CN113594393B - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN113594393B CN113594393B CN202111016186.6A CN202111016186A CN113594393B CN 113594393 B CN113594393 B CN 113594393B CN 202111016186 A CN202111016186 A CN 202111016186A CN 113594393 B CN113594393 B CN 113594393B
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- 239000010410 layer Substances 0.000 claims abstract description 203
- -1 amine compounds Chemical class 0.000 claims abstract description 52
- 239000000758 substrate Substances 0.000 claims abstract description 23
- 239000012044 organic layer Substances 0.000 claims abstract description 19
- 229910010272 inorganic material Inorganic materials 0.000 claims abstract description 13
- 239000011147 inorganic material Substances 0.000 claims abstract description 13
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 42
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 claims description 4
- 229910001635 magnesium fluoride Inorganic materials 0.000 claims description 4
- 239000011775 sodium fluoride Substances 0.000 claims description 4
- 235000013024 sodium fluoride Nutrition 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 3
- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 claims description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 2
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 claims description 2
- 229910001632 barium fluoride Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 230000000694 effects Effects 0.000 abstract description 8
- 238000002310 reflectometry Methods 0.000 abstract description 5
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 49
- 150000001875 compounds Chemical group 0.000 description 49
- 238000003786 synthesis reaction Methods 0.000 description 49
- 239000000463 material Substances 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 238000002347 injection Methods 0.000 description 27
- 239000007924 injection Substances 0.000 description 27
- 238000001819 mass spectrum Methods 0.000 description 26
- 238000000034 method Methods 0.000 description 26
- 238000004128 high performance liquid chromatography Methods 0.000 description 24
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000001624 naphthyl group Chemical group 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 5
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 5
- 125000005549 heteroarylene group Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 150000002220 fluorenes Chemical class 0.000 description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 238000006757 chemical reactions by type Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 2
- IJVBYWCDGKXHKK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetraphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IJVBYWCDGKXHKK-UHFFFAOYSA-N 0.000 description 2
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 2
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 2
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 2
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- SPHIBPCYNZKATL-UHFFFAOYSA-N 4-(4-anilino-2-methylphenyl)-3-methyl-2-naphthalen-1-yl-N-phenylaniline Chemical compound C1(=CC=CC2=CC=CC=C12)C=1C(=C(C=CC=1NC1=CC=CC=C1)C1=C(C=C(NC2=CC=CC=C2)C=C1)C)C SPHIBPCYNZKATL-UHFFFAOYSA-N 0.000 description 2
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 2
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 2
- HTJPPQKJCPTAED-UHFFFAOYSA-N 9-n,10-n-bis(4-methylphenyl)-9-n,10-n-diphenylanthracene-9,10-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC=CC=2)C=2C=CC(C)=CC=2)=C2C=CC=CC2=1)C1=CC=CC=C1 HTJPPQKJCPTAED-UHFFFAOYSA-N 0.000 description 2
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-N aluminum;2-methylquinolin-8-ol;4-phenylphenol Chemical compound [Al+3].C1=CC=C(O)C2=NC(C)=CC=C21.C1=CC=C(O)C2=NC(C)=CC=C21.C1=CC(O)=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-N 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol 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-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000004653 anthracenylene group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 239000010936 titanium Substances 0.000 description 1
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- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
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- 229940105963 yttrium fluoride Drugs 0.000 description 1
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention provides an organic electroluminescent device, and belongs to the technical field of organic electroluminescence. The organic electroluminescent device comprises a substrate, an anode, an organic layer, a cathode and a cover layer, wherein the cover layer comprises a low refractive layer and a high refractive layer, the low refractive layer comprises fluorene compounds and inorganic materials, and the high refractive layer comprises amine compounds, and as the three layers are used together as the cover layer, light rays are prevented from directly reaching air from the cathode, a larger refractive index difference value is generated at the interface of the low refractive layer and the high refractive layer in the cover layer, the overall reflectivity of the cover layer can be improved, the reflectivity of the cover layer becomes larger, the resonance effect of the device is improved, the increase of microcavity effect is maximized, and the luminous efficiency is also effectively improved. The organic electroluminescent device has good application effect and industrialization prospect.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device.
Background
An organic electroluminescent device is a display unit utilizing an organic self-luminescence phenomenon, which has excellent properties of a wide viewing angle, a lighter weight, a high luminance luminescence at a low driving voltage, a fast response speed, and the like as compared with a liquid crystal display unit, and has recently been expected as a full-color display unit or an application of illumination. The principle is that electrons injected from a cathode and holes injected from an anode are recombined in an organic layer clamped by two stages to form excitons, and the excitons emit light when the excitons are changed from an excited state to a ground state.
The organic electroluminescent devices can be classified into bottom emission and top emission according to the direction of extraction of emitted light. In the top emission system, the anode is a reflective electrode, the cathode is a semitransparent electrode, and light is extracted through the cathode side opposite to the substrate, and in this case, since there is no area loss due to the thin film transistor on the substrate side, the light emission area of the top emission system is greatly increased compared to that of the bottom emission system.
In the top emission system, both the anode and the cathode function as emission layers for light emitted from the light-emitting layer, the optical film thickness of the organic layer between the anode and the cathode is in the wavelength range, the self-light-emitting molecules are emitted toward a certain reflection layer and reflected by the reflection layer to the positions of the light-emitting molecules, and the reflected light is in a wave-overlapped state in which the phases are identical, and therefore, the self-light-emitting molecules emit light toward the side opposite to the reflection layer and are coherent with light traveling in the same direction, and optical interference is performed. There are the following phenomena: since the conditions of optical interference vary depending on the film thickness of each organic layer, the intensity or spectrum of light extracted to the outside varies greatly depending on the film thickness of each organic layer, but if the film thickness of each organic layer is adjusted in order to adjust the conditions of optical interference, the carrier transport balance in the device varies poorly. A method is therefore proposed for this case: in the top emission mode, a capping layer is deposited on the cathode, and the optical interference condition is optimized by the capping layer, thereby improving the light emission efficiency of the device.
Disclosure of Invention
In order to further improve the luminous efficiency of the device, the invention provides an organic electroluminescent device, which comprises a substrate, an anode, an organic layer, a cathode and a cover layer, wherein the cover layer comprises a low-refraction layer and a high-refraction layer, the low-refraction layer comprises fluorene compounds and inorganic materials, the high-refraction layer comprises amine compounds, and the special cover layer configuration of the organic electroluminescent device improves the resonance effect of the device, so that the luminous efficiency of the device is greatly improved.
