements as described above.
[ Prior Art literature ]
(patent document 1) korean patent laid-open No. 10-2012-032572
Disclosure of Invention
Technical problem
The present specification describes compounds and organic light emitting devices comprising the same.
Solution to the problem
The present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
a1 and A2 are the same or different from each other and each independently is cyano, or phenyl substituted with cyano,
either one of R5 and R6 or R is a bond with,
r1 to R4, and R5 and R6 which are not bonded thereto, are identical to or different from each other and are each independently deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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, or are bonded to each other with adjacent groups to form a substituted or unsubstituted ring,
y is an aryl group substituted or unsubstituted with 1 or more substituents selected from cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, and substituted or unsubstituted heteroaryl; or a substituted or unsubstituted heteroaryl group containing O or S as a heteroatom,
R which is not bonded is a substituted or unsubstituted aryl,
n1 to n6 are each integers of 0 to 4, n1+n2+n3+n4+n5+n6 is 1 or more,
when n1 to n6 are each an integer of 2 or more, substituents in parentheses of 2 or more are the same or different from each other.
In addition, the present specification provides an organic light emitting element, 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 a compound represented by the chemical formula 1.
Effects of the invention
The compound described in this specification can be used as a material for an organic layer of an organic light-emitting element.
In manufacturing an organic light-emitting element including the compound according to one embodiment of the present specification, an organic light-emitting element which is excellent in light-emitting efficiency and has a low driving voltage, high efficiency, and long lifetime can be obtained.
Drawings
Fig. 1 illustrates an example of an organic light-emitting element constituted by a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 10.
Fig. 2 illustrates an example of an organic light-emitting element constituted by a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6, an electron transport layer 8, and a cathode 10.
Fig. 3 illustrates an example of an organic light-emitting element constituted by a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 9, and a cathode 10.
[ description of the symbols ]
1: substrate board
2: anode
3: hole injection layer
4: hole transport layer
5: electron blocking layer
6: light-emitting layer
7: hole blocking layer
8: electron transport layer
9: electron injection and transport layers
10: cathode electrode
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
a1 and A2 are the same or different from each other and each independently is cyano, or phenyl substituted with cyano,
either one of R5 and R6 or R is a bond with,
r1 to R4, and R5 and R6 which are not bonded thereto, are identical to or different from each other and are each independently deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron 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, or are bonded to each other with adjacent groups to form a substituted or unsubstituted ring,
Y is an aryl group substituted or unsubstituted with 1 or more substituents selected from cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, and substituted or unsubstituted heteroaryl; or a substituted or unsubstituted heteroaryl group containing O or S as a heteroatom,
r which is not bonded is a substituted or unsubstituted aryl,
n1 to n6 are each integers of 0 to 4, n1+n2+n3+n4+n5+n6 is 1 or more,
when n1 to n6 are each an integer of 2 or more, substituents in parentheses of 2 or more are the same or different from each other.
The compound represented by the above chemical formula 1 is a delayed fluorescent substance. Unlike phosphorescent materials, which convert light by replacing singlet excitons with triplet excitons, fluorescent materials are materials which convert light by replacing triplet excitons with singlet excitons, and thus exhibit delayed fluorescence. The delayed fluorescence (also referred to as thermally activated delayed fluorescence: thermally Activated Delayed Fluorescence: hereinafter, appropriately abbreviated as "TADF") phenomenon is a phenomenon in which 75% of triplet excitons generated by electroluminescence cross-over between singlet exciton reverse systems (Reverse Intersystem Crossing: hereinafter, appropriately abbreviated as "RISC") at room temperature or a light emitting layer temperature in a light emitting element. The singlet excitons generated by the reverse intersystem crossing emit fluorescence in the same manner as the 25% singlet excitons generated by the direct excitation, and thus 100% internal quantum efficiency can be achieved.
In theory, the delayed fluorescent substance can convert both singlet excitons and triplet excitons into light, and thus can achieve 100% internal quantum efficiency, and thus can overcome the limits of lifetime and efficiency possessed by phosphorescent substances.
According to an embodiment of the present specification, the compound represented by chemical formula 1 above may be included in a light emitting layer of an organic light emitting element. The compound represented by chemical formula 1 has a small energy difference between the triplet state and the singlet state, and thus the exciton generated in the triplet state increases in proportion and speed by Reverse intersystem crossing (RISC) to the singlet state, and the time in which the exciton stays in the triplet state decreases, and thus has a delayed fluorescence (TADF: thermally Activated Delayed Fluorescence) characteristic, and thus has advantages of increased efficiency and lifetime when applied to a light emitting layer of an organic light emitting element.
In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components 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 another 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, cyano 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.
Examples of the above substituents are described below, but are not limited thereto.
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-SiY a Y b Y c The chemical formula of (A) is shown in the specification, Y is shown in the specification a 、Y b And Y c May each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl 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-BY d Y e The chemical formula of (A) is shown in the specification, Y is shown in the specification d And Y e May each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl 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 10 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 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 of the portion containing an alkyl group other than them described in this specification are all included in a straight-chain or branched-chain shape.
