CA2002865A1 - Phthalimide compounds for forming amorphous layers by vacuum deposition - Google Patents
Phthalimide compounds for forming amorphous layers by vacuum depositionInfo
- Publication number
- CA2002865A1 CA2002865A1 CA 2002865 CA2002865A CA2002865A1 CA 2002865 A1 CA2002865 A1 CA 2002865A1 CA 2002865 CA2002865 CA 2002865 CA 2002865 A CA2002865 A CA 2002865A CA 2002865 A1 CA2002865 A1 CA 2002865A1
- Authority
- CA
- Canada
- Prior art keywords
- compounds
- groups
- phthalimide
- vacuum deposition
- phthalimide compounds
- 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.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
PHTHALIMIDE COMPOUNDS FOR FORMING
AMORPHOUS LAYERS BY VACUUM DEPOSITION
Abstract There are disclosed phthalimide compounds of the structure:
AMORPHOUS LAYERS BY VACUUM DEPOSITION
Abstract There are disclosed phthalimide compounds of the structure:
Description
20028G~
P~THALIMIDE COMPOUNDS FOR FORMING
AMORPHOUS LAYERS BY VACUUM DEPOSITION
Technical Field The present invention relates to new compounds that are useful in the preparation of layers of transparent materials which provide an optic function. The compounds are phthalimides that can be vacuum deposited to provide the transparent layer.
Back~round Art Transparent layers for optical tevices can serve a variety of optical functions. For example, the optical performance of a len~ can be improved by providing an antireflecting coating. Such a coating, for example, can improve the contrast of the lens in a variety of conditions. Such antireflecting coatings are made by depositing a layer or layers of material having predetermined indices of refraction in predetermined thicknesses to achieve the desired antireflective condition.
Processes wherein polymers or monomers are solvent coated on the support, suffer from many disadvantages. First, solution coating, whether it be of the polymer or the monomers, produces layers which are of less than desired uniformity for optical applications. Further, these processes inevitably leave residual solvent in the layer which is disadvantageous for long term storage or subsequent process steps. In addition, multiple layers are difficult if not impossible since the solvent used to coat the second layer often attacks the first layer or will not wet the surface of the first layer.
It is common to coat inorganic materials using vacuum coating techniques. Thi~ type of coating is capable of producing uniform coatings without solvents. Multiple layers are more easily achieved than with solvent coating. However, vacuum - .
. .
.. . . .
-, , -, :, - ' . . :, . - .
.
200286j~
coating is not possible with these organic polymeric materials. The organic polymers do not have sufficient vapor pressure to evaporate even under high vacuum conditions. If the temperature of the polymer is raised to increase the vapor pressure, the polymer decomposes.
Thus, the problem to be solved by the present invention is to provide ne~ compounds that can be vacuum coated to provide useful optical layers.
~i8closure of the Invention In accordance with the present invention, there are provided phthalimide compounds of the structure:
Rl-~- 0 wherein R and Rl are independently selected from the group consisting of nitro, foramido groups, carbamoyl groups and heterocyclic groups derived from amino or carboxyl groups.
The phthalimide compounds of the invention have the structure:
Rl ~ ~o -~
wherein R and Rl are independently selected from the group consisting of nitro, foramido groups, carbamoyl groups and heterocyclic groups derived from amino or carboxyl groups.
The parent amino and carboxyl compounds are ~nown in the art. Reference iB made to CA 93:95691h where it is disclosed that these compounds are used as monomers to form polymers by polycondensation with aromatic difunctional compounds. There i8 no : , : . -. . .: . .
,::.. . .
200Z8~
suggestion that the compounds or derivatives of them could be vacuum evaporated to form useful layers for optical devices.
Useful foramido and carbamoyl groups are represented by the formulae -NHCOR2 and -CoNR2R3 respectively, wherein R2 and R3 are independently selected from the group con~isting of unsubstituted and substituted aliphatic, aromatic and heterocyclic groups such that the molecular weight of the compound is less than about 1000.
Useful aliphatic groups include alkenes such as ethyl, propyl and nonyl; branched aliphatic groups such as 2,2-dimethyl propyl; cycloaliphatic such as cyclohexyl; substituted aliphatic such as aliphatic 8ub8tituted with halogen, alkoxy, cyano and aromatic groups such as perfluoropropyl, 2-methoxyethyl and phenyl methyl; and unsaturated aliphatic groups such as 2-propenyl and l-cyclohexenyl.
