CN109843854A - Compound and its application containing crosslinked group - Google Patents
Compound and its application containing crosslinked group Download PDFInfo
- Publication number
- CN109843854A CN109843854A CN201780059502.3A CN201780059502A CN109843854A CN 109843854 A CN109843854 A CN 109843854A CN 201780059502 A CN201780059502 A CN 201780059502A CN 109843854 A CN109843854 A CN 109843854A
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- China
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- atom number
- carbon atom
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- organic
- aryl
- Prior art date
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- Granted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 162
- 125000003118 aryl group Chemical group 0.000 claims abstract description 95
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 71
- 229910052799 carbon Inorganic materials 0.000 claims description 171
- 125000004429 atom Chemical group 0.000 claims description 95
- 239000000463 material Substances 0.000 claims description 92
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- -1 alkane thioether Chemical class 0.000 claims description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 28
- 239000010408 film Substances 0.000 claims description 27
- 239000012188 paraffin wax Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 230000004888 barrier function Effects 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 150000001924 cycloalkanes Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 230000005669 field effect Effects 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 230000003111 delayed effect Effects 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 230000005284 excitation Effects 0.000 claims description 3
- 238000013086 organic photovoltaic Methods 0.000 claims description 3
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims description 3
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 238000006884 silylation reaction Methods 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 description 106
- 239000010410 layer Substances 0.000 description 90
- 238000007639 printing Methods 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- 239000000758 substrate Substances 0.000 description 25
- 238000004770 highest occupied molecular orbital Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 150000004982 aromatic amines Chemical class 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 230000006870 function Effects 0.000 description 14
- 230000005540 biological transmission Effects 0.000 description 13
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 13
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 239000002346 layers by function Substances 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 10
- 125000005504 styryl group Chemical group 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 9
- 230000009477 glass transition Effects 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 238000003775 Density Functional Theory Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 125000003107 substituted aryl group Chemical group 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000004065 semiconductor Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 230000027756 respiratory electron transport chain Effects 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 150000002240 furans Chemical class 0.000 description 5
- 238000007641 inkjet printing Methods 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 4
- IYTXKIXETAELAV-UHFFFAOYSA-N Aethyl-n-hexyl-keton Natural products CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000005286 illumination Methods 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 description 4
- 239000013110 organic ligand Substances 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 238000010020 roller printing Methods 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 4
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 235000009854 Cucurbita moschata Nutrition 0.000 description 3
- 240000001980 Cucurbita pepo Species 0.000 description 3
- 235000009852 Cucurbita pepo Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229920000547 conjugated polymer Polymers 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 3
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Natural products CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000004210 ether based solvent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002220 fluorenes Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000004088 simulation Methods 0.000 description 3
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- 235000020354 squash Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UWRZIZXBOLBCON-UHFFFAOYSA-N styrylamine group Chemical group C(=CC1=CC=CC=C1)N UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 2
- AGIQIOSHSMJYJP-UHFFFAOYSA-N 1,2,4-Trimethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1 AGIQIOSHSMJYJP-UHFFFAOYSA-N 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical group CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical group CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- JRRDISHSXWGFRF-UHFFFAOYSA-N 1-[2-(2-ethoxyethoxy)ethoxy]-2-methoxyethane Chemical compound CCOCCOCCOCCOC JRRDISHSXWGFRF-UHFFFAOYSA-N 0.000 description 2
- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 2
- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-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
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 2
- RERATEUBWLKDFE-UHFFFAOYSA-N 1-methoxy-2-[2-(2-methoxypropoxy)propoxy]propane Chemical compound COCC(C)OCC(C)OCC(C)OC RERATEUBWLKDFE-UHFFFAOYSA-N 0.000 description 2
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 2
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- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
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- 125000003003 spiro group Chemical group 0.000 description 1
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- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Disclose a kind of compound containing crosslinked group and its application.The compound has structure formula (I)Wherein, SG has structure formula (II)The heteroaryl that Ar is the aryl that annular atom number is 5~20 or annular atom number is 5~20；CLG is crosslinked group；O is 0 or 1；P is the integer more than or equal to 2；A has formula II IThe above-mentioned compound containing crosslinked group can make the electronic device with greater efficiency.
Description
The present invention relates to electronic fields, more particularly to a kind of compound containing crosslinked group and its application.
Organic Light Emitting Diode (OLEDs, Organic Light-Emitting Diodes) (Appl.Phys.Lett.1987,51:913-15. since the invention；Nature, 1990,347:539-541), the optics and electric property for having diversity, manufacturing cost relatively low and excellent in synthesis due to organic material, there is very big potentiality (Chem Rev in the application aspect of photoelectric device (such as flat-panel monitor and illumination), 2009,109:897-1091；Chem Mater,2011,23:326-340).
OLED device mostly uses greatly multilayer device structure, i.e., other than luminescent layer, also contains one or more layers hole transport/implanted layer or electron-transport/implanted layer.Therefore, in addition to developing excellent luminescent material, develop excellent electron-transport/injection material and hole transport/injection material be also realize high-performance OLED key (J Mater Chem, 2008,18:4495-4509.；Acc Chem Res,2005,38:632-643.；Adv Mater,2007,19:810-814).
To small molecule vacuum evaporation OLEDs, it is easy to multilayer, complicated efficient OLEDs device are obtained by vacuum deposition method, but due to vacuum deposition method have the shortcomings that it is expensive, time-consuming, waste material, be difficult to realize large-area applications.In comparison, solution processing type OLEDs is with a wide range of applications and commercial value due to the advantages that capable of preparing large area, flexible device by Solution processing techniques such as cheap inkjet printing, printings.Since general organic photoelectrical material has similar dissolubility, i.e. organic/polymer luminescent material, hole injection/transmission material, electron injection/transmission material have good dissolubility in the organic solvents such as toluene, chloroform, chlorobenzene, o-dichlorohenzene, ortho-xylene, tetrahydrofuran, therefore when Solution processing techniques prepare multilayer, complicated OLED, the problems such as that there are interfaces is miscible, interface attack.Such as when solution processable polymer or small molecule luminescent layer, used solvent can dissolve following hole transmission layer, and the problems such as causing miscible interface, interface attack (J Mater Chem, 2008,18:4495-4509.；Chem S℃Rev,2010,39:2500-2521).
Using conventional crosslinked group such as Freon C318 base, styryl, epoxy butane base, silicone base is acrylate-based, benzocyclobutane alkenyl.When decorating conjugated polymer, crosslinked group on polymer is in illumination, the conditions such as heating can cause crosslinked group Freon C318 base (Adv.Funct.Mater., 2002, 12, 745), styryl (Adv.Mater., 2007, 19, 300), epoxy butane base (Nature, 2003, 421, 829.), silicone base (Acc.Chem.Res., 2005, 38, 632), acrylate-based (Chem.Mater., 2003, 15, 1491), benzocyclobutane alkyl (Chem.Mater., 2007, 19, 4827.) reaction is crosslinked, form insoluble insoluble interpenetrating net polymer film, with excellent solvent resistance Can, can, interface attack miscible to avoid interface the problems such as (TW201406810A, US7592414B2).
But the cross-linking high polymer reported so far is all based on conjugated polymer.Conjugated polymer has lower triplet mostly, and adjacent emissive layers can be quenched, and as having the exciton of more high triplet energy (relatively much shorter wavelength) in green light emitting layer, while will not play the role of exciton barrier-layer.These all constrain the raising of the performance of OLED device, are not able to satisfy actual demand.
Summary of the invention
Based on this, a kind of compound containing crosslinked group and its application that can make the electronic device with greater efficiency must be provided by having.
The compound containing crosslinked group of one embodiment has the following structure formula (I):
Wherein, SG has structure formula (II):
The heteroaryl that Ar is the aryl that annular atom number is 5~20 or annular atom number is 5~20；
CLG is crosslinked group；
O is 0 or 1；
P is the integer more than or equal to 2；
The formula II I of A are as follows:
Wherein, R1For F, Cl, Br, I, D, CN, NO2、CF3、B(OR2)2、Si(R2)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be 3~10 cycloalkyl group, R2For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl,
- L- is singly-bound or carbon atom number is 5~40 conjugation aryl,
Ar1For annular atom number be 5~40 aromatic group or annular atom number be 5~40 heteroaryl,
The integer that y is 0~5,
Ar0Selected from one of following structural formula:
Wherein, Ar2For annular atom number be 5~40 aromatic group or annular atom number be 5~40 heteroaromatic base,
The integer that X is 0~4, the integer that X1 is 0~3,
- Z- is not present or for one of singly-bound and two bridging bases,
M is selected from 0~10 integer,
R9For F, Cl, Br, I, D, CN, NO2、CF3、B(OR14)2、Si(R14)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be 3~10 cycloalkane, R14For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl；
Dotted line in formula II I indicates L and Ar0It connects, the dotted line and circle in structural formula (IIIa) indicate that L can be with any carbon atom or Ar of two phenyl ring in circle2Structural formula in include aromatic rings or hetero-aromatic ring the connection of any carbon atom, the dotted line in structural formula (IIIb) and structural formula (IIIc) indicates that L can be connected on any carbon atom for the phenyl ring that dotted line passes through.
The above-mentioned compound containing crosslinked group is comprising organic functional architecture unit and crosslinkable groups, the dissolubility having had and film forming.The compound can make intermolecular crosslinkable groups crosslink reaction by heat treatment or ultraviolet irradiation, so that the compound cures be made to form film.Simultaneously, since above compound has preferable dissolubility and film forming, so that the composition containing the compound has preferable printing and filming performance, so that the performance with higher of the electronic device containing the compound or the composition, finally makes the manufacturing cost of electronic device low, high-efficient.
Fig. 1 is the structural schematic diagram of the Organic Light Emitting Diode of an embodiment.
To facilitate the understanding of the present invention, below to invention is more fully described.But the invention can be realized in many different forms, however it is not limited to embodiment described herein.It is made the disclosure of the present invention more thorough and comprehensive on the contrary, purpose of providing these embodiments is.
Unless otherwise defined, all technical and scientific terms used herein and the skill for belonging to technical field of the invention
The normally understood meaning of art personnel is identical.Term as used herein in the specification of the present invention, which is only for the purpose of describing specific embodiments, is not intended to limit the present invention.
In following implementation, if not otherwise specified, aryl refers to the alkyl for containing at least one aromatic ring, including monocyclic aryl and polyaromatic.Polyaromatic may be thick aryl, i.e., with the aryl of two or more rings, and wherein two neighboring ring shares two carbon atoms (i.e. condensed ring).Aryl for example can be benzene, naphthalene, anthracene, phenanthrene, perylene, aphthacene, pyrene, BaP, triphenylene, acenaphthene, fluorenes, spiro fluorene or derivatives thereof.It should be noted that being considered as aryl in the present embodiment when the H in aryl is substituted with a substituent.
Heteroaryl refers to comprising at least one heteroatomic aromatic group base, including bicyclic heteroaryl and polyheteroaromatic.Wherein, hetero atom for example can be selected from least one of Si, P, O, N, S and Ge；Further, hetero atom is selected from least one of Si, P, O, N and S；Further, hetero atom is selected from least one of O, N and S.Polyheteroaromatic may be thick heteroaryl, that is, include at least one heteroatomic thick aryl.Heteroaryl for example can be furans, benzofuran, dibenzofurans, thiophene, benzothiophene, dibenzothiophenes, pyrroles, pyrazoles, triazole, imidazoles, oxazole, oxadiazoles, thiazole, tetrazolium, indoles, carbazole, pyrrolo- imidazoles, pyrrolopyrrole, Thienopyrroles, thienothiophene, furans and pyrroles, furans and furans, thienofuran, benzo isoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinolin, cinnoline, quinoxaline, phenanthridines, primary pyridine, quinazoline, quinazolinone or derivatives thereof.It should be noted that being considered as heteroaryl in the present embodiment when the H in heteroaryl is substituted with a substituent.