The invention provides an organic electroluminescent device, which comprises a substrate, an anode, an organic layer, a cathode and a cover layer, wherein the cover layer comprises a low-refraction layer and a high-refraction layer, the low-refraction layer comprises fluorene compounds shown in chemical formula 1 and inorganic materials, the high-refraction layer comprises amine compounds shown in chemical formula 2,
At least one of Ar 1～Ar4 is selected from the group shown in chemical formula 3 or chemical formula 4, and the rest is the same or different from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
The ring A and the ring B are the same or different and are selected from one of substituted or unsubstituted C6-C12 aryl and substituted or unsubstituted C2-C15 heteroaryl; n and m are the same or different and are selected from integers of 1-11;
the L 0 is selected from none or a single bond;
The L 1 is selected from one of substituted or unsubstituted C6-C25 arylene and substituted or unsubstituted C2-C20 heteroarylene;
The R 1～R4 is the same or different and is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl; the a 1 is an integer from 0 to 5; the a 2～a4 are the same or different and are selected from integers from 0 to 4; when a plurality of substituents are present, the plurality of substituents may be the same or different from each other, or adjacent two substituents may be linked to form a ring;
The L 2、L6～L9 is the same or different and is selected from one of single bond, substituted or unsubstituted C6-C25 arylene and substituted or unsubstituted C2-C15 heteroarylene;
the X 0 is one selected from O, S;
the ring C is selected from one of an unsubstituted, substituted or unsubstituted benzene ring and a substituted or unsubstituted naphthalene ring;
Ar 5 is selected from substituted or unsubstituted C10-C18 thick aryl;
Ar 6 is selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
the L 3～L5 is the same or different and is selected from one of single bond, substituted or unsubstituted C6-C25 arylene and substituted or unsubstituted C2-C20 heteroarylene;
The R 5 is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl; the a 5 is selected from integers from 0 to 4; when a 5 is greater than 1, a plurality of R 5 may be the same or different from each other, or two adjacent R 5 may be connected to form a ring.
The invention has the beneficial effects that:
The organic electroluminescent device comprises a substrate, an anode, an organic layer, a cathode and a cover layer, wherein the cover layer comprises a low refractive layer and a high refractive layer, the low refractive layer comprises fluorene compounds and inorganic materials, and the high refractive layer comprises amine compounds, and as the three layers are used together as the cover layer, light rays are prevented from directly reaching air from the cathode, a larger refractive index difference value is generated at the interface of the low refractive layer and the high refractive layer in the cover layer, the overall reflectivity of the cover layer can be improved, the reflectivity of the cover layer becomes larger, the resonance effect of the device is improved, the increase of microcavity effect is maximized, and the luminous efficiency is also effectively improved.
Drawings
Detailed Description
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.
In the present description of the invention,Meaning a moiety attached to another substituent.
In this specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example, the number of the cells to be processed,Can representAnd so on.
The alkyl group in the present invention means a hydrocarbon group having at least one hydrogen atom in an alkane molecule, and may be a straight chain alkyl group, a branched chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, particularly preferably 1 to 4 carbon atoms, and examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, etc., but are not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl or tert-butyl.
Cycloalkyl in the present invention means a hydrocarbon group having at least one hydrogen atom in the cycloparaffin molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 10 carbon atoms, particularly preferably 3 to 6 carbon atoms, and examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and the like, but are not limited thereto. The alkyl group is preferably a cyclohexyl group, an adamantyl group, or a norbornyl group.
Aryl according to the invention refers to a monovalent group remaining after removal of one hydrogen atom from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, preferably having from 6 to 30 carbon atoms, more preferably from 6 to 18 carbon atoms, particularly preferably from 6 to 14 carbon atoms, most preferably from 6 to 12 carbon atoms, and may be substituted or unsubstituted. Examples may include phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, and,A group, perylene group, indenyl group, fluoranthenyl group, fluorenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, 9-methyl-9-phenylfluorenyl group, spirofluorenyl group, benzofluorenyl group, and the like, but is not limited thereto. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a spirofluorenyl group, or a benzofluorenyl group.
Heteroaryl according to the present invention refers to a group in which one or more of the aromatic nucleus carbons in the aryl group is replaced by a heteroatom including, but not limited to, oxygen, sulfur, nitrogen, silicon atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 12 carbon atoms, most preferably 3 to 8 carbon atoms, and the heteroaryl may be substituted or unsubstituted. Examples may include, but are not limited to, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, pyridyl, pyrimidinyl, triazinyl, thienyl, furanyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, carbazolyl, 9-phenylcarbazolyl, benzimidazolyl, benzoxazolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like. The heteroaryl group is preferably thienyl, furyl, indolyl, carbazolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl.
The arylene group according to the invention is defined as a divalent radical remaining after removal of two hydrogen atoms from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, preferably having from 6 to 30 carbon atoms, more preferably from 6 to 18 carbon atoms, particularly preferably from 6 to 14 carbon atoms, most preferably from 6 to 12 carbon atoms, and may be substituted or unsubstituted. Examples may include phenylene, biphenylene, terphenylene, etc., naphthylene, anthrylene, triphenylene, pyrenylene, fluoranthrylene, perylene, fluorenylene, 9-dimethylfluorenylene, 9-diphenylfluorenylene, 9-methyl-9-phenylfluorenylene, spirofluorenylene, benzofluorenylene, etc., but are not limited thereto. The arylene group is preferably a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a triphenylene group, a pyrenylene group, a fluorenylene group, a 9, 9-dimethylfluorenylene group, a 9, 9-diphenylfluorenylene group, a spirofluorenylene group, or a benzofluorenylene group.
Heteroaryl ene according to the present invention refers to a group in which one or more of the aromatic nucleus carbons in the arylene group is replaced by a heteroatom including, but not limited to, oxygen, sulfur, nitrogen, silicon atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 12 carbon atoms, most preferably 3 to 8 carbon atoms, which heteroaryl ene may be substituted or unsubstituted. Examples may include, but are not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, an indolylene group, a carbazolylene group, a furanylene group, a thiophenylene group, a quinolinylene group, an isoquinolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a phenothiazinylene group, a phenoxazinylene group, and the like. The heteroarylene group is preferably an indolylene group, a carbazolylene group, a furanylene group, a thienylene group, a dibenzofuranylene group, a dibenzothienyl group, a phenothiazinylene group, or a phenoxazinylene group.
"Substituted" as used herein means that a hydrogen atom in a compound group is replaced with another atom or group, and the position of substitution is not limited.
"Substituted or unsubstituted" as used herein means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen atom, amino group, cyano group, nitro group, C1-C30 alkyl group, C3-C20 cycloalkyl group, C6-C60 aryl group, C2-C60 heteroaryl group, C6-C60 arylamine group, C6-C60 aryloxy group, preferably deuterium, halogen atom, cyano group, C1-C12 alkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano group, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornyl, phenyl, tolyl, mesityl, penta-deuterophenyl, biphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, pyrenyl, triphenylenyl,A group, perylene group, fluoranthenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, 9-methyl-9-phenylfluorenyl group, carbazolyl group, 9-phenylcarbazolyl group, spirobifluorenyl group, carbazoloindolyl group, pyrrolyl group, furyl group, thienyl group, benzofuryl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, pyridyl group, pyrimidyl group, pyridazinyl group, pyrazinyl group, triazinyl group, oxazolyl group, thiazolyl group, benzoxazolyl group, benzothiazolyl group, benzotriazole group, benzimidazolyl group, quinolyl group, isoquinolyl group, phenothiazinyl group, phenoxazinyl group, acridinyl group and the like, but is not limited thereto. Or when the substituents are plural, adjacent substituents may be bonded to form a ring; when the substituent is plural, plural substituents are the same or different from each other.