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 40 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, perylenyl, and the like,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 above fluorenyl group is substituted, it may beIs 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 36 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuryl, 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.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a hydrocarbon ring, or a heterocyclic ring.
The hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring, and may be selected from the cycloalkyl group or the aryl group, in addition to the 2-valent group.
In the present specification, the above description of the aryl group can be applied to the aromatic hydrocarbon ring other than the 2-valent aromatic hydrocarbon ring.
The heterocyclic ring may be a 2-valent one, and the above description of the heterocyclic group may be applied.
According to an embodiment of the present specification, A1 and A2 are the same or different from each other, and each is independently cyano or phenyl substituted with cyano.
According to another embodiment, each of A1 and A2 above is cyano.
According to another embodiment, each of A1 and A2 above is phenyl substituted with cyano.
According to another embodiment, any one of A1 and A2 above is cyano, and the remaining one is phenyl substituted with cyano.
According to an embodiment of the present specification, the above Y is an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl and substituted or unsubstituted heteroaryl; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, which contains O or S as a hetero atom.
According to another embodiment, the above Y is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with 1 or more substituents selected from cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl and substituted or unsubstituted heteroaryl; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, which contains O or S as a heteroatom.
In another embodiment, Y is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. When Y is an aryl group substituted or unsubstituted with 1 or more substituents selected from a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted heteroaryl group, an element having high efficiency and lifetime can be obtained when the element is applied to an organic light-emitting element, as compared with an aryl group substituted with other substituents.
Specifically, when Y is an aryl group substituted with a substituent containing a double bond, a radical is formed in the organic light-emitting element when exposed to electrons, and therefore the light-emitting lifetime is lower than that of the compound of the present invention. In addition, the compound of the present invention has a wider portion of the interlace (overlap) between the energy levels of HOMO (highest occupied molecular orbital ) and LUMO (lowest unoccupied molecular orbital, lowest unoccupied molecular orbital) than the above-described compound in which Y is cyano, and thus has high fluorescence quantum efficiency (PLQY, photoluminescence Quantum Yield), and thus has high efficiency when applied to an organic light-emitting element.
According to another embodiment, the above Y is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from a cyano group and an alkyl group having 1 to 20 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms which contains O or S as a hetero atom which is substituted or unsubstituted.
In another embodiment, Y is a phenyl group substituted or unsubstituted with 1 or more substituents selected from a cyano group and an alkyl group having 1 to 20 carbon atoms, a naphthyl group substituted or unsubstituted with 1 or more substituents selected from a cyano group and an alkyl group having 1 to 20 carbon atoms, a fluorenyl group substituted or unsubstituted with an alkyl group selected from a cyano group and an alkyl group having 1 to 20 carbon atoms, a dibenzofuranyl group substituted or unsubstituted, or a dibenzothiophenyl group substituted or unsubstituted.
According to another embodiment, the above Y is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from cyano, methyl and butyl; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, which contains O or S as a heteroatom.
According to another embodiment, the above Y is phenyl substituted or unsubstituted with 1 or more substituents selected from cyano, methyl and butyl; naphthyl substituted or unsubstituted with 1 or more substituents selected from cyano, methyl, and butyl; fluorenyl substituted or unsubstituted with 1 or more substituents selected from cyano, methyl, and butyl; substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothienyl group.
In another embodiment, Y is phenyl substituted or unsubstituted with 1 or more substituents selected from cyano, methyl, and butyl; naphthyl substituted or unsubstituted with 1 or more substituents selected from cyano, methyl, and butyl; fluorenyl substituted with methyl; dibenzofuranyl; or dibenzothienyl.
In another embodiment, Y is phenyl substituted or unsubstituted with 1 or more substituents selected from cyano, methyl, and butyl; a naphthyl group; fluorenyl substituted with methyl; dibenzofuranyl; or dibenzothienyl.
In another embodiment, Y is phenyl substituted with cyano, phenyl substituted with methyl, phenyl substituted with tert-butyl, naphthyl, 9-dimethylfluorenyl, dibenzofuranyl, or dibenzothiophenyl.
According to an embodiment of the present specification, when n1 to n6 are integers of 0 to 4, n1+n2+n3+n4+n5+n6 is 1 or more, and n1 to n6 are integers of 2 or more, substituents in brackets of 2 or more are the same or different from each other. The compound represented by the above chemical formula 1 has a substituent group in 1 or more of 3 carbazole groups bonded to benzene or 2 or more substituent groups bonded to each other to form a ring, and thus has an advantage of having excellent light-emitting efficiency and long-life characteristics when applied to an organic light-emitting element, compared to a compound having no substituent group bonded to carbazole and a compound containing no carbazole condensed with a ring.
According to an embodiment of the present description, n1+n2+n3+n4+n5+n6 is 1 to 24.
According to an embodiment of the present description, n1+n2+n3+n4+n5+n6 is 1 to 16.
According to an embodiment of the present description, n1+n2+n3+n4+n5+n6 is 1 to 8.
According to an embodiment of the present description, n1+n2+n3+n4+n5+n6 is 1 to 6.
According to an embodiment of the present description, n1+n2+n3+n4+n5+n6 is 1 to 4.
