Electroactive polymeric arylenes and intermediates useful for making such polymers are disclosed. The present invention also provides electroactive compositions comprising the electroactive polymeric arylenes, organic electronic devices which comprise these polymers and compositions, and methods of
Electroactive polymeric arylenes and intermediates useful for making such polymers are disclosed. The present invention also provides electroactive compositions comprising the electroactive polymeric arylenes, organic electronic devices which comprise these polymers and compositions, and methods of fabricating these devices.
대표청구항▼
What is claimed is: 1. An electroactive polymeric arylene comprising: a conjugated internal region, and end capping groups; wherein the conjugated internal region comprises three or more arylene units, each of said arylene units being covalently bonded to two adjacent arylene units, or to an adjace
What is claimed is: 1. An electroactive polymeric arylene comprising: a conjugated internal region, and end capping groups; wherein the conjugated internal region comprises three or more arylene units, each of said arylene units being covalently bonded to two adjacent arylene units, or to an adjacent arylene unit and to an end capping group; wherein one or more of the arylene units of the internal region have the structure of Formula I wherein Ar1 is a phenylene or naphthylene group arylene that is unsubstituted or substituted with one or more groups selected from alkyl, alkenyl, alkoxy, fluoro, aryl, fluoroalkyl, heteroalkyl, heteroaryl, and hydrocarbyl containing one or more S, N, O, P, or Si atoms; wherein a is 1 or 2; wherein each Ey is independently selected from groups having the structures of Formulas II and III wherein X is O, S, or NR1, where R1 is alkyl, aryl, heteroaryl, or heteroalkyl; wherein each R2 is independently alkyl, alkoxy, fluoro, aryl, fluoroalkyl, heteroalkyl, or heteroaryl; wherein b is 0, 1, or 2; wherein Ar2 is a carbocyclic aryl group that is unsubstituted or substituted with one or more substituents selected from alkyl, alkenyl, alkoxy, fluoro, aryl, fluoroalkyl, heteroalkyl, heteroaryl, alkyloxadiazolyl, aryloxadiazolyl, alkyltriazolyl, aryltriazolyl, and hydrocarbyl containing one or more S, N, O, P, or Si atoms; wherein the end capping groups are each independently selected from carbocyclic aryl, heteroaryl, and tertiary aromatic amino aryl groups that are electrochemically stable; wherein each end capping group is conjugated to the conjugated internal region; and wherein each end capping group is unsubstitued or substituted with one or more groups selected from alkyl, alkenyl, alkoxy, aryl, fluoroalkyl, heteroalkyl, heteroaryl, and hydrocarbyl containing one or more S, N, O, P, or Si atoms. 2. The electroactive polymeric arylene of claim 1 further comprising a soft segment; wherein each end capping group is conjugated to the conjugated internal region or bonded to the soft segment; and wherein the soft segment is bonded to one or more arylene units of the internal region, or to an end capping group, or to an arylene unit of the internal region and to an end capping group. 3. The electroactive polymeric arylene of claim 1 wherein each Ar2 is independently selected from groups of Formulas XLIV-LIV wherein R3 is independently in each case hydrogen, C1-30 alkyl, C1-30 alkenyl, C6-20 aryl, C3-20 heteroaryl, or C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; wherein one or more of the aromatic rings in the groups of Formulas XLIV-LIV are independently unsubstituted or substituted with one or more groups Rz; wherein Rz is independently in each case fluoro, C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C1-20 alkenyl, C6-20 aryl, C3-20 heteroaryl, C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; C3-30 alkyloxadiazolyl, C3-30 aryloxadiazolyl, C3-30 alkyltriazolyl, C3-30 aryltriazolyl; wherein X is O, S, or NR1; and wherein R1 is alkyl, aryl, heteroaryl, or heteroalkyl. 4. The electroactive polymeric arylene of claim 1 wherein the structure of Formula I is selected from the divalent groups of Formulas XI-XLIII wherein each of the groups of Formulas XI-XLIII is unsubstituted or substituted on one or more of the aromatic rings with one or more groups (Ry); wherein R3 is independently in each case hydrogen, C1-30 alkyl, C1-30 alkenyl, C6-20 aryl, C3-20 heteroaryl, or C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; and wherein Ry is independently in each case fluoro, C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C1-20 alkenyl, C6-20 aryl, C3-20 heteroaryl, or C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms. 5. The electroactive polymeric arylene of claim 1 wherein the electroactive polymeric arylene is a polymer of the Formula V wherein each EC is an end capping group independently selected from carbocyclic aryl, heteroaryl, and tertiary aromatic amino aryl groups that are electrochemically stable, and n is an integer in the range of 3 to 100,000. 