The term "bonded to form a cyclic structure" as used herein means that two groups are attached to each other by a chemical bond and optionally aromatized. As exemplified below:
In the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a condensed ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclopentane, cyclohexane acene, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
The term "integer selected from 0 to M" as used herein means any one of the integers selected from 0 to M, including 0,1,2 … M-2, M-1, M. For example, "a 1 is an integer from 0 to 5" means that a 1 is selected from 0,1,2,3,4,5; "a 2～a4 is the same or different and is selected from an integer of 0 to 4" means that a 2～a4 is the same or different and is selected from 0,1,2,3,4; "a 5 is an integer from 0 to 4" means that a 1 is selected from 0,1,2,3,4; "n, m are the same or different and are selected from integers from 1 to 11" means that n, m are the same or different and are selected from 1,2,3,4,5,6,7,8,9, 10, 11; "n 1、m1 is the same or different and is selected from integers from 1 to 5" means that n 1、m1 is the same or different and is selected from 1,2,3,4,5; "n 2、m2 is the same or different and is selected from integers from 1 to 4" means that n 2、m2 is the same or different and is selected from 1,2,3,4; "n 3、m3 is the same or different and is selected from integers from 1 to 3" means that n 3、m3 is the same or different and is selected from 1,2,3; "n 4、m4 is the same or different and is selected from integers from 1 to 7" means that n 4、m4 is the same or different and is selected from 1,2,3,4,5,6,7; "b 1 is an integer from 0 to 4" means that b 1 is selected from 0,1,2,3,4; "b 2 is an integer from 0 to 3" means that b 2 is selected from 0,1,2,3; "b 3 is an integer from 0 to 2" means that b 3 is selected from 0,1,2; "b 4 is an integer from 0 to 6" means that b 4 is selected from 0,1,2,3,4,5,6; "r is an integer from 0 to 5" means that r is selected from 0,1,2,3,4,5; "s is an integer from 0 to 4" means that s is selected from 0,1,2,3,4; "t is an integer from 0 to 3" means that t is selected from 0,1,2,3; "w is an integer from 0 to 2" means that w is selected from 0,1,2; "q 1 is an integer from 0 to 7" means that q 1 is selected from 0,1,2,3,4,5,6,7; "q 2 is an integer from 0 to 6" means that q 2 is selected from 0,1,2,3,4,5,6; "q 3 is an integer from 0 to 4" means that q 3 is selected from 0,1,2,3,4; and so on.
The term "at least one" as used herein means one, two, three, four, and more where allowed.
The invention provides an organic electroluminescent device, which comprises a substrate, an anode, an organic layer, a cathode and a covering layer.
Preferably, the cover layer includes a low refractive layer and a high refractive layer.
Preferably, the low refractive layer includes a first low refractive layer and a second low refractive layer.
Preferably, the first low refractive layer includes a structure shown in chemical formula 1, and the second low refractive layer includes an inorganic material.
Preferably, the high refractive layer includes a structure shown in chemical formula 2.
Preferably, the high refractive layer is located outside the cathode, and the first low refractive layer is located between the high refractive layer and the second low refractive layer.
Preferably, the organic electroluminescent device sequentially comprises a substrate, an anode, an organic layer, a cathode, a high refractive layer, a first low refractive layer and a second low refractive layer.
The organic layer comprises at least one layer of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. However, the structure of the organic electroluminescent device of the present invention is not limited to the above-described structure, and if necessary, a plurality of organic layers may be omitted or simultaneously provided. For example, an electron blocking layer may be further provided between the hole transport layer and the light emitting layer, and a hole blocking layer may be further provided between the electron transport layer and the light emitting layer; the organic layers having the same function may be formed into a laminated structure of two or more layers.
The light-emitting layer according to the present invention may include a host material, a dopant material, or the like, and may be formed of a single-layer structure or a multilayer structure in which the above layers are stacked.
The organic electroluminescent device of the invention has the structure that:
a substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/high refractive layer/first low refractive layer/second low refractive layer;
A substrate/anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/high refractive layer/first low refractive layer/second low refractive layer;
a substrate/anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/high refractive layer/first low refractive layer/second low refractive layer;
a substrate/anode/hole injection layer/hole transport layer/light emitting auxiliary layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/high refractive layer/first low refractive layer/second low refractive layer;
A substrate/anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode/first capping layer/high refractive layer/first low refractive layer/second low refractive layer;
However, the structure of the organic electroluminescent device is not limited thereto. The organic electroluminescent device can be selected and combined according to the device parameter requirement and the material characteristics, partial organic layers can be added or omitted, and the organic layers with the same function can be made into a laminated structure with more than two layers.
The organic electroluminescent device of the present invention is generally formed on a substrate. The substrate may be a substrate made of glass, plastic, polymer film, silicon, or the like, as long as it is not changed when an electrode is formed or an organic layer is formed.
In the organic electroluminescent device according to the present invention, the anode material may be selected from metals such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., and alloys thereof; metal oxides such as indium oxide, zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), aluminum zinc oxide, and the like; the conductive polymer is, for example, polyaniline, polypyrrole, poly (3-methylthiophene), or the like. In addition to the above materials and combinations thereof, the anode material may also include other known materials suitable for use as an anode. Preferably, the anode of the present invention is selected from the group consisting of ITO, ITO-Ag-ITO, and the like.
In the organic electroluminescent device of the present invention, the hole injection material may be selected from silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, etc., copper phthalocyanine (CuPc), 4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene (HAT-CN), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), etc. In addition to the above materials and combinations thereof, the hole injection material may include other known materials suitable for use as a hole injection layer. Preferably, the hole injection layer of the present invention is selected from copper phthalocyanine (CuPc), 4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like.
In the organic electroluminescent device according to the present invention, the hole transporting material may be selected from the group consisting of N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB), N '-bis (naphthalene-1-yl) -N, N' -di (phenyl) -2,2 '-dimethylbenzidine (α -NPD), N' -diphenyl-N, N '-bis (3-methylphenyl) -1,1' -biphenyl-4, 4 '-diamine (TPD), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), and the like. In addition to the above materials and combinations thereof, the hole transport material may also include other known materials suitable for use as a hole transport layer. Preferably, the hole transport layer of the present invention is selected from the group consisting of N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB), N '-bis (naphthalen-1-yl) -N, N' -bis (phenyl) -2,2 '-dimethylbenzidine (α -NPD), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), and the like.
In the organic electroluminescent device of the present invention, the light emitting layer material comprises a light emitting layer host material AND a light emitting layer guest material, AND the light emitting layer host material may be selected from 4,4' -bis (9-Carbazolyl) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphtyl) anthracene (α -AND), 1,3, 5-tris (9-carbazolyl) benzene (TCP), AND the like. In addition to the above materials and combinations thereof, the luminescent layer host material may also include other known materials suitable for use as a luminescent layer. Preferably, the host material of the light emitting layer of the present invention is selected from 9, 10-bis (2-naphthyl) Anthracene (ADN), 9'- (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), AND the like. The guest material of the light emitting layer of the present invention is classified into a blue light emitting material, a green light emitting material, and a red light emitting material. The light-emitting layer guest may be selected from the group consisting of (6- (4- (diphenylamino (phenyl) -N, 2,5,8, 11-tetra-tert-butylperylene (TBPe), 4 '-bis [4- (di-p-tolylamino) styryl ] biphenyl (DPAVBi), bis (4, 6-difluorophenylpyridine-C2, N) picolinated iridium (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy) 3), bis (2-phenylpyridine) iridium (Ir (ppy) 2 (acac)), 9, 10-bis [ N- (p-tolyl) anilino ] anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N ] iridium (III) (Ir (piq) 3), bis (1-phenylisoquinoline) (acetylacetone) iridium (Ir (piq) 2 (acac)), and the like, and the light-emitting layer may include the above materials in addition to the above materials, and the light-emitting layer may be preferably selected from the group consisting of the materials of di- (4, 4' -p-toluylamino) anilino ] anthracene (TBPE), 4- (4-dimethylaminostyryl) -4H-pyran, tri-C, tri (1-phenylisoquinoline-C2, N) iridium (DPAVBi), bis (Ir), bis [ 1-phenylisoquinoline (Pi) 2, N) and the luminescent layer may be selected from the group consisting of the preferred luminescent layer 4-p-butyl perylene (PYP), 9, 10-bis [ N- (p-tolyl) anilino ] anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), and the like.
