CN111675707B - Organic electroluminescent material and device thereof - Google Patents
Organic electroluminescent material and device thereof Download PDFInfo
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- CN111675707B CN111675707B CN201910177494.3A CN201910177494A CN111675707B CN 111675707 B CN111675707 B CN 111675707B CN 201910177494 A CN201910177494 A CN 201910177494A CN 111675707 B CN111675707 B CN 111675707B
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- 239000000463 material Substances 0.000 title claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 125000004432 carbon atom Chemical group C* 0.000 claims description 125
- 239000010410 layer Substances 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 19
- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000012044 organic layer Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 239000004973 liquid crystal related substance Substances 0.000 claims description 8
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- 150000001412 amines Chemical class 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
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- 238000000034 method Methods 0.000 claims description 6
- 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 claims description 5
- 150000002527 isonitriles Chemical class 0.000 claims description 5
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 1
- -1 phosphino groups Chemical group 0.000 description 70
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
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- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- 238000006243 chemical reaction Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 7
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical group C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 239000011521 glass Substances 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
- 150000002894 organic compounds Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910000085 borane Inorganic materials 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
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- 125000002950 monocyclic group Chemical group 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 229940125904 compound 1 Drugs 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
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- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
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- 239000007943 implant Substances 0.000 description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 230000007704 transition Effects 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- WDIQKCMPSJFFDH-UHFFFAOYSA-N 1,2-dimethyl-5H-benzo[b][1]benzosilole Chemical compound CC1=C(C2=C([SiH2]C3=C2C=CC=C3)C=C1)C WDIQKCMPSJFFDH-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- HMLURENDJQQGCM-UHFFFAOYSA-N 1-benzothiophene;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2SC=CC2=C1 HMLURENDJQQGCM-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- IEBQZJXMAOMNBO-UHFFFAOYSA-N 1h-indole;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2NC=CC2=C1 IEBQZJXMAOMNBO-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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Abstract
An organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material is a novel triarylamine-aza carbazole quinazoline compound. These compounds are useful as host materials in electroluminescent devices and provide better device performance.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic electroluminescent devices. And more particularly, to a novel organic compound having an azacarbazole structure, and an organic electroluminescent device and a compound formulation including the same.
Background
Organic electronic devices include, but are not limited to, the following: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLEDs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.
In 1987, tang and Van Slyke of Isomandah reported a double-layered organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters,1987,51 (12): 913-915). Once biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). Most advanced OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Because OLEDs are self-emitting solid state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in flexible substrate fabrication.
OLEDs can be divided into three different types according to their light emission mechanism. The OLED of the Tang and van Slyke invention is a fluorescent OLED. It uses only singlet light emission. The triplet states generated in the device are wasted through non-radiative decay channels. Thus, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation prevents commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs using triplet emission from heavy metals containing complexes as emitters. Thus, both singlet and triplet states can be harvested, achieving a 100% IQE. Because of its high efficiency, the discovery and development of phosphorescent OLEDs has contributed directly to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency by Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons by reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymeric OLEDs depending on the form of the materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of the small molecules can be large as long as they have a precise structure. Dendrimers with a defined structure are considered small molecules. Polymeric OLEDs include conjugated polymers and non-conjugated polymers having pendant luminescent groups. Small molecule OLEDs can become polymeric OLEDs if post-polymerization occurs during fabrication.
Various methods of OLED fabrication exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymeric OLEDs are manufactured by solution processes such as spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be fabricated by solution processes if the material can be dissolved or dispersed in a solvent.
The emission color of an OLED can be achieved by the structural design of the luminescent material. The OLED may include a light emitting layer or layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full color OLED displays typically employ a mixing strategy using blue fluorescent and phosphorescent yellow, or red and green. Currently, a rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
Carbazole-based organic semiconductor materials are widely used in OLEDs because of their excellent photoelectric properties, redox properties, stability, and the like.
US20150325794A1 discloses organic compounds of the formula and organic light emitting devices comprising said compounds: 
In many examples, a compound of the formula:
however, compounds having an azacarbazole structural unit are not disclosed.
