CN115403586A - Triazine-containing compound and organic electroluminescent device comprising same - Google Patents
Triazine-containing compound and organic electroluminescent device comprising same Download PDFInfo
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- CN115403586A CN115403586A CN202110595172.8A CN202110595172A CN115403586A CN 115403586 A CN115403586 A CN 115403586A CN 202110595172 A CN202110595172 A CN 202110595172A CN 115403586 A CN115403586 A CN 115403586A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 78
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000010410 layer Substances 0.000 claims description 117
- 239000000463 material Substances 0.000 claims description 67
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 19
- 229910052805 deuterium Inorganic materials 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 14
- -1 cyano, nitro, amino Chemical group 0.000 claims description 12
- 239000002346 layers by function Substances 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000000376 reactant Substances 0.000 description 69
- 238000002360 preparation method Methods 0.000 description 48
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- 239000002994 raw material Substances 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 239000000758 substrate Substances 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 125000004986 diarylamino group Chemical group 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 150000003918 triazines Chemical class 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 2
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940125877 compound 31 Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical class CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- OMDTUSYJJFBYMG-UHFFFAOYSA-N 2,4-bis(9,9-dimethylfluoren-2-yl)-6-naphthalen-2-yl-1,3,5-triazine Chemical compound C1=CC=C2C(C)(C)C3=CC(C=4N=C(N=C(N=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 OMDTUSYJJFBYMG-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- SWUBEMMFTUPINB-UHFFFAOYSA-N 9-[3-carbazol-9-yl-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=C(C=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)=N1 SWUBEMMFTUPINB-UHFFFAOYSA-N 0.000 description 1
- BQFIIADCVFHAKC-UHFFFAOYSA-N 9-[3-carbazol-9-yl-5-[2-phenyl-6-(4-phenylphenyl)pyrimidin-4-yl]phenyl]carbazole Chemical compound C1=CC=CC=C1C1=CC=C(C=2N=C(N=C(C=2)C=2C=C(C=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=C1 BQFIIADCVFHAKC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- LCYXYLLJXMAEMT-SAXRGWBVSA-N Pyridinoline Chemical class OC(=O)[C@@H](N)CCC1=C[N+](C[C@H](O)CC[C@H](N)C([O-])=O)=CC(O)=C1C[C@H](N)C(O)=O LCYXYLLJXMAEMT-SAXRGWBVSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 159000000006 cesium salts Chemical class 0.000 description 1
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Chemical class 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002210 silicon-based material Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001894 space-charge-limited current method Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- TYHJXGDMRRJCRY-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) tin(4+) Chemical compound [O-2].[Zn+2].[Sn+4].[In+3] TYHJXGDMRRJCRY-UHFFFAOYSA-N 0.000 description 1
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention relates to a triazine-containing compound and an organic electroluminescent device containing the same, belonging to the technical field of semiconductors, wherein the structure of the compound is shown as a general formula (1);
after the compound is applied to a light-emitting layer of an OLED device, the device has long service life, particularly longer high-temperature service life.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a triazine-containing compound and an organic electroluminescent device comprising the triazine-containing compound.
Background
A hole transport region may exist between an anode and a light emitting layer of the organic electroluminescent device, and an electron transport region may exist between the light emitting layer and a cathode. Holes from the anode may migrate through the hole transport region to the light emitting layer, electrons from the cathode may migrate through the electron transport region to the light emitting layer, and the holes and the electrons are recombined in the light emitting layer and generate excitons. According to the quantum mechanics principle, the organometallic compound material as the doping material can realize 100% internal quantum yield.
Nevertheless, there is still a need for improvements in device voltage, current efficiency and lifetime for triplet-emissive phosphorescent OLEDs. The properties of the host material in the light-emitting layer generally affect the above-mentioned key properties of the organic electroluminescent device to a large extent. According to the prior art, the compounds used as host materials generally comprise triazine groups. When the existing triazine derivatives are used as main materials, the requirements on improvement of device voltage and current efficiency, especially on starting voltage and device service life are met.
For phosphorescent OLEDs, the emissive layer is typically not balanced with holes and electrons, and the roll-off in device efficiency at high current densities is a serious problem. The invention also provides a combination of two main materials, which can effectively solve the defects.
Disclosure of Invention
The invention provides a triazine-containing compound, which is applied to an organic electroluminescent device and enables the device to have long service life, especially longer high-temperature service life.
The technical scheme of the invention is as follows: a triazine-containing compound having the structure shown in formula (1):
in the general formula (1), L and L 0 、L 1 Each independently represents a single bond or phenylene;
Z 1 is represented by C-R 3 Or N;
Z 2 is represented by C-R 4 Or N, Z at the junction 1 、Z 2 Is represented as C;
R 0 one of R is represented by a structure shown by a general formula (1-1) or (1-2), and the other is represented by H;
in the general formula (1-1) and the general formula (1-2), m and n respectively represent 0,1 or 2;
when R is 0 When represented as H, L 0 Represented by phenylene;
when L is 1 When represents a single bond, at least one Z 1 Is represented as N;
when L is 1 When represented by phenylene, R 0 Represented by the general formula (1-1) or (1-2), L 0 Is a single bond and has at least one Z 2 Is represented as N;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl, cyano.
