TWI534172B - 含有醛基團之聚合物,此聚合物的反應及交聯,交聯聚合物,及含有此聚合物之電致發光裝置 - Google Patents
含有醛基團之聚合物,此聚合物的反應及交聯,交聯聚合物,及含有此聚合物之電致發光裝置 Download PDFInfo
- Publication number
- TWI534172B TWI534172B TW099105323A TW99105323A TWI534172B TW I534172 B TWI534172 B TW I534172B TW 099105323 A TW099105323 A TW 099105323A TW 99105323 A TW99105323 A TW 99105323A TW I534172 B TWI534172 B TW I534172B
- Authority
- TW
- Taiwan
- Prior art keywords
- polymer
- group
- organic
- base
- structural unit
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims description 152
- 125000003172 aldehyde group Chemical group 0.000 title claims description 32
- 229920006037 cross link polymer Polymers 0.000 title claims description 27
- 238000004132 cross linking Methods 0.000 title claims description 21
- 238000006243 chemical reaction Methods 0.000 title description 9
- -1 dihydrophenanthrenyl Chemical group 0.000 claims description 63
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 33
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 22
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 229910052786 argon Inorganic materials 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 229930192474 thiophene Natural products 0.000 claims description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- XXPBFNVKTVJZKF-UHFFFAOYSA-N 9,10-dihydrophenanthrene Chemical class C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 238000013086 organic photovoltaic Methods 0.000 claims description 6
- 150000004032 porphyrins Chemical class 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- IJVCSMSMFSCRME-KBQPJGBKSA-N Dihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-KBQPJGBKSA-N 0.000 claims description 3
- 150000001454 anthracenes Chemical class 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 230000005525 hole transport Effects 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- YYDBAOWUXOFJCG-UHFFFAOYSA-N 1,2,3,4-tetrahydrobenzo[b]triphenylene Chemical class C1CCCC2=C1C1=CC=3C=CC=CC3C=C1C1=C2C=CC=C1 YYDBAOWUXOFJCG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 2
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002800 charge carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical class C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 claims description 2
- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 claims description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002926 oxygen Chemical class 0.000 claims description 2
- 150000002987 phenanthrenes Chemical class 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 239000003451 thiazide diuretic agent Substances 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 claims description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 6
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 4
- 125000003943 azolyl group Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 229960005181 morphine Drugs 0.000 claims 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 3
- 235000001258 Cinchona calisaya Nutrition 0.000 claims 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 claims 2
- 125000005561 phenanthryl group Chemical group 0.000 claims 2
- 229960000948 quinine Drugs 0.000 claims 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 239000010410 layer Substances 0.000 description 70
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
- 238000006116 polymerization reaction Methods 0.000 description 24
- 239000000178 monomer Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 13
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000007239 Wittig reaction Methods 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- XKTABYOWTSPKHT-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C21.N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound N1=CC=CC2=CC=CC=C21.N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 XKTABYOWTSPKHT-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- JRFGJQVSDCDWOW-UHFFFAOYSA-N 1,2,3-benzothiadiazole;thiophene Chemical compound C=1C=CSC=1.C1=CC=C2SN=NC2=C1 JRFGJQVSDCDWOW-UHFFFAOYSA-N 0.000 description 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 3
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 3
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 3
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 3
- QJQGMOIUEXCUOH-UHFFFAOYSA-N 1,3-oxazole;1h-pyrrole Chemical group C=1C=CNC=1.C1=COC=N1 QJQGMOIUEXCUOH-UHFFFAOYSA-N 0.000 description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 3
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 3
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 3
- MHIITNFQDPFSES-UHFFFAOYSA-N 25,26,27,28-tetrazahexacyclo[16.6.1.13,6.18,11.113,16.019,24]octacosa-1(25),2,4,6,8(27),9,11,13,15,17,19,21,23-tridecaene Chemical compound N1C(C=C2C3=CC=CC=C3C(C=C3NC(=C4)C=C3)=N2)=CC=C1C=C1C=CC4=N1 MHIITNFQDPFSES-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N 3H-indole Chemical compound C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical compound C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 description 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical group C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YHBTXTFFTYXOFV-UHFFFAOYSA-N Liquid thiophthene Chemical compound C1=CSC2=C1C=CS2 YHBTXTFFTYXOFV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 3