WO2010110553A2 discloses organic compounds of the formula and organic light emitting devices comprising said compounds:
wherein ring A and ring B each represent a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5-or 6-membered heteroaromatic ring fused to an aromatic ring, or a monocyclic or polycyclic aromatic ring fused to a 5-or 6-membered heteroaromatic ring. In many examples, a compound of the formula: />
However, compounds in which carbazole units are linked to quinazolines are not disclosed, and the device data disclosed therein show that the device driving voltage is as high as that of a hole transporting or hole injecting layerAbove 5v, the corresponding luminous efficiency is also lower.
However, the carbazole organic semiconductor materials reported at present have certain limitations on carrier transmission capacity, efficiency, service life and the like in photoelectric devices. Therefore, the application potential of the material is worth continuing to be deeply researched and developed. The invention discloses novel aza-carbazole linked quinazoline compounds which provide better device performance.
Disclosure of Invention
The present invention aims to address at least part of the above problems by providing a series of compounds having a novel azacarbazole-quinazoline structure. The compounds are useful as host materials in organic electroluminescent devices. The novel compounds are applied to organic light emitting devices and can provide lower driving voltage, higher efficiency and longer service life.
According to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed:
wherein Ar is 1 And Ar is a group 2 Each independently selected from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms;
wherein L is 1 Is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
wherein X is 1 To X 5 Each independently selected from CR 1 Or N;
wherein Y is 1 To Y 4 Each independently selected from C, CR 2 Or N;
wherein Y is 5 To Y 8 Each independently selected from CR 2 Or N;
wherein Y is 1 To Y 8 At least one of which is N;
R 1 and R is 2 Each independently selected fromThe group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including the compound having the structure of formula 1.
According to another embodiment of the present invention, a compound formulation is also disclosed, comprising the compound having the structure of formula 1.
The novel compound with the aza-carbazole structure disclosed by the invention can be used as a main body material in an electroluminescent device. These novel compounds are a class of bipolar host materials comprising both electron donor triarylamine units having excellent hole transport capabilities and electron acceptor quinazoline units having excellent electron transport capabilities in their structure. In addition, the introduction of the azacarbazole not only maintains the higher triplet energy level, but also further balances the hole and electron transmission capability. Therefore, the novel compounds can be applied to organic light-emitting devices to provide lower driving voltage, higher efficiency and longer service life.
Drawings
FIG. 1 is a schematic diagram of an organic light emitting device that may contain the compounds and compound formulations disclosed herein.
Fig. 2 is a schematic diagram of another organic light emitting device that may contain the compounds and compound formulations disclosed herein.
Fig. 3 is structural formula 1 showing a compound as disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically illustrates, without limitation, an organic light-emitting device 100. The drawings are not necessarily to scale, and some of the layer structures in the drawings may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the layers described. The nature and function of the layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F in a 50:1 molar ratio 4 m-MTDATA of TCNQ as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1 as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of cathodes are disclosed in U.S. Pat. nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, including composite cathodes having a thin layer of metal, such as Mg: ag, with an overlying transparent, electrically conductive, sputter deposited ITO layer. The barrier layer is described in more detail in U.S. Pat. No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entiretyPrinciple and use. Examples of implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided by way of non-limiting example. The function of the OLED may be achieved by combining the various layers described above, or some of the layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sublayers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, such as the organic light emitting device 200 shown schematically and without limitation in fig. 2, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film packages are described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptops, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and taillights.
The materials and structures described herein may also be used in other organic electronic devices as listed above.
As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" on "the second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photosensitive" when it is believed that the ligand directly contributes to the photosensitive properties of the emissive material. When it is believed that the ligand does not contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary," but ancillary ligands may alter the properties of the photosensitive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by spin statistics that delay fluorescence by more than 25%. Delayed fluorescence can be generally classified into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. The P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
On the other hand, the E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between the triplet states and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have very small mono-triplet gaps in order for the conversion between the energy states. The thermal energy may activate a transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the delay component increases with increasing temperature. The fraction of backfill singlet excited states may reach 75% if the reverse intersystem crossing (iric) rate is sufficiently fast to minimize non-radiative decay from the triplet states. The total singlet fraction may be 100%, well in excess of 25% of the spin statistics of the electrically generated excitons.