It should be noted that aryl or heteroaryl can also include at least two aromatic rings or hetero-aromatic ring by the group that non-aromatic ring group connects and constitutes, wherein the quantity of the non-H atom in non-aromatic ring group is less than 10%.In a wherein embodiment, the quantity of the non-H atom in non-aromatic ring group is less than 5%.In a wherein embodiment, non-aromatic ring group is C atom, N atom or O atom.
The compound containing crosslinked group of one embodiment has the following structure formula (I):
Wherein, SG has structure formula (II):
The heteroaryl that Ar is the aryl that annular atom number is 5~20 or annular atom number is 5~20；
CLG is crosslinked group；
O is 0 or 1；
P is the integer more than or equal to 2；
The formula II I of A are as follows:
Wherein, R1For F, Cl, Br, I, D, CN, NO2、CF3、B(OR2)2、Si(R2)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be 3~10 cycloalkane R2For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl,
- L- is singly-bound or carbon atom number is 5~40 conjugation aryl,
Ar1For annular atom number be 5~40 aromatic group or annular atom number be 5~40 heteroaromatic group,
The integer that y is 0~5,
Ar0Selected from one of following structural formula:
Wherein, Ar2For annular atom number be 5~40 aromatic group or annular atom number be 5~40 heteroaromatic base,
The integer that X is 0~4, the integer that X1 is 0~3,
- Z- is not present or for one of singly-bound and two bridging bases,
M is selected from 0~10 integer,
R9For F, Cl, Br, I, D, CN, NO2、CF3、B(OR14)2、Si(R14)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be 3~10 cycloalkane, each group can be by one or more active group R14Replace, and one or more non-adjacent methylene (CH2) can be replaced by following group, they include R14C=CR14, C=C, Si (R14)2、Ge(R14)2、Sn(R14)2, C=O, C=S, C=Se, C=N (R14), O, S ,-COO- or CONR14, wherein one or more H atoms can be by D, F, Cl, Br, I, CN, N2, active group R14Substituted aromatic amine, the aromatic amine that aryl replaces, the aromatic amine replacement of heteroaryl substitution, substitution or the replacement of unsubstituted carbazole.R14For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl.It should be noted that the dotted line in formula II I indicates L and Ar0It connects, the dotted line and circle in structural formula (IIIa) indicate that the L can be with any carbon atom or Ar of two phenyl ring in circle2Structural formula in include aromatic rings or hetero-aromatic ring the connection of any carbon atom, the dotted line in structural formula (IIIb) and structural formula (IIIc) indicates that L can be connected on any carbon atom for the phenyl ring that dotted line passes through.
Ar is the aryl that annular atom number is 6~20 or the heteroaryl that annular atom number is 6~20 in one of the embodiments,.Further, Ar is the aryl that annular atom number is 6~16 or the heteroaryl that annular atom number is 6~16.Further, Ar is the aryl that annular atom number is 6~12 or the heteroaryl that annular atom number is 6~12.
Ar is the substituted aryl that annular atom number is 6~20 or the substituted heteroaryl that annular atom number is 6~20 in one of the embodiments,.Further, Ar is the substituted aryl that annular atom number is 6~16 or the substituted heteroaryl that annular atom number is 6~16.Further, Ar is the substituted aryl that annular atom number is 6~12 or the substituted heteroaryl that annular atom number is 6~12.
Ar is the aryl that annular atom number is 5~18 or the heteroaryl that annular atom number is 5~18 in one of the embodiments,.Further, Ar is the aryl that annular atom number is 5~15 or the heteroaryl that annular atom number is 5~15.Further, Ar is the aryl that annular atom number is 5~18 or the heteroaryl that annular atom number is 5~15.
Ar is the substituted aryl that annular atom number is 5~18 or the substituted heteroaryl that annular atom number is 5~18 in one of the embodiments,.Further, Ar is the substituted aryl that annular atom number is 5~15 or the substituted heteroaryl that annular atom number is 5~15.Further, Ar is the substituted aryl that annular atom number is 5~18 or the substituted heteroaryl that annular atom number is 5~15.
Ar is selected from one of benzene, biphenyl, triphenyl, benzo, fluorenes, indoles fluorenes and its derivative in one of the embodiments,.
In one of the embodiments, Ar is selected from triphenylamine, dibenzothiophenes, dibenzofurans, dibenzo selenophen, furans, thiophene, benzofuran, benzothiophene, benzo selenophen, carbazole, indole carbazole, pyridine indoles, pyrrolo- bipyridyl, pyrazoles, imidazoles, triazole type, oxazole, thiazole, oxadiazoles, dislike triazole, dioxazole, thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, triazines, oxazines, dislike thiazine, oxadiazines, indoles, benzimidazole, indazole, benzisoxazole, dibenzo oxazole, isoxazole, benzothiazole, quinoline, isoquinolin, cinnoline, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, azophenlyene, phenthazine, phenoxazine, benzofuran and pyridine, two pyrido furans, benzothiophene and pyridine, two pyridine bithiophenes, benzo selenophen and pyridine and two pyrido selenophens One of.
Ar is selected from one of following structural formula in one of the embodiments:
Wherein, X2For C-R15Or N,
Y2For C-R16-R17、Si-R18-R19、N-R20, C (=O), S (=O) 2, O or S,
-R15、-R16、-R17、-R18、-R19And-R20It is respectively and independently selected from as H, D, F ,-CN ,-NO2、-CF3, alkenyl, alkynyl, amido, acyl group, amide groups, cyano, isocyano group, alkoxy, hydroxyl, carbonyl, sulfuryl, the alkyl of carbon atom number 1~60, carbon atom number be 3~60 naphthenic base, carbon atom number be 6~60 aryl, carbon atom number be 3~60 heteroaryl, carbon atom number be 7~60 fused ring aryl, carbon atom number be 4~60 condensed hetero ring aryl and above-mentioned group in one of at least two combination groups being interconnected to form.
In a wherein embodiment ,-R15、-R16、-R17、-R18、-R19And-R20It itself can form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
In a wherein embodiment ,-R15Can respectively with-R16、-R17、-R18、-R19And-R20Form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
In a wherein embodiment ,-R20Can respectively with-R16、-R17、-R18、-R19And-R15Form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
In a wherein embodiment ,-R16With-R17Between can mutually form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
In a wherein embodiment ,-R18With-R19Between can mutually form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
- R in one of the embodiments,15、-R16、-R17、-R18、-R19And-R20Be respectively and independently selected from for the substituted alkyl of carbon atom number 1~60, carbon atom number be 3~60 substituted naphthenic base, carbon atom number be 6~60 substituted aryl, carbon atom number be 3~60 substituted heteroaryl, carbon atom number be 7~60 substituted fused ring aryl, carbon atom number be 4~60 substituted condensed hetero ring aryl.
CLG is cyclic monoene base, linear mono alkenyl, linear dialkylene, alkynyl, alkenyloxy group, two alkenyloxy groups, acrylic, propylene oxide base, Oxyranyle, silylation or cyclobutane base in one of the embodiments,.CLG enables the compound containing crosslinked group to crosslink reaction, and then increases the solvent resistance containing crosslinked group compound.Specifically, CLG energy
Enough in the environment of at least 100 DEG C, exclusion of water and oxygen, make to crosslink reaction by CLG between the compound containing crosslinked group.Above-mentioned cross-linking reaction can be enhanced by illumination in one of the embodiments,.Further, above-mentioned cross-linking reaction can be enhanced by UV illumination (i.e. ultraviolet lighting).
CLG is selected from one of following group in one of the embodiments:
Wherein, R10、R11、R12And R13It is respectively and independently selected from F, Cl, Br, I, D, CN, NO2、CF3、B(OR21)2、Si(R21)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be one of 3~10 cycloalkane, R21For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl；
Ar12For annular atom number be 5~40 aromatic group or annular atom number be 5~40 heteroaryl；
S is the integer more than or equal to 0, and t is the integer more than or equal to 0；
Dotted line in structure above indicates the connection of CLG and other groups.
O is 0 in one of the embodiments,.
O is 1 in one of the embodiments,.
The integer that p is 2~20 in one of the embodiments,.Further, the integer that p is 2~10.Further, the integer that p is 2~8.Further, the integer that p is 2~5.Further, the integer that p is 3~4.
- L- is the conjugation aryl that linking group, singly-bound or carbon atom number are 5~40 in one of the embodiments,.
Further, it is 5~40 by R that L, which is carbon atom number,22Substituted conjugation aryl, R22For F, Cl, Br, I, D, CN, NO2、CF3、B(OR23)2、Si(R23)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be 3~10 cycloalkane, each group can be by one or more active group R23Replace, and one or more non-adjacent methylene (CH2) can be replaced by following group, they include R14C=CR14, C=C, Si (R23)2、Ge(R23)2、Sn(R23)2, C=O, C=S, C=Se, C=N (R23), O, S ,-COO- or CONR23, wherein one or more H atoms can be by D, F, Cl, Br, I, CN, N2, active group R14Substituted aromatic amine, the aromatic amine that aryl replaces, the aromatic amine replacement of heteroaryl substitution, substitution or the replacement of unsubstituted carbazole.R23For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl.
L is the linking group with a phenyl ring in one of the embodiments,.
Further, the structural formula of L is selected from one kind of following structural formula:
Wherein, R25For F, Cl, Br, I, D, CN, NO2、CF3、B(OR24)2、Si(R24)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be 3~10 cycloalkane, each group can be by one or more active group R24Replace, and one or more non-adjacent methylene (CH2) can be replaced by following group, they include R24C=CR24, C=C, Si (R24)2、Ge(R24)2、Sn(R24)2, C=O, C=S, C=Se, C=N (R24), O, S ,-COO- or CONR24, wherein one or more H atoms can be by D, F, Cl, Br, I, CN, N2, active group R14Substituted aromatic amine, the aromatic amine that aryl replaces, the aromatic amine replacement of heteroaryl substitution, substitution or the replacement of unsubstituted carbazole.R24For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl；
The integer that x3 is 0~4；
Dotted line in structure above indicates the connection of L and other groups.
Ar in one of the embodiments,1And Ar2It is respectively and independently selected from the aryl that annular atom number is 6~40 or the heteroaryl that annular atom number is 6~30.Further, Ar1And Ar2It is respectively and independently selected from the aryl that annular atom number is 6~30 or the heteroaryl that annular atom number is 6~30.Further, L, Ar1And Ar2It is respectively and independently selected from the aryl that annular atom number is 6~25 or the heteroaryl that annular atom number is 6~25.
L, Ar in one of the embodiments,1And Ar2It is respectively and independently selected from the aryl that annular atom number is 5~40 or the heteroaryl that annular atom number is 5~40.Further, L, Ar1And Ar2It is respectively and independently selected from the aryl that annular atom number is 5~30 or the heteroaryl that annular atom number is 5~30.Further, L, Ar1And Ar2It is respectively and independently selected from the aryl that annular atom number is 5~20 or the heteroaryl that annular atom number is 5~20.Further, L, Ar1And Ar2It is respectively and independently selected from the aryl that annular atom number is 5~15 or the heteroaryl that annular atom number is 5~15.