6. The electroactive polymeric arylene of claim 5 wherein one or both of Ar2 and EC is substituted with one or more groups selected from fluoro, fluoroalkyl, and perfluoroalkyl, with the proviso that when EC is phenyl the fluoro group is not in the para position. 7. The electroactive polymeric arylene of claim 1 wherein the carbocyclic aryl end capping groups are each independently selected from phenyl, naphthyl, acenaphthyl, phenanthryl, anthracenyl, fluorenyl, 9-silafluorenyl, dihydrophenathrenyl, tetrahydropyrenyl, perylenyl, spirobisfluorenyl, fluoranthenyl, pyrenyl, rubrenyl, chrysenyl, biphenyl, and benzo[g,h,i]perylenyl; wherein the heteroaryl end capping groups are each independently selected from furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuryl, benzothiophenyl, indolyl, carbazoyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, benzothiadiazolyl, benzotriazinyl, phenazinyl, phenanthridinyl, acridinyl, indazolyl, and siloles; wherein the tertiary aromatic amino aryl end capping groups are each independently selected from monovalent aromatic ring radicals of tertiary aromatic amines selected from diarylanilines, alkylcarbazole, arylcarbazole, tetraarylediamines, N,N,N'N'-tetraarylbenzidines, N,N,N',N'-tetraaryl-1,4-phenylenediamines, N,N,N'N'-tetraryl-2,7-diaminofluorenes, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine, N,N'-bis(3-naphthalen-2-yl)-N,N'-bis(phenyl)benzidine, 1,4-bis(carbazolyl)biphenyl, peraryltriamines, starburst amines, 4,4',4"-tris(N,N-diarylamino)triphenylamines, 1,3,5-tris(4-diarylaminophenyl)benzenes, 4,4',4"-tris(N,N-diphenylamino)triphenylamine, 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine; 1,3,5-Tris(4-diphenylaminophenyl)benzenes, dendridic amines, and spiro amines; and wherein the end capping groups are unsubstituted or substituted with one or more groups selected from the group consisting of C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C1-20 alkenyl, C6-20 aryl, C3-20 heteroaryl, C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms, C3-30 alkyloxadiazolyl, C3-30 aryloxadiazolyl, C3-30 alkyltriazolyl, and C3-30 aryltriazolyl. 8. The electroactive polymeric arylene of claim 1 wherein the structure of Formula I is selected from the divalent groups of Formulas XI-XLIII wherein each of the groups of Formulas XI-XLIII is unsubstituted or substituted on one or more of the aromatic rings with one or more groups (Ry); wherein Ry is independently in each case fluoro, C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C1-20 alkenyl, C6-20 aryl, C3-20 heteroaryl, or C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; wherein R3 is independently in each case hydrogen, C1-30 alkyl, C1-30 alkenyl, C6-20 aryl, C3-20 heteroaryl, or C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; wherein each Ar2 is independently selected from groups of Formulas XLIV-LIV wherein one or more of the aromatic rings in the groups of Formulas XLIV-LIV are independently unsubstituted or substituted with one or more groups Rz; wherein Rz is independently in each case fluoro, C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C1-20 alkenyl, C6-20 aryl, C3-20 heteroaryl, C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; C3-30 alkyloxadiazolyl, C3-30 aryloxadiazolyl, C3-30 alkyltriazolyl, C3-30 aryltriazolyl; wherein X is O, S, or NR1; wherein R1 is alkyl, aryl, heteroaryl, or heteroalkyl; wherein R3 is independently in each case hydrogen, C1-30 alkyl, C1-30 alkenyl, C6-20 aryl, C3-20 heteroaryl, or C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; wherein the carbocyclic aryl end capping groups are each independently selected from phenyl, naphthyl, acenaphthyl, phenanthryl, anthracenyl, fluorenyl, 9-silafluorenyl, dihydrophenathrenyl, tetrahydropyrenyl, perylenyl, spirobisfluorenyl, fluoranthenyl, pyrenyl, rubrenyl, chrysenyl, biphenyl, and benzo[g,h,i]perylenyl; wherein the heteroaryl end capping groups are each independently selected from furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, isothiazolyl, pyridinyl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzofuryl, benzothiophenyl, indolyl, carbazoyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, benzothiadiazolyl, benzotriazinyl, phenazinyl, phenanthridinyl, acridinyl, indazolyl, and siloles; wherein the tertiary aromatic amino aryl end capping groups are each independently selected from monovalent aromatic ring radicals of tertiary aromatic amines selected from diarylanilines, alkylcarbazole, arylcarbazole, tetraarylediamines, N,N,N'N'-tetraarylbenzidines, N,N,N',N'-tetraaryl-1,4-phenylenediamines, N,N,N'N'-tetraryl-2,7-diaminofluorenes, N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine, N,N'-bis(3-naphthalen-2-yl)-N,N'-bis(phenyl)benzidine, 1,4-bis(carbazolyl)biphenyl, peraryltriamines, starburst amines, 4,4',4"-tris(N,N-diarylamino)triphenylamines, 1,3,5-tris(4-diarylaminophenyl)benzenes, 4,4',4"-tris(N,N-diphenylamino)triphenylamine, 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine; 1,3,5-Tris(4-diphenylaminophenyl)benzenes, dendridic amines, and spiro amines; and wherein the end capping groups are unsubstituted or substituted with one or more groups selected from the group consisting of C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C1-20 alkenyl, C6-20 aryl, C3-20 heteroaryl, C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms, C3-30 alkyloxadiazolyl, C3-30 aryloxadiazolyl, C3-30 alkyltriazolyl, and C3-30 aryltriazolyl. 