CA2344084A1 - Derives conjugues de polycarbazole utilises dans des diodes electroluminescentes organiques - Google Patents
Derives conjugues de polycarbazole utilises dans des diodes electroluminescentes organiques Download PDFInfo
- Publication number
- CA2344084A1 CA2344084A1 CA002344084A CA2344084A CA2344084A1 CA 2344084 A1 CA2344084 A1 CA 2344084A1 CA 002344084 A CA002344084 A CA 002344084A CA 2344084 A CA2344084 A CA 2344084A CA 2344084 A1 CA2344084 A1 CA 2344084A1
- Authority
- CA
- Canada
- Prior art keywords
- oled
- poly
- transport layer
- carbazole
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title 1
- 229920001088 polycarbazole Polymers 0.000 title 1
- -1 poly(ethyleneoxy) Polymers 0.000 claims abstract 9
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- 239000011149 active material Substances 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 5
- 150000001408 amides Chemical class 0.000 claims abstract 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 230000005525 hole transport Effects 0.000 claims 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 claims 3
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 claims 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 239000000178 monomer Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims 2
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical class N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 claims 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims 1
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000005264 aryl amine group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- FGGAOQTXQHKQOW-UHFFFAOYSA-N n,n-diphenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 FGGAOQTXQHKQOW-UHFFFAOYSA-N 0.000 claims 1
- 125000004957 naphthylene group Chemical group 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 1
- 150000004866 oxadiazoles Chemical class 0.000 claims 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 150000003217 pyrazoles Chemical class 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 claims 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims 1
- 150000004655 tetrazenes Chemical class 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 150000003918 triazines Chemical class 0.000 claims 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims 1
- 238000001228 spectrum Methods 0.000 abstract 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2344084A CA2344084C (fr) | 2001-04-12 | 2001-04-12 | Derives conjugues de polycarbazole utilises dans des diodes electroluminescentes organiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2344084A CA2344084C (fr) | 2001-04-12 | 2001-04-12 | Derives conjugues de polycarbazole utilises dans des diodes electroluminescentes organiques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2344084A1 true CA2344084A1 (fr) | 2002-10-12 |
| CA2344084C CA2344084C (fr) | 2011-07-19 |
Family
ID=4168831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2344084A Expired - Fee Related CA2344084C (fr) | 2001-04-12 | 2001-04-12 | Derives conjugues de polycarbazole utilises dans des diodes electroluminescentes organiques |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2344084C (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7655809B2 (en) | 2004-05-18 | 2010-02-02 | University Of Ottawa | Compounds comprising a linear series of five fused carbon rings, and preparation thereof |
| US7935836B2 (en) | 2004-05-18 | 2011-05-03 | Alexander Graham Fallis | Compounds comprising a linear series of five fused carbon rings, and preparation thereof |
| CN115073461A (zh) * | 2022-07-14 | 2022-09-20 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及其在有机发光元件中的应用 |
| CN115093414A (zh) * | 2022-07-14 | 2022-09-23 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及包含它的有机发光元件 |
| CN115417885A (zh) * | 2022-09-19 | 2022-12-02 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及其在有机发光元件中的应用 |
-
2001
- 2001-04-12 CA CA2344084A patent/CA2344084C/fr not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7655809B2 (en) | 2004-05-18 | 2010-02-02 | University Of Ottawa | Compounds comprising a linear series of five fused carbon rings, and preparation thereof |
| US7935836B2 (en) | 2004-05-18 | 2011-05-03 | Alexander Graham Fallis | Compounds comprising a linear series of five fused carbon rings, and preparation thereof |
| CN115073461A (zh) * | 2022-07-14 | 2022-09-20 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及其在有机发光元件中的应用 |
| CN115093414A (zh) * | 2022-07-14 | 2022-09-23 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及包含它的有机发光元件 |
| CN115073461B (zh) * | 2022-07-14 | 2024-01-02 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及其在有机发光元件中的应用 |
| CN115093414B (zh) * | 2022-07-14 | 2024-02-13 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及包含它的有机发光元件 |
| CN115417885A (zh) * | 2022-09-19 | 2022-12-02 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及其在有机发光元件中的应用 |
| CN115417885B (zh) * | 2022-09-19 | 2023-12-29 | 上海八亿时空先进材料有限公司 | 一种咔唑衍生物及其在有机发光元件中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2344084C (fr) | 2011-07-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6630254B2 (en) | Conjugated polycarbazole derivatives in Organic Light Emitting Diodes | |
| US10439147B2 (en) | Heterocyclic compounds and their use in electro-optical or opto-electronic devices | |
| US7887933B2 (en) | Electroluminescent materials and devices | |
| US9437828B2 (en) | Electroluminescent device using azomethine-lithium-complex as electron injection layer | |
| US20040247937A1 (en) | Organic electroluminescent devices with a doped co-host emitter | |
| US20040214036A1 (en) | Electron transport agents for organic electronic devices | |
| US20070107835A1 (en) | Ethynyl containing electron transport dyes and compositions | |
| KR20010062711A (ko) | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 | |
| KR20170134076A (ko) | 유기 화합물과 이를 이용한 발광다이오드 및 유기발광다이오드 표시장치 | |
| US7455917B2 (en) | Organic compound and organic light emitting device using the same | |
| US8642188B2 (en) | Phenanthroline compounds and electroluminescent devices using the same | |
| KR20130098227A (ko) | 유기 발광 소자 | |
| CA2344084A1 (fr) | Derives conjugues de polycarbazole utilises dans des diodes electroluminescentes organiques | |
| WO2008012581A2 (fr) | Revêtement de cathode | |
| KR20210032290A (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| US20100145050A1 (en) | Orthogonally fixed compounds for electrooptical applications | |
| KR102511680B1 (ko) | 유기 발광 소자 | |
| WO2009090423A1 (fr) | Substrat revêtu d'une barrière et dispositif électro-optique | |
| JP2000268975A (ja) | 有機エレクトロルミネッセンス素子 | |
| KR100827639B1 (ko) | 아민 화합물 및 이를 포함하는 유기 발광 다이오드 | |
| KR20210021762A (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| KR20210021761A (ko) | 화합물 및 이를 포함하는 유기 발광 소자 | |
| JP2002167579A (ja) | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160412 |