Above-mentioned aryl includes 6~15 carbon atoms in one of the embodiments,.Further, above-mentioned aryl includes 6~10 carbon atoms.Further, above-mentioned heteroaryl includes 2~15 carbon atoms.Further, above-mentioned heteroaryl includes 2~10 carbon atoms and at least one hetero atom, and condition is that carbon atom and heteroatomic sum are at least 4.
L, Ar in one of the embodiments,1And Ar2It is respectively and independently selected from one kind of following group:
Wherein, X5For C-R30Or N,
Y5For C-R31-R32、Si-R33-R34、N-R35, C (=O), S (=O) 2, O or S,
-R30、-R31、-R32、-R33、-R34And-R35It is respectively and independently selected from as H, D, F ,-CN ,-NO2、-CF3, alkenyl, alkynyl, amido, acyl group, amide groups, cyano, isocyano group, alkoxy, hydroxyl, carbonyl, sulfuryl, the alkyl of carbon atom number 1~60, carbon atom number be 3~60 naphthenic base, carbon atom number be 6~60 aryl, carbon atom number be 3~60 heteroaryl, carbon atom number be 7~60 fused ring aryl, carbon atom number be 4~60 condensed hetero ring aryl and above-mentioned group in one of at least two combination groups being interconnected to form.
In a wherein embodiment ,-R30、-R31、-R32、-R33、-R34And-R35It itself can form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
In a wherein embodiment ,-R35Can respectively with-R30、-R31、-R32、-R33And-R34Form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
In a wherein embodiment ,-R20Can respectively with-R16、-R17、-R18、-R19And-R15Form monocyclic aliphatic ring
The aryl or polycyclic aryl of base, polycyclic aliphatic ring group, monocycle.
In a wherein embodiment ,-R31With-R32Between can mutually form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
In a wherein embodiment ,-R33With-R34Between can mutually form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
- R in one of the embodiments,30、-R31、-R32、-R33、-R34And-R35Be respectively and independently selected from for the substituted alkyl of carbon atom number 1~60, carbon atom number be 3~60 substituted naphthenic base, carbon atom number be 6~60 substituted aryl, carbon atom number be 3~60 substituted heteroaryl, carbon atom number be 7~60 substituted fused ring aryl, carbon atom number be 4~60 one of substituted condensed hetero ring aryl.
L, Ar in one of the embodiments,1And Ar2It is respectively and independently selected from one kind of following structural formula:
Wherein, the number below structure above (such as C36) only represents the serial number of corresponding construction formula, does not have other meanings, in structure above, a kind of one substance of formula, between adjacent structure formula is staggeredly only document typesetting problem, does not have other meanings；
-R3Selected from-H ,-F ,-Cl ,-Br ,-I ,-D ,-CN ,-NO2、-CF3、B(OR40)2、Si(R40)3, linear paraffin, alkane ether, carbon atom number be 1~10 alkane thioether, branched paraffin, naphthenic carbon atomicity be one of 6~10 aryl, R40For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl；
One in 0~2 integer of u, one in 0~3 integer of v, one in 0~4 integer of w, one in 0~5 integer of t；
Dotted line in structure above indicates the connection of the structural formula and other groups.
Z is not present in one of the embodiments, and the structural formula of A are as follows:
Wherein, one in 0~5 integer of X4, other symbols are identical as the above-mentioned meaning pointed out.
When Z is two bridging base in one of the embodiments ,-Z- is one of following structural formula:
Wherein, R4、R5、R6With R7It is respectively and independently selected from F, Cl, Br, I, D, CN, NO2、CF3、B(OR25)2、Si(R25)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be one of 3~10 group of cycloalkane, R25For H, D, carbon atom number be 1~10 aliphatic alkane base, aromatic hydrocarbon base, annular atom number be 5~10 aryl or annular atom number be 5~10 heteroaryl；Dotted line in above-mentioned group indicates that Z can be with Ar0Two phenyl ring connections in structural formula I.
In a wherein embodiment, the structural formula of A is selected from one kind such as flowering structure:
In structure above, an a kind of A of formula, between adjacent structure formula is staggeredly only document typesetting problem, does not have other meanings.
SG is selected from one of following structural formula in one of the embodiments:
Wherein, R8The straight chained alkyl for being 1~20 selected from carbon atom number, the alkoxy that carbon atom number is 1~20, the thio alkoxy that carbon atom number is 1~20, the branched alkyl that carbon atom number is 3~20, the cyclic alkyl that carbon atom number is 3~20, the alkoxy that carbon atom number is 3~20, the thio alkoxy that carbon atom number is 3~20, the silicyl that carbon atom number is 3~20, the ketone group that carbon atom number is 1~20, the alkoxy carbonyl that carbon atom number is 2~20, the aryloxycarbonyl that carbon atom number is 7~20, cyano group (- CN), carbamoyl (- C (=O) NH2), halogen formoxyl (- C (=O)-X, wherein X represents halogen atom), formoxyl (- C (=O)-H), isocyano group, isocyanate group, thiocyanate groups, isothiocyanate group, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, carbon atom number be 5~40 aryl, carbon atom number be 5~40 heteroaryl, carbon atom number be 5~40 aryloxy group, carbon atom number be 5~40 heteroaryloxy and above-mentioned group in one of at least two combination groups being interconnected to form；
N is the integer greater than 0；
-L1Indicate singly-bound or linking group；
Dotted line in structure above indicates the connection of SG and other groups.
R in one of the embodiments,8It itself can form the aryl or polycyclic aryl of monocyclic aliphatic ring group, polycyclic aliphatic ring group, monocycle.
R in one of the embodiments,8For carbon atom number be 1~20 straight chained alkyl, carbon atom number be 1~20 alkoxy, carbon atom number be 3~20 branched alkyl or carbon atom number be 3~20 alkoxies.
L in one of the embodiments,1For aryl or heteroaryl.L in one of the embodiments,1Selected from one of following structural formula:
Dotted line in structure above indicates the connection of the structural formula and other groups.
Individual H atom or CH in structural formula I in one of the embodiments,2Group can be by L1Replace
Individual H atom or CH in structural formula I in one of the embodiments,2Group can be by R41Replace, R41For the alkyl with 1~40 C atom.Wherein, R41One of group selected from the following: methyl, ethyl, n-propyl, isopropyl, cyclopropyl, normal-butyl, isobutyl group, sec-butyl, tert-butyl, cyclobutyl, methyl butyl, n-pentyl, sec-amyl, cyclopenta, n-hexyl, cyclohexyl, n-heptyl, suberyl, n-octyl, cyclooctyl, ethylhexyl, trifluoromethyl, pentafluoroethyl group, trifluoroethyl, vinyl, acrylic, cyclobutenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl group, heptenyl, cycloheptenyl, octenyl, cyclo-octene base, acetenyl, propinyl, butynyl, pentynyl, hexin base and octynyl.Further, the alkoxy with 1~40 C atom is methoxyl group, trifluoromethoxy, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or methyl butoxy.
The above-mentioned compound containing crosslinked group is small molecule in one of the embodiments, i.e., is not the molecule of polymer, oligomer, dendritic or copolymer.
The above-mentioned compound containing crosslinked group has the function of hole transport in one of the embodiments, so that the compound can be applied in organic electronic device.Further, the above-mentioned compound containing crosslinked group can be as the material of the hole transmission layer in OLED.
In one of the embodiments, the above-mentioned LUMO with higher of the compound containing crosslinked group (Lowest Un DEG C cupied Molecular Orbital, lowest unoccupied molecular orbital) energy level can be used in organic electronic device so that the compound has the function of electronic blocking.Further, the above-mentioned compound containing crosslinked group can be as the material of the electronic barrier layer in OLED.It should be noted that, higher lumo energy in the present embodiment refers to that the lumo energy of the functional layer containing the compound is higher than the lumo energy of adjacent functional layer, such as in OLED, when material of the compound as electronic barrier layer, the lumo energy of electronic barrier layer is higher than the lumo energy of luminescent layer.
The above-mentioned compound containing crosslinked group triplet (T with higher in one of the embodiments,1), so that the compound has triplet excitons barrier functionality, can be used in organic electronic device.Further, the above-mentioned compound containing crosslinked group can be as the material of the exciton barrier-layer in OLED.It should be noted that the higher T in the present embodiment1Refer to the T of the functional layer containing the compound1Higher than the T of adjacent functional layer1, such as in phosphorescent OLED, when material of the compound as exciton barrier-layer, the T of exciton barrier-layer1Higher than the T of luminescent layer1。
The above-mentioned compound containing crosslinked group singlet energy level S with higher in one of the embodiments,1, so that the compound has singlet exciton barrier functionality, can be used in organic electronic device.Further, the above-mentioned compound containing crosslinked group can be as the material of the exciton barrier-layer in OLED.It should be noted that the higher S in the present embodiment1Refer to the S of the functional layer containing the compound1Higher than the S of adjacent functional layer1, such as in fluorescence OLED, when material of the compound as exciton barrier-layer, the S of exciton barrier-layer1Higher than the S of luminescent layer1。
After structure formula (I) saves CLG in one of the embodiments, structural formula (I-1) is obtained:
The compound LUMO with higher of structural formula (I-1) in one of the embodiments,.Further, the compound of structural formula (I-1) is greater than or waits -2.7eV.Further, the compound of structural formula (I-1) is greater than or waits -2.6eV.Further, the compound of structural formula (I-1) is greater than or waits -2.5eV.Further, the compound of structural formula (I-1) is greater than or waits -2.4eV.
The HOMO of the compound of structural formula (I-1) is less than or equal to -5.0eV in one of the embodiments, wherein HOMO indicates HOMO highest occupied molecular orbital.Further, the HOMO of the compound of structural formula (I-1) is less than or equal to -5.1eV.Further, the HOMO of the compound of structural formula (I-1) is less than or equal to -5.2eV.
(the HOMO-1)-HOMO of the compound of structural formula (I-1) is greater than or equal to 0.3eV in one of the embodiments, wherein (HOMO-1) indicates that second high has accounted for track.Further, (the HOMO-1)-HOMO of the compound of structural formula (I-1) is greater than or equal to 0.35eV.Further, (the HOMO-1)-HOMO of the compound of structural formula (I-1) is greater than or equal to 0.4eV.Further, (the HOMO-1)-HOMO of the compound of structural formula (I-1) is greater than or equal to 0.45eV.
Triplet (the T of the compound of structural formula (I-1) in one of the embodiments,1) it is greater than or equal to 2.5eV.Further, the T of the compound of structural formula (I-1)1More than or equal to 2.6eV.Further, the T of the compound of structural formula (I-1)1More than or equal to 2.7eV.
In a wherein embodiment, HOMO energy level and lumo energy can be measured by photoelectric effect, such as XPS (x-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), also it can be measured by CV (cyclic voltammetry), it can also each be measured by quantum chemical methods, such as DFT (density functional theory).
In a wherein embodiment, triplet T1 can be measured by low temperature time- resolved emission spectrometry, it can also be calculated by quantum simulation, such as be simulated by Time-dependent DFT and calculate or calculated by business software Gaussian 03W (Gaussian Inc.) simulation.Wherein, specific analogsimulation method can be found in WO2011141110.