The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and a functional layer located between the first electrode and the second electrode, at least one functional layer in the organic electroluminescent device comprising the triazine-containing compound.
Compared with the prior art, the invention has the beneficial technical effects that:
1) The compound provided by the invention has proper HOMO and LUMO energy levels, can ensure the efficient injection and recombination of current carriers in a light-emitting layer, and ensures the low voltage and high efficiency of a device.
2) The compound provided by the invention has a higher T1 energy level, and can ensure the energy transfer efficiency between a host and an object.
3) The compound provided by the invention has strong stereoselectivity and weak intermolecular interaction, so that the compound has the characteristics of difficult crystallization of molecules, low evaporation temperature, good film forming property and the like, and has excellent industrial processability.
4) The device life, especially the high-temperature device life, has always restricted the popularization of the OLED display in various application fields. The compound provided by the invention has higher chemical stability, is beneficial to reducing the efficiency roll-off under high current density, and is also beneficial to prolonging the service life of a device and the service life of a high-temperature device.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is an electron transport layer, 8 is an electron injection layer, 9 is a cathode layer, and 10 is a CPL layer.
Detailed Description
The principles and features of this invention are described below in conjunction with the accompanying drawings and examples, which are set forth to illustrate the invention and are not intended to limit the scope of the invention.
In the present invention, HOMO means the highest occupied orbital of a molecule and LUMO means the lowest unoccupied orbital of a molecule, unless otherwise specified. Further, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between the energy levels is also a comparison of the magnitude of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level is, the lower the energy of the energy level is.
In the present invention, when describing electrodes and organic electroluminescent devices, and other structures, "upper", "lower", "top", and "bottom" and the like used to indicate orientation only indicate orientation in a certain specific state, and do not mean that the related structures can exist only in the orientation; conversely, if the structure is repositioned, e.g., inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of the electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is further from the substrate is the "top" side.
A compound represented by the general formula (1)
In the general formula (1), L and L 0 、L 1 Each independently represents a single bond or phenylene;
Z 1 is represented by C-R 3 Or N;
Z 2 is represented by C-R 4 Or N, Z at the junction 1 、Z 2 Is represented as C;
R 0 one of R is represented by a structure shown by a general formula (1-1) or (1-2), and the other is represented by H;
in the general formula (1-1) and the general formula (1-2), m and n respectively represent 0,1 or 2;
when R is 0 When represented as H, L 0 Represented by phenylene;
when L is 1 When represents a single bond, at least one Z 1 Is represented as N;
when L is 1 When represented by phenylene, R 0 Represented by the general formula (1-1) or (1-2), L 0 Is a single bond and has at least one Z 2 Is represented as N;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl or cyano.
In a preferred technical scheme, the structure of the compound is shown as a general formula (1):
in the general formula (1), L and L 0 Each independently represents a single bond or phenylene;
Z 1 is represented by C, N or C-R 3 And at least one Z 1 Is represented as N;
Z 2 is represented by C, N or C-R 4 Z at the junction 1 、Z 2 Is represented as C;
R 0 one of R is represented by a structure shown by a general formula (1-1) or (1-2), and the other is represented by H;
in the general formula (1-1) and the general formula (1-2), m and n respectively represent 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl or cyano.
The preferred technical scheme is that in the general formula (1), two Z groups exist 1 Denoted as N.
In the general formula (1), there is one and only one Z 1 Denoted by N, having and only one Z 2 Denoted as N.
In a preferred embodiment, the structure of the compound is represented by any one of general formulae (2-1) to (2-4):
in the general formulae (2-1) to (2-4), L and L 0 Each independently represents a single bond or phenylene;
Z 1 is represented by C-R 3 Or N, and at least one Z 1 Is represented as N;
Z 2 is represented by C-R 4 Or N, Z at the junction 1 、Z 2 Is represented as C;
R 0 r represents H;
and R 0 Linked L 0 Represented by phenylene;
m and n are respectively 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl, cyano;
in the general formulae (2-5) and (2-6), L represents a single bond or phenylene;
Z 1 is represented by C-R 3 Or N;
Z 2 is represented by C-R 4 Or N, and at least one Z 2 Is represented as N; z of the joint 1 、Z 2 Is represented as C;
r represents H;
m and n are respectively 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl or cyano.
In a preferred embodiment, the compound structure is represented by any one of general formulae (3-1) to (3-12):
in the general formulae (3-1) to (3-12),
Z 1 is represented by C-R 3 Or N, and at least one Z 1 Is represented as N;
Z 2 is represented by C-R 4 Or N, Z at the junction 1 、Z 2 Is represented as C;
m and n are respectively 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl, cyano;
in the general formulae (3-13) and (3-16),
Z 1 is represented by C-R 3 Or N;
Z 2 is represented by C-R 4 Or N, and at least one Z 2 Is represented as N; z of the joint 1 、Z 2 Is represented as C;
m and n are respectively 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl or cyano.