According to an embodiment of the present description, n1+n2+n3+n4+n5+n6 is 1 to 3.
According to an embodiment of the present description, n1+n2+n3+n4+n5+n6 is 1 or 2.
According to an embodiment of the present disclosure, n1+n2+n3+n4+n5+n6 is 2 or more.
According to an embodiment of the present disclosure, n1+n2+n3+n4+n5+n6 is 3 or more.
According to an embodiment of the present disclosure, n1+n2+n3+n4+n5+n6 is 4 or more.
In one embodiment of the present specification, any one of R5 and R6 or R is bonded.
According to an embodiment of the present disclosure, R not bonded to the above is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In another embodiment, R not bonded to the above is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, R not bonded to the above is a substituted or unsubstituted phenyl group.
In another embodiment, R not bonded to the above is phenyl.
According to an embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 2 or 3.
[ chemical formula 2]
[ chemical formula 3]
In the above-mentioned chemical formulas 2 and 3,
r1 to R6, n1 to n6, Y, A1 and A2 are as defined in the above chemical formula 1,
r' is a substituted or unsubstituted aryl group.
According to one embodiment of the present specification, R' is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In another embodiment, R' is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, R' above is a substituted or unsubstituted phenyl group.
In another embodiment, R' is phenyl.
According to an embodiment of the present disclosure, R1 to R4, and R5 and R6 which are not bonded to each other are the same or different and are each independently deuterium, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or are bonded to each other with an adjacent group to form a substituted or unsubstituted ring having 6 to 30 carbon atoms.
According to an embodiment of the present disclosure, R1 to R4, and R5 and R6 not bonded thereto are the same or different from each other, and are each independently deuterium, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or substituted or unsubstituted aryl having 6 to 30 carbon atoms, 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.
According to an embodiment of the present specification, the above R1 to R4, and R5 and R6 which are not bonded to each other are the same or different from each other, and are each independently deuterium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted benzocarbazolyl, or are bonded to each other with adjacent groups to form a ring, thereby constituting any one of the following structures.
In the above-described structure, the first and second heat exchangers,
r11 is a substituted or unsubstituted aryl group,
r12 and R13 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group.
The above structure may be substituted or unsubstituted with deuterium, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.
According to another embodiment, the above R1 to R4, and R5 and R6 not bonded thereto are the same or different from each other, each independently deuterium, cyano, methyl, isopropyl, tert-butyl, phenyl, carbazolyl, or benzocarbazolyl substituted with deuterium or unsubstituted, or are bonded to each other to form a ring, thereby constituting any one of the following structures.
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In the above-described structure, the first and second heat exchangers,
r11 is a substituted or unsubstituted aryl group,
r12 and R13 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group,
the above structure may be substituted or unsubstituted with deuterium, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.
According to an embodiment of the present specification, the above structure may be substituted or unsubstituted with deuterium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted benzocarbazolyl.
According to an embodiment of the present specification, the above structure may be substituted or unsubstituted with deuterium, cyano, methyl substituted or unsubstituted with deuterium, isopropyl, tert-butyl, phenyl, carbazolyl, or benzocarbazolyl.
According to one embodiment of the present disclosure, the above structure may be substituted with deuterium, cyano, CH 3 、CD 3 Isopropyl, tert-butyl, phenyl, carbazolyl, and,Or a benzocarbazolyl group, substituted or unsubstituted.
According to one embodiment of the present specification, R11 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, R11 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.
In another embodiment, R11 is phenyl or biphenyl.
According to an embodiment of the present specification, the above-mentioned R12 and R13 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
In another embodiment, R12 and R13 are the same or different from each other and are each independently a substituted or unsubstituted methyl group.
According to another embodiment, R12 and R13 are methyl.
According to an embodiment of the present specification, at least one of the above R1 to R4, and R5 and R6 not bonded to each other and an adjacent group are bonded to each other to form a ring, thereby constituting a benzocarbazole ring.
According to an embodiment of the present specification, at least one of the above R1 to R4, and R5 and R6 not bonded to each other and an adjacent group are bonded to each other to form a ring, thereby constituting a benzocarbazole ring which is one of the following structures.
According to an embodiment of the present specification, the above chemical formula 1 is represented by any one of the following structures.
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According to an embodiment of the present specification, the triplet (triplet) level of the compound represented by the above chemical formula 1 is 2.1eV or more, preferably, 2.1eV or more and 3.0eV or less, 2.2eV or more and 3.0eV or less, and 2.4eV or more and 2.9eV or less. When the triplet (triplet) level of the compound represented by the above chemical formula 1 satisfies the above range, electron injection becomes easy, and the formation ratio of excitons increases, so that there is an advantage in that the light emitting efficiency increases.
According to an embodiment of the present specification, the difference between the singlet (single) level and the triplet (triplet) level of the compound represented by the above chemical formula 1 is 0eV or more and 0.3eV or less, preferably 0eV or more and 0.2eV or less. When the difference between the singlet (single) and triplet (triplet) levels of the compound represented by the above chemical formula 1 satisfies the above range, the rate and speed at which excitons generated in the triplet migrate to the singlet state through reverse intersystem crossing (RISC) increase, thereby reducing the time for which the excitons stay in the triplet state, and thus, there is an advantage in that the efficiency and lifetime of the organic light emitting element increase.