Certainly, it should be noted that the absolute value of HOMO, LUMO and T1 depend on measurement method used, calculation method or evaluation method.Therefore, rationally significant comparison should be carried out with identical measurement method and identical evaluation method.The energy level value that distinct methods determine should be demarcated mutually.In the present embodiment, the value of HOMO, LUMO and T1 are the simulations based on Time-dependent DFT, but do not influence the application of other measurement methods or calculation method.
In one of the embodiments, in the compound containing crosslinked group, SP3The total amount of the group of hydridization is less than or equal to the 30% of total molecular weight.Less SP3The presence of hetero radicals can effectively ensure that the thermal stability of the above-mentioned compound containing crosslinked group, and then guarantee the stability of the device including the compound.Further, in the compound containing crosslinked group, SP3The total amount of the group of hydridization is less than or equal to the 20% of total molecular weight.Further, in the compound containing crosslinked group, SP3The total amount of the group of hydridization is less than or equal to the 10% of total molecular weight.
The glass transition temperature of the compound containing crosslinked group is less than or equal to 100 DEG C in one of the embodiments,.Further, the glass transition temperature of the compound containing crosslinked group is less than or equal to 120 DEG C.Further, the glass transition temperature of the compound containing crosslinked group is less than or equal to 140 DEG C.Further, the glass transition temperature of the compound containing crosslinked group is less than or equal to 160 DEG C.Further, the glass transition temperature of the compound containing crosslinked group is less than or equal to 180 DEG C.
The molal weight of the compound containing crosslinked group is greater than or equal to 700g/mol in one of the embodiments, enables the compound as the raw material of printed form OLED.Further, molal weight is greater than or equal to 800g/mol.Further, the molal weight of the compound containing crosslinked group is greater than or equal to 900g/mol.Further, the molal weight of the compound containing crosslinked group is greater than or equal to 1000g/mol.Further, the molal weight of the compound containing crosslinked group is greater than or equal to 1100g/mol.
Solubility of the compound containing crosslinked group at 25 DEG C in toluene is greater than or equal to 10mg/mL in one of the embodiments,.Further, solubility of the compound containing crosslinked group at 25 DEG C in toluene is greater than or equal to 15mg/mL.Solubility of the compound containing crosslinked group at 25 DEG C in toluene is greater than or equal to 20mg/mL.
The structural formula of the compound containing crosslinked group is selected from one of following structural formula in one of the embodiments:
In structure above, an a kind of substance of formula, between adjacent structure formula is staggeredly only document typesetting problem, does not have other meanings.
The above-mentioned compound containing crosslinked group at least has the advantages that
(1) the above-mentioned compound containing crosslinked group is comprising organic functional architecture unit and crosslinkable groups, the dissolubility having had and film forming.The compound can make intermolecular crosslinkable groups crosslink reaction by heat treatment or ultraviolet irradiation, so that the compound cures be made to form film.Simultaneously, since above compound has preferable dissolubility and film forming, so that the composition containing the compound has preferable printing and filming performance, so that the electronic device containing the compound or the composition has a longer life expectancy and higher performance, finally make the manufacturing cost of electronic device low, high-efficient；
(2) the above-mentioned compound containing crosslinked group has the function of hole transport, so that the compound can be applied in organic electronic device；
(3) the above-mentioned lumo energy with higher of the compound containing crosslinked group can be used in organic electronic device so that the compound has the function of electronic blocking；
(4) the above-mentioned triplet with higher of the compound containing crosslinked group can be used in organic electronic device so that the compound has triplet excitons barrier functionality；
(5) the above-mentioned singlet energy level with higher of the compound containing crosslinked group can be used in organic electronic device so that the compound has singlet exciton barrier functionality；
(6) in the above-mentioned compound containing crosslinked group, SP3The total amount of the group of hydridization is less than or equal to the 30% of total molecular weight, less SP3The presence of hetero radicals can effectively ensure that the thermal stability of the above-mentioned compound containing crosslinked group, and then guarantee the stability of the device including the compound.
When the above-mentioned preparation containing crosslinked group, reacted using the raw material containing active group.
The raw material containing active group includes the structural unit A and structural unit SG and at least one leaving group in the above-mentioned structural formula of compound (I) containing crosslinked group in one of the embodiments,.
Leaving group is bromine, iodine, boric acid or borate in one of the embodiments,.
It should be noted that the reaction for forming C-C connection is reaction well known to those skilled in the art, details are not described herein again.Further, the reaction for forming C-C connection is coupling reaction.Further, the reaction for forming C-C connection is SUZUKI coupling reaction (suzuki reaction), STILLE coupling reaction (Shi Dile reaction) or HECK coupling reaction (Heck reaction).
The mixture of one embodiment, the compound and organic functional material containing crosslinked group including above embodiment.
Organic functional material is selected from least one of hole-injecting material (HIM), hole mobile material (HTM), hole barrier materials (HBM), electron injection material (EIM), electron transport material (ETM), electron-blocking materials (EBM), organic host materials (Host), singlet emitters (fluorescent illuminant), triplet emitters (phosphorescent emitter), thermal excitation delayed fluorescence material (TADF material) and organic dyestuff in one of the embodiments,.
Mixture includes above-mentioned compound and fluorescent illuminant containing crosslinked group in one of the embodiments,.It should be noted that the above-mentioned compound containing crosslinked group can be used as material of main part or and other materials collectively as material of main part.
Mixture includes the above-mentioned compound containing crosslinked group and TADF material in one of the embodiments,.
Some more detailed descriptions (but not limited to this) are made to singlet emitters, triplet emitters and TADF material below.
Singlet emitters (Singlet Emitter)
Singlet emitters often have longer conjugated pi electron system.So far, there are many examples, such as the styrylamine disclosed in JP2913116B and WO2001021729A1 and its derivative, the indenofluorene disclosed in WO2008/006449 and WO2007/140847 and its derivative.
Singlet emitters are unitary styrylamine, binary styrylamine, ternary styrylamine, quaternary styrylamine, styrene phosphine, styrene ether or arylamine in one of the embodiments,.
Unitary styrylamine is comprising unsubstituted or substitution styryl and at least one amine a compound.Further, the amine in unitary styrylamine is aromatic amine.Binary styrylamine is comprising two unsubstituted or substitution styryl and at least one amine compounds.Further, the amine in binary styrylamine is aromatic amine.Ternary styrylamine is comprising three unsubstituted or substitution styryl and at least one amine compounds.Further, the amine in ternary styrylamine is aromatic amine.Quaternary styrylamine is comprising four unsubstituted or substitution styryl and at least one amine compounds.Further, the amine in quaternary styrylamine is aromatic amine.Styrene phosphine is the compound comprising styryl He at least one phosphine.Styrene ether includes the compound of styryl and at least one ether.
Styryl is diphenylethyllene in one of the embodiments,.It should be noted that the diphenylethyllene replaced can also be used as the styryl of the present embodiment.
Aromatic amine is the compound that the aryl for directly coupling the unsubstituted of nitrogen or substitution comprising three or three directly couple the unsubstituted of nitrogen or the heteroaryl replaced.Further, a condensed ring is at least contained in the aryl or heteroaryl in aromatic amine, and the annular atom number in aryl or heteroaryl is at least 14.Further, aromatic amine is fragrant anthranylamine, fragrant anthradiamine, fragrant pyrene amine, fragrant pyrene diamines, fragrance amine in the wrong or fragrance diamines in the wrong.Fragrant anthranylamine is the compound that a binary aromatic amino is directly connect with anthracene.Specifically, fragrant anthranylamine is the compound that a binary aromatic amino is directly connect with No. 9 carbon atoms of anthracene.Fragrant anthradiamine is the compound that two binary arylamine groups are directly connect with anthracene.Specifically, fragrant anthranylamine is the compound that two binary aromatic aminos are connect with No. 9 of anthracene and No. 10 carbon atoms respectively.Fragrant pyrene amine is the compound that a binary aromatic amino is directly connect with pyrene.Specifically, fragrant pyrene amine is the compound that a binary aromatic amino is directly connect with No. 1 carbon atom of pyrene.Fragrant pyrene diamines is the compound that two binary aromatic aminos are directly connect with pyrene.Specifically, aromatic diamines are the compound that two binary aromatic aminos are connect with No. 1 of pyrene and No. 6 carbon atoms respectively.Fragrance amine in the wrong is compound of the binary aromatic amino directly with connection in the wrong.Specifically, fragrant pyrene amine is the compound that a binary aromatic amino is directly connect with No. 1 carbon atom in the wrong.Fragrance diamines in the wrong is compound of two binary aromatic aminos directly with connection in the wrong.Specifically, fragrance diamines in the wrong is the compound that two binary aromatic aminos are connect in the wrong No. 1 and No. 6 carbon atoms respectively.
Specifically, the singlet emitters based on vinylamine or the singlet emitters based on arylamine for example can be WO
2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549, WO 2007/115610,7,250,532 102,005,058,557 1,583,691 08,053,397 6,251,531 2006/210830 singlet emitters of A, the EP 1957606 in A1 and 2008/0113101 A1 of US of B1, US of A, US of A, JP of A1, CN of B2, DE of US.Singlet emitters in above-mentioned patent document can be used as the singlet emitters of present embodiment.
Singlet emitters based on stibene extremely derivative for example can be the singlet emitters in US 5121029A.
Singlet emitters are indenofluorene-amine or indenofluorene-diamines, the singlet emitters as disclosed in WO 2006/122630 in one of the embodiments,.Further, singlet emitters are benzo indenofluorene-amine or benzo indenofluorene-diamines, the singlet emitters as disclosed in WO 2008/006449.Further, singlet emitters are dibenzo indenofluorene-amine or dibenzo indenofluorene-diamines, the singlet emitters as disclosed in WO2007/140847.
It should be noted that polycyclic aromatic hydrocarbon compounds and its derivative can be used as the material of singlet emitters.Such as it can be anthracene [such as 9, 10- bis- (2- naphthanthracene)], naphthalene, four benzene, xanthene, it is luxuriant and rich with fragrance, pyrene (such as 2, 5, 8, tetra--t- butyl of 11-), indeno pyrene, penylene (such as 4, 4 '-bis- (9- ethyl -3- carbazole vinyl) -1, 1 '-biphenyl), two indeno pyrenes, decacyclene, coronene, fluorenes, two fluorenes of spiral shell, aryl pyrene (such as US20060222886A), arylene ethylene (such as US5121029A, US5130603A), cyclopentadiene (tetraphenyl cyclopentadiene), rubrene, cumarin, rhodamine, quinacridone, pyrans (such as 4 (dicyano methylene) -6- (4- is to dimethylaminostyryl -2- methyl) -4H- pyrans, DCM), thiapyran, bis- (azine) imines boronations are closed Object (2007/0092753 A1 of US), bis- (azine) methylene compounds, carbostyryl compound, oxazinone, benzoxazoles, benzothiazole, benzimidazole, pyrrolo-pyrrole-dione and above compound derivative.The material of some singlet emitters can be found in following patent documents: 20,070,252,517 4,769,292 6,020,078 2007/0252517 A1 and 2007/0252517 A1 of US of A, US of A, US of A1, US of US.The material of the singlet emitters in the above-mentioned patent document listed is incorporated in present embodiment as reference hereby.