In a preferred embodiment, the structure of the compound is represented by the general formula (4-1):
in the general formula (4-1), Z 1 Is shown asC. N or C-R 3 And at least one Z 1 Is represented as N; z is a linear or branched member 2 Is represented by C, N or C-R 4 Z at the junction 1 、Z 2 Is represented as C;
m and n are respectively 0,1 or 2;
R 1 、R 3 、R 4 independently represent hydrogen, deuterium, phenyl or cyano.
According to a preferred technical scheme, the specific structure of the compound is any one of the following structures:
organic electroluminescent device
The invention provides an organic electroluminescent device comprising a first electrode, a second electrode and functional layers, wherein the functional layers are positioned between the first electrode and the second electrode, and at least one functional layer in the organic electroluminescent device contains a triazine-containing compound represented by a general formula (1).
In a preferred embodiment of the present invention, the functional layer includes a light-emitting layer containing a triazine-containing compound represented by general formula (1).
In a preferred embodiment of the present invention, the light-emitting layer contains a light-emitting host material which is obtained by mixing a triazine-containing compound represented by the general formula (1) and a compound represented by the general formula (A) or (B),
in the general formula (A), A 1 To A 4 Independently of one another, represent substituted or unsubstituted C 6 -C 20 The aromatic ring of (a) is,
X 1 represents O, S, N (R) a )、C(R b )(R c ) Wherein R is a Is substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, wherein R b And R c Independently of one another, hydrogen, substituted or unsubstituted C 1 -C 6 Alkyl, substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted C 3 -C 30 Heteroaryl radical, R b And R c Which may be the same or different from each other,
L 1 represents the following group: single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 3 -C 30 A heteroarylene group, a heteroaryl group,
b1, b2, b3, b4, b5 independently of one another represent 0,1, 2,3 or 4;
R 5 represents substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 (ii) a heteroaryl group, wherein,
R 6 to R 9 Independently of one another, represents hydrogen, deuterium, halogen, hydroxy, cyano, nitro, amino, substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 3 -C 30 A heteroaryl group;
in the general formula (B), in the formula (B),
Ar 1 and Ar 2 Independently a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 2 -C 30 A hetero-arylene group,
R 14 and R 15 Independently is substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 A heterocyclic group,
R 10 -R 13 independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 A heterocyclic group.
In a preferred embodiment of the present invention, the functional layer of the organic electroluminescent device comprises a light-emitting layer, wherein the light-emitting layer contains a light-emitting host material, the light-emitting host material comprises a first host material and a second host material, the first host material is selected from triazine-containing compounds represented by a general formula (1), the second host material is selected from any one or more of compounds GH-1-GH-170, and specific structures of the compounds GH-1 to GH-170 are as follows:
in an exemplary embodiment of the present invention, an organic electroluminescent device may include an anode, a hole transport region, a light emitting region, an electron transport region, and a cathode. In addition to using the aza-dibenzofuran-modified triazines of the present invention in the organic electroluminescent device, the organic electroluminescent device can be prepared by conventional methods and materials for preparing organic electroluminescent devices.
As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices can be used. Examples are transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; flexible PI film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. The direction of use varies depending on the nature of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
A first electrode is formed on the substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide (ZnO), indium Tin Zinc Oxide (ITZO), or the like. When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include Ag, mg, al, pt, pd, au, ni, nd, ir, cr, or a metal mixture. The thickness of the first electrode layer depends on the material used and is typically 50-500nm, preferably 70-300nm and more preferably 100-200nm.
The organic functional material layer arranged between the first electrode and the second electrode sequentially comprises a hole transmission area, a light emitting layer and an electron transmission area from bottom to top.
Herein, the hole transport region constituting the organic electroluminescent device may be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.
As the materials of the hole injection layer, the hole transport layer, and the electron blocking layer, any materials can be selected from known materials used for OLED devices.
Examples of the above-mentioned materials may be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrylanthracene derivatives, styrylamine derivatives and like styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline-based copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene ethylene and derivatives thereof, polythiophene and derivatives thereof, conductive polymer oligomers such as poly-N-vinylcarbazole derivatives and thiophene oligomers, aromatic tertiary amine compounds, styrene amine compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1 '-bis (4-diarylaminophenyl) cyclohexane, 4' -bis (diarylamine) biphenyls, and the like bis [4- (diarylamino) phenyl ] methanes, 4 '-bis (diarylamino) terphenyls, 4' -bis (diarylamino) tetrabiphenyls, 4 '-bis (diarylamino) diphenyl ethers, 4' -bis (diarylamino) diphenylsulfanes, bis [4- (diarylamino) phenyl ] dimethylmethanes, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes, 2-diphenylethylene compounds, and the like.
Furthermore, according to the matching requirements of the devices, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a superposition structure of a plurality of hole transport materials. In this context, the film thickness of the hole carrier conducting film layer having the above-described various functions is not particularly limited.
The hole injection layer comprises a host organic material that conducts holes and also comprises a P-type dopant material with a deep HOMO level (and correspondingly a deep LUMO level). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO level of the host organic material used for conducting holes in the buffer layer at the anode interface must have certain characteristics with the P-doped material, so that the generation of a charge transfer state between the host material and the doped material is expected to be achieved, ohmic contact between the buffer layer and the anode is achieved, and efficient injection from the electrode to hole injection conduction is achieved, which is summarized as follows: the HOMO energy level of the host material-the LUMO energy level of the P doping material is less than or equal to 0.4eV.