Type E delayed fluorescence features can be found in excitation complex systems or in single compounds. Without being bound by theory, it is believed that E-delayed fluorescence requires a luminescent material with a small mono-triplet energy gap (Δe S-T ). Organic non-metal containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor Charge Transfer (CT) type emission. The spatial separation of HOMO from LUMO in these donor-acceptor compounds generally results in a small Δe S-T . These states may include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
Definition of terms for substituents
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-includes straight and branched alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. The carbon in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferred.
Cycloalkyl-as used herein, includes cyclic alkyl. Preferred cycloalkyl groups are cycloalkyl groups containing 4 to 10 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, cycloalkyl groups may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.
Alkenyl-as used herein, covers both straight chain and branched alkene groups. Preferred alkenyl groups are alkenyl groups containing 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl and 3-phenyl-1-butenyl. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, covers both straight and branched chain alkynyl groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. Preferred aryl groups are those containing from 6 to 60 carbon atoms, more preferably from 6 to 20 carbon atoms, and even more preferably from 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chicory, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl groups may be optionally substituted. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-3-yl, p-triphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl-4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-tetrabiphenyl.
Heterocyclyl or heterocycle-as used herein, aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups are contemplated that may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and even more preferably 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzothiophene pyridine, thienodipyridine, benzothiophene bipyridine, benzoselenophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-1, 3-aza-borane, 1-borane, 4-borane, and the like. In addition, heteroaryl groups may be optionally substituted.
Alkoxy-is represented by-O-alkyl. Examples of alkyl groups and preferred examples are the same as described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentoxy and hexoxy groups. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.
Aryloxy-is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of the aryloxy group having 6 to 40 carbon atoms include phenoxy and diphenoxy.
Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, aralkyl groups may be optionally substituted. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthyl-ethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthyl-ethyl, 2- β -naphthyl-ethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-chlorophenyl, 1-isopropyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl.
The term "aza" in aza-dibenzofurans, aza-dibenzothiophenes and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.
In the present disclosure, when any one of the terms from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted nitrile, substituted isonitrile, substituted sulfanyl, substituted sulfinyl, substituted sulfonyl, substituted phosphino, substituted aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl and phosphino groups, any one or more of which may be substituted with one or more groups selected from deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted cycloalkyl having 1 to 20 carbon atoms, unsubstituted alkyl having 7 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, 3 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, aryl having 3 to 30 carbon atoms, aryl having 3 carbon atoms, 3 to 30 carbon atoms, aryl having 3 to 20 carbon atoms, sulfinyl, sulfonyl, phosphino, and combinations thereof.
It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.
In the compounds mentioned in this disclosure, the hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because of their enhanced efficiency and stability of the device.
In the compounds mentioned in this disclosure, polysubstituted means inclusive of disubstituted up to the maximum available substitution range. When a substituent in a compound mentioned in this disclosure means multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may be present at a plurality of available substitution positions on its linking structure, and the substituent present at each of the plurality of available substitution positions may be of the same structure or of different structures.
In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless adjacent substituents are defined to be optionally linked to form a ring. The expression that adjacent substituents can optionally be linked to form a ring is intended to mean that the two groups are linked to each other by a chemical bond. This is exemplified by the following formula:
furthermore, the expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that in the case where one of the two groups represents hydrogen, the second group is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
according to one embodiment of the present invention, a compound having formula 1 is disclosed:
wherein Ar is 1 And Ar is a group 2 Each independently selected from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms;
wherein L is 1 Selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
wherein X is 1 To X 5 Each independently selected from CR 1 Or N;
wherein Y is 1 To Y 4 Each independently selected from C, CR 2 Or N;
wherein Y is 5 To Y 8 Each independently of the otherGround is selected from CR 2 Or N;
wherein Y is 1 To Y 8 At least one of which is N;
R 1 and R is 2 Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
It should be noted that in formula 1, adjacent substituents are not limited to being optionally linked to form a ring. That is, in formula 1, X is included 1 To X 5 ，Y 1 To Y 8 ，L 1 ，Ar 1 ，Ar 2 Within this, none of the adjacent substituents can join to form a ring. For example, when Y in formula 1 5 ，Y 6 At the same time CR 2 When two R 2 Cannot be connected to form a ring; also for example, when L in formula 1 1 Attached to Y 2 And Y is 3 And Y 4 At the same time CR 2 When two R 2 Cannot be connected to form a ring; also for example, when X in formula 1 1 ，X 2 At the same time CR 1 When two R 1 Are not connected to form a ring; also for example, L 1 ，Ar 1 And Ar is a group 2 None of which is linked to other substituents to form a ring.