Useful aromatic groups include phenyl and naphthyl and substituted aromatic such as aromatic substituted with halogen, alkyl, cyano, alkoxy and hydroxy such as 4-methoxy phenyl and 3,4-dichloro phenyl.
Useful heterocyclic groups include pyridyl, furanyl, thiophenyl, quinolyl and piperidyl; and substituted heterocyclic such as heterocyclic sub8tituted with alkyl, halogen and alkoxy such as 5-butylpyrityl.
Heterocyclic groups derived from amino or carboxyl group8 are those groups that can be formed by reacting the amino or carboxyl group with another reagent to form the heterocycle. Useful groups therefore include the following, which can be substituted, for example, with aliphatic groups;
halogen; alkoxy and nitro:
. , .
. : .
' ' ' ' ' ZOOX~
-N\ O I - N\ ~0~ ~I ~ 0~
H
--~O' ~I and --~ O ~I
The symmetrically substituted compounds, that is R = Rl, are made starting with nitro phthalic anhydride. This is reacted with a lS nitroaniline to give a tinitro-N-phenyl-phthalimide.
This in turn is reduced to the corresponding diamino compound which i~ then reacted with the oxychloride of the desired side chain.
The similar unsymmetrical compounds are made by reacting the appropriately substituted aniline with the proper nitro-phthalic anhydride followed by reduction to the corresponding amine. The amine is then reacted with the desired acid chloride.
The following compounds are illustrative of the compounds within the scope of the invention.
They were made by methods similar to the detailed method described in Example 1 below.
I.
=-\ Index: 1.703 Br-~ ~^-CONH O (second sample index ~ = 1.705) I O ~N--~ ~. mp: > 240 ~ \NHCO--~ ~---Br O ._.
: . .
:.: : - . ,, ... .. . - .
: . . : . . ....... - . ~ , ~ : ::, - - ~ . .~ :: . :
- - , - . - . , - .: - . . .
: ~ ....... ~ , - ' ~ - .
, . . : : ~
zoo~
--5-- .
II.
.=. 0 Intex: 1.776 ~ Br ~ ~o~ \N / ~ ~
C0-.~ ~--Br III.
(CH3)3CCH2CONH 0 Index: 1.578 lo I o \N~ . mp: 197 - 200O
~ ~NHC0CH2c(cH3)3 IV.
0 Intex: 1.747 ~ ~ -C0 ~ ~ ~ ~U ~ > 240-O /-=-:( 20 V.
Cl~ Index: 1.737 NHC0--~ ~--Cl ; 25 VI
. 0 Index: 1.744 ~ --C0 ~ (50:50 mixture co-:l \.=.~ N ~ ~ -=-\ evaporated from ~ ,0~ - 80urces) `' ~- ~ \NHC0-~
+
? 35 cll~-~ co~ - cl ~ o . .
i r-. ., , ,~ ~
,~, ...
X , '' , I
'~ ' - , .. . ... . .
. ~ . ' . . , ~' ''' ~. . . ' . ' ' ' -,, , ' 20028~i5 VII.
OIndex: 1.739 ~ ~ CO-.~ ~.
VIII.
~ Index: 1.751 ~ 0~ . mp: 231 - 235 ~ ~ CO--~ ~--Br IX.
OIndex: 1.704 ~ 2 O mp: > 260 C~I O ~N /--\
~ CONH--~ ~--Br ~.
O ._.
XI.
_ ~ NHC-I o >~ ./ ~
~I ~co-O /-=-\
.~ ~.
One of the advantages of the described compounds is that the index of refraction can be changed by changing the side chain. In addition, with the vacuum coating technique, the compounds can be easily mixed. Thus, the index of refraction of the layer can be carefully selected for the .... . - -, . - .. , . . :~.
. . . . .
, . ~ . . .
.
-, 20~
particular application. Still further, by providing two or more sources of different compounds in the vacuum chamber, a top-to-bottom gradient of intex of refraction can be provided in the layer by varying the proportions of the compounds that are evaporated during the deposition of the layer. These properties are either difficult or impossible to provide with other methods using organic materials.