In view of the above empirical summary, for the hole-type host materials with different HOMO levels, different P-doped materials need to be selected and matched to realize ohmic contact at the interface, so as to improve the hole injection effect.
Thus, in one embodiment of the present invention, for better hole injection, the hole injection layer further comprises a P-type dopant material having charge conductivity selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4"- ((1E, 1' E) -cyclopropane-1, 2, 3-trimethylenetri (cyanoformylidene)) tris (2, 3,5, 6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type dopant material used is 99 to 95, preferably 99 to 97.
The thickness of the hole injection layer of the present invention may be 5 to 100nm, preferably 5 to 50nm and more preferably 5 to 20nm, but the thickness is not limited to this range.
The thickness of the hole transport layer of the present invention may be 5 to 200nm, preferably 10 to 150nm and more preferably 20 to 100nm, but the thickness is not limited to this range.
The thickness of the electron blocking layer of the present invention may be 1 to 20nm, preferably 5 to 10nm, but the thickness is not limited to this range.
After the hole injection layer, the hole transport layer, and the electron blocking layer are formed, a corresponding light emitting layer is formed over the electron blocking layer.
The triazine-containing compound represented by general formula (1) of the present invention is used as the host material of the light-emitting layer.
In addition, the light emitting material may further include a phosphorescent material. Specific examples of the phosphorescent material include metal complexes of iridium, platinum, and the like. For example, ir (ppy) 3 [ fac-tris (2-phenylpyridine) iridium]And the like, blue phosphorescent materials such as FIrpic and FIr6, and red phosphorescent materials such as Btp2Ir (acac).
In the light-emitting layer of the present invention, the ratio of the host material to the guest material used is 99.
The thickness of the light emitting layer may be adjusted to optimize light emitting efficiency and driving voltage. A preferable range of the thickness is 5nm to 50nm, further preferably 10 to 50nm, and more preferably 15 to 30nm, but the thickness is not limited to this range.
In the present invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed over the light emitting layer, in this order, but is not limited thereto.
The hole blocking layer is used for blocking holes injected from the anode from passing through the light emitting layerAn optical layer into the cathode, thereby extending the lifetime and enhancing the performance of the device. The hole blocking layer of the present invention may be disposed over the light emitting layer. As the hole-blocking layer material of the organic electroluminescent device of the present invention, compounds having a hole-blocking effect known in the art, for example, phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis (2-methyl-8-quinoline) -4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and 9,9'- (5- (6- ([ 1,1' -biphenyl ] derivatives)]-4-yl) -2-phenylpyrimidin-4-yl) -1, 3-phenylene) bis (9H-carbazole) (CAS No.:1345338-69-3) And pyrimidine derivatives. The hole blocking layer of the present invention may have a thickness of 2 to 200nm, preferably 5 to 150nm, and more preferably 10 to 100nm, but the thickness is not limited to this range.
The electron transport layer may be disposed over the light-emitting layer or, if present, the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, an electron transport layer material for organic electroluminescent devices known in the art, for example, in Alq, can be used 3 Metal complexes of hydroxyquinoline derivatives represented by BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS No.: 1459162-51-6), 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]Imidazole derivatives such as imidazole (CAS number: 561064-11-7, commonly known as LG 201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, and the like. The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, and more preferably 25 to 45nm, but the thickness is not limited to this range.
The electron injection layer may be disposed over the electron transport layer. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
The second electrode may be disposed over the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may comprise, for example, li, yb, ca, liF/Al, mg, baF, ba, ag, or compounds or mixtures thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, mg, yb, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Al, mo, ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used and is generally from 10 to 50nm, preferably from 15 to 20nm.
In order to improve the light extraction efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be further added on the second electrode of the device. According to the principle of optical absorption and refraction, the CPL cover layer material should have a higher refractive index as well as a better refractive index, and the absorption coefficient should be smaller as well. Any material known in the art may be used as the CPL layer material, such as Alq3, or N4, N4' -diphenyl-N4, N4' -bis (9-phenyl-3-carbazolyl) biphenyl-4, 4' -diamine. The CPL capping layer is typically 5-300nm, preferably 20-100nm and more preferably 40-80nm thick.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layers of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.
The organic electroluminescent device may be any element that converts electrical energy into light energy or converts light energy into electrical energy without particular limitation, and may be, for example, an organic electroluminescent device, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum. Herein, the organic light emitting diode is described as one example of the organic electroluminescent device (but the present invention is not limited thereto), and may be applied to other organic electroluminescent devices in the same manner.
In the case where the organic electroluminescent device is of a top emission type, the first electrode may be a reflective electrode, and the second electrode may be a transmissive electrode or a semi-transmissive electrode. In the case where the organic electroluminescent device is of a bottom emission type, the first electrode may be a transmissive electrode or a semi-transmissive electrode, and the second electrode may be a reflective electrode.