Singlet emitters are selected from one of following structural formula in one of the embodiments:
Triplet emitters (phosphorescent emitter)
Triplet emitters are also referred to as phosphorescent emitter.
Triplet emitters are metal complex in one of the embodiments, and structural formula is M (L) n；Wherein, M is metallic atom, and L is organic ligand, and L is connected in a manner of chemical bond or coordinate bond one or more positions and G；N is the integer greater than 1.Further, 1,2,3,4,5 or 6 n.It should be noted that metal complex, which is connected to the compound that polymer obtains by one or more positions, can also be used as triplet emitters.Specifically, polymer is organic ligand.
M is transition metal element, lanthanide series or actinides in one of the embodiments,.Further, M Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag.Further, M Os, Ir, Ru, Rh, Re, Pd or Pt.
Triplet emitters include cheland in one of the embodiments,.Cheland is conducive to improve the stability of metal complex.Specifically, cheland is coordinated by least two binding sites and metallic atom.Further, triplet emitters include 2~3 identical or different bidentates or multidentate ligand.
Organic ligand is phenylpyridine derivative, 7,8- benzoquinoline derivative, 2 (2- thienyl) pyridine derivates, 2 (1- naphthalene) pyridine derivates or 2 phenylchinoline derivatives in one of the embodiments,.Above-mentioned organic ligand is substituted with a substituent.Substituent group is, for example, to contain methyl fluoride or trifluoromethyl.It further include assistant ligand when triplet emitters are metal complex in one of the embodiments,.Specifically, assistant ligand is acetic acid acetone or picric acid.
It can be used as the metal complex of triplet emitters in one of the embodiments, just like flowering structure formula:
Wherein, G is metallic atom；Ar1' it is to contain at least one the cyclic group of donor atom (atom for having a lone pair electrons), and Ar1' connect by donor atom with G；Ar1' include at least the cyclic group for having a C atom, and Ar2' connect by C atom with G；Ar1' and Ar2' by being covalently keyed；L' is assistant ligand；M' is 1,2 or 3；N' is 0,1 or 2.
Specifically, Ar1' and Ar2' it can carry one or more substituent groups.Wherein, substituent group is oxygen, phenyl or dibenzofurans, Ar1' and Ar2' can be connected by the substituent group of the two.Further, in a structural formula of triplet emitters, m' Ar1' it can be identical group, or different groups；M' Ar2' it can be identical group, or different groups；N' L' can be identical group, or different groups.
Further, Ar1' it is when containing at least one the cyclic group of donor atom, donor atom is nitrogen or phosphorus.
Further, m' is 2 or 3.Further, 3 m'.
Further, n' is 0 or 1.Further, 0 n'.
The material of some triplet emitters and its example of application can be found in following patent documents and document in one of the embodiments: WO 200070655, WO 200141512, WO 200202714, WO 200215645, EP 1191613, EP 1191612, EP 1191614, WO 2005033244, WO 2005019373, US 2005/0258742, WO 2009146770, WO 2010015307, WO 2010031485, WO 2010054731, WO 2010054728, WO 2010086089, WO 2010099852, WO 2010102709, US 20070087219 A1, US 20090061681 A1, US 20010053462 A1, Baldo, Thompson et al.Nature 403, (2000), 20,090,061,681 20090061681 A1 of A1, US of 750-753, US, Adachi et al.Appl.Phys.Lett.78 (2001), 1622-1624, J.Kido et al.Appl.Phys.Lett.65 (1994), 2124, Ki Do et al.Chem.Lett.657,1990,2007/0252517 A1 of US, Johnson et al., JACS 105,1983,1795, Wrighton, JACS 96,1974,998, Ma et al., Synth.Metals 94,1998,245, US 6824895, US 7029766, US 6835469, US 6830828,20010053462 A1 of US, WO 2007095118A1, US 2012004407A1, WO 2012007088A1, WO20 12007087A1, WO 2012007086A1, US 2008027220A1, WO 2011157339A1, CN 102282150A, WO 2009118087A1.The material of the triplet emitters in the above-mentioned patent document and document listed is incorporated in present embodiment hereby.
Triplet emitters can be selected from such as one of structural formula in following table in one of the embodiments:
Thermal excitation delayed fluorescence luminescent material (TADF material)
Traditional organic fluorescence materials can only be shone using 25% singlet exciton to be formed is electrically excited, and the internal quantum efficiency of device is lower (up to 25%).Although phosphor material passes through between being since the strong SO coupling in heavy atom center enhances, it can efficiently use and be electrically excited the singlet exciton to be formed and Triplet exciton, the internal quantum efficiency of device is made to reach 100%.But phosphor material is expensive, and stability of material is poor, and device efficiency the problems such as serious of roll-offing limits its application in OLED.Hot activation delayed fluorescence luminescent material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.Such material generally has small singlet-triplet poor (Δ Est), triplet excitons can by it is counter be between pass through be transformed into singlet exciton shine.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation.Device internal quantum efficiency can reach 100%.Material structure is controllable simultaneously, and property is stablized, cheap woth no need to noble metal, in having a extensive future for the field OLED.
TADF material needs to have lesser singlet-triplet poor (i.e. Δ Est).Specifically, the Δ Est of TADF material is less than 0.3eV.Further, the Δ Est of TADF material is less than 0.2eV.Further, the Δ Est of TADF material is less than 0.1eV.TADF has preferable fluorescence quantum efficiency.Some TADF materials can be found in following patent documents: CN103483332 (A), TW201309696 (A), TW201309778 (A), TW201343874 (A), TW201350558 (A), US20120217869 (A1), WO2013133359 (A1), WO2013154064 (A1), Adachi, et.al.Adv.Mater., 21,2009,4802, Adachi, et.al.Appl.Phys.Lett., 98,2011,083302, Adachi, et.al.Appl.Phys.Lett. , 101,2012,093306, Adachi, et.al.Chem.Commun., 48,2012,11392, Adachi, et.al.Nature Photonics, 6,2012,253, Adachi, et.al.Nature, 492,2012,234, Adachi, et.al.J.Am.Chem.S DEG C, 134,2012,14706, Adachi, et.al.Angew.Chem.Int.Ed, 51,2012,11311, Adachi, et.al.Chem.Commun., 48,2012,9580, Adachi, et.al.Chem.Commun., 48,2013,10385, Adachi, et.al.Adv.Mater., 25,2013,3319, Adachi, et.al.Adv.Mater., 25,2013,3707, Adachi, et.al.Chem.Mater., 25,2013,3038, Adachi, et.al.Chem.Mater., 25,2013,3766, Adachi, et.al.J.Mater.Chem.C., 1,2013,4599, Adachi, et.al.J.Phys.Chem. A., 117,2013,5607.Whole TADF materials in the above-mentioned patent listed or article file are incorporated in present embodiment hereby.
TADF material can be selected from one of structural formula of following table in one of the embodiments:
In structure above, a kind of TADF material of a formula, between adjacent structure formula is staggeredly only document typesetting problem, does not have other meanings.The organic functional material publication for organic functions structural unit appeared above is that disclosed purpose is incorporated herein in way of reference.
One of mixture of the composition of one embodiment, the compound containing crosslinked group including above embodiment and above embodiment, organic solvent.Wherein, organic solvent is selected from least one of arsol, Fang Za race solvent, ketones solvent, ether solvent and esters solvent.Further, organic solvent is selected from least one of arsol, the cyclosubstituted arsol of aliphatic, aromatics ketone solvent and the aromatic ether solvents that aliphatic chain replaces.
Specifically, arsol or Fang Za race solvent are to diisopropyl benzene, penta benzene, naphthane, cyclohexyl benzene, chloronaphthalene, 1, 4- dimethylnaphthalene, 3- isopropyl biphenyl, p-Methylisopropylbenzene, diamyl benzene, 3 penta benzene, amyl toluene, ortho-xylene, meta-xylene, paraxylene, adjacent diethylbenzene, NSC 62102, p-Diethylbenzene, 1, 2, 3, 4- durene, 1, 2, 3, 5- durene, 1, 2, 4, 5- durene, butylbenzene, detergent alkylate, dihexyl benzene, dibutyl benzene, to diisopropyl benzene, 1- methoxynaphthalene, cyclohexyl benzene, dimethylnaphthalene, 3- isopropyl biphenyl, p-Methylisopropylbenzene, 1- methyl naphthalene, 1, 2, 4- trichloro-benzenes, 1, 3- dipropoxy benzene, 4, 4- difluoro-diphenylmethane, 1, 2- dimethoxy-4 '-(1- acrylic) benzene, two Phenylmethane, 2- phenylpyridine, 3- phenylpyridine, N- methyldiphenylamine, 4- isopropyl biphenyl, α, α-dichloro diphenyl methane, 4- (3- phenyl propyl) pyridine, Ergol, 1, bis- (3,4- 3,5-dimethylphenyl) ethane of 1-, 2- isopropyl naphthalene or benzyl ether.
Ketone solvent is the derivative of 1-tetralone, 2- tetralone, 2- (phenyl epoxy) tetralone, 6- (methoxyl group) tetralone, acetophenone, propiophenone, benzophenone and these compounds, derivative for example can be 4- methyl acetophenone, 3- methyl acetophenone, 2- methyl acetophenone, 4- methyl phenyl ketone, 3- methyl phenyl ketone, 2- methyl phenyl ketone, isophorone, 2,6,8- trimethyl -4- nonanone, fenchone, methyl n-heptyl ketone, 3- nonanone, butyl ketone, 2- decanone, 2,5- acetyl butyryl, phorone or two n-pentyl ketone.
Ether solvents are 3- phenoxytoluene, butyl phenyl ether, benzyl butyl benzene, p-anisaldehyde dimethyl-acetal, tetrahydro -2- phenoxy group -2H- pyrans, 1, 2- dimethoxy-4 '-(1- acrylic) benzene, 1, 4- benzdioxan, 1, 3- dipropyl benzene, 2, 5- dimethoxy-p, this ether of 4- ethyl, 1, 2, 4- trimethoxy-benzene, 4- (1- acrylic) -1, 2- dimethoxy benzene, 1, 3- dimethoxy benzene, glycidyl phenyl ether, dibenzyl ether, 4- tert-butyl anisole, trans--anethole, 1, 2- dimethoxy benzene, 1- methoxynaphthalene, diphenyl ether, 2- phenoxy group methyl ether, 2- phenoxy group tetrahydrofuran, ethyl -2- naphthyl ether, amyl ether c hexyl ether, dioctyl ether, butyl cellosolve, diethylene glycol diethyl ether, Diethylene glycol butyl methyl ether, dibutyl ethylene glycol ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether or tetraethyleneglycol dimethyl ether.
Ester solvent is sad alkyl ester, decanedioic acid alkyl ester, stearic acid alkyl ester, benzoic acid alkyl esters, phenylacetic acid alkyl ester, cinnamic acid alkyl ester, oxalic acid alkyl ester, maleic acid alkyl ester, alkane lactone or oleic acid alkyl ester.
Ketone solvent is methyl n-heptyl ketone, 3- nonanone, butyl ketone, 2- decanone, 2,5- acetyl butyryl, 2,6,8- trimethyl -4- nonanone, phorone or two n-pentyl ketone.Ether solvents are amyl ether, hexyl ether, dioctyl ether, butyl cellosolve, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, dibutyl ethylene glycol ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether or tetraethyleneglycol dimethyl ether.