Example 1: ~reyara~ion of 4-(4-bromophenylcarbon-10,a,mido~-N-(3-r4-bromophenylcarbonamidol-phenyl~phthalimide A solution of 4-nitrophthalic anhydride (24.6 g., 0.127 mole) and 3-nitroaniline (17.5 g., 0.127 mole) in acetonitrile (300 ml) was heated at reflux for 84 hours, cooled and filtered. The solid was washed with cold acetonitrile, dissolved in acetic anhydride (200 ml), and heated at reflux for 3 -hours. The reaction mixture was cooled, the solid filtered and rinsed with acetonitrile and dried.
~` 20 Yield of N-(3-nitrophenyl)-4-nitrophthalimide was 20.6 g. (51.7Z); m.p. 245-246. Calcd. for C14H7N306: C, 53.7; H, 2.3; N, 13-4-1 Found: C, S3.6; H, 2.5; N, 13.5.
q A solution of N-(3-nitrophenyl)-4-nitro-phthalimide (5.0 g. ) in tetrahydrofuran (300 ml) was reduced under hydrogen (45 psi) using platinum oxide ' catalyst (0.2 g.) for 18 hours. The solution was j dried (MgS04), filtered through Celite, and the 1` solvent evaporated under reduced pressure to yield 4-amino-N-(3-aminophenyl)phthalimide; 3.8 g. (93.1%);
M ~ 228-231- Calcd- for C14HllN3 2 66.4; H, 4.4; N, 16.6. Found: C, 66.9; ~, 4.9; N, 16Ø
To a stirred solution of 4-amino-N-(3-amino-phenyl)phthalimide (4.0 g., 0.016 mole) and triethyl-amine (3.6 g., 0.036 mole) in tetrahydrofuran (300 ml) was added dropwise a solution of 4-bromobenzoyl ;~
.`~
..... . . .. . . . . .
~, .. : ,.. . . ... . .. .. . . .
x, . ~
: . :
. . . .
. ~ -.
. .
.
. .
Z00~8~5 chloride (7.4 g., 0.034 mole) in tetrahydrofuran (50 ml). After 1 hour the solution was filteret and the solvent was removed from the filtrate under reduced pressure. After several recrystallizations from a variety of solvents, a fluorescent impurity still remained. The solid was finally stirred in hot dichloromethane for several hours, filtered and dried in a vacuum oven overnight. TLC showed no more fluorescent impurity. Yield 2.22 g. (22.4%), m.p.
>240 Calcd. for C28H17Br2N3 4 54.3; ~, 2.8; N, 6.8. Found: C, 52.1; ~, 2.4; N, 6.3.
j Other compounds mentioned above were made in : a similar manner. Characterizing refractive index and melting point data for these compounds arealso mentioned above.
Example 2:
A series of compounds were vacuum deposited on quartz supports in a vacuum coating apparatus.
The pertinent conditions for the deposition were:
chamber pressure less than 1 x 10 6 mm Hg;
substrate temperature was room temperature or about 22-C; deposition rate of between 0.4 to 1.0 nm/sec;
substrate height was 65 cm. The thicknesses of the - 25 films were between 0.10 ~m and 1.0 ~m.
The geometric thickness and the refractive ' index was determined by ellipsometry and waveguide ; analysis. This is described in detail in Rabolt et al, IBM J. Res. Develop. , Vol 26 No. 2 pg. 209, 1982.
The refractive indexes for compounds I
through IX mentioned above were measured from these coated samples. Each of these coated samples would be useful, for example, as an optical wave guide.
~ Industrial Applicability i 35 The present invention thus provides organic compounds which can be vacuum evaporated to produce useful optical elements.
;
.
.. . . . .
.. - . - . . , :
, ' : .
;., , ' ' .. ~: ,.. ' . . , ,. -' ,. :;
:- ' ' ':
-:~ j ' . . , ' .
: : ' ; . . ` ' ~ , :'
P~THALIMIDE COMPOUNDS FOR FORMING
AMORPHOUS LAYERS BY VACUUM DEPOSITION
Technical Field The present invention relates to new compounds that are useful in the preparation of layers of transparent materials which provide an optic function. The compounds are phthalimides that can be vacuum deposited to provide the transparent layer.