In the organic electroluminescent device of the present invention, the doping ratio of the host material and the guest material in the light emitting layer is determined according to the materials used. Preferably, the doping film thickness proportion of the guest material of the light-emitting layer is 0.5-10%.
In the organic electroluminescent device according to the present invention, the electron transport material may be selected from 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq 3), 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), etc., and may include other known materials suitable for an electron transport layer in addition to the above materials and combinations thereof. Preferably, the electron transport layer of the present invention is selected from 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq 3), 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), and the like.
In the organic electroluminescent device according to the present invention, the electron injection material may be selected from Li, na, K, rb, cs, be, mg, ca, lithium fluoride (LiF), sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, lithium oxide, lithium tetra (8-hydroxyquinoline) boron, lithium 8-hydroxyquinoline, etc., and may include other known materials suitable for an electron injection layer in addition to the above materials and combinations thereof. Preferably, the electron injection layer of the present invention is selected from lithium fluoride (LiF), 8-hydroxyquinoline-lithium (Liq), and the like.
In the organic electroluminescent device according to the present invention, the cathode material may be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, etc., and alloys thereof; the multilayered metal material is, for example, liF/Al, mg/Ag, li/Al, liO2/Al, baF2/Al, or the like. In addition to the above materials and combinations thereof, the cathode material may also include other known materials suitable for use as a cathode. Preferably, the cathode according to the invention is selected from a semitransparent cathode, such as Ag or Mg-Ag alloy or thin Al.
The invention relates to an organic electroluminescent device, wherein the cover layer comprises a low refractive layer and a high refractive layer, the low refractive layer comprises fluorene compounds and inorganic materials shown in chemical formula 1, the high refractive layer comprises amine compounds shown in chemical formula 2,
At least one of Ar 1～Ar4 is selected from the group shown in chemical formula 3 or chemical formula 4, and the rest is the same or different from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
The ring A and the ring B are the same or different and are selected from one of substituted or unsubstituted C6-C12 aryl and substituted or unsubstituted C2-C15 heteroaryl; n and m are the same or different and are selected from integers of 1-11;
the L 0 is selected from none or a single bond;
The L 1 is selected from one of substituted or unsubstituted C6-C25 arylene and substituted or unsubstituted C2-C20 heteroarylene;
The R 1～R4 is the same or different and is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl; the a 1 is an integer from 0 to 5; the a 2～a4 are the same or different and are selected from integers from 0 to 4; when a plurality of substituents are present, the plurality of substituents may be the same or different from each other, or adjacent two substituents may be linked to form a ring;
The L 2、L6～L9 is the same or different and is selected from one of single bond, substituted or unsubstituted C6-C25 arylene and substituted or unsubstituted C2-C15 heteroarylene;
the X 0 is one selected from O, S;
the ring C is selected from one of an unsubstituted, substituted or unsubstituted benzene ring and a substituted or unsubstituted naphthalene ring;
Ar 5 is selected from substituted or unsubstituted C10-C18 thick aryl;
Ar 6 is selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
the L 3～L5 is the same or different and is selected from one of single bond, substituted or unsubstituted C6-C25 arylene and substituted or unsubstituted C2-C20 heteroarylene;
The R 5 is selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl; the a 5 is selected from integers from 0 to 4; when a 5 is greater than 1, a plurality of R 5 may be the same or different from each other, or two adjacent R 5 may be connected to form a ring.
Preferably, the fluorene compound represented by chemical formula 1 is selected from one of structures shown below,
Preferably, at least one of Ar 1～Ar4 is selected from one of the following groups derived from chemical formula 3 or chemical formula 4,
The Ra is selected from one of hydrogen, cyano, methyl, trifluoromethyl and phenyl; the Rb is selected from one of hydrogen, fluorine, methyl, trifluoromethyl and phenyl;
N 1、m1 is the same or different and is selected from integers of 1 to 5; n 2、m2 is the same or different and is selected from integers from 1 to 4; n 3、m3 is the same or different and is selected from integers from 1 to 3; n 4、m4 is the same or different and is selected from integers from 1 to 7;
B 1 are the same or different and are selected from integers from 0 to 4; b 2 are the same or different and are selected from integers from 0 to 3; b 3 are the same or different and are selected from integers from 0 to 2; b 4 are the same or different and are selected from integers from 0 to 6.
Preferably, at least two of Ar 1～Ar4 are selected from the group shown in chemical formula 3 or chemical formula 4, and the rest are the same or different selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
preferably, ar 1、Ar2 is the same or different from the group shown in chemical formula 3 or chemical formula 4, ar 3、Ar4 is the same or different from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
preferably, ar 1、Ar3 is the same or different from the group shown in chemical formula 3 or chemical formula 4, ar 2、Ar4 is the same or different from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
Preferably, ar 1、Ar4 is the same or different from the group shown in chemical formula 3 or chemical formula 4, ar 2、Ar3 is the same or different from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl; preferably, at least three of Ar 1～Ar4 are selected from the group shown in chemical formula 3 or chemical formula 4, and the rest are the same or different selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
Preferably, ar 1～Ar3 is the same or different and is selected from the group shown in chemical formula 3 or chemical formula 4, ar 4 is selected from one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C2-C20 heteroaryl;
preferably, ar 1～Ar4 is the same or different and is selected from the group shown in chemical formula 3 or chemical formula 4;
Preferably, at least one of Ar 1～Ar4 (preferably Ar 1) is selected from one of the structures shown below,
Preferably, ar 1～Ar4 (preferably Ar 2～Ar4) is the same or different and is selected from one of chemical formula 3, chemical formula 4 or a structure shown below,
The R 7、R8 is the same or different and is selected from one of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tertiary butyl, adamantyl, phenyl, tolyl, mesityl, pentadeuterated phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirobifluorenyl, 9-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl and benzimidazolyl;
R 9 is selected from one of phenyl, tolyl, pentadeuterated phenyl, biphenyl and naphthyl;
R is an integer from 0 to 5; s is an integer from 0 to 4; the t is selected from integers of 0 to 3; the w is selected from integers of 0-2; when R, s, t, w is greater than 1, the plurality of R 7、R8 are the same or different from each other.