Above-mentioned composition also includes another organic solvent in one of the embodiments,.Another organic solvent is selected from methanol, ethyl alcohol, 2-methyl cellosolve, methylene chloride, chloroform, chlorobenzene, o-dichlorohenzene, tetrahydrofuran, methyl phenyl ethers anisole, morpholine, toluene, ortho-xylene, meta-xylene, paraxylene, 1,4 dioxanes, acetone, methyl ethyl ketone, 1,2 dichloroethanes, 3- phenoxytoluene, 1,1,1- trichloroethanes, 1,1, at least one of 2,2- tetrachloroethanes, ethyl acetate, butyl acetate, dimethylformamide, dimethyl acetamide, dimethyl sulfoxide, naphthane, naphthalane and indenes.
Above-mentioned composition is solution in one of the embodiments,.
Above-mentioned composition is suspension in one of the embodiments,.
It should be noted that above-mentioned composition can also include one of other components when above-mentioned composition is solution or suspension.Other components are used to adjust viscosity, filming performance or raising adhesion of solution or suspension etc..Other components for example can be surface active cpd, lubricant, wetting agent, dispersing agent, hydrophobing agent or bonding agent." the printing of Helmut Kipphan chief editor is referred in relation to printing technique and its to the details of the related request (such as solvent, concentration and viscosity) in relation to solution
Media handbook: technology and production method " (Handbook of Print Media:Technologies and Production Methods), ISBN 3-540-67326-1.
Above-mentioned composition can be used as ink, for printing.When for printing technology, viscosity, the surface tension of ink are important parameter.Suitable surface tension enables ink to be suitable for specific substrate and specific printing process.
Ink is 19dyne/cm~50dyne/cm in operating temperature or the surface tension at 25 DEG C in one of the embodiments,.Further, ink is 22dyne/cm~35dyne/cm in operating temperature or the surface tension at 25 DEG C.Further, ink is 25dyne/cm~33dyne/cm in operating temperature or the surface tension at 25 DEG C.
Viscosity of the ink at operating temperature or 25 DEG C is 1cps~100cps in one of the embodiments, and lower viscosity enables ink to be suitable for ink jet printing.Further, viscosity of the ink at operating temperature or 25 DEG C is 1cps~50cps.Further, viscosity of the ink at operating temperature or 25 DEG C is 1.5cps~20cps range.Further, viscosity of the ink at operating temperature or 25 DEG C is 4.0cps~20cps.
It should be noted that viscosity can be adjusted by different methods, such as choose the concentration of functional material in suitable solvent or ink, wherein functional material is selected from least one of the compound containing crosslinked group and organic functional material.Above-mentioned ink can adjust the concentration of the functional material in ink according to printing process used in one of the embodiments,.Specifically, the content of the functional material in ink is 0.3wt%~30wt% range.Further, the content of the functional material in ink is 0.5wt%~20wt%.The content of functional material in ink is 0.5wt%~15wt%.The content of functional material in ink is 0.5wt%~10wt%.The content of functional material in ink is 1wt%~5wt%.
Above-mentioned ink is used to prepare organic electronic device.
Above-mentioned ink is used to prepare the method for organic electronic device as printing or coating in one of the embodiments,.
Further, printing or coating technique are coated with including (but not limited to) inkjet printing, spray printing (Nozzle Printing), typographic printing, silk-screen printing, dip-coating, rotary coating, blade coating, roller printing, torsion roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brushing, bat printing, jet printing (Nozzle printing) and slit-type squash type.Further, printing or coating technique include ink jet printing, the coating of slit-type squash type, jet printing and intaglio printing.
The organic Functional Materials, Thin Films of one embodiment, including the above-mentioned compound containing crosslinked group.
Organic Functional Materials, Thin Films are prepared by the method that solution is processed in one of the embodiments,.Organic Functional Materials, Thin Films can be used in organic electronic device.
The preparation method of the organic Functional Materials, Thin Films of one embodiment includes the following steps (1)~step (4):
Step (1), preparation contain the film liquid of the above-mentioned compound containing crosslinked group.
Specifically, the organic component comprising the above-mentioned compound containing crosslinked group is dissolved in solvent, obtained solution.
Film liquid is prepared film forming layer by step (2).
Specifically, above-mentioned film liquid is coated on substrate with the method for printing or coating and forms film layer.Wherein, printing or coating method it is optional in, but it is not limited to, inkjet printing, spray printing (Nozzle Printing), typographic printing, silk-screen printing, dip-coating, rotary coating, blade coating, roller printing, torsion roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brushing, bat printing and the coating of slit-type squash type etc..
Step (3) makes the compound in film layer containing crosslinked group crosslink reaction, obtains cured film.
Specifically, the substrate containing film layer is placed at least 100 DEG C and is heated, so that the compound in film layer containing crosslinked group is crosslinked reaction, obtain cured film.It should be noted that ultraviolet lighting can also be carried out to film layer, so that the compound in film layer containing crosslinked group is crosslinked reaction, obtain cured film.
Step (4) cleans cured film with organic solvent, to remove uncrosslinked cured compound, obtains organic functional thin film.It should be noted that obtained cured film can satisfy actual demand, step (4) be can be omitted.
The thickness of organic functional thin film is at least the 50% of thicknesses of layers in one of the embodiments,.Further, the thickness of organic functional thin film is at least the 60% of thicknesses of layers.Further, the thickness of organic functional thin film is at least the 70% of thicknesses of layers.Further, the thickness of organic functional thin film is at least the 85% of thicknesses of layers.
Based on above compound, the present invention also provides a kind of application of the compound containing crosslinked group in organic electronic device as described above.The organic electronic device it is optional in, but it is not limited to, Organic Light Emitting Diode (OLED), organic photovoltaic battery (OPV), organic light emission battery (OLEEC), organic field-effect tube (OFET), organic light-emitting field effect pipe, organic laser, organic spin electric device, organic sensor or organic phasmon emitting diode (Organic Plasmon Emitting Diode) etc..Further, organic electronic device OLED.In one of the embodiments, by the change containing crosslinked group
Object is closed in the hole transmission layer, hole injection layer or luminescent layer of OLED.Further, the compound containing crosslinked group is used for the hole transmission layer of OLED.
Further, the present invention relates to a kind of organic electronic device, organic electronic device includes at least one compound containing crosslinked group.Organic electronic device includes functional layer in one of the embodiments, and functional layer is prepared by above-mentioned composition.Further, organic electronic device includes at least cathode, anode and the functional layer between cathode and anode, includes at least one as described above containing the compound of crosslinked group in functional layer.
In one of the embodiments, organic electronic device is Organic Light Emitting Diode (OLED), organic photovoltaic battery (OPV), organic light emission battery (OLEEC), organic field-effect tube (OFET), organic light-emitting field effect pipe, organic laser, organic spin electric device, organic sensor or organic phasmon emitting diode (Organic Plasmon Emitting Diode).
Organic electronic device is electroluminescent device in one of the embodiments,.Further, as shown in Figure 1, organic electronic device is OLED100 (as shown in figure), OLED100 includes substrate 101, anode 102, luminescent layer 104 and cathode 106.It should be noted that OLED100 further includes hole transmission layer 103, electron transfer layer 105.
Substrate 101 is transparent substrate or opaque substrate.Transparent substrate can be used to manufacture transparent light emitting component, see, for example, the Nature such as Bulovic 1996,380, p29, Gu etc., Appl.Phys.Lett.1996,68, p2606.Substrate can be rigid or elasticity.Substrate can be plastics, metal, semiconductor wafer or glass.Further, substrate has a smooth surface, and substrate free of surface defects is especially desirable selection.Substrate flexible can be thin polymer film or plastics in one of the embodiments,.Further, the glass transition temperature Tg of substrate 101 is greater than 150 DEG C.Further, the glass transition temperature Tg of substrate 101 is greater than 200 DEG C.Further, the glass transition temperature Tg of substrate 101 is greater than 250 DEG C.Further, the glass transition temperature Tg of substrate 101 is greater than 300 DEG C.The example of suitable flexible base board has poly- (ethylene glycol terephthalate) (PET) and polyethylene glycol (2,6- naphthalene) (PEN).
Anode (102) is conductive metal, metal oxide or conducting polymer.Anode 102 can be easily injected into hole into hole injection layer (HIL), hole transmission layer (HTL) or luminescent layer.In the shown embodiment, anode 102 is laminated in the side of substrate 101.In wherein one embodiment, the absolute value of the difference of the HOMO energy level or valence-band level of the work function of anode 102 and the illuminator in luminescent layer 104 or the p-type semiconductor material as HIL or HTL or electronic barrier layer (EBL) is less than 0.5eV.Further, the absolute value of the difference of the HOMO energy level or valence-band level of the illuminator 104 in the work function and luminescent layer of anode 102 or the p-type semiconductor material as HIL or HTL or electronic barrier layer (EBL) is less than 0.3eV.Further, the absolute value of the difference of the HOMO energy level or valence-band level of the work function of anode 102 and the illuminator in luminescent layer 104 or the p-type semiconductor material as HIL or HTL or electronic barrier layer (EBL) is less than 0.2eV.Can include but is not limited to as the example of the material of anode 102: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminium-doped zinc oxide (AZO) etc..Other be properly used as the material of anode 102 be it is known, those of ordinary skill in the art are readily able to select use.Any suitable technology deposition can be used in anode 102, such as physical vaporous deposition, physical vaporous deposition include rf magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) etc..In certain embodiments, anode 102 is patterning.Patterned ITO electrically-conductive backing plate is commercially available, and can be used to prepare device according to the present invention.
Cathode 106 is conductive metal or metal oxide.Cathode 106 can be easily injected into electronics into EIL, ETL or luminescent layer 104.In the shown embodiment, cathode 106 is laminated in side of the anode 102 far from substrate 101.In wherein one embodiment, the absolute value of the difference of the lumo energy or conduction level of illuminator 104 or the n-type semiconductor as electron injecting layer (EIL) or electron transfer layer (ETL) or hole blocking layer (HBL) is less than 0.5eV in the work function and luminescent layer of cathode 106.Further, the absolute value of the difference of the lumo energy or conduction level of illuminator or the n-type semiconductor as electron injecting layer (EIL) or electron transfer layer (ETL) or hole blocking layer (HBL) is less than 0.3eV in the work function of cathode 106 and luminescent layer 104.The absolute value of the difference of the lumo energy or conduction level of illuminator or the n-type semiconductor as electron injecting layer (EIL) or electron transfer layer (ETL) or hole blocking layer (HBL) is less than 0.2eV in the work function and luminescent layer 104 of cathode 106.In principle, the material of all cathodes that can be used as OLED all may be as the cathode material of device of the present invention.Can include but is not limited to as the example of the material of cathode 106: Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF2/Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO etc..Any suitable technology deposition can be used as the material of cathode 106, such as physical vaporous deposition, physical vaporous deposition include rf magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam) etc..
In the shown embodiment, luminescent layer 104 is laminated in side of the anode 102 far from substrate 101, and is located at cathode 106 close to the side of anode 102.In wherein one embodiment, luminescent layer 104 is by the above-mentioned composition system containing crosslinked group
It is standby to form.Specifically, luminescent layer 104 is prepared by printing above-mentioned composition.