According to one embodiment of the invention, wherein X 1 To X 5 Each independently selected from CR 1 WhereinR 1 Each independently selected from: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
According to one embodiment of the invention, wherein X 1 Is CR (CR) 1 And R is 1 Selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted pyridyl group; x is X 2 To X 5 Are CH.
According to one embodiment of the invention, wherein X 1 Is CR (CR) 1 And R is 1 Selected from phenyl, cyanophenyl, dimethylfluorenyl, pyridinyl, biphenyl; x is X 2 To X 5 Are CH.
According to one embodiment of the invention, wherein Y 1 To Y 4 At least one of which is N.
According to one embodiment of the invention, wherein Y 1 -Y 3 Each independently selected from C or CR 2 ，Y 4 Is N, Y 5 -Y 8 Each independently selected from CR 2 。
According to one embodiment of the invention, wherein Y 5 To Y 8 At least one of which is N.
According to one embodiment of the invention, wherein Y 1 -Y 4 Each independently selected from C or CR 2 ，Y 5 Is N, Y 6 -Y 8 Each independently selected from CR 2 。
According to one embodiment of the invention, wherein Y 1 To Y 8 At least two of which are N.
According to one embodiment of the invention, wherein Y 1 -Y 3 Each independently selected from C or CR 2 ，Y 4 And Y 5 Is N, Y 6 -Y 8 Each independently selected from CR 2 。
According to one embodiment of the invention, wherein Ar 1 And Ar is a group 2 Each independently selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzoSilol, biphenyl, terphenyl, phenanthryl, triphenylene, spirobifluorenyl, dibenzofuranyl, dibenzothienyl or dibenzoselenophenyl, azadibenzofuranyl, azadibenzothienyl, and combinations thereof.
According to one embodiment of the invention, wherein Ar 1 And Ar is a group 2 Each independently selected from the group consisting of: phenyl, cyanophenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzosilol, dimethyldibenzosilol, diphenyldibenzosilol, biphenyl, terphenyl, phenanthryl, triphenylene, spirobifluorenyl, dibenzofuranyl, dibenzothienyl or dibenzoselenophenyl, azadibenzofuranyl, azadibenzothienyl, and combinations thereof.
According to one embodiment of the invention, wherein L 1 Selected from phenylene, pyridylene or pyrimidinylene.
According to one embodiment of the invention, wherein R 2 Is hydrogen.
According to one embodiment of the invention, wherein L 1 And Y is equal to 2 And (5) connection.
According to one embodiment of the invention, wherein L 1 And Y is equal to 3 And (5) connection.
According to an embodiment of the invention, wherein the compound is selected from the group consisting of compound 1 to compound 498, wherein the specific structure of the compound 1 to compound 498 is presented in claim 10.
According to an embodiment of the present invention, there is also disclosed an electroluminescent device including:
an anode is provided with a cathode,
a cathode electrode, which is arranged on the surface of the cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having formula 1:
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 and Ar is a group 2 Each independently selected from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms;
wherein L is 1 Selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
wherein X is 1 To X 5 Each independently selected from CR 1 Or N;
wherein Y is 1 To Y 4 Each independently selected from C, CR 2 Or N;
wherein Y is 5 To Y 8 Each independently selected from CR 2 Or N;
wherein Y is 1 To Y 8 At least one of which is N;
wherein R is 1 And R is 2 Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to one embodiment of the invention, in the device, the organic layer is a light emitting layer and the compound is a host material.