The present invention also relates to a method of preparing an organic electroluminescent device comprising sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, LITI, or the like may be used, but are not limited thereto. In the present invention, it is preferable that the respective layers are formed by a vacuum evaporation method. The individual process conditions in the vacuum evaporation process can be routinely selected by the person skilled in the art according to the actual requirements.
Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used in a generic and descriptive sense only and not for purposes of limitation. In some instances, features, characteristics and/or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics and/or elements described in connection with other embodiments, unless specifically indicated otherwise, as will be apparent to one of ordinary skill in the art upon submission of the present application. Accordingly, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention.
The starting materials referred to in the synthetic examples of the present invention are either commercially available or obtained by preparation methods conventional in the art.
Preparation of reactant B-1:
raw material H-1 (50 mmol), raw material S-1 (50 mmol) and potassium carbonate (150 mmol) were added to a mixture solvent of 300mL of toluene and 150mL of distilled water, stirred, and charged with N 2 Blowing for 30min, and adding Pd (pph) 3 ) 4 (1.0 mmol) was added to the solution, the mixed solution was refluxed for 24h, the mixed solution was cooled to room temperature, extracted with ethyl acetate and distilled water, the organic layer was dried over anhydrous magnesium sulfate, rotary evaporated in vacuo to give a crude product, purified by silica gel column chromatography using n-hexane/ethyl acetate (3;
intermediate G-1 (35 mmol), tetrahydrofuran (60 mL) and glacial acetic acid (90 mL) are mixed and stirred at-10 ℃ for 20min, nitroso-tert-butyl ester (105 mmol) is added through a syringe within 20min, after stirring at-10 ℃ for l h, the temperature is raised to 0 ℃, stirring is carried out for 12h, the reaction mixture is heated to room temperature, diluted with 150mL of water, and the precipitated material is filtered and dried to obtain intermediate T-1.
In a three-neck flask, under the protection of nitrogen, 3mmol of intermediate T-1, 6mmol of pinacol diboron, 9mmol of potassium acetate, 0.6mmol of Sphos and 0.12mmol of Pd 2 (dba) 3 Added to 150mL of dioxane, refluxed for 8h, the reaction system was cooled to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure, and purified by silica gel column chromatography using n-heptane/ethyl acetate (9).
Preparation of reactant B-2:
the preparation of the reactant B-2 was carried out in the same manner as the preparation of the reactant B-1 except that the starting material H-1 was replaced with the starting material H-2.
Preparation of reactant B-3:
the preparation method of the reactant B-3 is the same as that of the reactant B-1, except that the raw material S-1 is replaced by the raw material S-2, and the raw material H-1 is replaced by the raw material H-3.
Preparation of reactant B-4:
the process for producing the reactant B-4 is the same as that for producing the reactant B-1 except that the raw material S-1 is replaced with the raw material S-3 and the raw material H-1 is replaced with the raw material H-4.
Preparation of reactant B-5:
the preparation method of the reactant B-5 is the same as that of the reactant B-1 except that the raw material S-4 is used in place of the raw material S-1.
Preparation of reactant B-6:
the reactant B-6 was prepared in the same manner as the reactant B-3 except that the starting material H-3 was replaced with the starting material H-5.
Preparation of reactant B-7:
the reactant B-7 was prepared in the same manner as the reactant B-3 except that the starting material H-3 was replaced with the starting material H-6.
Preparation of reactant B-8:
the preparation method of the reactant B-8 is the same as that of the reactant B-3, except that the raw material S-2 is replaced by the raw material S-5, and the raw material H-3 is replaced by the raw material H-7.
Preparation of reactant B-9:
the reactant B-9 was prepared in the same manner as the reactant B-3 except that the starting material H-3 was replaced with the starting material H-7.
Preparation of reactant B-10:
the preparation method of the reactant B-10 is the same as that of the reactant B-3, except that the raw material S-2 is replaced by the raw material S-6, and the raw material H-3 is replaced by the raw material H-8.
Example 1: preparation of compound 15:
in a 500mL three-necked flask, 0.01mol of the reactant A-1,0.01mol of the reactant B-1,0.03mol of sodium carbonate, 150mL of toluene, 30mL of ethanol and 30mL of water are added under the protection of nitrogen, stirred and mixed, and then 1.5X 10 -4 mol Pd(pph 3 ) 4 Heating to 105 ℃, refluxing for 10 hours, taking a sample, completely reacting, naturally cooling to room temperature, filtering, subjecting the filtrate to reduced pressure rotary evaporation (-0.09MPa, 85 ℃), passing through a neutral silica gel column (silica gel 100-200 mesh, eluent: chloroform: n-hexane =1 (volume ratio)) to obtain compound 15.
Example 2: preparation of compound 16:
compound 16 was prepared by the same method as in preparation example 1, except that reactant B-1 was replaced with reactant B-2.
Example 3: preparation of compound 26:
compound 26 was prepared as in preparation example 1, except that reactant B-1 was replaced with reactant B-3.
Example 4: preparation of compound 31:
compound 31 was prepared as in preparation example 1, except that reactant B-4 was used in place of reactant B-1.
Example 5: preparation of compound 79:
compound 79 was prepared as in preparation example 1, except that reactant B-5 was used in place of reactant B-1.