Back~round Art Transparent layers for optical tevices can serve a variety of optical functions. For example, the optical performance of a len~ can be improved by providing an antireflecting coating. Such a coating, for example, can improve the contrast of the lens in a variety of conditions. Such antireflecting coatings are made by depositing a layer or layers of material having predetermined indices of refraction in predetermined thicknesses to achieve the desired antireflective condition.
Processes wherein polymers or monomers are solvent coated on the support, suffer from many disadvantages. First, solution coating, whether it be of the polymer or the monomers, produces layers which are of less than desired uniformity for optical applications. Further, these processes inevitably leave residual solvent in the layer which is disadvantageous for long term storage or subsequent process steps. In addition, multiple layers are difficult if not impossible since the solvent used to coat the second layer often attacks the first layer or will not wet the surface of the first layer.
It is common to coat inorganic materials using vacuum coating techniques. Thi~ type of coating is capable of producing uniform coatings without solvents. Multiple layers are more easily achieved than with solvent coating. However, vacuum - .
. .
.. . . .
-, , -, :, - ' . . :, . - .
.
200286j~
coating is not possible with these organic polymeric materials. The organic polymers do not have sufficient vapor pressure to evaporate even under high vacuum conditions. If the temperature of the polymer is raised to increase the vapor pressure, the polymer decomposes.
Thus, the problem to be solved by the present invention is to provide ne~ compounds that can be vacuum coated to provide useful optical layers.
~i8closure of the Invention In accordance with the present invention, there are provided phthalimide compounds of the structure:
Rl-~- 0 wherein R and Rl are independently selected from the group consisting of nitro, foramido groups, carbamoyl groups and heterocyclic groups derived from amino or carboxyl groups.
The phthalimide compounds of the invention have the structure:
Rl ~ ~o -~
wherein R and Rl are independently selected from the group consisting of nitro, foramido groups, carbamoyl groups and heterocyclic groups derived from amino or carboxyl groups.
The parent amino and carboxyl compounds are ~nown in the art. Reference iB made to CA 93:95691h where it is disclosed that these compounds are used as monomers to form polymers by polycondensation with aromatic difunctional compounds. There i8 no : , : . -. . .: . .
,::.. . .
200Z8~
suggestion that the compounds or derivatives of them could be vacuum evaporated to form useful layers for optical devices.
Useful foramido and carbamoyl groups are represented by the formulae -NHCOR2 and -CoNR2R3 respectively, wherein R2 and R3 are independently selected from the group con~isting of unsubstituted and substituted aliphatic, aromatic and heterocyclic groups such that the molecular weight of the compound is less than about 1000.
Useful aliphatic groups include alkenes such as ethyl, propyl and nonyl; branched aliphatic groups such as 2,2-dimethyl propyl; cycloaliphatic such as cyclohexyl; substituted aliphatic such as aliphatic 8ub8tituted with halogen, alkoxy, cyano and aromatic groups such as perfluoropropyl, 2-methoxyethyl and phenyl methyl; and unsaturated aliphatic groups such as 2-propenyl and l-cyclohexenyl.
Useful aromatic groups include phenyl and naphthyl and substituted aromatic such as aromatic substituted with halogen, alkyl, cyano, alkoxy and hydroxy such as 4-methoxy phenyl and 3,4-dichloro phenyl.
Useful heterocyclic groups include pyridyl, furanyl, thiophenyl, quinolyl and piperidyl; and substituted heterocyclic such as heterocyclic sub8tituted with alkyl, halogen and alkoxy such as 5-butylpyrityl.
Heterocyclic groups derived from amino or carboxyl group8 are those groups that can be formed by reacting the amino or carboxyl group with another reagent to form the heterocycle. Useful groups therefore include the following, which can be substituted, for example, with aliphatic groups;
halogen; alkoxy and nitro:
. , .
. : .
' ' ' ' ' ZOOX~
-N\ O I - N\ ~0~ ~I ~ 0~
H
--~O' ~I and --~ O ~I
The symmetrically substituted compounds, that is R = Rl, are made starting with nitro phthalic anhydride. This is reacted with a lS nitroaniline to give a tinitro-N-phenyl-phthalimide.
This in turn is reduced to the corresponding diamino compound which i~ then reacted with the oxychloride of the desired side chain.
The similar unsymmetrical compounds are made by reacting the appropriately substituted aniline with the proper nitro-phthalic anhydride followed by reduction to the corresponding amine. The amine is then reacted with the desired acid chloride.