In the present specification, the triplet energy can be measured by a spectrometer such as JASCO FP-8600 capable of measuring fluorescence or phosphorescence, and 10 is produced under the condition of measurement by using toluene or Tetrahydrofuran (THF) as a solvent at an ultralow temperature by using liquefied nitrogen -6 M concentration solution, and irradiating the solution with a light source having an absorption wavelength range of a substance, thereby confirming the elimination of singlet emission by spectroscopic analysis of luminescenceSpectrum of light emitted in triplet state other than light. If electrons from the light source are excited, separation of the two components can be achieved in an ultralow temperature state because the electrons stay in the triplet state for a much longer time than in the singlet state.
In the present specification, the singlet energy is measured by a fluorescent device such as JASCO FP-8600, and the light source is irradiated at normal temperature, unlike the triplet energy measurement method described above.
In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In the present invention, the HOMO and LUMO levels of the compounds can also be adjusted by introducing various substituents into the core structure of the structure described above.
In addition, an organic light-emitting element according to the present specification is 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 above-mentioned compound.
The organic light-emitting element of the present specification can be manufactured by a general method and material for manufacturing an organic light-emitting element, 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 including an organic layer represented by chemical formula 1, the organic layer may be formed not only by a vacuum 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 element 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 element 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 injection simultaneously as organic layers. However, the structure of the organic light emitting element of the present specification is not limited thereto, and may include a smaller or larger number of organic layers.
In the organic light emitting element of the present specification, the organic layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1.
In another organic light emitting element 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 the chemical formula 1.
In another organic light emitting element of the present specification, the organic layer includes a light emitting layer, and the light emitting layer may include a compound represented by the 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.
According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the compound as a dopant of the light emitting layer.
In one embodiment of the present specification, the organic layer includes a light-emitting layer including the compound as a dopant of the light-emitting layer, and may further include a host. At this time, the content of the above dopant may be contained in an amount of 1 to 60 parts by weight, preferably 30 to 50 parts by weight, based on 100 parts by weight of the main body.
According to an embodiment of the present specification, the organic layer includes a light-emitting layer including any one or more selected from an aromatic condensed ring derivative and a heterocyclic compound as a host of the light-emitting layer.
According to an embodiment of the present specification, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and as the heterocyclic compound, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but not limited thereto.
According to an embodiment of the present specification, the light emitting layer may include the compound as a dopant, and may include a compound represented by the following chemical formula F as a host, but is not limited thereto.
[ chemical formula F ]
In the above-mentioned chemical formula F,
l13 is a substituted or unsubstituted (b+1) valent aryl group, or a substituted or unsubstituted (b+1) valent heteroaryl group,
g11 and G12 are the same or different from each other and are each independently hydrogen, deuterium, cyano, or heteroaryl containing O or S,
b13 is an integer of 1 to 3, and when b13 is 2 or more, L13 are the same or different from each other,
b is 1 or 2, b is 2,the same as or different from each other.
According to an embodiment of the present specification, the organic layer includes a light emitting layer including a dopant including the compound and a host represented by the chemical formula F at a weight ratio of 1:99 to 50:50.
In one embodiment of the present specification, in the above chemical formula F, L13 is a substituted or unsubstituted aryl group having a (b+1) valence of 6 to 16 or a substituted or unsubstituted heteroaryl group having a (b+1) valence of 2 to 16.
In one embodiment of the present specification, in the above chemical formula F, L13 is a substituted or unsubstituted aryl group having a (b+1) valence of 6 to 12 or a substituted or unsubstituted heteroaryl group having a (b+1) valence of 2 to 12.
In an embodiment of the present specification, in the above chemical formula F, L13 is a substituted or unsubstituted (b+1) valent phenyl group, a substituted or unsubstituted (b+1) valent biphenyl group, a substituted or unsubstituted (b+1) valent dibenzofuranyl group, or a substituted or unsubstituted (b+1) valent pyridyl group.
In one embodiment of the present specification, in the case where L13 is a substituted (b+1) -valent aryl group in the chemical formula F, the substituent of the (b+1) -valent aryl group is an aryl group substituted with a heteroaryl group.
In one embodiment of the present specification, in the above chemical formula F, G11 and G12 are the same or different from each other, and each is independently hydrogen or cyano.
In one embodiment of the present specification, b13 is 1 in the above chemical formula F.
In one embodiment of the present specification, b13 is 2 in the above chemical formula F.
In one embodiment of the present specification, the compound represented by the above chemical formula F is any one selected from the following compounds.
According to an embodiment of the present disclosure, the organic layer includes a light-emitting layer including the compound and a fluorescent light-emitting substance. In this case, the content of the fluorescent substance may be contained in an amount of 0 to 10 parts by weight based on 100 parts by weight of the compound. Since the fluorescent substance is allowed to function to receive excitons from the compound and finally emit light, the color purity of the element can be improved by using a fluorescent substance having a narrow half width, and there is an advantage in that quenching of excitons and polarons of the compound can be prevented to increase the lifetime of the element. The half width refers to a width of a peak (peak) having a height of half (1/2) of a maximum emission peak (peak) height on an emission spectrum.