- FZICDBOJOMQACG-UHFFFAOYSA-N benzo[h]isoquinoline Chemical compound C1=NC=C2C3=CC=CC=C3C=CC2=C1 FZICDBOJOMQACG-UHFFFAOYSA-N 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- NCLXSHBFMBBSOK-UHFFFAOYSA-N hydrazine;pyrimidine Chemical compound NN.C1=CN=CN=C1 NCLXSHBFMBBSOK-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 3
- KIUJQVAFYAWQDX-UHFFFAOYSA-N naphthalene;1,3-oxazole Chemical compound C1=COC=N1.C1=CC=CC2=CC=CC=C21 KIUJQVAFYAWQDX-UHFFFAOYSA-N 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical group C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 3
- 150000003536 tetrazoles Chemical group 0.000 description 3
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- MMQFYDQGJNKDBV-UHFFFAOYSA-N 1h-imidazole;1h-indole Chemical compound C1=CNC=N1.C1=CC=C2NC=CC2=C1 MMQFYDQGJNKDBV-UHFFFAOYSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- MDZDEBKCEOKKHL-UHFFFAOYSA-N 4,5-dihydro-1h-indole Chemical class C1=CCCC2=C1NC=C2 MDZDEBKCEOKKHL-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000005427 anthranyl group Chemical group 0.000 description 2
- 238000004630 atomic force microscopy Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000004376 1,2-dimethylbutylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- BLMBNEVGYRXFNA-UHFFFAOYSA-N 1-methoxy-2,3-dimethylbenzene Chemical compound COC1=CC=CC(C)=C1C BLMBNEVGYRXFNA-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000006052 Horner reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 238000003527 Peterson olefination reaction Methods 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- MEEWSBNOBXBASQ-UHFFFAOYSA-M fluoromethanesulfonate Chemical compound [O-]S(=O)(=O)[CH]F MEEWSBNOBXBASQ-UHFFFAOYSA-M 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920006150 hyperbranched polyester Polymers 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical compound C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 description 1
- RRBYUSWBLVXTQN-VZCHMASFSA-N tricyclene Natural products C([C@@H]12)C3C[C@H]1C2(C)C3(C)C RRBYUSWBLVXTQN-VZCHMASFSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/30—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0672—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
-
- 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
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/148—Side-chains having aromatic units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
- C08G2261/3162—Arylamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
- C08G2261/522—Luminescence fluorescent
- C08G2261/5222—Luminescence fluorescent electrofluorescent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2365/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Chemical & Material Sciences (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Description
本發明係有關一種聚合物,其包含至少一種含有至少一個醛基之結構單元,且有關製備可交聯及/或交聯聚合物(包括含有醛基之聚合物)之方法。本發明用以製備交聯聚合物(包括含有醛基之聚合物)之方法產生具有優異之交聯程度的聚合物。本發明因此亦有關一種藉由本發明方法製備之交聯聚合物,有關此交聯聚合物於電子裝置中之用途,尤其是在有機電致發光裝置中,所謂OLED(OLED=有機發光二極體),且有關包含此交聯聚合物之電致發光層裝置。本發明亦有關本發明含有醛基之聚合物用以製備含有乙烯基或烯基之聚合物或交聯聚合物的用途。
於光電子裝置諸如OLED中,尤其是PLED(聚合物發光二極體),需要具有不同功能性之組份。於PLED中,不同功能性一般係存在於不同聚合物層中。此情況下,使用術語多層OLED系統。此等多層OLED系統尤其包含電荷輸送層,諸如電子-及電洞導體層,及包含發光組份之層。此等多層OLED系統通常係藉由連續層狀塗覆包含具有各種功能性之聚合物的聚合物溶液,且將所塗覆之個別聚合物層交聯,以使其在塗覆下一層之前變成不可溶。該等方法係描述於例如EP 0 637 899及WO 96/20253中。
大部分情況下,交聯基係直接鍵結於單體,其隨後經由聚合而變成可交聯聚合物的一部分。此種用於交聯聚合物之製備路徑係描述於例如WO 2006/043087、WO 2005/049689、WO 2005/052027及US 2007/0228364中。在聚合期間,與已帶有可交聯基團之單體聚合有關的問題係不期望之交聯,即使在製備聚合物之期間。為了避免此等缺點,因此可交聯基團需要在聚合條件保持安定且不進行反應,以便隨後僅能具體地有助於交聯。一般聚合條件諸如例如在Stille、Suzuki或Yamamoto偶聯中,需要高於室溫之溫度。在此等溫度下,可交聯基團可(即使在聚合期間)與其他交聯單體及/或任何其他存在之共聚單體進行不想要之副反應。此點可能限制聚合物之可加工性,造成材料缺陷且降低形成之裝置的性能及/或能力。先前技術所使用之方法無法令人滿意地解決此等問題。
是故,本發明之目的係發現避免可交聯基團在單體聚合期間之副反應的方式,使得聚合係於不受干擾的情況下進行,且所得聚合物具有所欲數量之可交聯基。
本發明目的首先藉由提供本身不帶有任何可交聯基團但含有可輕易且定量轉化成可交聯基之基團的聚合物而達成。
本發明因此係有關一種聚合物,其包含至少一種下式(I)之結構單元:
其特徵為至少一個來自Ar及Ar'之代表者(較佳係Ar')含有醛基,其中所使用符號及下標具有以下意義:Ar及Ar‘彼此獨立地表示經取代或未經取代、單環或多環之芳族或雜芳族環系統;X 係表示共價單鍵或直鏈、分支鏈或環狀C1-10-伸烷基、C1-10-伸烯基或C1-10-伸炔基,其中一或多個H原子可由F置換且其中一或多個CH2基團可由O、NH或S置換;且n 係為1、2、3或4,較佳係1或2且特佳為1;且虛線係表示對聚合物之下一結構單元的鍵結。
本發明中,術語"結構單元"係用以意指藉由位在兩端之鍵形成反應併入聚合物骨架內以作為其中一部分的單體單元,因此在所製備聚合物中係以重現單元存在。
本申請案中,術語聚合物係用以同時意指聚合物化合物、寡聚物化合物及樹枝狀聚合物。本發明聚合物化合物較佳係包含10至10,000,特佳係20至5000,且尤其是50至2000個結構單元。本發明寡聚物化合物較佳係包含3至9個結構單元。在此聚合物分支因素係介於0(直鏈聚合物,無分支點)及1(完全分支樹枝狀聚合物)之間。
本申請案中,術語"樹枝狀聚合物"要用以表示自多官能性中心(核心)構成之高度分支化合物,分支單體以規則結構鍵結於該核心,產生樹狀結構。核心及單體兩者在此處皆可採用任何所欲之分支結構,其係由純有機單元及有機金屬化合物或配位化合物兩者構成。"樹枝狀聚合物"在此大體上預期被理解為例如M.Fischer and F.Vögtle(Angew.Chem.,Int.Ed.1999,38,885)所述。
本發明中,"經取代或未經取代、單環或多環之芳族環系統"係用以意指芳族環系統,較佳係具有6至60,尤其較佳係6至30,極佳係6至14且特佳係6至10個芳族環原子,其並非必要僅含有芳族基,而是其中附加地複數個芳族單元可間雜有非芳族性短單元(<10%之非H原子,較佳<5%之非H原子),諸如例如sp3-混成C原子或O或N原子、CO基等。因此,例如,諸如9,9‘-螺聯茀、9,9-二芳基茀等之系統亦用為芳族環系統。
芳族環系統可為單環或多環,即其可含有一個環(例如苯基)或複數個環,其亦可縮合(例如萘基)或共價鍵結(例如聯苯基)或含有縮合及鍵結環之組合。然而,特佳係完全縮合系統。
較佳芳族環系統係為例如苯基、聯苯基、聯三苯基、1,1':3',1"-聯三苯基-2'-基、萘基、蒽、聯萘基、菲、二氫菲、芘、二氫芘、、苝、稠四苯、稠五苯、苯並芘、茀、茚、茚並茀及螺聯茀。
本發明中,術語"經取代或未經取代、單環或多環之雜芳族環系統"係用以意指芳族環系統,較佳係具有5至60,尤其較佳係5至30,極佳係5至20且特佳係5至9個芳族環原子,其中一或多個此等原子係為雜原子。
"經取代或未經取代、單環或多環之雜芳族環系統"並非必然僅含芳族基團,而是亦可間雜有非芳族性短單元(<10%之非H原子,較佳<5%之非H原子),諸如例如sp3-混成C原子或O或N原子、CO基等。
雜芳族環系統可為單環或多環,即其可含一個環或複數個環,此等環亦可為稠合或共價鍵結(例如吡啶基苯基)或含有稠合及鍵結環之組合。較佳者係完全共軛雜芳基。然而,特佳者係完全稠合系統。