9. The electroactive polymeric arylene of claim 1 wherein the end capping groups are each independently selected from the group of Formulas LXVIII-LXXXVII wherein R3 is independently in each case hydrogen, C1-30 alkyl, C1-30 alkenyl, C6-20 aryl, C3-20 heteroaryl, or C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms, and wherein any of the aromatic or aliphatic rings can be independently substituted one or more times with fluoro, C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C1-20 alkenyl, C6-20 aryl, C3-20 heteroaryl, or C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms. 10. The electroactive polymeric arylene of claim 1 wherein the electroactive polymeric arylene is a copolymer; wherein one or more of the arylene units are comonomer units independently selected from carbocyclic arylene, heteroarylene, and tertiary aromatic amino arylene; wherein the comonomer units are conjugated with Ar1; and wherein the comonomer units are unsubstituted or substituted with one or more groups independently selected from alkyl, alkenyl, alkoxy, fluoro, aryl, fluoroalkyl, heteroalkyl, heteroaryl, and hydrocarbyl containing one or more S, N, O, P, or Si atoms. 11. The electroactive polymeric arylene of claim 10 wherein the electroactive polymeric arylene is a copolymer of Formula VI, VII, or VIII wherein Ar3 and Ar4 are comonomer units, each independently selected from C6-20 carbocyclic arylenes, C3-20 heteroarylenes, and C18-60 tertiary aromatic amino arylenes; where Ar3 and Ar4 are unsubstituted or substituted with one or more substituents selected from alkyl, fluoro, fluoroalkyl, aryl, heteroaryl, and hydrocarbyl containing one or more S, N, O, P, or Si atoms; wherein m and n are integers in the range of 2 to 100,000; wherein EC are end capping groups which are the same or different and which are electrochemically stable carbocyclic aryl, heteroaryl, or tertiary aromatic amino aryl groups; and wherein the copolymer is a random, alternating, or block copolymer. 12. The electroactive polymeric arylene of claim 11 wherein the copolymer comprises a soft segment. 13. The electroactive polymeric arylene of claim 11 wherein one or more of Ar2, EC, Ar3, and Ar4 are substituted with one or more groups independently selected from fluoro, fluoroalkyl, and perfluoroalkyl with the proviso that when EC is phenyl the fluoro group is not in the para position. 14. The electroactive polymeric arylene of claim 11 wherein one or both of Ar3 and Ar4 are fluorenylene of Formula LXXXIX wherein R3 is independently in each case selected from hydrogen, C1-30 alkyl, C1-30 alkenyl, C6-20 aryl, C3-20 heteroaryl, and C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; wherein Ry is independently in each case selected from fluoro, C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C1-20 alkenyl, C6-20 aryl, C3-20 heteroaryl, and C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms; and wherein n is 0, 1, or 2. 15. The electroactive polymeric arylene of claim 11 wherein the electroactive polymeric arylene is an alternating or block copolymer. 16. The electroactive polymeric arylene of claim 11 wherein Ar3 and Ar4 are independently selected from phenylene group arylene and naphthalene group arylene; wherein each phenylene group arylene and naphthalene group arylene is independently unsubstituted or substituted with one or more substituents selected independently in each case from fluoro, C1-20 fluoroalkyl, C1-20 perfluoroalkyl, C1-20 alkyl, C6-20 aryl, C3-20 heteroaryl, and C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms. 17. The electroactive polymeric arylene of claim 11 wherein Ar3 and Ar4 are independently selected from condensed polycyclic arylene, heteroarylene, and tertiary aromatic amino arylene; wherein each condensed polycyclic arylene, heteroarylene, and tertiary aromatic amino arylene is independently unsubstituted or substituted with one or more substituents selected independently in each case from C1-20 alkyl, C6-20 aryl, C3-20 heteroaryl, and C1-30 hydrocarbyl containing one or more S, N, O, P, or Si atoms. 18. The electroactive polymeric arylene of claim 1 wherein the electroactive polymeric arylene remains amorphous at temperatures above its glass transition temperature. 19. The electroactive polymeric arylene of claim 1 wherein the electroactive polymeric arylene is light emitting; and wherein the color of the light emission is stable during thermal aging. 20. The electroactive polymeric arylene of claim 19 wherein the color is blue.