Example 6: preparation of compound 87:
compound 87 was prepared by the same method as in preparation example 1, except that reactant B-1 was replaced with reactant B-6.
Example 7: preparation of compound 105:
compound 105 was prepared as in preparation example 1, except that reactant A-1 was replaced with reactant A-2 and reactant B-1 was replaced with reactant B-7.
Example 8: preparation of compound 106:
compound 106 is prepared as in preparation example 1, except that reactant A-1 is replaced with reactant A-2 and reactant B-1 is replaced with reactant B-2.
Example 9: preparation of compound 108:
compound 108 was prepared as in preparation example 1, except that reactant A-1 was replaced with reactant A-2 and reactant B-1 was replaced with reactant B-3.
Example 10: preparation of compound 143:
the preparation method of the intermediate T-10 is the same as that of the intermediate T-1, except that the raw material S-1 is replaced by the raw material S-10, and the raw material H-1 is replaced by the raw material H-10 to obtain the intermediate T-10;
adding 0.01mol of raw material M-10,0.01mol of intermediate T-10,0.03mol of sodium carbonate, 150mL of toluene, 30mL of ethanol and 30mL of water into a 500mL three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 1.5 multiplied by 10 -4 mol Pd(pph 3 ) 4 Heating to 105 deg.C, reflux reacting for 10 hr, taking sample, cooling to room temperature, filtering, and rotary evaporating the filtrate under reduced pressure (-0.09MPa, 85 deg.C) to neutralSilica gel column (silica gel 100-200 mesh, eluent: chloroform: N-hexane =1 (volume ratio)) to give intermediate N-10;
0.01mol of starting material D-1 and 0.012mol of intermediate N-10 were added to 150mL of toluene solvent at 5X 10 - 5 mol Pd 2 (dba) 3 ，5×10 -5 mol P(t-Bu) 3 0.03mol of sodium tert-butoxide, and the reaction is carried out for 24 hours under the reflux at 105 ℃ in a nitrogen atmosphere. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, rinsed with chloroform, and the resulting filtrate was evaporated in vacuo. Passing the crude product through a silica gel column to obtain a compound 143;
example 11: preparation of compound 157:
compound 157 was prepared in the same manner as in preparation example 10, except that the starting material S-10 was replaced with the starting material S-11.
Example 12: preparation of compound 247:
in a 500mL three-necked flask, 0.01mol of the reactant A-3,0.01mol of the reactant B-3,0.03mol of sodium carbonate, 150mL of toluene, 30mL of ethanol and 30mL of water are added under the protection of nitrogen, stirred and mixed, and then 1.5X 10 -4 mol Pd(pph 3 ) 4 Heating to 105 ℃, carrying out reflux reaction for 10 hours, taking a sample, completely reacting, naturally cooling to room temperature, filtering, carrying out reduced pressure rotary evaporation on the filtrate (-0.09MPa, 85 ℃), passing through a neutral silica gel column (silica gel 100-200 meshes, eluent: chloroform: n-hexane =1 (volume ratio)) to obtain an intermediate F-1;
in a 500mL three-necked flask, 0.01mol of intermediate F-1,0.01mol of raw material D-2,0.03mol of sodium carbonate, 150mL of toluene, 30mL of ethanol, and 30mL of water were added under nitrogen protection, and stirred and mixed, and then 1.5X 10 was added -4 mol Pd(pph 3 ) 4 Heating to 105 ℃, refluxing for 10 hours, taking a sample, completely reacting, naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (-0.09MPa, 85 ℃), and passing through a neutral silica gel column (silica gel 100-200 meshes, eluent: chloroform: n-hexane =1 (volume ratio)) to obtain a compound 247;
example 13: preparation of compound 291:
compound 291 is prepared by the same method as in preparation example 1, except that reactant A-1 is replaced with reactant A-4.
Example 14: preparation of compound 306:
compound 306 is prepared as in preparation example 1, except that reactant B-8 is used in place of reactant B-1.
Example 15: preparation of compound 307:
compound 307 is prepared by the same method as in preparation example 1 except that reactant B-1 is replaced with reactant B-9.
Example 16: preparation of compound 308:
compound 308 is prepared as in preparative example 1 except that reactant A-1 is replaced with reactant A-5 and reactant B-1 is replaced with reactant B-10.
Example 17: preparation of compound 309:
compound 309 is prepared as in preparation example 1, except that reactant A-1 is replaced with reactant A-5 and reactant B-1 is replaced with reactant B-11.
The reactants B-8, B-9 and B-11 can also be obtained by conventional reaction using conventional compounds (such as CAS:2407622-24-4, 1589534-43-9 and 2271177-16-1) as raw materials and a boron reagent.
For structural analysis of the compounds prepared in the examples, the molecular weights were measured by LC-MS as shown in table 1:
TABLE 1
The compound of the present invention is used in a light-emitting device, and can be used as a material for a light-emitting layer. The compounds prepared in the above examples of the present invention were tested for physicochemical and optoelectronic properties, respectively, and the results are shown in table 2:
TABLE 2
Note: the triplet state energy level T1 is measured by Fluorolog-3 series fluorescence spectrometer of Horiba, and the material test sample is 2 x 10 -5 A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter of Germany Chi-resistant company), and the heating rate is 10 ℃/min; highest occupied molecular orbital HOMO energyThe stage is tested by an ionization energy testing system (IPS-3), and the test is in an atmospheric environment; eg was tested by a two-beam uv-vis spectrophotometer (model: TU-1901) with LUMO = HOMO + Eg. The electron mobility test is to make the material of the invention into a single charge device and measure the device by an SCLC method.