較佳雜芳族環系統係為例如5員環,諸如吡咯、吡唑、咪唑、1,2,3-三唑、1,2,4-三唑、四唑、呋喃、噻吩、硒吩、唑、異唑、1,2-噻唑、1,3-噻唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、6員環諸如吡啶、嗒、嘧啶、吡、1,3,5-三、1,2,4-三、1,2,3-三、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四或稠合基團,諸如吲哚、異吲哚、吲、吲唑、苯並咪唑、苯並三唑、嘌呤、萘並咪唑、菲並咪唑、吡啶並咪唑、吡並咪唑、喹啉並咪唑、苯並唑、萘並唑、蒽咪唑、菲並唑、異唑、苯並噻唑、苯並呋喃、異苯並呋喃、二苯並呋喃、喹啉、異喹啉、喋啶、苯並-5,6-喹啉、苯並-6,7-喹啉、苯並-7,8-喹啉、苯並異喹啉、吖啶、啡噻、啡、苯並嗒、苯並嘧啶、喹啉、啡、啶、氮雜咔唑、苯並咔啉、啡啶、菲啉、噻吩並[2,3b]噻吩、噻吩並[3,2b]噻吩、二噻吩並噻吩、異苯並噻吩、二苯並噻吩、苯並噻二唑噻吩或此等基團之組合。雜芳基亦可經烷基、烷氧基、烷硫基、氟、氟烷基或其他芳基或雜芳基取代。
經取代或未經取代單環或多環芳族或雜芳族環系統視情況具有一或多個取代基,該取代基較佳係選自矽基、磺基、磺醯基、甲醯基、胺、亞胺、腈、巰基、硝基、鹵素、C1-12-烷基、C6-12-芳基、C1-12-烷氧基、羥基或此等基團之組合。
較佳取代基係為例如增進溶解度之基團,諸如烷基或烷氧基、拉電子基團,諸如氟、硝基或腈,或用以增加聚合物玻璃轉移溫度(Tg)之取代基,尤其是龐大基團,諸如例如第三丁基或視情況經取代之芳基。
特佳取代基係為例如F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)N(R)2、-C(=O)Y1、-C(=O)R及-N(R)2,其中R係彼此獨立地為H、具有1至20個C原子之脂族或芳族烴基,且Y1係表示鹵素、視情況經取代之矽基、具有4至40個(較佳6至20個)C原子之芳基、或具有1至22C原子之直鏈或分支鏈烷基、烷氧基、烷基羰基、烷氧基羰基、烷基羰基氧基或烷氧基羰基氧基,其中一或多個H原子可視情況置換為F或Cl。
就本發明之目的而言,術語"芳族單元"係用以意指本身形成芳族系統之原子團,該系統根據HCKEL定義係為具有(4n+2)個π電子的環狀共軛系統,其中n表示整數。
"直鏈、分支鏈或環狀C1-10-伸烷基、C1-10-伸烯基或C1-10-伸炔基"係用以意指飽和或不飽和脂族烴,其較佳係含有1至10個碳原子,尤其較佳係1至6個碳原子,其中另外一或多個CH2基團可置換為NH、O或S,且另外一或多個H原子可由F置換。在此特佳者係具有1至6個碳原子之直鏈飽和烴。具有1至10個碳原子之脂族烴的實例包括下列者:亞甲基、伸乙基、伸正丙基、伸異丙基、伸正丁基、伸異丁基、伸第二丁基(1-甲基伸丙基)、伸第三丁基、伸異戊基、伸正戊基、伸第三戊基(1,1-二甲基丙基)、1,2-二甲基伸丙基、2,2-二甲基伸丙基(新戊基)、1-乙基伸丙基、2-甲基伸丁基、伸正己基、伸異己基、1,2-二甲基伸丁基、1-乙基-1-甲基伸丙基、1-乙基-2-甲基伸丙基、1,1,2-三甲基伸丙基、1,2,2-三甲基伸丙基、1-乙基伸丁基、1-甲基伸丁基、1,1-二甲基伸丁基、2,2-二甲基伸丁基、1,3-二甲基伸丁基、2,3-二甲基伸丁基、3,3-二甲基伸丁基、2-乙基伸丁基、1-甲基伸戊基、2-甲基伸戊基、3-甲基伸戊基、伸環戊基、伸環己基、伸環庚基、伸環辛基、2-乙基伸己基、三氟亞甲基、五氟伸乙基、2,2,2-三氟伸乙基、伸乙烯基、伸丙烯基、伸丁烯基、伸戊烯基、二伸環戊烯基、伸己烯基、伸環己烯基、伸庚烯基、伸環庚烯基、伸辛烯基、伸環辛烯基、伸乙炔基、伸丙炔基、伸丁炔基、伸戊炔基、伸己炔基及伸辛炔基。
基於存在聚合物中作為結構單元之所有共聚單體為100 mol%,式(I)可交聯結構單元於聚合物中之比例係於0.01至95 mol%範圍內,較佳係於0.1至70 mol%範圍內,尤其較佳係於0.5至50 mol%範圍內,且特佳係於1至30 mol%範圍內。
本發明其他較佳具體實施態樣中,本發明聚合物在一或多種式(I)結構單元之外,亦包含至少一種異於式(I)結構單元之其他結構單元。此等尤其是於WO 02/077060 A1及WO 2005/014689 A2中所廣泛揭示及列示者。此等刊物係以引用方式併入本發明。其他結構單元可源自例如以下類型:第1組:增進聚合物之電洞注入及/或電洞傳輸性質的單元;第2組:增進聚合物之電子注入及/或電子傳輸性質的單元;第3組:具有來自第1組及第2組之個別單元的組合之單元;第4組:將發光特徵修改至可得到電致磷光而非電致螢光之程度;第5組:改善自所謂單重態成為三重態之轉變的單元;第6組:影響形成之聚合物的發光顏色的單元;第7組:通常作為骨架之單元;第8組:影響形成之聚合物的薄膜形態及/或流變性質的單元。
本發明較佳聚合物係為其中至少一種結構單元具有電荷傳送性質者,即其包含來自第1組及/或第2組之單元者。
來自第1組具有電洞注入及/或電洞傳輸性質之結構單元有例如三芳基胺、聯苯胺、四芳基-對-苯二胺、三芳基膦、啡噻、啡、二氫啡、噻蒽、二苯並-對-戴奧辛、啡噻、咔唑、薁、噻吩、吡咯及呋喃衍生物及其他具有高HOMO之其他含O-、S-或N-之雜環(HOMO=最高佔據分子軌域)。此等芳基胺及雜環較佳係於聚合物中造成大於-5.8 eV(相對於真空等級),尤其較佳係大於-5.5 eV之HOMO。
來自第2組具有電子注入及/或電子傳輸性質之結構單元有例如吡啶、嘧啶、嗒、吡、二唑、喹啉、喹啉、蒽、苯並蒽、芘、苝、苯並咪唑、三、酮、氧化膦及啡衍生物,但亦可為三芳基硼烷及其他具有低LUMO之含O、S或N的雜環(LUMO=最低未佔據分子軌域)。聚合物中此等單元較佳產生低於-2.5 eV之LUMO(相對於真空等級),尤其較佳係低於-2.7 eV。
本發明聚合物可較佳包含來自第3組之單元,其中增加電洞移動性之結構及增加電子移動性之結構(即來自第1及2組之單元)係直接彼此鍵結或鍵結至同時增加電洞移動性及電子移動性兩者之結構。此等單元中有些可以作為發光劑,將發光顏色偏移成綠色、黃色或紅色。因此,其用途是適用於例如自原始發射藍光聚合物製造其他發光顏色。
來自第4組之結構單元係為可於高效率下自三重態發光者,即使於室溫下亦然,即展現電致磷光而非電致螢光,經常造成能量效率增高。適於此目的者首先為含有原子序大於36之重原子的化合物。較佳者係符合前述條件之含有d-或f-過渡金屬的化合物。此處特佳者係含有第8至10族之元素(Ru、Os、Rh、Ir、Pd、Pt)的對應結構單元。此處適於本發明聚合物之結構單元有例如WO 02/068435 A1、WO 02/081488 A1、EP 1239526 A2及WO 2004/026886 A2所述之各種錯合物。對應之單體係描述於WO 02/068435 A1及WO 2005/042548 A1中。
來自第5組之結構單元係為改善自單重態成為三重態之轉變者,用以支撐來自第4組之結構單元,改善此等結構單元之磷光性質。適用於此目的者尤其有咔唑及橋聯咔唑二聚體單元,如例如WO 2004/070772 A2及WO 2004/113468 A1所述。亦適用於此目的者有酮、氧化膦、亞碸、碸、矽烷衍生物或類似化合物,如例如WO 2005/040302 A1所述。
在前述者以外,來自第6組之結構單元係為具有至少一種不在前述之其他芳族結構或另一共軛結構,即對電荷載流子移動性僅具極小之影響、非有機金屬錯合物或不影響單重態-三重態轉變者。此類結構元素可影響形成之聚
合物的發光顏色。視該單元而定,其因此亦可作為發光體。在此較佳者係為具有6至40個C原子之芳族結構,以及二苯乙炔、二苯乙烯或雙苯乙烯基伸芳基衍生物,其各可經一或多個基團R所取代。此處特佳者係納入1,4-伸苯基、1,4-伸萘基、1,4-或9,10-伸蒽基、1,6-,2,7-或4,9-伸芘基、3,9-或3,10-伸苝基、4,4'-伸聯苯基、4,4"-伸聯三苯基、4,4'-聯-1,1'-伸萘基、4,4‘-伸二苯乙炔基、4,4'-伸二苯乙烯基、4,4"-雙苯乙烯基伸芳基、苯並噻二唑及對應之氧衍生物、喹啉、啡噻、啡、二氫啡、雙(噻吩基)伸芳基、寡聚(伸噻吩基)、啡、紅螢烯、稠五苯或苝衍生物,其較佳係經取代,或較佳共軛之推拉系統(由供體及受體取代基所取代之系統)或諸如方酸(squarine)或喹吖酮(較佳係經取代)之系統。
來自第7組之結構單元係為含有具有6至40個C原子的芳族結構,其通常作為聚合物骨架。此等有例如4,5-二氫芘衍生物、4,5,9,10-四氫芘衍生物、茀衍生物、9,9‘-螺聯茀衍生物、菲衍生物、9,10-二氫菲衍生物、5,7-二氫二苯並呯衍生物及順式與反式茚並茀衍生物。
來自第8組之結構單元係為影響聚合物之薄膜形態及/或流變性質者,諸如例如矽氧烷、長烷基鏈或氟化基團,但亦特別為剛性或可撓性單位,諸如例如液晶形成性單元或可交聯基團。
較佳者是在式(I)結構單元外同時另外包含一或多個選自第1至8組之單元的本發明聚合物。同時存在多於一
種來自一組之其他結構單元亦可能較佳。
較佳者係為在至少一種式(I)式(I)結構單元之外,亦包含來自第7組之單元,尤其較佳係以聚合物中結構單元總數計至少50mol%之此等單元的聚合物。
本發明聚合物亦佳者係含有改善電荷傳輸或電荷注入的單元,即來自第1及/或2組之單元;比例為0.5至30mol%之此等單元特佳;比例為1至10mol%之此等單元極佳。
本發明聚合物另外特佳係包含來自第7組之結構單元及來自第1及/或2組之單元,尤其是至少50mol%來自第7組之單元及0.5至30mol%之來自第1及/或2組之單元。
本發明聚合物係為包含式(I)結構單元之均聚物或共聚物。本發明聚合物可為直鏈或分支鏈,較佳係直鏈。除一或多個式(I)結構單元之外,本發明共聚物有可能具有一或多個來自前文所示第1至8組之其他結構。
本發明共聚物可具有雜亂、交替或嵌段狀結構,或亦具有複數個交替之此等結構。本發明共聚物特佳係具有雜亂或交替結構。共聚物特佳係雜亂或交替共聚物。其中可製得具有嵌段狀結構之共聚物的方式及其他結構元素特別有利於此目的之方式係詳述於例如WO 2005/014688 A2中。後者係以引用方式併入本文。亦應再次於此點著重於聚合物亦可具有樹枝狀結構。
另一具體實施態樣中,式(I)中Ar'較佳係為選自以下之經取代或未經取代單元:伸苯基、伸聯苯基、伸聯三苯基、1,1':3',1"-聯三
苯-2'-伸基、伸萘基、蒽、伸聯萘基、菲、二氫菲、芘、二氫芘、、苝、稠四苯、稠五苯、苯並[a]芘、茀、茚、茚並茀、螺聯茀、吡咯、吡唑、咪唑、1,2,3-三唑、1,2,4-三唑、四唑、呋喃、噻吩、硒吩、唑、異唑、1,2-噻唑、1,3-噻唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、吡啶、嗒、嘧啶、吡、1,3,5-三、1,2,4-三、1,2,3-三、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、吲哚、異吲哚、吲、吲唑、苯並咪唑、苯並三唑、嘌呤、萘並咪唑、菲並咪唑、吡啶並咪唑、吡並咪唑、喹啉並咪唑、苯並唑、萘並唑、蒽並咪唑、菲並唑、異唑、苯並噻唑、苯並呋喃、異苯並呋喃、二苯並呋喃、喹啉、異喹啉、喋啶、苯並-5,6-喹啉、苯並-6,7-喹啉、苯並-7,8-喹啉、苯並異喹啉、吖啶、啡噻、啡、苯並嗒、苯並嘧啶、喹啉、啡、啶、氮雜咔唑、苯並咔啉、啡啶、菲啉、噻吩並[2,3b]噻吩、噻吩並[3,2b]噻吩、二噻吩並噻吩、異苯並噻吩、二苯並噻吩及苯並噻二唑噻吩,其中該視情況選用之取代基係為前文針對芳族及雜芳族環系統所述者。伸萘基及伸苯基係特佳,而伸苯基係特佳。
再另一具體實施態樣中,式(I)結構單元中之X較佳地為共價單鍵。
本發明另一具體實施態樣係亦為一種聚合物,其包含至少一種以下式(II)之結構單元:
其特徵為單元Ar1至Ar6中至少一個Ar含有醛基,其中所使用符號及下標具有以下意義:Ar1至Ar6係相同或相異且彼此獨立地表示具有5至25個環原子之經取代或未經取代、單環或多環之芳族或雜芳族環系統;m 係為0或1;n’ 係為0、1或2;虛線係表示對聚合物之下一結構單元的鍵結;其限制條件為若n’=1,則該兩N原子係鍵結至同一芳族環系統之不同C原子。
當n’=2時,出現於對應之方括弧中之兩結構元素可串聯配置,產生直鏈之式(II)結構單元,或可並聯配置(即兩者皆位於Ar2或Ar4),產生分支鏈之式(II)結構單元。
本發明另一具體實施態樣中,較佳係Ar1至Ar6係彼此獨立地相同或相異地選自:伸苯基、伸聯苯基、伸聯三苯基、1,1':3',1"-聯三苯-2'-伸基、伸萘基、蒽、伸聯萘基、菲、二氫菲、芘、二氫芘、、苝、稠四苯、稠五苯、苯並[a]芘、茀、茚、茚並茀、螺聯茀、吡咯、吡唑、咪唑、1,2,3-三唑、1,2,4-三唑、四唑、呋喃、噻吩、硒吩、唑、異唑、1,2-噻