The fluorescent substance may be represented by an anthracene compound, a pyrene compound, a fluoranthene compound, a perylene compound, a boron compound, or the following structure, but is not limited thereto.
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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.
The organic light-emitting element may have a laminated structure as shown below, for example, 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 element of the present specification may have the structure shown in fig. 1 to 3, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light-emitting element in which an anode 2, a light-emitting layer 6, and a cathode 10 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 6.
Fig. 2 illustrates a structure of an organic light-emitting element in which an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6, an electron transport layer 8, and a cathode 10 are sequentially stacked on a substrate 1.
Fig. 3 illustrates a structure of an organic light-emitting element in which an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 9, and a cathode 10 are sequentially stacked on a substrate 1.
For example, the organic light emitting element 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 varpor 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 these methods, an organic light-emitting element 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, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various 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, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well 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), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers. 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 degradation 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 the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
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 light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
When the light-emitting layer emits red light, as the light-emitting dopant, PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonide, bis (1-phenylisoquinoline) iridium acetylacetonate), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate may be usedIridium complex), PQIR (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant 3 Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum), anthracene compounds, pyrene compounds, and boron compounds, but not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F 2 ppy) 2 Examples of the fluorescent substance include phosphorescent substances such as Irpic, 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.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting material is a material that can well inject electrons from the cathode and transfer the electrons to the light-emitting layer, and is suitable for a material 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 the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for improving the movement of electrons can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, a capability of preventing excitons generated in the light emitting layer from migrating to a hole injecting layer, and a capability of forming a thin filmExcellent compounds. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,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 generally under the same conditions as those of 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 element according to the present invention 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 invention
In the following, examples will be given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present application is not to be construed as limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
< production example >
The compound represented by the above chemical formula 1 can be produced based on various types of isophthalonitrile substituted with a halide as follows. Various compounds in specific examples were synthesized by the following production methods.
Production example 1-1: synthesis of Compound 1-A
20g (68.1 mmol) of 2-bromo-4, 6-dichloro-5-fluoroisophthalonitrile, 70mmol of (4-cyanophenyl) boric acid, 200mL of THF, 100mL of water and 204mmol of potassium carbonate were mixed and heated to 70 ℃. Tetrakis (triphenylphosphine) palladium (1.3 mmol) was added and stirred under reflux for 3 hours. After the reaction, the aqueous layer was removed from the reaction solution which was returned to room temperature, and the organic layer was purified by chloroform/hexane (2:3) column chromatography, whereby 19.8g of compound 1-a was obtained (yield 92%).
MS[M+H] + ＝316
Production examples 1 to 2: synthesis of Compound 1-B
20g (68.1 mmol) of 2-bromo-4, 6-dichloro-5-fluoroisophthalonitrile, 70mmol of naphthalen-2-ylboronic acid, 200mL of THF, 100mL of water and 204mmol of potassium carbonate were mixed and heated to 70 ℃. Tetrakis (triphenylphosphine) palladium (1.3 mmol) was added and stirred under reflux for 3 hours. After the reaction, the aqueous layer was removed from the reaction solution which was returned to room temperature, and the organic layer was purified by chloroform/hexane (2:3) column chromatography, whereby 20.2g of compound 1-B was obtained (yield 87%).
MS[M+H] + ＝341
Production examples 1 to 3: synthesis of Compound 1-C
20g (68.1 mmol) of 2-bromo-4, 6-dichloro-5-fluoroisophthalonitrile, 70mmol of dibenzo [ b, d ] furan-2-ylboronic acid, 200mL of THF, 100mL of water and 204mmol of potassium carbonate were mixed and heated to 70 ℃. Tetrakis (triphenylphosphine) palladium (1.3 mmol) was added and stirred under reflux for 3 hours. After the reaction, the aqueous layer was removed from the reaction solution which was returned to room temperature, and the organic layer was purified by chloroform/hexane (2:3) column chromatography, whereby 21.8g of compound 1-C was obtained (yield 84%).
MS[M+H] + ＝381
Production examples 1 to 4: synthesis of Compound 1-D
20g (68.1 mmol) of 5-bromo-4, 6-dichloro-2-fluoroisophthalonitrile, 70mmol of p-tolueneboronic acid, 200mL of THF, 100mL of water and 204mmol of potassium carbonate were mixed and heated to 70 ℃. Tetrakis (triphenylphosphine) palladium (1.3 mmol) was added and stirred under reflux for 3 hours. After the reaction, the aqueous layer was removed from the reaction solution which was returned to room temperature, and the organic layer was purified by chloroform/hexane (2:3) column chromatography, whereby 17.9g of compound 1-D was obtained (yield 86%).