As can be seen from the above data, the organic compound of the present invention has a high glass transition temperature (Tg), which can improve the phase stability and high temperature stability of the material film; the organic compound has proper HOMO and LUMO energy levels, can reduce the injection barrier of current carriers, reduces the voltage of a device and improves the efficiency of the device. The organic compound has a high T1 energy level, can ensure the energy transfer efficiency between a host and an object when used as a host material, and inhibits energy loss, and also has higher electron mobility.
The application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-29 and device comparative examples 1-8. Compared with the device example 1, the device examples 2 to 29 and the device comparative examples 1 to 8 of the present invention have the same manufacturing process, adopt the same substrate material and electrode material, and keep the film thickness of the electrode material consistent, except that the luminescent layer in the device is replaced.
Device example 1
As shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the anode layer 2 (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)) is washed, i.e., washed with a detergent (SemiClean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 were deposited by a vacuum deposition apparatus as the hole injection layer 3, the film thickness was 10nm, and the mass ratio of HT-1 to P-1 was 97. HT-1 was then evaporated as a hole transport layer 4 to a thickness of 130nm. EB-1 was then evaporated as an electron blocking layer 5 with a thickness of 40nm. After the evaporation of the electron blocking layer material is finished, the light-emitting layer 6 of the OLED light-emitting device is manufactured, the structure of the OLED light-emitting device comprises the following components, wherein the components 15 and GH-1 used in the OLED light-emitting layer 6 are used as host materials, GD-1 is used as a doping material, the mass ratio of the compound 15. After the light-emitting layer 6, ET-1 and Liq were continuously vacuum-evaporated, the mass ratio of ET-1 to Liq was 1, the film thickness was 35nm, and this layer was an electron-transporting layer 7. On the electron transport layer 7, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 8. On the electron injection layer 8, a vacuum deposition apparatus was used to produce a 15 nm-thick Mg: the Ag electrode layer has a Mg-Ag mass ratio of 1. On the cathode layer 9, CP-1 was vacuum-deposited as a CPL layer 10 with a thickness of 70nm. The organic electroluminescent device 1 is obtained.
The molecular structural formula of the related material is shown as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected using a well-known driving circuit, and the voltage, current efficiency, light emission spectrum, and device lifetime of the device were measured. Device examples and comparative examples prepared in the same manner are shown in table 3; voltage, current efficiency and 20mA/cm of the resulting device 2 The following LT95 lifetime test results are shown in table 4.
TABLE 3
TABLE 4
Note: the voltage and current efficiency are 10mA/cm at the current density 2 Tested under conditions using an IVL (current-voltage-brightness) test system (forskod scientific instruments, suzhou); the life test system is an EAS-62C type OLED device life tester of Japan System research company; the device lifetime LT95 is defined as the current density at which the current is 20mA/cm 2 The time it takes for the device luminance to decay to 95% of the initial luminance; the high temperature device lifetime LT95 refers to a current density of 20mA/cm 2 And when the temperature is 85 ℃, the time for the brightness of the device to decay to 95 percent of the initial brightness; the turn-on voltage refers to a driving voltage of the device at a luminance of 1nit of the device.
As can be seen from the device data results of table 4: the organic light-emitting devices using the compounds of the present invention showed a very significant improvement in device lifetime compared to device comparative examples 1 to 4 and device comparative examples 5 to 8, and the degree of such improvement was unexpected.
In order to compare the efficiency attenuation of different devices under high current density, the efficiency attenuation coefficient phi, phi = (mu) of each device is defined m -μ 50 )/μ m (ii) a Wherein mu m Expressed as the maximum current efficiency, μ, of the device 50 Indicating a drive current of 50mA/cm 2 The current efficiency of the device. The larger the value phi is, the more serious the efficiency roll-off of the device is, and on the contrary, the problem that the device rapidly decays under high current density is controlled. The efficiency attenuation coefficient φ of the devices obtained in device examples 1-29 and device comparative examples 1-8 was measured, and the results are shown in Table 5:
TABLE 5
As can be seen from the data in table 5, the organic light emitting device prepared by using the compound of the present invention has a smaller efficiency decay coefficient than the comparative example, which shows that the organic electroluminescent device prepared by using the compound of the present invention can effectively reduce the efficiency roll-off of the device at high current density.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A triazine-containing compound, wherein the compound has a structure represented by general formula (1):
in the general formula (1), L and L 0 、L 1 Each independently represents a single bond or phenylene;
Z 1 is represented by C-R 3 Or N;
Z 2 is represented by C-R 4 Or N, Z at the junction 1 、Z 2 Is represented as C;
R 0 one of R is represented by a structure shown by a general formula (1-1) or (1-2), and the other is represented by H;
in the general formula (1-1) and the general formula (1-2), m and n respectively represent 0,1 or 2;
when R is 0 When represented as H, L 0 Represented by phenylene;
when L is 1 When represents a single bond, at least one Z 1 Is represented as N;
when L is 1 When it represents a phenylene group, R 0 Represented by the general formula (1-1) or (1-2), L 0 Is a single bond and has at least one Z 2 Is represented as N;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl or cyano.