Preferably, ar 1～Ar4 (preferably Ar 2～Ar4) is the same or different and is selected from one of chemical formula 3, chemical formula 4 or a structure shown below,
Preferably, the L 1 is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted 9, 9-dimethylfluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted 9, 9-diphenylfluorenyl, substituted or unsubstituted 9-methyl-9-phenylfluorenyl, substituted or unsubstituted 9, 9-spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl;
Preferably, L 1 is selected from one of the structures shown below,
Preferably, L 1 is selected from one of the structures shown below,
Preferably, the high refractive layer is selected from one of chemical formulas 2-1 to 2-12 as shown below,
The L 3-L5、Ar6 is as previously defined;
The R 6 is selected from one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, isopropyl, tertiary butyl, substituted or unsubstituted phenyl and substituted or unsubstituted naphthyl;
Q1 is an integer from 0 to 7; q2 is an integer from 0 to 6; and q3 is an integer from 0 to 4.
Preferably, ar 6 is selected from one of the structures shown below,
R 7、R8 is the same or different and is selected from one of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tertiary butyl, phenyl, tolyl, mesityl, pentadeuterated phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirobifluorenyl, 9-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl and benzimidazolyl;
R 9 is selected from one of phenyl, tolyl, pentadeuterated phenyl, biphenyl and naphthyl;
The r 1 is an integer from 0 to 5; s 1 is an integer from 0 to 4; the t 1 is an integer from 0 to 3; the w 1 is selected from integers of 0-2; when R 1、s1、t1、w1 is greater than 1, a plurality of R 7、R8 are the same or different from each other.
Preferably, ar 6 is selected from one of the structures shown below,
Preferably, L 2～L9 is the same or different and is selected from a single bond or one of the structures shown below,
Preferably, the R 1～R5 is the same or different and is selected from one of hydrogen, deuterium, halogen, cyano, methyl, ethyl, isopropyl, tertiary butyl, substituted or unsubstituted phenyl and substituted or unsubstituted naphthyl; the a 1、a5 are the same or different and are selected from integers of 0 to 5; the a 2～a4 are the same or different and are selected from integers from 0 to 4; when a plurality of substituents are present, the plurality of substituents may be the same as or different from each other, or adjacent two substituents may be linked to form a ring.
Preferably, the fluorene compound represented by chemical formula 1 is selected from one of structures shown below,
Preferably, the amine compound of formula 2 is selected from one of the structures shown below,
Preferably, the inorganic material is selected from one or a combination of at least two of halides, oxides and nitrides;
Preferably, the inorganic material is selected from one or a combination of at least two of lithium fluoride, calcium fluoride, sodium fluoride, aluminum fluoride, magnesium fluoride, barium fluoride, ytterbium fluoride, yttrium fluoride, praseodymium fluoride, gadolinium fluoride, lanthanum fluoride, neodymium fluoride, cerium fluoride, silicon oxide, aluminum oxide, tungsten oxide and Na 5Al3F14、Na3AlF6.
Preferably, the inorganic material is selected from one of lithium fluoride, calcium fluoride, sodium fluoride and magnesium fluoride;
preferably, the inorganic material is selected from lithium fluoride.
The invention also provides a preparation method of the structures of the chemical formula 1 and the chemical formula 2,
The preparation method of the structure in the chemical formula 1 comprises the following steps:
when-N (Ar 1)(Ar2) is the same as-N (Ar 3)(Ar4), the reaction is as follows:
[ reaction type 1]
When-N (Ar 1)(Ar2) is different from-N (Ar 3)(Ar4), the reaction is as follows:
[ reaction type 2]
Ar1～Ar4、R1～R4、L1、L2、L6～L9、a1～a4 The limitations are the same as those described above,
The reaction types involved in the preparation process of the chemical formula 1 are Suzuki reaction and Buchwald reaction.
The preparation method of the structure of the chemical formula 2 comprises the following steps:
Ar 5～Ar6, ring C, X 0、R5、L3～L5、a5 are as defined above,
The type of reaction involved in the preparation process of chemical formula 1 in the present invention is the Buchwald reaction.
The present invention may bond the above substituents by a method known in the art, and the kind and position of substituents or the number of substituents may be changed according to a technique known in the art.
The thickness of each organic layer of the organic electroluminescent device is not particularly limited, and may be any thickness commonly used in the art.
The organic electroluminescent device of the present invention may be any one of a vacuum evaporation method, a spin coating method, a vapor deposition method, a blade coating method, a laser thermal transfer method, an electrospray coating method, a slit coating method, and a dip coating method, and in the present invention, a vacuum evaporation method is preferably used.
The organic electroluminescent device can be widely applied to the fields of panel display, illumination light sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, indication boards, signal lamps and the like.
The present invention is explained more fully by the following examples, but is not intended to be limited thereby. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue burden.
Preparation and characterization of the Compounds
Description of the starting materials, reagents and characterization equipment:
the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis uses a Vario EL cube type organic elemental analyzer of Elementar, germany, and the mass of the sample is 5-10 mg;
Nuclear magnetic resonance (1 H NMR spectrum) A Bruker-510 nuclear magnetic resonance spectrometer (Bruker, germany) was used, 600MHz, CDCl 3 as solvent, TMS as internal standard.
Synthesis example 1 Synthesis of Compound 1-1
Preparation of intermediate c-1:
Raw material a-1 (81.01 mmol,7.54 g), raw material b-1 (77.16 mmol,19.05 g), palladium acetate (0.77 mmol,0.17 g), bis (diphenylphosphino) ferrocene (0.77 mmol,0.42 g), sodium t-butoxide (92.59 mmol,8.88 g) and 300mL toluene were sequentially added to a reaction flask under the protection of argon, the mixture was stirred, and the mixed solution of the above reactants was heated at 90℃for 4 hours; after the reaction, naturally cooling, extracting with 400mL of dichloromethane, layering, drying the extract with anhydrous sodium sulfate, filtering, steaming the filtrate in a rotary manner, and purifying by a silica gel column to obtain an intermediate c-1 (16.8 g, yield 84%); the HPLC purity is more than or equal to 99.55 percent. Mass spectrum m/z:259.0441 (theoretical value: 259.0420).
Preparation of intermediate f-1:
Raw material d-1 (33.01 mmol,11.96 g), raw material e-1 (32.37 mmol,7.31 g), tetraphenylphosphine palladium (0.32 mmol,0.37 g), potassium acetate (48.55 mmol,4.76 g), 100mL toluene, 50mL ethanol, 50mL water and argon were sequentially added to a reaction flask under the protection of argon, the mixture was stirred, and the mixture was heated under reflux for 4.5 hours; after the completion of the reaction, the mixture was extracted with toluene, and the organic phase was washed with saturated brine, dried, and purified by column chromatography to give intermediate f-1 (12.45 g, yield 83%); HPLC purity is more than or equal to 99.64%. Mass spectrum m/z:462.0918 (theoretical value: 462.0942).