It should be noted that, OLED100 can also include other function layer, such as hole injection layer (HIL), hole transmission layer 103 (HTL), electronic barrier layer (EBL), electron injecting layer (EIL), electron transfer layer 105 (ETL) or hole blocking layer (HBL).It is described later in detail in WO2010135519A1, US20090134784A1 and WO2011110277A1 suitable for the material in these functional layers, the full content in this 3 patent documents is incorporated to present embodiment as reference hereby.In the shown embodiment, hole transmission layer 103 is laminated in side of the anode 102 far from substrate 101, and is located at luminescent layer 104 close to the side of anode 102.Electron transfer layer 105 is laminated in side of the luminescent layer 104 far from hole transmission layer 103, and is located at cathode 106 close to the side of luminescent layer 104.
In wherein one embodiment, hole transmission layer 103 is prepared by the above-mentioned composition containing crosslinked group.
In wherein one embodiment, the emission wavelength of above-mentioned electronic light emitting devices is 300nm~1000nm.Further, the emission wavelength of above-mentioned electronic light emitting devices is 350nm~900nm.Further, the emission wavelength of above-mentioned electronic light emitting devices is 400nm~800nm.
The application of above-mentioned organic electronic device in electronic equipment of various.Electronic equipment is display equipment, lighting apparatus, light source or sensor in one of the embodiments,.It should be noted that electronic equipment is not limited to above equipment, it can also include other electronic equipments.
The following are specific embodiment parts:
Embodiment 1: the synthesis of compound 1 (i.e. HTM1):
Successively the intermediate b of the intermediate a and 9.19g (0.018mol) of 13.6g (0.018mol) are dissolved in the toluene of 300mL at room temperature, sequentially add tetra-triphenylphosphine palladium 1.2g, potassium carbonate 10g (0.74mol), water 60mL, ethyl alcohol 60mL, it is heated to 110 DEG C to react 15 hours, TLC plate shows fully reacting.It is extracted three times after reaction solution is added to the water with methylene chloride, organic phase drying is then concentrated to get crude product, the solid after column chromatography is compound 1, and obtained compound 1 is 13.0g, yield 68%.
Embodiment 2: the synthesis of compound 2 (i.e. HTM2)
Successively the intermediate b of the intermediate a and 13.3g (0.018mol) of 13.6g (0.018mol) are dissolved in the toluene of 300mL at room temperature, sequentially add tetra-triphenylphosphine palladium 1.2g, potassium carbonate 9.7g (0.074mol), water 60mL, ethyl alcohol 60mL, it is heated to 110 DEG C to react 15 hours, TLC plate shows fully reacting.It is extracted three times after reaction solution is added to the water with methylene chloride, organic phase drying is then concentrated to get crude product, the solid after column chromatography is compound 2, and obtained compound 1 is 15.1g, yield 65%.
Embodiment 3: the synthesis of compound 3 (i.e. HTM3)
5.0mmol intermediate a is dissolved in dry tetrahydrofuran (THF) solution of 200mL, under nitrogen environment protection, reaction solution stirs at a temperature of being placed in -78 DEG C, the methylene triphenyl phosphorus (Wittig reagent) of 8.0mmol is added dropwise, after to be added, it is gradually increased to room temperature, continue to be stirred at room temperature overnight, add water quenching reaction, all reaction solutions are extracted with dichloromethane, organic phase is washed with water, finally merge organic phase, it is dry with anhydrous sodium sulfate, filtering, it is evaporated organic solvent, products therefrom silica gel column purification, mobile phase is methylene chloride: petroleum ether=1:2, finally obtain the compound 3 of 3.5mmol.Dried for standby under vacuum environment.Wherein, the MS (APCI) of compound 3 is 754.0.
Embodiment 4: the synthesis of compound 4 (i.e. HTM4)
5.0mmol intermediate a is dissolved in dry tetrahydrofuran (THF) solution of 200mL, under nitrogen environment protection, reaction solution stirs at a temperature of being placed in -78 DEG C, the methylene triphenyl phosphorus (Wittig reagent) of 8.0mmol is added dropwise, after to be added, it is gradually increased to room temperature, continue to be stirred at room temperature overnight, add water quenching reaction, all reaction solutions are extracted with dichloromethane, organic phase is washed with water, finally merge organic phase, it is dry with anhydrous sodium sulfate, filtering, it is evaporated organic solvent, products therefrom silica gel column purification, mobile phase is methylene chloride: petroleum ether=1:2, finally obtain the compound 4 of 3.9mmol.Dried for standby under vacuum environment.Wherein, the MS (APCI) of compound 4 is 754.0.
Embodiment 5: the synthesis of compound 5 (i.e. HTM5)
5.0mmol intermediate a is dissolved in dry tetrahydrofuran (THF) solution of 200mL, under nitrogen environment protection, reaction solution stirs at a temperature of being placed in -78 DEG C, the methylene triphenyl phosphorus (Wittig reagent) of 8.0mmol is added dropwise, after to be added, it is gradually increased to room temperature, continue to be stirred at room temperature overnight, add water quenching reaction, all reaction solutions are extracted with dichloromethane, organic phase is washed with water, finally merge organic phase, it is dry with anhydrous sodium sulfate, filtering, it is evaporated organic solvent, products therefrom silica gel column purification, mobile phase is methylene chloride: petroleum ether=1:2, finally obtain 3.0mmol compound 5.Dried for standby under vacuum environment.Wherein, the MS (APCI) of compound 5 is 1023.3.
Test:
1, energy-structure is measured
For the energy level of compound using TD-DFT (time-depentent DFT) by Gaussian09W (Gaussian Inc.), specific analogy method can be found in WO2011141110.Specifically, with density function method " Ground State/DFT/Default
The energy-structure of the geometry of Spin/B3LYP " and base group " 6-31G (d) " (Charge 0/Spin Singlet) Lai Youhua compound, compound calculates " TD-SCF/DFT/Default Spin/B3PW91 " and base group " 6-31G (d) " (Charge 0/Spin Singlet) by TD-DFT (time-depentent DFT) method.HOMO and lumo energy are calculated according to following calibration equation (1) and (2), and S1 and T1 are directly used.
HOMO (eV)=[(HOMO (G) × 27.212) -0.9899]/1.1206 calibration equations (1),
Wherein, HOMO (G) passes through the direct calculated result of Gaussian 03W, unit Hartree；
LUMO (eV)=((LUMO (G) × 27.212) -2.0041)/1.385 calibration equations (2),
Wherein, LUMO (G) passes through the direct calculated result of Gaussian 03W, unit Hartree.
NPB is standard material, the structural formula of NPB are as follows:
Respectively measure Examples 1 to 5 compound and HOMO energy level, lumo energy, T1Energy level and S1Energy level
1 level structure of table
| HOMO[eV] | LUMO[eV] | T1[eV] | S1[eV] | |
| Embodiment 1 | -5.16 | -2.17 | 2.60 | 3.10 |
| Embodiment 2 | -5.17 | -2.17 | 2.61 | 3.15 |
| Embodiment 3 | -5.14 | -2.25 | 2.47 | 3.20 |
| Embodiment 4 | -5.26 | -2.19 | 2.59 | 3.22 |
| Embodiment 5 | -5.21 | -2.28 | 2.58 | 3.20 |
| NPB | -5.18 | -2.34 | 2.44 | 3.07 |
As can be seen from Table 2, the energy level difference of the HOMO and LUMO of the compound of Examples 1 to 5 are smaller, illustrate that the stability of the compound of Examples 1 to 5 is preferable, meanwhile, the Δ E of the compound of Examples 1 to 5ST[i.e. Δ (S1-T1), the energy level difference between singlet energy level and triplet] it is smaller, illustrate include the material of the compound of Examples 1 to 5 luminous efficiency it is higher.
2, material influence to the service life of OLED of the compound and Poly-TFB (i.e. Poly-Trifluroboran) of Examples 1 to 5 as hole transmission layer.
The material of luminescent layer is as follows:
Wherein, H1 is total material of main part, and synthesis is referring to application No. is the Chinese patents of CN201510889328.8；H2 is total material of main part, and synthesis is referring to patent WO201034125A1；E1 is phosphorescence auxiliary material, and synthesis is referring to patent CN102668152；
OLED device preparation step is as follows:
1) cleaning of ito transparent electrode (anode) glass substrate: ito transparent electrode glass substrate is ultrasonically treated 30 minutes using the aqueous solution containing 5%Decon90 cleaning solution, then deionized water is cleaned by ultrasonic 3 times, then isopropanol is cleaned by ultrasonic 15 minutes, is dried with nitrogen；It is handled 5 minutes under oxygen plasma, to clean ito transparent electrode glass substrate surface and promote the work function of ito transparent electrode；
2) preparation of HIL and HTL: by spin coating PEDOT:PSS (Clevios in the processed glass substrate of oxygen gas plasmaTMPEDOT:PSS Al4083), obtain the film of 80nm, after the completion of spin coating in air 150 DEG C anneal 20 minutes, then spin coating obtains the material of htl layer on PEDOT:PSS layer, the htl layer of 20nm is obtained, then at 180 DEG C
Hot plate on handle 60 minutes；
3) prepared by luminescent layer: being first dissolved in H1, H2, E1 in toluene according to the weight ratio of 40:40:20, the concentration of solution is 20mg/mL, and by this solution, spin coating obtains 60nm film in nitrogen glove box, is then annealed 10 minutes at 120 DEG C.
4) prepared by cathode: the device that spin coating is completed being put into vacuum evaporation cavity, the barium of 2nm and the aluminium of 100nm is successively deposited, obtains OLED.
5) device is placed in nitrogen glove box, is encapsulated using ultraviolet-curing resin plus glass cover-plate.
Wherein, when prepared by htl layer, the material of htl layer is respectively that (CAS:223569-31-1 is purchased from Lumtec.Corp to Poly-TFB；5mg/mL toluene solution), the compound of Examples 1 to 5.Wherein, when using the compound of Examples 1 to 5 as the material of htl layer, before the thickness for measuring htl layer, htl layer is rinsed twice with toluene.
The I-E characteristic and external quantum efficiency of device are measured by Keithley236 Current Voltage-measuring system and a corrected silicon photo diode.Wherein, the external quantum efficiency of the OLED of the compound containing Examples 1 to 5 is the relative value of the external quantum efficiency of the OLED containing Poly-TFB.As a result see Table 2 for details.