唑、1,3-噻唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、吡啶、嗒、嘧啶、吡、1,3,5-三、1,2,4-三、1,2,3-三、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、吲哚、異吲哚、吲、吲唑、苯並咪唑、苯並三唑、嘌呤、萘並咪唑、菲並咪唑、吡啶並咪唑、吡並咪唑、喹啉並咪唑、苯並唑、萘並唑、蒽並咪唑、啡並唑、異唑、苯並噻唑、苯並呋喃、異苯並呋喃、二苯並呋喃、喹啉、異喹啉、喋啶、苯並-5,6-喹啉、苯並-6,7-喹啉、苯並-7,8-喹啉、苯並異喹啉、吖啶、啡噻、啡、苯並嗒、苯並嘧啶、喹啉、啡、啶、氮雜咔唑、苯並咔啉、啡啶、菲啉、噻吩並[2,3b]噻吩、噻吩並[3,2b]噻吩、二噻吩並噻吩、異苯並噻吩、二苯並噻吩及苯並噻二唑噻吩,其中視情況存在之取代基係前文針對芳族及雜芳族環系統所描述者。伸萘基及伸苯基係特佳,而伸苯基係尤佳。
本發明另一具體實施態樣中,特佳係式(I)中Ar或式(II)中Ar1、Ar2、Ar4及Ar5選自以下之經取代或未經取代之單元:4,5-二氫芘、4,5,9,10-四氫茀、9,9‘-螺聯茀、茀、菲、9,10-二氫菲、5,7-二氫二苯並呯、順式-茚並茀、反式-茚並茀、伸苯基、噻吩、苯並蒽,咔唑、苯並咪唑、呯及三。
此外,較佳者係本發明聚合物包含作為其他結構單元之式(I)及/或(II)結構單元,然而,其不含醛基。
此外,本發明聚合物之式(II)中結構單元較佳係於基團Ar3及/或Ar6上含有醛基,且本發明聚合物之式(I)中結構單元Ar'含有醛基。基團Ar3、Ar6及Ar‘較佳係表示可能含有醛基之苯基。醛基可位於相對苯基成鄰位、間位或對位之位置。醛基較佳係為對位。
本發明另一具體實施態樣中,較佳者係當式(II)中m及n等於零時,基團Ar1、Ar2及Ar3中之一者不為苯基。此情況下,Ar1及/或Ar2較佳係不為苯基。
特佳具體實施態樣中,本發明聚合物係包含至少一種以下結構單元:
本發明另一具體實施態樣中,聚合物較佳係包含一或多種以下結構單元:
其中虛線係表示對聚合物中其他結構單元之鍵結。芳族基團可再由一或多個取代基所取代。
包含著含有一或多個醛基之式(I)及/或(II)結構單元的本發明聚合物通常係藉由使一或多種類型之單體進行聚合而製備,其中至少一種單體形成聚合物中之式(I)及/或(II)結構單元。適當之聚合反應係熟習此技術者已知且係描述於文獻中。形成C-C或C-N連結的特別適當且特佳之聚合反應如下:
(A)SUZUKI聚合;
(B)YAMAMOTO聚合;
(C)STILLE聚合;
(D)HECK聚合;
(E)NEGISHI聚合;
(F)SONOGASHIRA聚合;
(G)HIYAMA聚合;及
(H)HARTWIG-BUCHWALD聚合。
可藉此等方法進行聚合之方式及可隨後自反應介質分離且純化聚合物之方式係熟習此技術者已知,且係詳述於文獻中,例如在WO 03/048225 A2、WO 2004/037887 A2及WO 2004/037887 A2中。
C-C連結反應較佳係選自SUZUKI偶合、YAMAMOTO偶合及STILLE偶合,且C-N連結反應較佳係為HARTWIG-BUCHWALD偶合。
本發明因此亦有關一種製備本發明聚合物之方法,其特徵為其係藉由SUZUKI聚合、YAMAMOTO聚合、STILLE聚合或HARTWIG-BUCHWALD聚合製備。
可藉由聚合轉化成本發明聚合物之單體係為在兩末端各含有彼此獨立地選自以下基團之單體:鹵素,較佳係Br及I,O-甲苯磺酸酯,O-三氟甲磺酸酯,O-SO2R1,B(OR1)2及Sn(R1)3。
R1較佳係每次出現各彼此獨立地選自:氫、具有1至20個C原子之脂族烴基及具有6至20個環原子之芳族單環性或多環性環系統,其中二或更多個基團R1可彼此形成環系統。具有1至20個碳原子之脂族烴在此係為直鏈、分支鏈或環狀烷基、烯基、炔基,其中一或多個碳原子可由O、N或S置換。此外,一或多個氫原子可由氟置換。具有1至20個碳原子之脂族烴的實例包括下列者:甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基(1-甲基丙基)、第三丁基、異戊基、正戊基、第三戊基(1,1-二甲基丙基)、1,2-二甲基丙基、2,2-二甲基丙基(新戊基)、1-乙基丙基、2-甲基丁基、正己基、異己基、1,2-二甲基-丁基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基丁基、1-甲基丁基、1,1-二甲基丁基、2,2-二甲基丁基、1,3-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、2-乙基丁基、1-甲基戊基、2-甲基戊基、3-甲基戊基、環戊基、環己基、環庚基、環辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基及辛炔基。
有關R1之術語"具有6至20個環原子之單環或多環芳族環系統"係具有與前文定義相同之意義,其中此時縮合芳族系統亦佳。較佳芳族環系統係為萘基及苯基,其中以苯基特佳。
當其中兩基團R1形成環系統時,此兩鍵合基團R1較佳係表示具有2至8個碳原子之二價脂族基團。其實例係為下式-CH2(CH2)nCH2-化合物,其中n=0、1、2、3、4、5或6,較佳係0、1、2或3。
當有多於兩個之基團R1彼此形成環系統時,此等基團R1連同另一者一起表示具有6至20個碳原子之分支鏈三-、四-、五-或多價脂族基團。
特佳具體實施態樣中,單體之終止基團係彼此獨立地選自Br、I及B(OR1)2。
本發明樹枝狀聚合物可藉熟習此技術者已知或與其類似之方法製備。適當之方法係描述於文獻中,諸如例如於Frechet,Jean M. J.;Hawker,Craig J.,"Hyperbranched polyphenylene and hyperbranched polyesters: new soluble,three-dimensional,reactive polymers",Reactive & Functional Polymers(1995),26(1-3),127-36;Janssen,H. M.;Meijer,E. W.,"The synthesis and characterisation of dendritic molecules",Materials Science and Technology(1999),20(Synthesis of Polymers),403-458;Tomalia,Donald A.,"Dendrimer molecules",Scientific American(1995),272(5),62-6、WO 02/067343 A1及WO 2005/026144 A1。
本發明另外有關包含著含有一或多個醛基之式(I)及/或(II)結構單元的聚合物用於製備可交聯聚合物之用途。可交聯基團較佳係為乙烯基或烯基。聚合物之醛基藉WITTIG反應或與WITTIG類似之反應轉化成乙烯基或烯基,較佳係丙烯基。
本發明因此亦有關一種方法,其包含以下步驟:
(a)提供包含著含有一或多個醛基之式(I)及/或(II)結構單元的聚合物;及
(b)將醛基轉化成乙烯基或烯基。
前述本發明方法中,將醛基轉化成乙烯基或烯基之化學轉化較佳係藉WITTIG反應、類似WITTIG反應、Emmons-Horner反應、Peterson反應或Tebbe亞甲基化而進行。
不論其是否含有醛基或已含有乙烯基或烯基,本發明聚合物皆可於純物質形式下使用,但亦可連同任何所需類型之其他聚合、寡聚、樹枝狀或低分子量物質一起以混合物形式使用。本發明中,低分子量物質係用以意指具有在100至3000 g/mol範圍內之分子量的化合物,較佳係200至2000 g/mol。此等其他物質可例如改善電子性質或其本身可發光。術語混合物在前文及下文中係適用於包含至少一種聚合物組份之混合物。依此方式,可製得由一或多種包含式(I)及/或(II)結構單元之本發明聚合物及視情況選用之一或多種其他聚合物與一或多個低分子量物質之混合物(摻合物)組成的一或多層聚合物層。
本發明因此另外有關一種聚合物摻合物,其包含一或多種本發明聚合物及一或多種其他聚合、寡聚、樹枝狀及/或低分子量物質。
本發明另外有關包含一或多種本發明聚合物或混合物於一或多種溶劑中之溶液及調配物。可製備此類型溶液之方式係熟習此技術者已知且描述於例如WO 02/072714 A1、WO 03/019694 A2及其中所列之文獻。
此等溶液可用以製造聚合物薄層,例如藉由面積塗覆方法(例如旋塗法)或藉印刷方法(例如噴墨印刷)。
包含著含有一或多個醛基之式(I)及/或(II)結構單元之聚合物在醛基轉化成烯基(較佳係乙烯基)後,特別適於製造薄膜或塗層,尤其是製造結構化塗層,例如藉由熱或光誘發原位交聯,諸如例如原位UV光聚合或光圖案化。此情況不僅可使用純物質形式之對應聚合物,但亦可使用此等前述聚合物之調配物或混合物。此等可在添加或不添加溶劑及/或黏合劑之情況下使用。適用於前述方法之材料、製程及裝置係描述於例如WO 2005/083812 A2中。可能之黏合劑係為例如聚苯乙烯、聚碳酸酯、聚(甲基)丙烯酸酯、聚丙烯酸酯、聚乙烯基丁醛及類似、光電子中性聚合物。
適當且較佳溶劑係為例如甲苯、苯甲醚、二甲苯、苯甲酸甲酯、二甲基苯甲醚、三甲苯、四氫萘、鄰二甲氧苯、四氫呋喃及氯苯及其混合物。
本發明另外有關一種聚合物之用途,該聚合物包含著含有一或多個醛基之式(I)及/或(II)結構單元,用以製備交聯聚合物。換言之,此聚合物之醛基係直接鏈接至已鍵結至另一聚合物或可依相同或類似方式鍵結至另一聚合物的化合物,或轉化成可交聯基團,接著與另外之可交聯基團反應,產生交聯聚合物。可交聯基團較佳係為乙烯基或烯基,且較佳係藉由WITTIG反應或類似WITTIG之反應併入聚合物內。若可交聯基團係為乙烯基或烯基,則可藉由自由基或離子聚合進行交聯,該聚合可由熱或由輻射引發。由熱引發之自由基聚合較佳,較佳係在低於250℃之溫度,尤其較佳係在低於200℃之溫度。
附加之苯乙烯單體係於交聯過程中視情況添加,以達到較高之交聯程度。所添加苯乙烯單體之比例基於以結構單元形式存在於聚合物中的所有已共聚單體的100 mol%計,較佳係於0.01至50 mol%範圍中,尤其較佳係0.1至30 mol%。
本發明因此亦有關一種製備交聯聚合物之方法,其係包含以下步驟:
(a) 提供包含著含有一或多個醛基之式(I)及/或(II) 結構單元的聚合物;
(b) 將醛基轉化成乙烯基或烯基;及
(c) 自由基或離子性交聯,較佳係自由基交聯,可由熱或由輻射引發,較佳係由熱引發。
本發明方法所製備之交聯聚合物不可溶於所有一般溶劑。依此方式,可製得限定層厚,其藉由施加後續層而不溶或仍部分溶解。
本發明因此亦有關一種交聯聚合物,其可藉前述方法製得。交聯聚合物-如前文所述-較佳係製備成交聯聚合物層形式。由於交聯聚合物於所有溶劑中皆不溶解,故可使用前述技術,自溶劑將包含式(I)及/或(II)結構單元之另一聚合物層施加於此類型交聯聚合物層表面。
本發明亦涵蓋所謂混成裝置,其中可存在一或多個聚合物層及藉低分子量物質氣相沈積所製得之層。
本發明交聯聚合物可使用於電子或光電子裝置或其製造。
本發明因此另外有關本發明交聯聚合物於電子或光電子裝置中之用途,較佳係有機或聚合物有機電致發光裝置(OLED,PLED)、有機場效電晶體(OFET)、有機積體電路(O-IC)、有機薄膜電晶體(TFT)、有機太陽能電池(O-SC)、有機雷射二極體(O-雷射)、有機光伏打(OPV)元件或裝置或有機感光體(OPC),特佳為有機或聚合有機電致發光裝置(OLED,PLED),尤其是聚合物有機電致發光裝置(PLED)。
若為前述混成裝置,則術語結合PLED/SMOLED(小分子有機發光二極體)系統係針對有機電致發光裝置使用。
可製造OLED或PLED之方式係熟習此技術者已知,且係以一般方法形式詳述於例如WO 2004/070772 A2,其應針對個別情況對應地調整。
如前文所述,本發明聚合物極適於在PLED或此方式製得之顯示器中作為電致發光材料。
就本發明之目的而言,電致發光材料係用以表示可作為活性層之材料。活性層表示該層可在施加電場時發光(發光層)且/或改善正及/或負電荷之注射及/或傳輸(電荷注射或電荷傳輸層)。
本發明因此亦佳係有關本發明交聯聚合物於PLED中之用途,尤其是作為電致發光材料。
本發明另外有關電子或光電子組件,較佳係有機或聚合有機電致發光裝置(OLED,PLED)、有機場效電晶體(OFET)、有機積體電路(O-IC)、有機薄膜電晶體(TFT)、有機太陽能電池(O-SC)、有機雷射二極體(O-雷射)、有機光伏打(OPV)元件或裝置及有機感光體(OPC),特佳係有機或聚合有機電致發光裝置,尤其是具有一或多層活性層之聚合物有機電致發光裝置,其中此等活性層中至少一層係包含一或多種本發明聚合物。活性層可為例如發光層、電荷傳輸層及/或電荷注入層。