연구과제 타임라인
LOADING...
LOADING...
LOADING...
LOADING...
LOADING...
이 특허에 인용된 특허 (42)
Woo Edmund P. ; Shiang William R. ; Inbasekaran Michael ; Roof Gordon R., 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers.
Denisevich ; Jr. Peter (Fairfax CA) Schroeder Albert H. (Richmond CA) Kurkov Victor P. (San Rafael CA) Suzuki Shigeto (San Francisco CA), Carbazole-oxadiazole electroactive polymers.
Mercer Frank W. (Belmont CA) Lau Aldrich N. K. (Palo Alto CA) Vo Lanchi P. (San Jose CA), Compounds having oxadiazole and triazene moieties, crosslinkable polymers therefrom, and methods therefor.
Hsieh Bing R. (Webster NY) Johnson Gordon E. (Webster NY) Antoniadis Homer (Rochester NY) McGrane Kathleen M. (Webster NY) Stolka Milan (Fairport NY), Electroluminescent devices containing a conjugated polymer obtained via halogen precursor route chemistry.
Manoj Nirmal ; Ha T. Le ; Martin B. Wolk ; Erika Bellmann ; Fred McCormick, Electronically active primer layers for thermal patterning of materials for electronic devices.
Kim Chung Yup,KRX ; Cho Hyun Nam,KRX ; Kim Dong Young,KRX ; Kim Young Chul,KRX ; Lee Jun Young,KRX ; Kim Jai Kyeong,KRX, Fluorene-based alternating copolymers for electroluminescence element and electroluminescence element using such copoly.
Kim Chung Yup,KRX ; Cho Hyun Nam,KRX ; Kim Dong Young,KRX ; Kim Young Chul,KRX ; Lee Jun Young,KRX ; Kim Jai Kyeong,KRX, Fluorene-based alternating polymers containing acetylene group and electroluminescence element using the same.
Woo Edmund P. ; Inbasekaran Michael ; Shiang William R. ; Roof Gordon R. ; Bernius Mark T. ; Wu Weishi, Fluorene-containing polymers and compounds useful in the preparation thereof.
Chang Jeffrey C. ; Staral John S. ; Tolbert William A. ; Wolk Martin B. ; Jalbert Claire A. ; Chou Hsin-hsin, Laser addressable thermal transfer imaging element with an interlayer.
Bellmann, Erika; Bentsen, James G.; Hsu, Yong; Manoj, Nirmal; Wolk, Martin B., Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein.
Staral John S. (Woodbury MN) Tolbert William A. (Woodbury MN) Chou Hsin Hsin (Woodbury MN) Li Wu Shyong (Woodbury MN), Polarizing mass transfer donor element and method of transferring a polarizing mass transfer layer.
Staral John S. ; Jalbert Claire A. ; Tolbert William A. ; Wolk Martin B. ; Martens Allan R. ; Isberg Thomas A., Process and materials for imagewise placement of uniform spacers in flat panel displays.
Guehler Paul F. ; Isberg Thomas A. ; Mizuno Kazuhiko,JPX ; Noda Kazuki,JPX ; Padiyath Raghunath ; Pokorny Richard J. ; Staral John S. ; Chang Jeffrey C., Process for making active substrates for color displays.
Isberg Thomas A. ; Jalbert Claire A. ; Staral John S. ; Tolbert William A. ; Wolk Martin B., Process for preparing high resolution emissive arrays and corresponding articles.
Miller Robert Dennis ; Klaerner Gerrit ; Scott John Campbell, Thermally and/or photochemically crosslinked electroactive polymers in the manufacture of opto-electronic devices.
Lipton, Michael G.; Polyakov, Ilya; Zarrabi, Alireza; Hui, Otto; Biggs, Silmon James; Kridl, Thomas A.; Russell, Gordon; Heim, Jonathan R.; Hitchcock, Roger; Weaber, Chris A., Method of manufacturing electroactive polymer transducers for sensory feedback applications.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.