The thickness and external quantum efficiency of the HTL of 2 OLED of table
| Compound | HTL thickness (nm) | External quantum efficiency (cd/A)@1000nits |
| Poly-TFB | 20 | 1 |
| HTM1 | 13 | 1.81 |
| HTM2 | 12 | 1.55 |
| HTM3 | 15 | 1.74 |
| HTM4 | 17 | 2.12 |
| HTM5 | 16 | 1.43 |
As can be seen from Table 2, the external quantum efficiency of the OLED of the compound containing Examples 1 to 5 is at least 1.43 times of the external quantum efficiency of the OLED containing Poly-TFB.Illustrate that the compound of Examples 1 to 5 more favorably improves the performance of OLED, it may be possible to due to containing cross-linking small molecule in the compound of Examples 1 to 5, so that these compounds triplet with higher, to have preferable barrier effect to triplet state.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, and but it cannot be understood as the limitations to patent of invention range.It should be pointed out that for those of ordinary skill in the art, without departing from the inventive concept of the premise, various modifications and improvements can be made, and these are all within the scope of protection of the present invention.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (16)
- A kind of compound containing crosslinked group, which is characterized in that have the following structure formula (I):Wherein, SG has structure formula (II):The heteroaryl that Ar is the aryl that annular atom number is 5~20 or annular atom number is 5~20；CLG is crosslinked group；O is 0 or 1；P is the integer more than or equal to 2；The formula II I of A are as follows:Wherein, R1For F, Cl, Br, I, D, CN, NO2、CF3、B(OR2)2、Si(R2)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be 3~10 cycloalkyl group, R2For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aromatics or annular atom number be 5~10 heteroaromatic group,- L- is singly-bound or carbon atom number is 5~40 aromatic groups,Ar1For annular atom number be 5~40 aromatic group or annular atom number be 5~40 heteroaromatic group,The integer that y is 0~5,Ar0Selected from one of following structural formula:Wherein, Ar2For annular atom number be 5~40 aromatic group or annular atom number be 5~40 heteroaromatic base,The integer that X is 0~4, the integer that X1 is 0~3,- Z- is not present or for one of singly-bound and two bridging bases,M is selected from 0~10 integer,R9For F, Cl, Br, I, D, CN, NO2、CF3、B(OR14)2、Si(R14)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 branched paraffin, total carbon atom number be 3~10 cycloalkane, R14For H, D, carbon atom number be 1~10 aliphatic alkane base, annular atom number be 5~10 aromatics or annular atom number be 5~10 heteroaromatic group；Dotted line in the formula II I indicates the L and Ar0It connects, the dotted line and circle in the structural formula (IIIa) indicate that the L can be with any carbon atom or Ar of two phenyl ring in circle2Structural formula in include aromatic rings or hetero-aromatic ring the connection of any carbon atom, the dotted line in the structural formula (IIIb) and the structural formula (IIIc) indicates that the L can be connected on any carbon atom for the phenyl ring that dotted line passes through.
- Compound according to claim 1 containing crosslinked group, which is characterized in that the Ar is selected from such as flowering structure One of formula:AndWherein, X2For C-R15Or N,Y2For C-R16-R17、Si-R18-R19、N-R20, C (=O), S (=O) 2, O or S,-R15、-R16、-R17、-R18、-R19And-R20It is respectively and independently selected from as H, D, F ,-CN ,-NO2、-CF3, alkenyl, alkynyl, amido, acyl group, amide groups, cyano, isocyano group, alkoxy, hydroxyl, carbonyl, sulfuryl, the alkyl of carbon atom number 1~60, carbon atom number be 3~60 naphthenic base, carbon atom number be 6~60 aryl, carbon atom number be 3~60 heteroaryl, carbon atom number be 7~60 fused ring aryl, carbon atom number be 4~60 condensed hetero ring aryl and above-mentioned group in one of at least two combination groups being interconnected to form.
- Compound according to claim 1 containing crosslinked group, it is characterized in that, the CLG is cyclic monoene base, linear mono alkenyl, linear dialkylene, alkynyl, alkenyloxy group, two alkenyloxy groups, acrylic, propylene oxide base, Oxyranyle, silylation or cyclobutane base.
- Compound according to claim 1 containing crosslinked group, which is characterized in that the CLG is selected from one of following group:AndWherein, R10、R11、R12And R13It is respectively and independently selected from F, Cl, Br, I, D, CN, NO2、CF3、B(OR21)2、Si(R21)3, carbon atom number be 1~10 linear paraffin, total carbon atom number be 1~10 alkane ether, total carbon atom number be 1~10 alkane thioether, total carbon atom number be 3~10 one of branched paraffin, the cycloalkane that total carbon atom number is 3~10, the group for the alkane ether for being 3~10 containing total carbon atom number and the group of alkane thioether for being 3~10 containing total carbon atom number, R21For H, D, the heteroaryl that the aryl or annular atom number that carbon atom number is 1~10 aliphatic alkane base, annular atom number are 5~10 are 5~10；Ar12For annular atom number be 5~40 aromatic group or annular atom number be 5~40 heteroaryl；S is the integer more than or equal to 0, and t is the integer more than or equal to 0；Dotted line in structure above indicates the connection of the CLG and other groups.
- Compound according to claim 1 containing crosslinked group, which is characterized in that the L, the Ar1And the Ar2It is respectively and independently selected from one kind of following group:AndWherein, X5For C-R30Or N,Y5For C-R31-R32、Si-R33-R34、N-R35, C (=O), S (=O) 2, O or S,- the R30,-the R31,-the R32,-the R33,-the R34And-the R35It is respectively and independently selected from as H, D, F ,-CN ,-NO2、-CF3, alkenyl, alkynyl, amido, acyl group, amide groups, cyano, isocyano group, alkoxy, hydroxyl, carbonyl, sulfuryl, the alkyl of carbon atom number 1~60, carbon atom number be 3~60 naphthenic base, carbon atom number be 6~60 aryl, carbon atom number be 3~60 heteroaryl, carbon atom number be 7~60 fused ring aryl, carbon atom number be 4~60 condensed hetero ring aryl and above-mentioned group in one of at least two combination groups being interconnected to form.
- Compound according to claim 1 containing crosslinked group, which is characterized in that the L, the Ar1And the Ar2It is respectively and independently selected from one kind of following structural formula:Wherein ,-R3Selected from-H ,-F ,-Cl ,-Br ,-I ,-D ,-CN ,-NO2、-CF3、B(OR40)2、Si(R40)3, linear paraffin, alkane ether, carbon atom number be 1~10 alkane thioether, branched paraffin, cycloalkane, carbon atom be 3~10 alkane ether, carbon atom number be one of 6~10 aryl, R40The aliphatic alkane for being 1~10 for H, D, carbon atom number The heteroaryl that the aryl or annular atom number that alkyl, annular atom number are 5~10 are 5~10；One in 0~2 integer of u, one in 0~3 integer of v, one in 0~4 integer of w, one in 0~5 integer of t, the dotted line in the structural formula indicate the connection of the structural formula and other groups.
- Compound according to claim 1 containing crosslinked group, which is characterized in that the structural formula of the A is selected from one kind of following structural formula:
- Compound according to claim 1 containing crosslinked group, which is characterized in that the SG is selected from one of following structural formula:AndWherein, R8The straight chained alkyl for being 1~20 selected from carbon atom number, the alkoxy that carbon atom number is 1~20, the thio alkoxy that carbon atom number is 1~20, the branched alkyl that carbon atom number is 3~20, the cyclic alkyl that carbon atom number is 3~20, the alkoxy that carbon atom number is 3~20, the thio alkoxy that carbon atom number is 3~20, the silicyl that carbon atom number is 3~20, the ketone group that carbon atom number is 1~20, the alkoxy carbonyl that carbon atom number is 2~20, the aryloxycarbonyl that carbon atom number is 7~20, cyano, carbamoyl, halogen formoxyl, formoxyl, isocyano group, isocyanate group, thiocyanate groups, isothiocyanate group, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, carbon atom number be 5~40 aryl, carbon atom number be 5~40 heteroaryl, carbon atom number be 5~40 aryloxy group, carbon atom number be 5~40 heteroaryloxy and above-mentioned group in at least two combination groups being interconnected to form；N is the integer greater than 0；-L1Indicate singly-bound or linking group；Dotted line in structure above indicates the connection of the SG and other groups.
- Compound according to claim 8 containing crosslinked group, which is characterized in that the L1Selected from one of following structural formula:AndDotted line in structure above indicates the L1With the connection of other groups.
- Compound according to claim 1 containing crosslinked group, which is characterized in that the compound containing crosslinked group can crosslink reaction at 100 DEG C or more.
- A kind of mixture, it is characterized in that, including the described in any item compounds and organic functional material containing crosslinked group of claim 1~10, the organic functional material is selected from least one of hole-injecting material, hole mobile material, hole barrier materials, electron injection material, electron transport material, electron-blocking materials, organic host materials, singlet emitters, triplet emitters, thermal excitation delayed fluorescence material and organic dyestuff.
- A kind of composition, it is characterized in that, including one of mixture described in the described in any item compounds and claim 11 containing crosslinked group of claim 1~10, organic solvent, the organic solvent is selected from least one of arsol, Fang Za race solvent, ketones solvent, ether solvent and esters solvent.
- The organic functional thin film that at least one of composition described in the described in any item compounds containing crosslinked group of claim 1~10, mixture and claim 12 described in claim 11 is prepared.
- A kind of preparation method of organic functional thin film, which comprises the steps of:Prepare the film liquid containing the described in any item compounds containing crosslinked group of claim 1~10；The film liquid is prepared into film forming layer；AndSo that the compound described in film layer containing crosslinked group is crosslinked reaction, obtains organic functional thin film.
- A kind of organic electronic device, which is characterized in that including the described in any item compounds containing crosslinked group of claim 1~10.
- Organic electronic device according to claim 15, it is characterized in that, the organic electronic device is machine light emitting diode, organic photovoltaic battery, organic light emission battery, organic field-effect tube, organic light-emitting field effect pipe, organic laser, organic spin electric device, organic sensor or organic phasmon emitting diode.
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| CN201611200084 | 2016-12-22 | ||
| CN2016112000849 | 2016-12-22 | ||
| PCT/CN2017/118065 WO2018113783A1 (en) | 2016-12-22 | 2017-12-22 | Compound containing cross-linking group and use thereof |
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| WO2019077051A1 (en) * | 2017-10-19 | 2019-04-25 | Cynora Gmbh | Lighting device for motor vehicles and increased operating temperatures |
| KR102218558B1 (en) | 2018-11-13 | 2021-02-19 | 주식회사 엘지화학 | Novel polymer and organic light emitting device comprising the same |
| CN111725414B (en) * | 2019-07-18 | 2024-03-01 | 广州华睿光电材料有限公司 | Organic electroluminescent device comprising light extraction layer |
| CN113410384B (en) * | 2021-06-28 | 2023-04-07 | 西南大学 | Preparation method of polymer dielectric layer for flexible field effect transistor |
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| JP2009016739A (en) * | 2007-07-09 | 2009-01-22 | Canon Inc | Organic light emitting device and its manufacturing method |
| JP2010021422A (en) * | 2008-07-11 | 2010-01-28 | Canon Inc | Organic light emitting element, and display with the same |
| US20100207105A1 (en) * | 2007-05-30 | 2010-08-19 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device, and illuminating device |
| CN102147577A (en) * | 2010-02-10 | 2011-08-10 | 富士施乐株式会社 | Electrophotographic photoreceptor, process cartridge and image forming apparatus |
| CN103650190A (en) * | 2011-07-11 | 2014-03-19 | 默克专利有限公司 | Compositions for organic electroluminescent devices |
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| WO2011093309A1 (en) * | 2010-01-28 | 2011-08-04 | コニカミノルタホールディングス株式会社 | Organic photoelectric conversion element |
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| US20100207105A1 (en) * | 2007-05-30 | 2010-08-19 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device, and illuminating device |
| JP2009016739A (en) * | 2007-07-09 | 2009-01-22 | Canon Inc | Organic light emitting device and its manufacturing method |
| JP2010021422A (en) * | 2008-07-11 | 2010-01-28 | Canon Inc | Organic light emitting element, and display with the same |
| CN102147577A (en) * | 2010-02-10 | 2011-08-10 | 富士施乐株式会社 | Electrophotographic photoreceptor, process cartridge and image forming apparatus |
| CN103650190A (en) * | 2011-07-11 | 2014-03-19 | 默克专利有限公司 | Compositions for organic electroluminescent devices |
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