MS[M+H] + ＝305
Production examples 1 to 5: synthesis of Compound 1-E
20g (68.1 mmol) of 5-bromo-4, 6-dichloro-2-fluoroisophthalonitrile, 70mmol of (4-cyanophenyl) boric acid, 200mL of THF, 100mL of water and 204mmol of potassium carbonate were mixed and heated to 70 ℃. Tetrakis (triphenylphosphine) palladium (1.3 mmol) was added and stirred under reflux for 3 hours. After the reaction, the aqueous layer was removed from the reaction solution recovered to room temperature, and the organic layer was purified by chloroform/hexane (2:3) column chromatography to obtain 18.3g of compound 1-E (yield 85%).
MS[M+H] + ＝316
Production examples 1 to 6: synthesis of Compound 1-F
20g (68.1 mmol) of 5-bromo-4, 6-dichloro-2-fluoroisophthalonitrile, 70mmol of dibenzo [ b, d ] thiophen-2-ylboronic acid, 200mL of THF, 100mL of water and 204mmol of potassium carbonate were mixed and heated to 70 ℃. Tetrakis (triphenylphosphine) palladium (1.3 mmol) was added and stirred under reflux for 3 hours. After the reaction, the aqueous layer was removed from the reaction solution which was returned to room temperature, and the organic layer was purified by chloroform/hexane (2:3) column chromatography, whereby 21.9g of compound 1-F was obtained (yield 81%).
MS[M+H] + ＝397
Production examples 1 to 7: synthesis of Compound 1-G
20g (68.1 mmol) of 5-bromo-4, 6-dichloro-2-fluoroisophthalonitrile, 70mmol of (4- (tert-butyl) phenyl) boronic acid, 200mL of THF, 100mL of water and 204mmol of potassium carbonate were mixed and heated to 70 ℃. Tetrakis (triphenylphosphine) palladium (1.3 mmol) was added and stirred under reflux for 3 hours. After the reaction, the aqueous layer was removed from the reaction solution recovered to room temperature, and the organic layer was purified by chloroform/hexane (2:3) column chromatography to obtain 20.3G of compound 1-G (yield 86%).
MS[M+H] + ＝347
Production example 2-1: synthesis of Compound 2-A
17.1g (54 mmol) of 1-A, 54mmol of 5H-benzo [ b ] carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution which had been returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 24.4g of Compound 2-A (yield 88%).
MS[M+H] + ＝513
Production example 2-2: synthesis of Compound 2-B
17.1g (54 mmol) of 1-A, 54mmol of 9H-carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 22.8g of Compound 2-B (yield 91%).
MS[M+H] + ＝463
Production example 2-3: synthesis of Compound 2-C
18.4g (54 mmol) of 1-B, 54mmol of 5H-benzo [ B ] carbazole, 160mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 25g of Compound 2-C (yield 86%).
MS[M+H] + ＝538
Production examples 2 to 4: synthesis of Compound 2-D
20.6g (54 mmol) of 1-C, 54mmol of 9H-carbazole, 180mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 25.4g of compound 2-D (yield 89%).
MS[M+H] + ＝528
Production examples 2 to 5: synthesis of Compound 2-E
16.5g (54 mmol) of 1-D, 54mmol of 9H-carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 22.2g of Compound 2-E (yield 91%).
MS[M+H] + ＝452
Production examples 2 to 6: synthesis of Compound 2-F
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16.5g (54 mmol) of 1-D, 54mmol of 5H-benzo [ b ] carbazole, 150mL of DMF and 108mmol of potassium carbonate are mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 22.8g of Compound 2-F (yield 84%).
MS[M+H] + ＝502
Production examples 2 to 7: synthesis of Compound 2-G
17.1g (54 mmol) of 1-E, 54mmol of 9H-carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 21.3G of compound 2-G (yield 85%).
MS[M+H] + ＝463
Production examples 2 to 8: synthesis of Compound 2-H
17.1g (54 mmol) of 1-E, 54mmol of 3, 6-diphenyl-9H-carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution which had been returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 26.6g of Compound 2-H (yield 80%).
MS[M+H] + ＝615
Production examples 2 to 9: synthesis of Compound 2-I
17.1g (54 mmol) of 1-E, 54mmol of 5-phenyl-5, 8-indolino [2,3-c ] carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution which had been returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 28.2g of Compound 2-I (yield 83%).
MS[M+H] + ＝628
Production examples 2 to 10: synthesis of Compound 2-J
21.5g (54 mmol) of 1-F, 54mmol of 9H-carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution which had been returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 25.6g of Compound 2-J (yield 87%).
MS[M+H] + ＝544
Production examples 2 to 11: synthesis of Compound 2-K
18.7G (54 mmol) of 1-G, 54mmol of 9H-carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 24.3g of Compound 2-K (yield 91%).
MS[M+H] + ＝494
Production examples 2 to 12: synthesis of Compound 2-L
18.7G (54 mmol) of 1-G, 54mmol of 3, 6-diphenyl-9H-carbazole, 150mL of DMF and 108mmol of potassium carbonate were mixed, heated to 100℃and stirred for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 30g of Compound 2-L (yield 86%).
MS[M+H] + ＝646
Production example 3-1: synthesis of Compound 1
19g (37 mmol) of 2-A, 74mmol of 9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized 2 times from tetrahydrofuran and ethanol to obtain 23.2g of compound 1 (yield 81%).