The following compounds are illustrative of the compounds within the scope of the invention.
They were made by methods similar to the detailed method described in Example 1 below.
I.
=-\ Index: 1.703 Br-~ ~^-CONH O (second sample index ~ = 1.705) I O ~N--~ ~. mp: > 240 ~ \NHCO--~ ~---Br O ._.
: . .
:.: : - . ,, ... .. . - .
: . . : . . ....... - . ~ , ~ : ::, - - ~ . .~ :: . :
- - , - . - . , - .: - . . .
: ~ ....... ~ , - ' ~ - .
, . . : : ~
zoo~
--5-- .
II.
.=. 0 Intex: 1.776 ~ Br ~ ~o~ \N / ~ ~
C0-.~ ~--Br III.
(CH3)3CCH2CONH 0 Index: 1.578 lo I o \N~ . mp: 197 - 200O
~ ~NHC0CH2c(cH3)3 IV.
0 Intex: 1.747 ~ ~ -C0 ~ ~ ~ ~U ~ > 240-O /-=-:( 20 V.
Cl~ Index: 1.737 NHC0--~ ~--Cl ; 25 VI
. 0 Index: 1.744 ~ --C0 ~ (50:50 mixture co-:l \.=.~ N ~ ~ -=-\ evaporated from ~ ,0~ - 80urces) `' ~- ~ \NHC0-~
+
? 35 cll~-~ co~ - cl ~ o . .
i r-. ., , ,~ ~
,~, ...
X , '' , I
'~ ' - , .. . ... . .
. ~ . ' . . , ~' ''' ~. . . ' . ' ' ' -,, , ' 20028~i5 VII.
OIndex: 1.739 ~ ~ CO-.~ ~.
VIII.
~ Index: 1.751 ~ 0~ . mp: 231 - 235 ~ ~ CO--~ ~--Br IX.
OIndex: 1.704 ~ 2 O mp: > 260 C~I O ~N /--\
~ CONH--~ ~--Br ~.
O ._.
XI.
_ ~ NHC-I o >~ ./ ~
~I ~co-O /-=-\
.~ ~.
One of the advantages of the described compounds is that the index of refraction can be changed by changing the side chain. In addition, with the vacuum coating technique, the compounds can be easily mixed. Thus, the index of refraction of the layer can be carefully selected for the .... . - -, . - .. , . . :~.
. . . . .
, . ~ . . .
.
-, 20~
particular application. Still further, by providing two or more sources of different compounds in the vacuum chamber, a top-to-bottom gradient of intex of refraction can be provided in the layer by varying the proportions of the compounds that are evaporated during the deposition of the layer. These properties are either difficult or impossible to provide with other methods using organic materials.
Example 1: ~reyara~ion of 4-(4-bromophenylcarbon-10,a,mido~-N-(3-r4-bromophenylcarbonamidol-phenyl~phthalimide A solution of 4-nitrophthalic anhydride (24.6 g., 0.127 mole) and 3-nitroaniline (17.5 g., 0.127 mole) in acetonitrile (300 ml) was heated at reflux for 84 hours, cooled and filtered. The solid was washed with cold acetonitrile, dissolved in acetic anhydride (200 ml), and heated at reflux for 3 -hours. The reaction mixture was cooled, the solid filtered and rinsed with acetonitrile and dried.
~` 20 Yield of N-(3-nitrophenyl)-4-nitrophthalimide was 20.6 g. (51.7Z); m.p. 245-246. Calcd. for C14H7N306: C, 53.7; H, 2.3; N, 13-4-1 Found: C, S3.6; H, 2.5; N, 13.5.
q A solution of N-(3-nitrophenyl)-4-nitro-phthalimide (5.0 g. ) in tetrahydrofuran (300 ml) was reduced under hydrogen (45 psi) using platinum oxide ' catalyst (0.2 g.) for 18 hours. The solution was j dried (MgS04), filtered through Celite, and the 1` solvent evaporated under reduced pressure to yield 4-amino-N-(3-aminophenyl)phthalimide; 3.8 g. (93.1%);
M ~ 228-231- Calcd- for C14HllN3 2 66.4; H, 4.4; N, 16.6. Found: C, 66.9; ~, 4.9; N, 16Ø
To a stirred solution of 4-amino-N-(3-amino-phenyl)phthalimide (4.0 g., 0.016 mole) and triethyl-amine (3.6 g., 0.036 mole) in tetrahydrofuran (300 ml) was added dropwise a solution of 4-bromobenzoyl ;~
.`~
..... . . .. . . . . .