本案內文及以下實施例主要係針對本發明聚合物有關PLED及對應之顯示器之用途。儘管有此描述之限制,但熟習此技術者仍可在無進一步發明步驟下使用本發明聚合物作為前述其他電子裝置中其他用途的半導體。
以下實施例係用以說明本發明,而非限制。尤其,基於特定化合物討論之特色、性質及優點亦可套用於未詳細描述但係落於申請專利範圍保護範圍內之其他化合物,除非另有陳述。
5 g之4-(N,N-二苯基胺基)苯甲醛(18.3 mmol)溶於270ml之無水THF中且冷卻至0℃。連續添加6.5 g之固體形式N-溴琥珀醯亞胺(36.6 mmol),溶液於0℃攪拌4小時。
濾出固體,將水及二氯甲烷添加至溶液。分相。有機相以水洗滌三次且以Na2SO4乾燥,然後過濾,於旋轉蒸發器中蒸發。產物自庚烷/甲苯再結晶數次。
1H NMR(CDCl3,δ(ppm),J(Hz)):7.02(d,4H,J=8.8),7.04(d,2H,J=8.8),7.44(d,4H,J=8.9),7.71(d,2H,J=8.8),9.84(s,1H)
4.9 g之N-(4-甲醯基苯基)咔唑(18.1 mmol)溶於270ml之無水THF且冷卻至0℃。連續添加6.4 g之固體形式N-溴琥珀醯亞胺(36.1 mmol),溶液於0℃攪拌4小時。
濾出固體,將水及二氯甲烷添加至溶液。分相。有機相以水洗滌三次且以Na2SO4乾燥,然後過濾,於旋轉蒸發器中蒸發。產物自乙酸乙酯再結晶數次。
1H NMR(C2D2Cl4,δ(ppm),J(Hz)):7.34(d,2H,J=8.6),7.55(d,2H,J=8.8),7.71(d,2H,J=8.3),8.13(d,2H,J=8.6),8.21(s,2H),10.10(s,1H)
本發明聚合物P1及P2係藉WO 03/048225所述方法由SUZUKI偶合下文所示之三種不同結構單元製備。此方式所製備之聚合物P1a、P1b及P1c與P2a、P2b及P2c在移除脫離基後包含所示百分比之三種結構單元(百分比數據=mol%)。
製備對照聚合物C1及C2,其在藉由如同實施例3a所述方法移除脫離基後包含所示百分比之兩種下述結構單元(百分比數據=mol%):
依照以下反應流程圖,藉WITTIG反應,自實施例3a所製備之聚合物P1a、P1b及P1c與P2a、P2b及P2c製備含有可交聯基團之聚合物P1a’、P1b’及P1c’與P2a’、P2b’及P2c’:P1之WITTIG反應:
P2之WITTIG反應:
為此目的,於50℃在氬下將聚合物P1a(1 g)溶於20ml之無水THF,且隨之冷卻至室溫。
2.86 g(8 mmol)溴化甲基三苯膦於0℃在氬下溶於20 ml之無水THF中,於0℃分批添加0.90 g(8 mmol)第三丁醇鉀。隨後於2℃使用注射筒緩緩添加聚合物溶液,混合物於室溫攪拌隔夜。溶液以水萃取三次,有機相於甲醇中沉澱。
聚合物P1b及P1c與P2a、P2b及P2c係類似地反應。
聚合物發光二極體之製造已多次描述於專利文獻中(參見例如WO 2004/037887)。為了藉實施例說明本發明,PLED係藉WO 2004/037887所述方法,使用對照聚合物C1,藉旋塗於ITO基板上而製得,該基板已預先塗覆PEDOT(PEDOT係為聚噻吩衍生物(Baytron P,得自H. C. Starck,Goslar))。經塗覆基板藉於180℃加熱10分鐘而乾燥。形成之中間層之層厚係為20 nm。隨後藉旋塗法塗覆80 nm發光層,此發光層係由聚合物基質C2及綠色磷光三重發光體T1(約20 mol%)構成。隨後藉氣相沈積塗覆Ba/Al陰極(金屬來自Aldrich),封裝PLED且測定電光學特徵。表1列示所得結果。
如實施例5所述般進行製造,使用聚合物P1a’置換對照聚合物C1,且使用聚合物P2a’、P2b’及P2c’置換對照聚合物C2。在旋塗法之後,在P1'及P2'之情況下,每一情況下各藉由於180℃加熱一小時而將塗層乾燥,以使聚合物交聯。包含聚合物P1a'之中間層的層厚係為20 nm,且包含聚合物C2、P2a’、P2b’及P2c’之發光層的層厚在每一情況下各發光層之厚度係為80 nm。PLED之電光學特徵測定係如同實施例5般地進行,且係描述於下文。結果總列於表1。
為測定電光學特徵,實施例5及6所製之PLED夾在特別針對基板尺寸製造且具有彈簧接點之支架中。具有眼睛響應濾器之光電二極體可直接安置於測量支架上,以排除外來光線之影響。
電壓一般係以0.2 V步階自0增加至最大20 V且再次降低。就各個測量點而言,流通PLED之電流及所得之光電流係藉光電二極體測量。依此方式,得到測試PLED之IUL數據。重要參數係為所測量之最大效率("eff."單位為cd/A)及100 cd/m2(U100)所需之電壓。
此外,為了得知試驗PLED之色彩及精確之電致發光光譜,在第一次測量之後,再次施加100 cd/m2所需之電壓,以光譜測量頭置換光電二極體。此者藉光學纖維連接至光譜儀(Ocean Optics)。色彩座標(CIE:Commission International de l′clairage,1931之標準觀測者)可自測量光譜演算出來。
包含交聯中間層及/或基質聚合物P1a’及P2a-c’之PLED的效率可相當於包含未交聯對照聚合物C1及C2之PLED的效率。電壓及色彩座標亦彼此相當。此點顯示交聯對於效率、電壓及色彩座標不具負面影響。然而,主要優勢係為本發明聚合物之交聯容許層厚明確地改變且準確地控制,因為交聯之層可不再部分溶解及洗除,此係更詳細說明於實施例8。因此,於PLED中達到多層結構,其中所有層皆係自溶液開始加工且具有限定層厚。此情況下,例如,亦可將限定層厚之第三層施加至交聯之發射綠光層(P2’包含20 mol%之T1),之後藉氣相沈積施加陰極,且將PLED封裝。若第三層亦可交聯,則可施加限定層厚之第四層。
如同實施例5及6般地進行製造。聚合物C1、P1a’、P1b’及P1c’藉旋塗法塗覆至已預先塗覆PEDOT之ITO基板上。塗覆P1a’、P1b’及P1c’之基板隨後各藉著於180℃加熱一小時加以乾燥,以使聚合物交聯。聚合物層厚度各為20 nm。隨後藉旋塗法塗覆厚度65 nm之發射藍光聚合物B1之層。(B1之製備係如同實施例3般地進行。B1在移除脫離基後,包含所列百分比之以下所示結構單元(百分比數據=mol%))。
隨後藉氣相沈積施加Ba/Al陰極,且將PLED封包起來。PLED之電光學特徵的測定係如實施例6所述般地進行。結果總列於表2。
包含交聯聚合物P1a’、P1b’及P1c’之PLED的效率等同於未交聯對照聚合物C1。電壓及色彩座標亦彼此相當。此點顯示中間層之交聯對於PLED之效率、電壓及色彩座標不具負面影響。然而,主要優勢係為本發明聚合物之交聯容許層厚明確地改變且準確地控制,因為交聯之層可不再部分溶解及洗除,此係更詳細說明於實施例8。因此,包含至少兩層之多層結構係於自溶液加工之PLED中自該等具有限定厚度之層的溶液達成。
聚合物C1、C2、P1a’、P1b’、P1c’、P2a’、P2b’及P2c’以如表2所述般之層厚旋塗於玻璃載體上。層厚係藉以針刮磨聚合物層而測得,刮麼係向下延伸至玻璃基板。刮麼深度及因此所得之聚合物層厚度隨之於至少兩個點借助AFM(原子力顯微鏡)測量兩次,且形成平均值(表3)。若為本發明聚合物P1’及P2’,則聚合物膜係藉由於180℃加熱一小時加以乾燥,以使該膜交聯。若為對照聚合物C1及C2,則聚合物膜係藉著於180℃加熱10分鐘加以乾燥。所有聚合物膜接著皆於旋塗器(旋轉速度1000 rpm)上以甲苯洗滌一分鐘,薄膜再次藉著於180℃加熱10分鐘加以乾燥,而移除溶劑。隨之再次如前文所述般測量層厚,以確認層厚是否改變(表3)。若層厚未減少,則聚合物不可溶,且因此係適當地交聯。
結果顯示本發明聚合物之交聯實質上為最大量。交聯基團比例愈高,交聯後之聚合物愈不可溶。若為20 nm之小值層厚,則聚合物中可交聯單體比例僅10%即可使該層適當地交聯而不被洗出。保留有95%原先施加之層厚(P1’),相對於非可交聯聚合物(C1)的20%。若層厚為80 nm,聚合物中比例為10%之可交聯單體單元已展現明顯改善。洗滌之後,保留約88%之交聯聚合物(P2a’)層厚,而非對應非可交聯聚合物(C2)的6%。若聚合物中有20%之可交聯單體單元,則保留>90%之原先施加層厚(P2b’,P2c’)。因此若為本發明可交聯聚合物,則可控制層厚。
Claims (11)
- 一種製備交聯聚合物之方法,其特徵為其係包含以下步驟:(a)提供含有醛基之聚合物;(b)將該醛基轉化成乙烯基或烯基;及(c)使該聚合物交聯,其中該聚合物包含基於存在聚合物中作為結構單元之所有共聚單體為100mol%之1至30mol%的至少一種下式(I)之結構單元:
- 如申請專利範圍第1項之方法,其中Ar‘係為選自以 下之經取代或未經取代之單元:苯基、聯苯基、聯三苯基、1,1':3',1"-聯三苯-2'-基、萘基、蒽基、聯萘基、菲基、二氫菲基、芘基、二氫芘基、基、苝基、稠四苯基、稠五苯基、苯並[a]芘基、茀基、茚基、茚並茀基、螺聯茀基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、四唑基、呋喃基、噻吩基、硒吩基、唑基、異唑基、1,2-噻唑基、1,3-噻唑基、1,2,3-二唑基、1,2,4-二唑基、1,2,5-二唑基、1,3,4-二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、吡啶基、嗒基、嘧啶基、吡基、1,3,5-三基、1,2,4-三基、1,2,3-三基、1,2,4,5-四基、1,2,3,4-四基、1,2,3,5-四基、吲哚基、異吲哚基、吲基、吲唑基、苯並咪唑基、苯並三唑基、嘌呤基、萘並咪唑基、菲並咪唑基、吡啶並咪唑基、吡並咪唑基、喹啉並咪唑基、苯並唑基、萘並唑基、蒽並咪唑基、啡並唑基、異唑基、苯並噻唑基、苯並呋喃基、異苯並呋喃基、二苯並呋喃基、喹啉基、異喹啉基、喋啶基、苯並-5,6-喹啉基、苯並-6,7-喹啉基、苯並-7,8-喹啉基、苯並異喹啉基、吖啶基、啡噻基、啡基、苯並嗒基、苯並嘧啶基、喹啉基、啡基、啶基、氮雜咔唑基、苯並咔啉基、啡啶基、啡啉基、噻吩並[2,3b]噻吩基、噻吩並[3,2b]噻吩基、二噻吩並噻吩基、異苯並噻吩基、二苯並噻吩基及苯並噻二唑噻吩基。
- 如申請專利範圍第1項之方法,其中式(I)結構單元係為下式(II)之結構單元:
- 如申請專利範圍第1或3項之方法,其中式(I)中Ar或式(II)中Ar1、Ar2、Ar4及Ar5係為選自以下之經取代或未經取代之單元:4,5-二氫伸芘基、4,5,9,10-四氫伸茀基、9,9‘-螺伸聯茀基、伸茀基、伸菲基、9,10-二氫伸菲基、5,7-二氫伸二苯並呯基、順式-伸茚並茀基、反式-伸茚並茀基、伸苯基、伸噻吩基、伸苯並蒽基、伸咔唑基、伸苯並咪唑基、伸呯基及伸三基。
- 如申請專利範圍第1項之方法,其中該其他結構單 元係為式(I)及/或(II)中來自Ar及Ar'之代表者不包含醛基之結構單元。
- 如申請專利範圍第1或3項之方法,其中式(I)中Ar‘或式(II)中Ar3及/或Ar6係含有醛基。
- 如申請專利範圍第3項之方法,其中式(II)結構單元係選自以下結構單元:
- 一種交聯聚合物,其特徵為其可藉由如申請專利範圍第1至7項中任一項之方法製得。
- 一種如申請專利範圍第8項之交聯聚合物於電子裝置中的用途。
- 一種有機電子裝置,其特徵為其包含如申請專利範圍第8項之交聯聚合物。
- 如申請專利範圍第10項之有機電子裝置,其中其係為有機或聚合有機電致發光裝置(OLED,PLED)、有機積體電路(O-IC)、有機場效電晶體(OFET)、有機薄膜電晶體(OTFT)、有機太陽能電池(O-SC)、有機雷射二極體(O-雷射)、有機光伏打(OPV)元件或裝置 或有機感光體(OPC)。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102009010713A DE102009010713A1 (de) | 2009-02-27 | 2009-02-27 | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