MS[M+H] + ＝775
Production example 3-2: synthesis of Compound 2
17.1g (37 mmol) of 2-B, 74mmol of 3, 6-dimethyl-9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 21.7g of compound 2 (yield 75%).
MS[M+H] + ＝781
Production example 3-3: synthesis of Compound 3
19.9g (37 mmol) of 2-C, 74mmol of 9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 23.1g of compound 3 (yield 78%).
MS[M+H] + ＝800
Production examples 3 to 4: synthesis of Compound 4
19.6g (37 mmol) of 2-D, 74mmol of 3, 6-dimethyl-9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 22.8g of compound 4 (yield 73%).
MS[M+H] + ＝847
Production examples 3 to 5: synthesis of Compound 5
16.7g (37 mmol) of 2-E, 74mmol of 3, 6-dimethyl-9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 20.2g of compound 5 (yield: 71%).
MS[M+H] + ＝770
Production examples 3 to 6: synthesis of Compound 6
18.6g (37 mmol) of 2-F, 74mmol of 9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 22.3g of compound 6 (yield 79%).
MS[M+H] + ＝764
Production examples 3 to 7: synthesis of Compound 7
17.1G (37 mmol) of 2-G, 74mmol of 3, 6-dimethyl-9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 21.1g of compound 7 (yield 73%).
MS[M+H] + ＝781
Production examples 3 to 8: synthesis of Compound 8
22.8g (37 mmol) of 2-H, 74mmol of 9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 25g of compound 8 (yield 77%).
MS[M+H] + ＝877
Production examples 3 to 9: synthesis of Compound 9
23.2g (37 mmol) of 2-I, 74mmol of 9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 25.7g of compound 9 (yield 78%).
MS[M+H] + ＝890
Production examples 3 to 10: synthesis of Compound 10
20.1g (37 mmol) of 2-J, 74mmol of 3, 6-dimethyl-9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 23g of compound 10 (yield: 72%).
MS[M+H] + ＝862
Production examples 3 to 11: synthesis of Compound 11
18.3g (37 mmol) of 2-K, 74mmol of 3, 6-dimethyl-9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized 2 times from tetrahydrofuran and ethanol to obtain 21g of compound 11 (yield: 70%).
MS[M+H] + ＝812
Production examples 3 to 12: synthesis of Compound 12
23.9g (37 mmol) of 2-L, 74mmol of 9H-carbazole, 180mL of xylene, 89mmol of sodium tert-butoxide and 1.8mmol of tetrakis (triphenylphosphine) palladium are mixed, refluxed and stirred for 2 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized from tetrahydrofuran and ethanol 2 times to obtain 24.9g of compound 12 (yield 74%).
MS[M+H] + ＝908
Comparative examples 1 to 1 ]
ITO (Indium 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, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. 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, each thin film was vacuum-deposited by vacuum deposition to a vacuum degree of 5.0X10 -4 The handkerchief is laminated. First, hexaazatriphenylene-capronitrile (HAT-CN) was added to ITO +.>And performing thermal vacuum evaporation to form a hole injection layer.
On the hole injection layer, the following is performedVacuum vapor deposition of NPB compound to form hole transport layer
On the hole transport layer, the film thickness is set to An electron blocking layer was formed by vacuum evaporation of the following compound EB1>
Then, on the electron blocking layer, the film thickness is set to beThe following compounds m-CBP and 4CzIPN were vacuum-evaporated at a weight ratio of 70:30 to form a light-emitting layer.
On the light-emitting layer, the film thickness is set toThe hole blocking layer was formed by vacuum evaporation of the following compound HB 1.
On the hole blocking layer, the following compound ET1 and compound LiQ (Lithium Quinolate, 8-hydroxyquinoline lithium) were vacuum-evaporated at a weight ratio of 1:1 to give a film of the following compoundForm an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And the thickness of the metal layer is evaporated to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintainedTo->Lithium fluoride maintenance of cathode>Is kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 To 5X 10 -6 The support is then fabricated to produce an organic light emitting device. />
< Experimental examples 1-1 to 1-12>
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the compound of table 1 below was used instead of the compound 4CzIPN in comparative example 1-1.
< comparative examples 1-2 to 1-4>
An organic light-emitting device was produced in the same manner as in comparative example 1-1 except that the following compounds T1 to T3 were used instead of the compound 4CzIPN in comparative example 1-1.
The organic light-emitting elements of experimental examples 1-1 to 1-12 and comparative examples 1-1 to 1-4 were subjected to a temperature of 10mA/cm 2 The driving voltage (V) and the current efficiency (cd/A) were measured at a current density of 3000cd/m 2 The CIE color coordinates were determined at a luminance of (c),and measured at 3000cd/m 2 Time when the lower luminance was reduced to 95% (T 95 ) The results are shown in table 1 below.
[ Table 1 ]
As shown in table 1, the elements of examples 1-1 to 1-12 using the compound of chemical formula 1 have lower voltage and higher efficiency than the element of comparative example 1-1 using the compound 4 CzIPN.