According to one embodiment of the invention, in the device, the organic layer further comprises a phosphorescent light emitting material.
According to one embodiment of the invention, in the device, the phosphorescent light emitting material is a metal complex having at least one ligand comprising a structure of any one of:
wherein, the liquid crystal display device comprises a liquid crystal display device,
R a ，R b and R is c May represent mono-, di-, tri-or tetra-substitution, or no substitution;
R a ，R b and R is c Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
X b Selected from the group consisting of: o, S, se, NR N1 ，CR C1 R C2
R N1 ，R C1 And R is C2 Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstitutedSubstituted or unsubstituted cycloalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted aryl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having from 3 to 20 carbon atoms, substituted or unsubstituted amine having from 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
in the ligand structure, adjacent substituents can optionally be linked to form a ring.
According to another embodiment of the present invention, a compound formulation comprising a compound represented by formula 1 is also disclosed. The specific structure of the compound is shown in any one of the previous embodiments.
Combined with other materials
The materials described herein for specific layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application 2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as useful for specific layers in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the hosts disclosed herein may be used in conjunction with a variety of light emitting dopants, hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. 2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
In the examples of material synthesis, all reactions were carried out under nitrogen protection, unless otherwise indicated. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structural confirmation and characterization testing using one or more equipment conventional in the art (including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai's optical technique fluorescence spectrophotometer, wuhan Koste's electrochemical workstation, anhui Bei Yi g sublimator, etc.), in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Frieda, st. John's, an ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.
Material synthesis examples:
the preparation method of the compound of the present invention is not limited, and is typically, but not limited to, exemplified by the following compounds, the synthetic routes and preparation methods thereof are as follows:
synthesis example 1: synthesis of Compound 5
Step 1: synthesis of intermediate B
Intermediate A (4.7 g,18.95 mmol) was dissolved in 200mL DMF and NaH (2.27 g,56.85 mmol) was added under ice-bath followed by 2-chloro-4-phenyl-quinazoline (6.85 g,28.43 mmol) and then allowed to react overnight at room temperature. After the reaction was completed, distilled water was added to precipitate a solid, which was filtered, and the solid was washed with water, ethanol and ethyl acetate in this order to obtain intermediate B (6.0 g,13.29 mmol) as a white solid in a yield of 70.1%.
Step 2: synthesis of Compound 5
Under nitrogen, intermediate B (2.9 g,6.43 mmol), intermediate C (3.7 g,7.07 mmol), pd 2 (dba) 3 (292.8mg，0.32mmol)，S-Phos(262.4g,0.64mmol)，K 2 CO 3 (1.77 g,12.8 mmol) and solvent (toluene/water 50/12 mL) were added to a three-necked flask, and the mixture was allowed to react overnight at 110 ℃. Distilled water was then added to precipitate a solid, which was filtered to give a solid which was purified by column chromatography (eluent: PE/dcm=1:1) to give compound 5 (4.5 g,5.86 mmol) as a pale yellow solid in 91.1% yield. The product was identified as the target product, molecular weight 768.
Synthesis example 2: synthesis of Compound 68
Step 1: synthesis of intermediate E:
under nitrogen, intermediate D (50 g,289 mmol), cuBr (45.1 g,317 mmol), CH 3 CN (1000 mL) was added to a three-necked flask, and tert-butyl nitrite (39 g,376 mmol) was slowly added dropwise at 65℃and reacted for 4 hours. After the reaction was completed, cooled to room temperature, quenched with dropwise aqueous sodium thiosulfate solution, the solvent was removed by spinning under reduced pressure, the mixture was extracted with ethyl acetate, the organic phase was washed with water, dried over anhydrous magnesium sulfate, the solvent was removed by spinning under reduced pressure, and purified by silica gel column chromatography (eluent: PE/dcm=8:1) to give intermediate E (30 g,126.3 mmol) as a pale yellow solid in 43.7% yield.