DE200910059985 DE102009059985A1 (de) | 2009-12-22 | 2009-12-22 | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201100459A TW201100459A (en) | 2011-01-01 |
TWI534172B true TWI534172B (zh) | 2016-05-21 |
Family
ID=42016981
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW099105323A TWI534172B (zh) | 2009-02-27 | 2010-02-24 | 含有醛基團之聚合物,此聚合物的反應及交聯,交聯聚合物,及含有此聚合物之電致發光裝置 |
Country Status (7)
Country | Link |
---|---|
US (2) | US9156939B2 (zh) |
EP (1) | EP2401316B1 (zh) |
JP (1) | JP5670353B2 (zh) |
KR (1) | KR101732199B1 (zh) |
CN (2) | CN102333809A (zh) |
TW (1) | TWI534172B (zh) |
WO (1) | WO2010097155A1 (zh) |
Families Citing this family (79)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013062605A1 (en) * | 2011-03-28 | 2013-05-02 | Hitachi Chemical Research, Inc. | Network conjugated polymers with enhanced solubility |
KR102008034B1 (ko) | 2011-07-11 | 2019-08-06 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 화합물 |
GB201223369D0 (en) * | 2012-12-24 | 2013-02-06 | Cambridge Display Tech Ltd | Polymer and device |
WO2013156125A1 (de) | 2012-04-17 | 2013-10-24 | Merck Patent Gmbh | Vernetzbare sowie vernetzte polymere, verfahren zu deren herstellung sowie deren verwendung |
CN104447566A (zh) * | 2013-09-13 | 2015-03-25 | 沈阳工业大学 | N1联苯相联的菲并咪唑化合物及其制备方法与应用 |
US10734587B2 (en) | 2014-03-13 | 2020-08-04 | Merck Patent Gmbh | Formulations of luminescent compounds |
DE102014008722B4 (de) | 2014-06-18 | 2024-08-22 | Merck Patent Gmbh | Zusammensetzungen für elektronische Vorrichtungen, Formulierung diese enthaltend, Verwendung der Zusammensetzung, Verwendung der Formulierung sowie organische elektronische Vorrichtung enthaltend die Zusammensetzung |
EP3026094B1 (en) | 2014-11-28 | 2017-07-19 | Basf Se | Novel materials for the photo-crosslinking of conjugated polymers for application in organic optoelectronics |
EP3026093B1 (en) | 2014-11-28 | 2017-09-27 | Basf Se | Novel materials for the thermal and photochemical solubility switch of conjugated polymers for application in organic electronics |
CN115838341A (zh) | 2014-12-12 | 2023-03-24 | 默克专利有限公司 | 具有可溶性基团的有机化合物 |
KR102433462B1 (ko) | 2014-12-30 | 2022-08-17 | 메르크 파텐트 게엠베하 | 적어도 하나의 폴리머 및 적어도 하나의 염을 포함하는 조성물 및 이 조성물을 포함하는 전계발광 디바이스 |
US10651388B2 (en) | 2014-12-30 | 2020-05-12 | Merck Patent Gmbh | Compositions comprising at least one polymer and at least one metal complex and to electroluminescent devices containing said compositions |
WO2016184540A1 (en) | 2015-05-18 | 2016-11-24 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
JP6596918B2 (ja) * | 2015-05-19 | 2019-10-30 | 住友化学株式会社 | 発光素子 |
WO2016188609A1 (en) | 2015-05-22 | 2016-12-01 | Merck Patent Gmbh | Formulation containing an organic semiconductor and a metal complex |
FR3041350B1 (fr) * | 2015-09-21 | 2019-05-10 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Electrolyte solide pour generateur electrochimique |
US11005044B2 (en) * | 2015-10-06 | 2021-05-11 | Sumitomo Chemical Company, Limited | Light emitting device |
JP6783121B2 (ja) * | 2015-12-24 | 2020-11-11 | 群栄化学工業株式会社 | アリル基含有樹脂、その製造方法、樹脂ワニスおよび積層板の製造方法 |
TWI745395B (zh) | 2016-07-08 | 2021-11-11 | 德商麥克專利有限公司 | 有機電致發光裝置用之材料 |
WO2018054798A1 (de) | 2016-09-21 | 2018-03-29 | Merck Patent Gmbh | Binukleare metallkomplexe für den einsatz als emitter in organischen elektrolumineszenzvorrichtungen |
KR102654996B1 (ko) | 2016-10-06 | 2024-04-05 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 재료 |
WO2018069196A1 (de) | 2016-10-12 | 2018-04-19 | Merck Patent Gmbh | Binukleare metallkomplexe sowie elektronische vorrichtungen, insbesondere organische elektrolumineszenzvorrichtungen, enthaltend diese metallkomplexe |
WO2018069197A1 (de) | 2016-10-12 | 2018-04-19 | Merck Patent Gmbh | Metallkomplexe |
KR102472249B1 (ko) | 2016-10-13 | 2022-11-29 | 메르크 파텐트 게엠베하 | 금속 착물 |
TWI781123B (zh) | 2016-11-25 | 2022-10-21 | 德商麥克專利有限公司 | 用於有機電激發光裝置之材料 |
WO2018095888A1 (en) | 2016-11-25 | 2018-05-31 | Merck Patent Gmbh | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
US20190296242A1 (en) | 2016-11-30 | 2019-09-26 | Merck Patent Gmbh | Polymers with asymmetric repeating units |
CN109996828A (zh) | 2016-12-22 | 2019-07-09 | 默克专利有限公司 | 用于电子器件的材料 |
JP7114596B2 (ja) | 2016-12-22 | 2022-08-08 | メルク パテント ゲーエムベーハー | 少なくとも2種の有機機能性化合物を含む混合物 |
CN110177855A (zh) | 2017-01-23 | 2019-08-27 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TW201920343A (zh) | 2017-06-21 | 2019-06-01 | 德商麥克專利有限公司 | 電子裝置用材料 |
TWI786143B (zh) | 2017-07-03 | 2022-12-11 | 德商麥克專利有限公司 | 有機電致發光裝置及其產製方法 |
CN108675975A (zh) | 2017-10-17 | 2018-10-19 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TWI838352B (zh) | 2017-11-24 | 2024-04-11 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
TWI820057B (zh) | 2017-11-24 | 2023-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
CN108084407B (zh) * | 2017-12-13 | 2019-12-03 | 华南协同创新研究院 | 含9,9,10,10-四氧-噻蒽七元稠环单元的聚合物及其制备方法与应用 |
TW201938761A (zh) | 2018-03-06 | 2019-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
TWI802656B (zh) | 2018-03-06 | 2023-05-21 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
WO2019224134A1 (en) | 2018-05-23 | 2019-11-28 | Merck Patent Gmbh | Semiconducting nanoparticle |
US20210198566A1 (en) | 2018-05-24 | 2021-07-01 | Merck Patent Gmbh | Formulation |
TW202028301A (zh) | 2018-07-11 | 2020-08-01 | 德商麥克專利有限公司 | 含有高度分枝聚合物之調合物、高度分枝聚合物、及含有此高度分枝聚合物的電光學裝置 |