Further, it was found that the element using the compound of the above chemical formula 1 was improved in voltage, efficiency, color purity and lifetime characteristics as compared with comparative examples 1-2 to 1-4 using compounds in which all of carbazole bound to phenylene was unsubstituted or only 2 carbazole were bound to phenylene.
Therefore, it was confirmed that the compound according to the present invention is excellent in light-emitting ability and high in color purity, and thus can be suitably used for a delayed fluorescence organic light-emitting element.
Comparative example 2-1 ]
ITO (Indium 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, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. 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, each thin film was vacuum-deposited by vacuum deposition to a vacuum degree of 5X 10 -4 Handkerchief layerAnd (3) stacking. First, hexaazatriphenylene-capronitrile (HAT-CN) was added to ITO +.>And performing thermal vacuum evaporation to form a hole injection layer.
Forming a hole transport layer by vacuum vapor deposition of the following compound NPB on the hole injection layer
On the hole transport layer, the film thickness is set to An electron blocking layer was formed by vacuum evaporation of the following compound EB1>
Then, on the electron blocking layer, the film thickness is set to beThe following compounds m-CBP, 4CzIPN and GD1 were vacuum-evaporated at a weight ratio of 68:30:2 to form a light-emitting layer.
On the light-emitting layer, the film thickness is set toThe hole blocking layer was formed by vacuum evaporation of the following compound HB 1.
On the hole blocking layer, the following compound ET1 and compound LiQ (Lithium Quinolate, 8-hydroxyquinoline lithium) were vacuum-evaporated at a weight ratio of 1:1 to give a film of the following compoundForm an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And the thickness of the metal layer is evaporated to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintainedTo->Lithium fluoride maintenance of cathode>Is kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 To 5X 10 -6 The support is then fabricated to produce an organic light emitting device.
/>
< Experimental examples 2-1 to 2-12>
An organic light-emitting device was produced in the same manner as in comparative example 2-1 except that the compound of table 2 below was used instead of compound 4CzIPN in comparative example 2-1.
< comparative examples 2-2 to 2-4>
An organic light-emitting device was produced in the same manner as in comparative example 2-1 except that the compound of table 2 below was used instead of compound 4CzIPN in comparative example 2-1.
The organic light-emitting elements of experimental examples 2-1 to 2-12 and comparative examples 2-1 to 2-4 were subjected to a temperature of 10mA/cm 2 The driving voltage (V) and the current efficiency (cd/A) were measured at a current density of 3000cd/m 2 The CIE color coordinates were measured at the luminance of (c) and the results are shown in table 2 below.
[ Table 2 ]
As shown in table 2, the elements of examples 2-1 to 2-12 using the compound of chemical formula 1 have lower voltage and higher efficiency than the element using the compound 4CzIPN of comparative example 2-1.
It is also found that the element using the compound of chemical formula 1 was improved in voltage and efficiency characteristics as compared with comparative examples 2-1 to 2-4 using compounds in which all of carbazole bonded to phenylene group was unsubstituted or only 2 carbazole were bonded to phenylene group.
Therefore, it was confirmed that the compound according to the present invention is excellent in light-emitting ability and capable of adjusting the light-emitting wavelength, thereby enabling realization of an organic light-emitting element of high color purity.
While the preferred examples of the present invention have been described above, the present invention is not limited to these examples, and may be modified and implemented in various forms within the scope of the invention as claimed and the detailed description of the invention, and the present invention is also within the scope of the invention.
Claims (7)
1. A compound represented by the following chemical formula 2:
chemical formula 2
Wherein, in the chemical formula 2,
a1 and A2 are each cyano groups,
r1 to R4, and R5 and R6 are the same or different from each other and are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, or are bonded to each other with the adjacent groups to form a phenyl-substituted or unsubstituted ring having 6 to 30 carbon atoms,
y is an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of a white cyano group and an alkyl group having 1 to 20 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms which contains O or S as a hetero atom,
n1 to n6 are each integers of 0 to 4, n1+n2+n3+n4+n5+n6 is 1 or more,
when n1 to n6 are each an integer of 2 or more, substituents in parentheses of 2 or more are the same or different from each other.
2. The compound according to claim 1, wherein R1 to R4, and R5 and R6 are the same or different from each other, each independently is an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms, or are combined with each other with adjacent groups to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with a phenyl group.
3. The compound of claim 1, wherein the chemical formula 2 is represented by any one of the following structures:
4. An organic light emitting element comprising:
a first electrode;
a second electrode provided opposite to the first electrode; and
comprises 1 or more organic layers between the first electrode and the second electrode,
wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 3.
5. The organic light-emitting element according to claim 4, wherein the organic layer comprises a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer containing the compound.
6. The organic light-emitting element according to claim 4, wherein the organic layer comprises an electron-transporting layer or an electron-injecting layer, the electron-transporting layer or the electron-injecting layer containing the compound.
7. The organic light-emitting element according to claim 4, wherein the organic layer comprises a light-emitting layer containing the compound.
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| CN116998242A (en) * | 2021-03-15 | 2023-11-03 | 出光兴产株式会社 | Organic electroluminescent element and electronic device |
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