Step 2: synthesis of intermediate F:
intermediate E (30 g,126.3 mmol), phenylboronic acid (23.18 g,190 mmol), pd (PPh) 3 ) 4 (4.4g，3.81mmol)，K 2 CO 3 (35g,254mmol)、THF(500mL)、H 2 O (100 mL) was placed in a three-necked flask and reacted at 60℃for 16h. After the reaction was completed, cooled to room temperature, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated to remove the solvent by spin-drying under reduced pressure, and purified by silica gel column chromatography (eluent: PE/dcm=5:1) to give intermediate F (20 g,81.1 mmol) as a pale yellow solid in 64.2% yield.
Step 3: synthesis of intermediate G:
intermediate F (10 g,42.7 mmol) and PPh were purged with nitrogen 3 (33.7 g,128.2 mmol) and o-dichlorobenzene (100 mL) were charged into a three-necked flask and reacted at 200℃for 16 hours. After the reaction was completed, cooled to room temperature, and the crude product was purified by silica gel column chromatography (eluent: PE/ea=1:1) to give intermediate G (7G, 34.5 mmol) as a white solid in 80.9% yield.
Step 4: synthesis of intermediate H:
intermediate G (4G, 19.8 mmol), 2-chloro-4-phenyl-quinazoline (7.1G, 29.7 mmol), naH (1.4G, 59.4 mmol) and DMF (100 mL) were each placed in a three-necked flask under nitrogen and reacted at 25℃for 5h. After the reaction was completed, distilled water was added to precipitate a solid, which was suction-filtered under reduced pressure and washed three times with ethyl acetate to give intermediate H (7 g,17.2 mmol) as a pale yellow solid, with a yield of 86.9%.
Step 5: synthesis of Compound 68:
under nitrogen, intermediate H (3.5 g,7.4 mmol), intermediate I (4.03 g,11.05 mmol), pd 2 (dba) 3 (340mg，0.37mmol)、Sphos(304mg，0.74mmol)、K 2 CO 3 (2.04 g,14.8 mmol), toluene (120 mL), water (30 mL) were added to a three-necked flask and reacted at 110℃for 16 hours. After the reaction was completed, cooled to room temperature, diluted with water, the mixture was extracted with dichloromethane, the organic phase was washed with water, the solvent was removed by spin-drying under reduced pressure, and the crude product was purified by column chromatography on silica gel (eluent: PE/dcm=3/1), toluene was recrystallized to give compound 68 (3 g,4.34 mmol) as a yellow solid in 58.6% yield. The product was identified as the target product, molecular weight 692.
Synthesis example 3: synthesis of Compound 137
Step 1: synthesis of intermediate K
Intermediate J (12.0 g,75.69 mmol), 4-chloro-phenylboronic acid (14.2 g,90.83 mmol) and Pd (PPh) were each reacted under nitrogen 3 ) 4 (2.62g，2.27mmol)，K 2 CO 3 (20.92g,151.38mmol)、Dioxane(240mL)、H 2 O (60 mL) was placed in a three-necked flask and heated at reflux overnight. After the reaction was completed, cooled to room temperature, distilled water was added, the mixture was extracted with DCM, the organic phase was washed with water, dried over anhydrous magnesium sulfate, the solvent was removed by spin-drying under reduced pressure, and purified by silica gel column chromatography (eluent: PE/dcm=1:1) to give intermediate K (17.3 g,73.73 mmol) as a bright yellow solid in 97.4% yield.
Step 2: synthesis of intermediate L
Under the protection of nitrogen, intermediate K (17.0 g,72.45 mmol) and PPh are reacted 3 (57.0 g,217.35 mmol) o-dichlorobenzene (90 mL) was added to the flask and reacted overnight at 200 ℃. After the reaction was completed, it was cooled to room temperature, the reaction solution was poured into a large amount of n-hexane, a large amount of solid was precipitated, suction filtration was performed under reduced pressure, and the solid was washed with DCM several times to obtain intermediate L (9.5 g,46.88 mmol) as a white solid, with a yield of 64.7%.