Preparation of Compound 1-1:
To a reaction flask were successively added, under argon, intermediate f-1 (23.73 mmol,11.0 g), intermediate c-1 (48.64 mmol,12.6 g), dibenzylideneacetone dipalladium (0.24 mmol,0.21 g), tri-tert-butylphosphine (0.48 mmol,0.1 mL), sodium tert-butoxide (59.32 mmol,5.69 g) and 150mL of toluene under argon, and the mixture was stirred, and the mixed solution of the above reactants was heated at 115℃for 3 hours; after the reaction, naturally cooling, extracting with 400mL of dichloromethane, layering, drying the extract with anhydrous sodium sulfate, filtering, steaming the filtrate, and purifying by a silica gel column to obtain a compound 1-1 (18.30 g, yield 85%); HPLC purity is more than or equal to 99.45%. Mass spectrum m/z:908.2213 (theoretical value: 908.2249). Theoretical element content (%) C 55H30F10N2: c,72.69; h,3.33; f,20.90; n,3.08. Measured element content (%): c,72.60; h,3.37; f,20.93; n,3.10. The above results confirm that the obtained product is the target product.
Synthesis example 2 Synthesis of Compounds 1 to 9
The same procedures as in Synthesis example 1 were repeated except for substituting b-1 for b-2 in equimolar amounts to give Compound 1-9 (18.80 g); HPLC purity is more than or equal to 99.65%. Mass spectrum m/z:978.2732 (theoretical value: 978.2716). Theoretical element content (%) C 65H30N12: c,79.74; h,3.09; n,17.17. Measured element content (%): c,79.78; h,3.06; n,17.15. The above results confirm that the obtained product is the target product.
Synthesis example 3 Synthesis of Compounds 1 to 17
The same procedures as in Synthesis example 1 were repeated except for substituting b-1 for equimolar b-3 to give Compound 1-17 (17.50 g); HPLC purity is more than or equal to 99.67%. Mass spectrum m/z:922.2321 (theoretical value: 922.2343). Theoretical element content (%) C 57H30F8N4: c,74.18; h,3.28; f,16.47; n,6.07. Measured element content (%): c,74.14; h,3.25; f,16.50; n,6.12. The above results confirm that the obtained product is the target product.
Synthesis example 4 Synthesis of Compounds 1 to 37
The same procedures as in Synthesis example 1 were repeated except for substituting b-1 for b-5 in equimolar amounts to give compounds 1 to 37 (17.01 g); the HPLC purity is more than or equal to 99.57 percent. Mass spectrum m/z:874.2313 (theoretical value: 874.2343). Theoretical element content (%) C 53H30F8N4: c,72.77; h,3.46; f,17.37; n,6.40. Measured element content (%): c,72.73; h,3.48; f,17.41; n,6.38. The above results confirm that the obtained product is the target product.
Synthesis example 5 Synthesis of Compounds 1 to 44
The same procedures as in Synthesis example 1 were repeated except for substituting d-1 for equimolar d-6 to give compounds 1 to 44 (18.06 g); HPLC purity is more than or equal to 99.68%. Mass spectrum m/z:906.2076 (theoretical value: 906.2093). Theoretical element content (%) C 55H28F10N2: c,72.85; h,3.11; f,20.95; n,3.09. Measured element content (%): c,72.89; h,3.06; f,20.97; n,3.07. The above results confirm that the obtained product is the target product.
Synthesis example 6 Synthesis of Compounds 1-74
The same procedures as in Synthesis example 1 were repeated except for substituting a-1 and b-1 with equimolar amounts of a-9 and b-8 to give Compound 1-74 (18.15 g); HPLC purity is not less than 99.51%. Mass spectrum m/z:944.3203 (theoretical value: 944.3214). Theoretical element content (%) C 67H42F2N2O2: c,85.15; h,4.48; f,4.02; n,2.96. Measured element content (%): c,85.19; h,4.42; f,4.05; n,2.94. The above results confirm that the obtained product is the target product.
Synthesis example 7 Synthesis of Compounds 1 to 107
The same procedures as in Synthesis example 1 were repeated except for substituting a-1 and b-1 with equimolar amounts of a-12 and b-12 to give Compound 1-107 (15.92 g); the HPLC purity is more than or equal to 99.46 percent. Mass spectrum m/z:828.3024 (theoretical value: 828.3001). Theoretical element content (%) C 59H36N6: c,85.48; h,4.38; n,10.14. Measured element content (%): c,85.51; h,4.36; n,10.10. The above results confirm that the obtained product is the target product.
Synthesis example 8 Synthesis of Compounds 1 to 112
The same procedures as in Synthesis example 1 were repeated except for substituting a-1 for equimolar a-13 to give Compound 1-112 (18.19 g); HPLC purity is not less than 99.43%. Mass spectrum m/z:958.2137 (theoretical value: 958.2154). Theoretical element content (%) C 57H28F10N4: c,71.40; h,2.94; f,19.81; n,5.84. Measured element content (%): c,71.44; h,2.92; f,19.78; n,5.86. The above results confirm that the obtained product is the target product.
Synthesis example 9 Synthesis of Compounds 1 to 137
The same procedures as in Synthesis example 1 were repeated except for using E1 in place of E14 in equimolar amount to give compounds 1 to 137 (19.15 g); HPLC purity is more than or equal to 99.60%. Mass spectrum m/z:984.2575 (theoretical value: 984.2562). Theoretical element content (%) C 61H34F10N2: c,74.39; h,3.48; f,19.29; n,2.84. Measured element content (%): c,74.31; h,3.50; f,19.34; n,2.87. The above results confirm that the obtained product is the target product.
Synthesis example 10 Synthesis of Compounds 1 to 142
Preparation of intermediate g-15:
Raw material d-1 (48.65 mmol,17.62 g), raw material e-15 (48.17 mmol,17.96 g), tetraphenylphosphine palladium (0.48 mmol,0.55 g), potassium acetate (72.25 mmol,7.08 g) and 100mL toluene, 50mL ethanol and 50mL water were sequentially added to a reaction flask under the protection of argon, and the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 4.5 hours; after the completion of the reaction, the mixture was extracted with toluene, and the organic phase was washed with saturated brine, dried, and purified by column chromatography to give intermediate g-15 (21.71 g, yield 80%); HPLC purity is more than or equal to 99.47%. Mass spectrum m/z:562.0932 (theoretical value: 562.0947)
Preparation of intermediate f-15:
Raw material g-15 (30.83 mmol,16.0 g), raw material h-15 (31.13 mmol,5.94 g), tetraphenylphosphine palladium (0.31 mmol,0.35 g), potassium acetate (46.24 mmol,4.53 g) and 70mL toluene, 35mL ethanol and 35mL water were sequentially added to a reaction flask under the protection of argon, the mixture was stirred, and the mixed solution of the above reactants was heated under reflux for 4.5 hours; after the completion of the reaction, the mixture was extracted with toluene, and the organic phase was washed with saturated brine, dried, and purified by column chromatography to give intermediate f-15 (15.72 g, yield 81%); HPLC purity is more than or equal to 99.64%. Mass spectrum m/z:628.1347 (theoretical value: 628.1361)
Preparation of Compounds 1-142:
To a reaction flask were successively added, under argon, intermediate f-15 (22.24 mmol,14.0 g), c-1 (45.59 mmol,11.81 g), dibenzylideneacetone dipalladium (0.22 mmol,0.20 g), tri-tert-butylphosphine (0.44 mmol,0.09 mL), sodium tert-butoxide (55.60 mmol,5.33 g) and 100mL of toluene under argon, and the mixture was stirred, and the mixed solution of the above reactants was heated at 115℃for 3 hours; after the reaction, naturally cooling, extracting with 300mL of dichloromethane, layering, drying the extract with anhydrous sodium sulfate, filtering, steaming the filtrate, and purifying by a silica gel column to obtain the compound 1-142 (19.84 g, yield 83%); the HPLC purity is more than or equal to 99.56 percent. Mass spectrum m/z:1074.2645 (theoretical value: 1074.2668). Theoretical element content (%) C 67H36F10N2 O: c,74.86; h,3.38; f,17.67; n,2.61. Measured element content (%): c,74.84; h,3.36; f,17.71; n,2.63. The above results confirm that the obtained product is the target product.