JP6866333B2 (ja) | 2018-08-16 | 2021-04-28 | エルジー・ケム・リミテッド | 4又は5位に芳香族アミノ基が置換したフルオレン誘導体を繰り返し単位として主鎖に含むポリマー、その正孔輸送材料としての使用、並びにそれを含む有機電子デバイス |
EP3844243B1 (en) | 2018-08-28 | 2022-06-22 | Merck Patent GmbH | Materials for organic electroluminescent devices |
TWI837167B (zh) | 2018-08-28 | 2024-04-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
TWI823993B (zh) | 2018-08-28 | 2023-12-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
GB201815338D0 (en) * | 2018-09-20 | 2018-11-07 | Sumitomo Chemical Co | Light-emitting particle |
WO2020078843A1 (en) | 2018-10-15 | 2020-04-23 | Merck Patent Gmbh | Nanoparticle |
EP3877369A1 (de) | 2018-11-05 | 2021-09-15 | Merck Patent GmbH | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
KR20210089199A (ko) | 2018-11-07 | 2021-07-15 | 메르크 파텐트 게엠베하 | 아민기 함유 반복 단위를 갖는 폴리머 |
WO2020099284A1 (en) | 2018-11-14 | 2020-05-22 | Merck Patent Gmbh | Nanoparticle |
JP7330018B2 (ja) * | 2018-12-06 | 2023-08-21 | 住友化学株式会社 | 高分子化合物の製造方法 |
US11370879B2 (en) | 2018-12-14 | 2022-06-28 | International Business Machines Corporation | Solution-processable indenofluorenes and methods to generate solution-processable indenofluorenes |
KR20210104121A (ko) | 2018-12-20 | 2021-08-24 | 메르크 파텐트 게엠베하 | 표면 개질된 반도체 발광 나노입자 및 이를 제조하는 방법 |
TW202035345A (zh) | 2019-01-17 | 2020-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
WO2020156969A1 (en) | 2019-01-29 | 2020-08-06 | Merck Patent Gmbh | Composition |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
TW202110935A (zh) | 2019-04-16 | 2021-03-16 | 德商麥克專利有限公司 | 含有可交聯聚合物之調配物 |
EP3959287A1 (en) | 2019-04-26 | 2022-03-02 | Merck Patent GmbH | Nanoparticle |
CN111875551B (zh) * | 2019-09-02 | 2022-04-15 | 广东聚华印刷显示技术有限公司 | 有机化合物、电子器件及相应的制备方法 |
TW202136471A (zh) | 2019-12-17 | 2021-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置用的材料 |
US20230157171A1 (en) | 2020-03-26 | 2023-05-18 | Merck Patent Gmbh | Cyclic compounds for organic electroluminescent devices |
EP4132939B1 (de) | 2020-04-06 | 2024-01-31 | Merck Patent GmbH | Polycyclische verbindungen für organische elektrolumineszenzvorrichtungen |
US20230312612A1 (en) | 2020-06-29 | 2023-10-05 | Merck Patent Gmbh | Heteroaromatic compounds for organic electroluminescent devices |
WO2022002771A1 (de) | 2020-06-29 | 2022-01-06 | Merck Patent Gmbh | Heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
KR20230043106A (ko) | 2020-07-22 | 2023-03-30 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
KR20230088748A (ko) | 2020-10-16 | 2023-06-20 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 헤테로원자를 포함하는 화합물 |
KR20230088415A (ko) | 2020-10-16 | 2023-06-19 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 복소환 화합물 |
US20240101560A1 (en) | 2020-12-18 | 2024-03-28 | Merck Patent Gmbh | Nitrogenous heteroaromatic compounds for organic electroluminescent devices |
KR20230122093A (ko) | 2020-12-18 | 2023-08-22 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 질소 함유 화합물 |
CN112679685B (zh) * | 2021-01-06 | 2021-09-28 | 上海交通大学 | 一种基于蒽单元的共轭有机框架材料cof-ta及其制备方法 |
CN112851895B (zh) * | 2021-01-06 | 2022-03-15 | 上海交通大学 | 一种基于薁的二维共价有机框架的合成方法及其在电化学二氧化氮传感器中的应用 |
WO2022214506A1 (en) | 2021-04-09 | 2022-10-13 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR20240127395A (ko) | 2021-12-21 | 2024-08-22 | 메르크 파텐트 게엠베하 | 전자 디바이스 |
WO2023117835A1 (en) | 2021-12-21 | 2023-06-29 | Merck Patent Gmbh | Electronic devices |
TW202340423A (zh) | 2022-01-20 | 2023-10-16 | 德商麥克專利有限公司 | 具有混合主體系統之有機電元件 |
CN118647622A (zh) | 2022-02-23 | 2024-09-13 | 默克专利有限公司 | 用于有机电致发光器件的芳族杂环 |
WO2023161167A1 (de) | 2022-02-23 | 2023-08-31 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2023213759A1 (de) | 2022-05-04 | 2023-11-09 | Merck Patent Gmbh | Polymere enthaltend speziell substituierte triarylamin-einheiten sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
WO2024115426A1 (de) | 2022-12-01 | 2024-06-06 | Merck Patent Gmbh | Polymere enthaltend spirotruxenderivate als wiederholungseinheit sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL9000101A (nl) | 1990-01-16 | 1991-08-16 | Dmv Campina Bv | Werkwijze voor bereiden van ijs-produkten. |
DE4325885A1 (de) | 1993-08-02 | 1995-02-09 | Basf Ag | Elektrolumineszierende Anordnung |
EP1801181B1 (en) | 1994-12-28 | 2011-12-28 | Cambridge Display Technology Limited | Polymers for use in optical devices |
GB0104177D0 (en) | 2001-02-20 | 2001-04-11 | Isis Innovation | Aryl-aryl dendrimers |
DE10109027A1 (de) | 2001-02-24 | 2002-09-05 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
JP4438042B2 (ja) | 2001-03-08 | 2010-03-24 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
WO2002072714A1 (de) | 2001-03-10 | 2002-09-19 | Covion Organic Semiconductors Gmbh | Lösung und dispersionen organischer halbleiter |
WO2002077060A1 (de) | 2001-03-24 | 2002-10-03 | Covion Organic Semiconductors Gmbh | Konjugierte polymere enthaltend spirobifluoren-einheiten und fluoren-einheiten und deren verwendung |
DE10116962A1 (de) | 2001-04-05 | 2002-10-10 | Covion Organic Semiconductors | Rhodium- und Iridium-Komplexe |
DE10141624A1 (de) | 2001-08-24 | 2003-03-06 | Covion Organic Semiconductors | Lösungen polymerer Halbleiter |
DE10159946A1 (de) | 2001-12-06 | 2003-06-18 | Covion Organic Semiconductors | Prozess zur Herstellung von Aryl-Aryl gekoppelten Verbindungen |
JP4218340B2 (ja) | 2001-12-28 | 2009-02-04 | 住友化学株式会社 | 高分子化合物の製造方法 |