Step 3: synthesis of intermediate M
Intermediate L (4.0 g,19.74 mmol), 2-chloro-4-phenyl-quinazoline (6.18 g,25.66 mmol), naH (1.18 g,49.35 mmol) and DMF (100 mL) were separately placed in three-necked flask under nitrogen and stirred overnight at room temperature. After the reaction was completed, distilled water was added to precipitate a solid, which was suction-filtered under reduced pressure and washed three times with ethyl acetate to give intermediate M (6.25 g,15.36 mmol) as a white solid in 77.8% yield.
Step 4: synthesis of Compound 137
Intermediate C (6.92 g,13.21 mmol), intermediate M (4.48 g,11.01 mmol), pd under nitrogen 2 (dba) 3 (0.30g，0.33mmol)，S-Phos(0.54g,1.32mmol)，K 3 PO 4 (4.67 g,22.02 mmol), toluene (48 mL), ethanol (12 mL), water (12 mL) were added to the three-necked flask, and heated under reflux overnight. Stopping heating, cooling to room temperature, transferring the reaction solution to a separating funnel, collecting the organic phase, adding DCM into the aqueous phase, extracting for several times, mixing the organic phase and anhydrous Na 2 SO 4 And (5) drying. The solvent was removed by rotary evaporation under reduced pressure, and column chromatography on silica gel (eluent: PE/ea=3:1) gave 137 (6.9 g,8.98 mmol) as a pale yellow solid with a yield of 81.6%. The product was identified as the target product, molecular weight 768.
Those skilled in the art will recognize that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other compound structures of the present invention.
Device embodiment
Example 1
First, a glass substrate having an 80nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was baked in a glove box to remove moisture. The substrate is then mounted on a substrate support and loaded into a vacuum chamber. The organic layer specified below was at a vacuum level of about 10 -8 The deposition was performed sequentially on the ITO anode by thermal vacuum deposition at a rate of 0.2 to 2 a/s in the case of a tray. The compound HI is used as a Hole Injection Layer (HIL). The compound HT serves as a Hole Transport Layer (HTL). Compound EB acts as an Electron Blocking Layer (EBL). Compound RD1 (5%) was then doped in compound 68 of the present invention and co-evaporated to serve as the light emitting layer (EML). Compound HB was used as a Hole Blocking Layer (HBL). On the hole blocking layer, the compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1nm was evaporated as an electron injection layer, and 120nm of aluminum was evaporated as a cathode. The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.
Comparative example 1
Comparative example 1 was prepared as in example 1, except that compound a was used in place of compound 68 of the present invention in the light-emitting layer (EML).
Example 2
The preparation method of example 2 was the same as in example 1, except that RD2 (2%) was co-evaporated in the compound 5 of the present invention doped in the light emitting layer (EML), instead of RD1 (5%) being co-evaporated in the compound 68 of the present invention doped.
Comparative example 2
Comparative example 2 was prepared as in example 2, except that compound B was used in place of compound 5 of the present invention in the light-emitting layer (EML).
The detailed device portion layering and thicknesses are shown in the following table. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
TABLE 1 device structure
The material structure used in the device is as follows:
table 2 shows the data at 1000cd/m 2 The measured λmax, voltage (V), external Quantum Efficiency (EQE) and CIE data, device lifetime was at 15mA/cm 2 Measured at constant current.
Table 2 device data
Discussion:
compound 68 and compound a were used as host materials in example 1 and comparative example 1, respectively. As shown in the data in table 2, CIE, amax is similar. Example 1 has a longer lifetime than comparative example 1, has a higher External Quantum Efficiency (EQE), and the voltage of example 1 is 0.21V lower than comparative example 1. It is very difficult to achieve the lifetime and efficiency of the present invention while enabling voltage reduction. In addition, at 1000cd/m 2 The external quantum efficiency of example 2 was 24.47% higher than that of comparative example 2, 23.84%. The data indicate that the bipolar host material of the compound of formula 1 is due to the structure thereof comprising the compound of formula 1In addition, the introduction of the azacarbazole maintains the higher triplet energy level and further balances the hole and electron transport capacity of the azacarbazole, so that the excellent comprehensive properties of low voltage, high efficiency and long service life can be obtained in the device.
It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. Thus, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. It is to be understood that the various theories as to why the present invention works are not intended to be limiting.