Synthesis example 11 preparation of Compound 2-1
Synthetic intermediate C-1:
To the reaction flask were successively added compound M-1 (13.65 g,62.23 mmol), L-1 (12.47 g,60.21 mmol), sodium t-butoxide (8.61 g,89.56 mmol), palladium acetate (0.27 g,1.20 mmol), triphenylphosphine (0.31 g,1.20 mmol) and 250ml toluene, under argon, and reacted for 4.5 hours under heating at 90 ℃. After the reaction was completed, the reaction mixture was cooled to room temperature, washed with deionized water, dried over anhydrous magnesium sulfate, concentrated to a small amount, and purified by silica gel column chromatography using N-hexane as a mobile phase to give intermediate N-1 (17.89 g, yield 86%), and the purity of the solid was ≡ 99.5% by HPLC. Mass spectrum m/z:359.15 67 (theoretical value: 359.1554).
Synthesis of Compound 2-1:
to a reaction flask were successively added intermediate N-1 (15.62 g,45.21. Mmol), X-1 (12.81 g,43.12 mmol), sodium t-butoxide (6.22 g,64.68 mmol), pd 2(dba)3 (0.79 g,0.86 mmol), X-Phos (0.41 g,0.86 mmol) and 200mL of toluene under the protection of argon, and the mixture of the above reactants was heated and refluxed for 4 hours, after the completion of the reaction, the reaction solution was poured into 500mL of water, 400mL of methylene chloride was added, the layers were separated, the aqueous layer was extracted 3 times with 200mL of methylene chloride, the organic phases were combined, the solvent was recovered under reduced pressure, and toluene was recrystallized to give compound 2-1 (20.34 g, yield 84%), and the purity of the solid was not less than 99.3% by HPLC detection. Mass spectrum m/z:561.2074 (theoretical value: 561.2093). Theoretical element content (%) C 42H27 NO: c,89.81; h,4.85; n,2.49. Measured element content (%): c,89.76; h,4.87; n,2.52.
Synthesis example 12 preparation of Compound 2-2
The same procedures as in Synthesis example 11 were repeated except for using M-1 and L-1 in place of M-2 and L-2 in equimolar amounts, to give Compound 2-2 (20.59 g, yield 85%) and a solid purity of ≡ 99.7% by HPLC. Mass spectrum m/z:561.2019 (theoretical value: 561.2093). Theoretical element content (%) C 42H27 NO: c,89.81; h,4.85; n,2.49. Measured element content (%): c,89.85; h,4.87; n,2.44.
Synthesis example 13 preparation of Compounds 2 to 9
The same procedures as in Synthesis example 11 were repeated except for using L-1 in Synthesis example 11 in place of L-3 in equimolar amount to give Compound 2-9 (22.83 g, yield 83%) and detecting the solid purity by HPLC ≡ 99.8%. Mass spectrum m/z:637.2425 (theoretical value: 637.2406). Theoretical element content (%) C 48H31 NO: c,90.40; h,4.90; n,2.20. Measured element content (%): c,90.43; h,4.86; n,2.23.
Synthesis example 14 preparation of Compounds 2-77
The same procedures as in Synthesis example 11 were repeated except for using X-1 in place of X-3 in equimolar amount to give Compound 2-77 (19.38 g, yield 80%) having a solid purity of ≡99.6% by HPLC. Mass spectrum m/z:561.2071 (theoretical value: 561.2093). Theoretical element content (%) C 42H27 NO: c,89.81; h,4.85; n,2.49. Measured element content (%): c,89.83; h,4.88; n,2.44.
Synthesis example 15 preparation of Compounds 2-107
The same procedures as in Synthesis example 11 were repeated except for using M-1 and X-1 in place of M-3 and X-4 in equimolar amounts, to give Compound 2-107 (21.73 g, yield 79%) and a solid purity of ≡ 99.5% by HPLC. Mass spectrum m/z:637.2443 (theoretical value: 637.2406). Theoretical element content (%) C 48H31 NO: c,90.40; h,4.90; n,2.20. Measured element content (%): c,90.43; h,4.86; n,2.22.
Synthesis example 16 preparation of Compounds 2-117
By the same process as in Synthesis example 11 except that L-1 and X-1 were replaced with equimolar L-3 and X-5, compound 2-117 (23.38 g, yield 85%) was obtained and the purity of the solid was ≡ 99.3% by HPLC detection. Mass spectrum m/z:637.2432 (theoretical value: 637.2406). Theoretical element content (%) C 48H31 NO: c,90.40; h,4.90; n,2.20. Measured element content (%): c,90.45; h,4.88; n,2.16.
Synthesis example 17 preparation of Compounds 2-134
The same procedures as in Synthesis example 11 were repeated except for using M-1, L-1 and X-1 as replaced with M-2, L-4 and X-6 in equimolar amounts to give Compound 2-134 (23.10 g, yield 84%) and solid purity. Mass spectrum m/z:637.2423 (theoretical value: 637.2406). Theoretical element content (%) C 48H31 NO: c,90.40; h,4.90; n,2.20. Measured element content (%): c,90.38; h,4.85; n,2.25.
Synthesis example 18 preparation of Compounds 2-194
The same procedures as in Synthesis example 11 were repeated except for using M-1, L-1 and X-1 as replaced with M-2, L-2 and X-7 in equimolar amounts to give Compound 2-194 (21.42 g, yield 86%) and solid purity by HPLC was. Mass spectrum m/z:577.1823 (theoretical value: 577.1864). Theoretical element content (%) C 42H27 NS: c,87.32; h,4.71; n,2.42. Measured element content (%): c,87.30; h,4.75; n,2.38.
Synthesis example 19 preparation of Compounds 2-237
The same procedures as in Synthesis example 11 were repeated except for using M-1 and L-1 in place of M-2 and L-5 in equimolar amounts, to give Compound 2-237 (21.89 g, yield 83%) and, as a result, a solid having a purity of ≡ 99.5% by HPLC. Mass spectrum m/z:611.2221 (theoretical value: 611.2249). Theoretical element content (%) C 46H29 NO: c,90.32; h,4.78; n,2.29. Measured element content (%): c,90.36; h,4.75; n,2.25.
Synthesis example 20 preparation of Compounds 2-240
The same procedures as in Synthesis example 11 were repeated except for using M-1 and L-1 in place of M-2 and L-6 in equimolar amounts, to give Compound 2-240 (23.11 g, yield 81%) and, as a result, a solid having a purity of ≡ 99.4% by HPLC. Mass spectrum m/z:661.2445 (theoretical value: 661.2406). Theoretical element content (%) C 50H31 NO: c,90.74; h,4.72; n,2.12. Measured element content (%): c,90.72; h,4.69; n,2.16.