AU2002367422A1 (en) | 2001-12-28 | 2003-07-24 | Sumitomo Chemical Company, Limited | Process for production of high-molecular compounds |
DE10238903A1 (de) | 2002-08-24 | 2004-03-04 | Covion Organic Semiconductors Gmbh | Rhodium- und Iridium-Komplexe |
DE10249723A1 (de) | 2002-10-25 | 2004-05-06 | Covion Organic Semiconductors Gmbh | Arylamin-Einheiten enthaltende konjugierte Polymere, deren Darstellung und Verwendung |
US6982179B2 (en) | 2002-11-15 | 2006-01-03 | University Display Corporation | Structure and method of fabricating organic devices |
DE10304819A1 (de) | 2003-02-06 | 2004-08-19 | Covion Organic Semiconductors Gmbh | Carbazol-enthaltende konjugierte Polymere und Blends, deren Darstellung und Verwendung |
DE10328627A1 (de) | 2003-06-26 | 2005-02-17 | Covion Organic Semiconductors Gmbh | Neue Materialien für die Elektrolumineszenz |
DE10337346A1 (de) | 2003-08-12 | 2005-03-31 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere enthaltend Dihydrophenanthren-Einheiten und deren Verwendung |
DE10337077A1 (de) | 2003-08-12 | 2005-03-10 | Covion Organic Semiconductors | Konjugierte Copolymere, deren Darstellung und Verwendung |
JPWO2005026144A1 (ja) | 2003-09-12 | 2006-11-16 | 住友化学株式会社 | デンドリマー化合物及びそれを用いた有機発光素子 |
EP2366752B1 (de) | 2003-10-22 | 2016-07-20 | Merck Patent GmbH | Neue materialien für die elektrolumineszenz und deren verwendung |
DE10350606A1 (de) | 2003-10-30 | 2005-06-09 | Covion Organic Semiconductors Gmbh | Verfahren zur Herstellung heteroleptischer, ortho-metallierter Organometall-Verbindungen |
WO2005049548A1 (en) | 2003-11-17 | 2005-06-02 | Sumitomo Chemical Company, Limited | Crosslinkable substituted fluorene compounds |
TW201219350A (en) | 2003-11-17 | 2012-05-16 | Sumitomo Chemical Co | Crosslinkable arylamine compounds |
DE102004009355A1 (de) | 2004-02-26 | 2005-09-15 | Covion Organic Semiconductors Gmbh | Verfahren zur Vernetzung organischer Halbleiter |
US8114316B2 (en) * | 2004-08-21 | 2012-02-14 | Merck Patent Gmbh | Monomers, oligomers and polymers of thieno[2,3-b]thiophene |
GB0423528D0 (en) * | 2004-10-22 | 2004-11-24 | Cambridge Display Tech Ltd | Monomer for making a crosslinked polymer |
JP2006152014A (ja) | 2004-11-25 | 2006-06-15 | Sumitomo Chemical Co Ltd | 高分子錯体化合物およびそれを用いた高分子発光素子 |
US8440324B2 (en) | 2005-12-27 | 2013-05-14 | E I Du Pont De Nemours And Company | Compositions comprising novel copolymers and electronic devices made with such compositions |
EP2069419A2 (en) | 2006-08-24 | 2009-06-17 | E.I. Du Pont De Nemours And Company | Hole transport polymers |
JP5625272B2 (ja) | 2008-07-29 | 2014-11-19 | 住友化学株式会社 | 1,3−ジエンを含む化合物及びその製造方法 |
EP2373759B1 (en) | 2008-12-05 | 2015-11-11 | General Electric Company | Functionalized polyfluorenes for use in optoelectronic devices |
US8512879B2 (en) * | 2009-11-10 | 2013-08-20 | General Electric Company | Polymer for optoelectronic device |
-
2010
- 2010-02-01 US US13/203,506 patent/US9156939B2/en active Active
- 2010-02-01 CN CN2010800096521A patent/CN102333809A/zh active Pending
- 2010-02-01 JP JP2011551425A patent/JP5670353B2/ja active Active
- 2010-02-01 EP EP10703414.2A patent/EP2401316B1/de active Active
- 2010-02-01 WO PCT/EP2010/000590 patent/WO2010097155A1/de active Application Filing
- 2010-02-01 CN CN201610389995.4A patent/CN106084187A/zh active Pending
- 2010-02-01 KR KR1020117022536A patent/KR101732199B1/ko active IP Right Grant
- 2010-02-24 TW TW099105323A patent/TWI534172B/zh not_active IP Right Cessation
-
2015
- 2015-07-20 US US14/803,398 patent/US9728724B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
JP5670353B2 (ja) | 2015-02-18 |
WO2010097155A1 (de) | 2010-09-02 |
EP2401316A1 (de) | 2012-01-04 |
CN102333809A (zh) | 2012-01-25 |
US20110303876A1 (en) | 2011-12-15 |
US9156939B2 (en) | 2015-10-13 |
JP2012519214A (ja) | 2012-08-23 |
KR20110137325A (ko) | 2011-12-22 |
TW201100459A (en) | 2011-01-01 |
US9728724B2 (en) | 2017-08-08 |
KR101732199B1 (ko) | 2017-05-02 |
US20150325793A1 (en) | 2015-11-12 |
EP2401316B1 (de) | 2017-05-24 |
CN106084187A (zh) | 2016-11-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI534172B (zh) | 含有醛基團之聚合物,此聚合物的反應及交聯,交聯聚合物,及含有此聚合物之電致發光裝置 | |
JP5726905B2 (ja) | エレクトロルミネッセンスポリマー、その調製方法、およびその使用 | |
JP5714488B2 (ja) | エレクトロルミネセンスポリマー、その調製方法およびその使用 | |
KR102055118B1 (ko) | 치환된 올리고트리아릴아민 단위를 함유하는 중합체, 및 이들 중합체를 포함하는 전자발광 소자 | |
JP6422861B2 (ja) | 2,7−ピレン構造単位を含むポリマー | |
JP5221537B2 (ja) | 1,4−ビス(2−チエニルビニル)ベンゼン誘導体及びその使用 | |
TW201114797A (en) | Polymers which contain substituted indenofluorene derivatives as structural unit, process for the preparation thereof, and the use thereof | |
TW201127867A (en) | Polymers comprising substituted anthracenyl units, blends comprising these polymers, and devices comprising these polymers or blends | |
JP5866355B2 (ja) | 置換ベンゾチオフェン単位を含むポリマー、これらポリマーを含むブレンドおよびこれらポリマーまたはブレンドを含む素子 | |
KR101676510B1 (ko) | 가교가능한 및 가교 중합체, 이의 제조 방법 및 이의 용도 | |
KR101660991B1 (ko) | 저 다분산성을 갖는 신규 중합체 | |
Vanjinathan et al. | Design, synthesis, photophysical, and electrochemical properties of DCM‐based conjugated polymers for light‐emitting devices | |
JP2015508119A (ja) | ジベンゾシクロヘプタン構造単位を含むポリマー | |
KR20180006423A (ko) | 금속 착물 및 이들 금속 착물을 포함하는 전계발광 소자 | |
JP7159874B2 (ja) | 枝分かれポリマーの製造方法、枝分かれポリマー、及び有機エレクトロニクス素子 | |
DE102009059985A1 (de) | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Annulment or lapse of patent due to non-payment of fees |