2. The compound of claim 1, wherein the compound has the structure of formula (1):
in the general formula (1), L and L 0 Each independently represents a single bond or phenylene;
Z 1 is represented by C, N or C-R 3 And at least one Z 1 Is represented as N;
Z 2 is represented by C, N or C-R 4 Z at the junction 1 、Z 2 Is represented as C;
R 0 one of R is represented by a structure shown by a general formula (1-1) or (1-2), and the other is represented by H;
in the general formula (1-1) and the general formula (1-2), m and n respectively represent 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl, cyano.
3. The compound of claim 2, wherein in formula (1) there is one and only one Z 1 Denoted by N, having and only one Z 2 Denoted as N.
4. The compound of claim 1, wherein the compound structure is represented by any one of general formulae (2-1) to (2-4):
in the general formulae (2-1) to (2-4), L and L 0 Each independently represents a single bond or phenylene;
Z 1 is represented by C-R 3 Or N, and at least one Z 1 Is represented as N;
Z 2 is represented by C-R 4 Or N, Z at the junction 1 、Z 2 Is represented as C;
R 0 r represents H;
and R 0 Linked L 0 Represented by phenylene;
m and n are respectively 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl, cyano;
in the general formulae (2-5) and (2-6), L represents a single bond or phenylene;
Z 1 is represented by C-R 3 Or N;
Z 2 is represented by C-R 4 Or N, and at least one Z 2 Is represented as N; z of the joint 1 、Z 2 Is represented as C;
r represents H;
m and n are respectively 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl or cyano.
5. The compound of claim 1, wherein the compound structure is represented by any one of general formulae (3-1) to (3-12):
in the general formulae (3-1) to (3-12),
Z 1 is represented by C-R 3 Or N, and at least one Z 1 Is represented as N;
Z 2 is represented by C-R 4 Or N, Z at the junction 1 、Z 2 Is represented as C;
m and n are respectively 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl, cyano;
in the general formulae (3-13) and (3-16),
Z 1 is represented by C-R 3 Or N;
Z 2 is represented by C-R 4 Or N, and at least one Z 2 Is represented as N; z of the joint 1 、Z 2 Is represented as C;
m and n are respectively 0,1 or 2;
R 1 -R 4 independently represent hydrogen, deuterium, phenyl or cyano.
6. The compound of claim 1, wherein the compound structure is represented by general formula (4-1):
in the general formula (4-1), Z 1 Is represented by C, N or C-R 3 And at least one Z 1 Is represented as N;
Z 2 is represented by C, N or C-R 4 Z at the junction 1 、Z 2 Is represented as C;
m and n are respectively 0,1 or 2;
R 1 、R 3 、R 4 independently represent hydrogen, deuterium, phenyl, cyano.
7. The compound of claim 1, wherein the specific structure of the compound is any one of the following structures:
8. an organic electroluminescent device comprising a first electrode, a second electrode and a functional layer which is present between the first electrode and the second electrode, characterized in that at least one of the functional layers in the organic electroluminescent device comprises a triazine-containing compound as claimed in any of claims 1 to 7.
9. The organic electroluminescent element according to claim 8, wherein the functional layer comprises a light-emitting layer, and the light-emitting layer contains a light-emitting host material comprising a mixture of the compound according to any one of claims 1 to 7 and a compound represented by the general formula (A) or (B),
in the general formula (A), A 1 To A 4 Independently of one another, represents substituted or unsubstituted C 6 -C 20 The aromatic ring of (a) is,
X 1 represents O, S, N (R) a )、C(R b )(R c ) Wherein R is a Is substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, wherein R is b And R c Independently of one another, hydrogen, substituted or unsubstituted C 1 -C 6 Alkyl, substituted or unsubstituted C 6 -C 30 Aryl or substituted or unsubstituted C 3 -C 30 Heteroaryl, R b And R c Which may be the same or different from each other,
L 1 represents the following group: single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 3 -C 30 A heteroarylene group, a heteroaryl group,
b1, b2, b3, b4, b5 independently of one another represent 0,1, 2,3 or 4;
R 5 represents substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 (ii) a heteroaryl group, wherein,
R 6 to R 9 Independently of one another, represents hydrogen, deuterium, halogen, hydroxy, cyano, nitro, amino, substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl radicalsSubstituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 6 -C 30 Aryloxy, substituted or unsubstituted C 3 -C 30 A heteroaryl group;
in the general formula (B), in the formula (B),
Ar 1 and Ar 2 Independently a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C 2 -C 30 A hetero-arylene group,
R 14 and R 15 Independently is substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 A heterocyclic group,
R 10 -R 13 independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 2 -C 30 A heterocyclic group.
10. The organic electroluminescent device according to claim 9, wherein the compounds represented by the general formulae (a) and (B) are selected from any one of the following specific structures:
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