Claims (11)
1. A compound having formula 1:
wherein Ar is 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms; wherein L is 1 Selected from phenylene substituted or unsubstituted with one or more deuterium;
wherein X is 1 Is CR (CR) 1 And R is 1 Selected from phenyl substituted or unsubstituted with one or more deuterium; x is X 2 To X 5 Each independently selected from CR 1 And R is 1 Selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof;
wherein Y is 4 Selected from N, Y 1 -Y 3 Each independently selected from C or CR 2 ，Y 5 -Y 8 Each independently selected from CR 2 The method comprises the steps of carrying out a first treatment on the surface of the And R is 2 Selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted, having 1-20 units Alkyl groups of carbon atoms and combinations thereof; wherein L is 1 And Y is equal to 2 Linking, or L 1 And Y is equal to 3 And (5) connection.
2. The compound of claim 1, wherein X 1 Is CR (CR) 1 Wherein R is 1 Selected from phenyl substituted or unsubstituted with one or more deuterium; x is X 2 To X 5 Are CH.
3. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently selected from the group consisting of: substituted or unsubstituted phenyl, biphenyl, terphenyl, and combinations thereof.
4. The compound of claim 1, wherein L 1 Is phenylene.
5. The compound of claim 1, wherein R 2 Is hydrogen.
6. The compound of claim 1, wherein the compound is selected from the group consisting of:
7. an electroluminescent device, comprising:
an anode is provided with a cathode,
a cathode electrode, which is arranged on the surface of the cathode,
an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having formula 1:
wherein, the liquid crystal display device comprises a liquid crystal display device,
Ar 1 and Ar is a group 2 Each independently selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;
wherein L is 1 Selected from phenylene substituted or unsubstituted with one or more deuterium;
wherein X is 1 Is CR (CR) 1 And R is 1 Selected from phenyl substituted or unsubstituted with one or more deuterium; x is X 2 To X 5 Each independently selected from CR 1 And R is 1 Selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof;
wherein Y is 4 Selected from N, Y 1 -Y 3 Each independently selected from C or CR 2 ，Y 5 -Y 8 Each independently selected from CR 2 The method comprises the steps of carrying out a first treatment on the surface of the And R is 2 Selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof;
wherein L is 1 And Y is equal to 2 Linking, or L 1 And Y is equal to 3 And (5) connection.
8. The device of claim 7, wherein the organic layer is a light emitting layer and the compound is a host material.
9. The device of claim 8, wherein the light emitting layer further comprises a phosphorescent light emitting material.
10. The device of claim 9, wherein the phosphorescent light emitting material is a metal complex having at least one ligand comprising a structure of any one of:
wherein, the liquid crystal display device comprises a liquid crystal display device,
R a ，R b and R is c May represent mono-, poly-, or unsubstituted;
R a ，R b and R is c Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
X b Selected from the group consisting of: o, S, se, NR N1 ,CR C1 R C2 ；
R N1 ,R C1 And R is C2 Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkenyl having 6 to 30 carbon atomsAryl groups of atoms, substituted or unsubstituted heteroaryl groups of 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups of 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups of 6 to 20 carbon atoms, substituted or unsubstituted amine groups of 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphine groups, and combinations thereof;
in the ligand structure, adjacent substituents can optionally be linked to form a ring.
11. A compound formulation comprising the compound of claim 1.
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| CN104364345A (en) * | 2012-06-13 | 2015-02-18 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR20160076882A (en) * | 2014-12-23 | 2016-07-01 | 주식회사 두산 | Organic compound and organic electroluminescent device comprising the same |
| CN108026111A (en) * | 2015-09-09 | 2018-05-11 | 德山新勒克斯有限公司 | Organic electric element compound, organic electric element and its electronic device using it |
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| CN104364345A (en) * | 2012-06-13 | 2015-02-18 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR20160076882A (en) * | 2014-12-23 | 2016-07-01 | 주식회사 두산 | Organic compound and organic electroluminescent device comprising the same |
| CN108026111A (en) * | 2015-09-09 | 2018-05-11 | 德山新勒克斯有限公司 | Organic electric element compound, organic electric element and its electronic device using it |
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