Device examples 1 to 15
Device example 1: an ITO-Ag-ITO glass substrate as an anode was ultrasonically washed with a solvent such as pure water, isopropyl alcohol, acetone, methanol, etc., and then washed by exposure to ultraviolet rays and ozone for 30 minutes, and the washed glass substrate was placed in a vacuum deposition apparatus.
And vacuum depositing m-MTDATA on the ITO-Ag-ITO glass substrate to form a hole injection layer with the thickness of 60nm, and vacuum depositing TAPC on the hole injection layer to form a hole transport layer with the thickness of 80 nm. CBP (green host) and GD (green doping) were co-deposited on the hole transport layer in a weight ratio of 95:5, forming a light emitting layer 30nm thick. Alq 3 is then deposited on the light-emitting layer to form an electron transport layer 40nm thick. Depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 1nm, and vacuum depositing Mg on the electron injection layer: ag (1:9) forms a cathode with a thickness of 15nm, the compound 2-1 of the invention is deposited on the cathode to form a high refractive layer with a thickness of 20nm, the compound 1-1 of the invention is deposited on the high refractive layer to form a first low refractive layer with a thickness of 50nm, and LiF is deposited on the first low refractive layer to form a second low refractive layer with a thickness of 15 nm.
Device examples 2 to 10: the same procedure as in device example 1 was used to prepare organic electroluminescent devices 2 to 10, except that compound 2-1 in device example 1 was replaced with inventive compounds 2-2, 2-77, 2-117, 2-237, 2-194, 2-240, 2-9, 2-107, 2-134, compound 1-1 in device example 1 was replaced with inventive compounds 1-9, 1-17, 1-37, 1-44, 1-74, 1-107, 1-112, 1-137, 1-142, and LiF was replaced with MgF 2.
Comparative example 1: an ITO-Ag-ITO glass substrate as an anode was ultrasonically washed with a solvent such as pure water, isopropyl alcohol, acetone, methanol, etc., and then washed by exposure to ultraviolet rays and ozone for 30 minutes, and the washed glass substrate was placed in a vacuum deposition apparatus.
And vacuum depositing m-MTDATA on the ITO-Ag-ITO glass substrate to form a hole injection layer with the thickness of 60nm, and vacuum depositing TAPC on the hole injection layer to form a hole transport layer with the thickness of 80 nm. CBP (green host) and GD (green doping) were co-deposited on the hole transport layer in a weight ratio of 95:5, forming a light emitting layer 30nm thick. Alq 3 is then deposited on the light-emitting layer to form an electron transport layer 40nm thick. Depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 1nm, and vacuum depositing Mg on the electron injection layer: ag (1:9) forms a cathode of 15nm thickness, and the compound 2-1 of the invention is deposited on the cathode to form a high refractive layer of 85nm thickness.
Comparative examples 2 to 5: comparative organic electroluminescent devices 2 to 5 were prepared by the same procedure as in comparative example 1, except that the compound 2-1 in comparative example 1 was replaced with the compounds 2-2, 2-77, 2-237, 2-240.
Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. The environment tested was atmospheric and the temperature was room temperature.
The results of the luminescence characteristic test of the obtained organic electroluminescent device are shown in table 1.
TABLE 1 test of luminescence characteristics of organic electroluminescent devices
As can be seen from the results of table 1, the organic electroluminescent device of the present invention exhibits an advantage of high luminous efficiency as compared with comparative examples 1 to 5. The organic electroluminescent device provided by the invention has a special cover layer configuration, light is prevented from directly reaching the air from the cathode, a larger refractive index difference is generated at the interface of the low refractive layer and the high refractive layer in the cover layer, the overall reflectivity of the cover layer is improved, and the resonance effect of the device is further improved, so that the increase of microcavity effect is maximized, and the luminous efficiency of the device is also effectively improved. The organic electroluminescent device has good industrialization prospect.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.
Claims (6)
1. The organic electroluminescent device is characterized by comprising a substrate, an anode, an organic layer, a cathode and a cover layer in sequence, wherein the cover layer comprises a low-refraction layer and a high-refraction layer, the low-refraction layer comprises a first low-refraction layer and a second low-refraction layer, the first low-refraction layer comprises fluorene compounds shown in chemical formula 1, the second low-refraction layer comprises an inorganic material, the high-refraction layer is selected from one of chemical formulas 2-1 to 2-6 shown in the following, the high-refraction layer is positioned between the cathode and the first low-refraction layer, the first low-refraction layer is positioned between the high-refraction layer and the second low-refraction layer,
；
At least one of Ar 1~Ar4 is selected from one of the following groups,
；
The Ra is selected from one of hydrogen, cyano, methyl, trifluoromethyl and phenyl; the Rb is selected from one of hydrogen, fluorine, methyl, trifluoromethyl and phenyl;
N 1、m1 are the same or different and are selected from integers of 1-5; n 2、m2 are the same or different and are selected from integers of 1-4; n 3、m3 are the same or different and are selected from integers of 1-3; n 4、m4 are the same or different and are selected from integers of 1-7;
B 1 are the same or different and are selected from integers of 0-4; b 2 are the same or different and are selected from integers of 0-3; b 3 are the same or different and are selected from integers of 0-2; b 4 are the same or different and are selected from integers of 0 to 6,
The rest Ar 1~Ar4 is the same or different and is selected from one of the structures shown in the following,
；
；
The R 7 are the same or different and are selected from one of hydrogen and deuterium;
R is an integer from 0 to 5; s is an integer of 0 to 4;
the L 0 is selected from none or a single bond;
The L 1 is selected from one of the structures shown below,
；；
The R 1~R4 are the same or different and are selected from one of hydrogen and deuterium; the a 1 is an integer from 0 to 5; the a 2~a4 are the same or different and are selected from integers of 0-4;
L 2 is selected from a single bond or one of the structures shown below,
；
The L 6~L9 is selected from single bonds;
；
R 6 is selected from one of hydrogen and deuterium;
Q 1 is an integer from 0 to 7; q 2 is an integer from 0 to 6; q 3 is an integer from 0 to 4;
Ar 6 is selected from one of the structures shown below,
；
；
；
The L 3~L5 are the same or different and are selected from one of single bond, deuterium substituted or unsubstituted phenylene;
the inorganic material is selected from one or a combination of at least two of lithium fluoride, calcium fluoride, sodium fluoride, aluminum fluoride, magnesium fluoride and barium fluoride.
2. An organic electroluminescent device as claimed in claim 1, wherein at least one of Ar 1~Ar4 is selected from one of the groups shown below,
；
The Ra is selected from one of hydrogen and cyano; the Rb is selected from one of hydrogen and fluorine.
3. An organic electroluminescent device as claimed in claim 1, wherein at least one of Ar 1~Ar4 is selected from one of the structures shown below,
。
4. An organic electroluminescent device as claimed in claim 1, wherein Ar 6 is selected from one of the structures shown below,。
5. The organic electroluminescent device as claimed in claim 1, wherein L 3~L5 is the same or different and is selected from a single bond or one of the structures shown below,。
6. An organic electroluminescent device according to claim 1, wherein the inorganic material is selected from one or a combination of two of lithium fluoride and magnesium fluoride.
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