~, .. : ,.. . . ... . .. .. . . .
x, . ~
: . :
. . . .
. ~ -.
. .
.
. .
Z00~8~5 chloride (7.4 g., 0.034 mole) in tetrahydrofuran (50 ml). After 1 hour the solution was filteret and the solvent was removed from the filtrate under reduced pressure. After several recrystallizations from a variety of solvents, a fluorescent impurity still remained. The solid was finally stirred in hot dichloromethane for several hours, filtered and dried in a vacuum oven overnight. TLC showed no more fluorescent impurity. Yield 2.22 g. (22.4%), m.p.
>240 Calcd. for C28H17Br2N3 4 54.3; ~, 2.8; N, 6.8. Found: C, 52.1; ~, 2.4; N, 6.3.
j Other compounds mentioned above were made in : a similar manner. Characterizing refractive index and melting point data for these compounds arealso mentioned above.
Example 2:
A series of compounds were vacuum deposited on quartz supports in a vacuum coating apparatus.
The pertinent conditions for the deposition were:
chamber pressure less than 1 x 10 6 mm Hg;
substrate temperature was room temperature or about 22-C; deposition rate of between 0.4 to 1.0 nm/sec;
substrate height was 65 cm. The thicknesses of the - 25 films were between 0.10 ~m and 1.0 ~m.
The geometric thickness and the refractive ' index was determined by ellipsometry and waveguide ; analysis. This is described in detail in Rabolt et al, IBM J. Res. Develop. , Vol 26 No. 2 pg. 209, 1982.
The refractive indexes for compounds I
through IX mentioned above were measured from these coated samples. Each of these coated samples would be useful, for example, as an optical wave guide.
~ Industrial Applicability i 35 The present invention thus provides organic compounds which can be vacuum evaporated to produce useful optical elements.
;
.
.. . . . .
.. - . - . . , :
, ' : .
;., , ' ' .. ~: ,.. ' . . , ,. -' ,. :;
:- ' ' ':
-:~ j ' . . , ' .
: : ' ; . . ` ' ~ , :'
Claims (3)
1. Phthalimide compounds of the structure:
wherein R and R1 are independently selected from the group consisting of nitro, foramido groups, carbamoyl groups and heterocyclic groups derived from amino or carboxyl groups.
wherein R and R1 are independently selected from the group consisting of nitro, foramido groups, carbamoyl groups and heterocyclic groups derived from amino or carboxyl groups.
2. A phthalimide compound according to claim 1 wherein R and R1 are the same.
3. A phthalimide compound according to claim 1 wherein said compound is: 4-(4-bromophenyl-carbonamido)-N-(3-[4-bromophenylcarbonamido]phenyl)-phthalimide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27355088A | 1988-11-21 | 1988-11-21 | |
| US273,550 | 1988-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2002865A1 true CA2002865A1 (en) | 1990-05-21 |
Family
ID=23044396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2002865 Abandoned CA2002865A1 (en) | 1988-11-21 | 1989-11-14 | Phthalimide compounds for forming amorphous layers by vacuum deposition |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA2002865A1 (en) |
| WO (1) | WO1990005722A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7320992B2 (en) | 2003-08-25 | 2008-01-22 | Amgen Inc. | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1278634B (en) * | 1964-02-25 | 1968-09-26 | Basf Ag | Process for the preparation of dyes of the anthraquinone series |
| GB1254345A (en) * | 1969-04-18 | 1971-11-17 | Ilford Ltd | Alkali-soluble colour couplers |
| JPS57209979A (en) * | 1981-06-19 | 1982-12-23 | Teijin Ltd | Ultraviolet light absorber and method for using same |
-
1989
- 1989-11-13 WO PCT/US1989/004974 patent/WO1990005722A1/en unknown
- 1989-11-14 CA CA 2002865 patent/CA2002865A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO1990005722A1 (en) | 1990-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5157541A (en) | Optical article for reflection modulation | |
| JPH03132729A (en) | High x(2) optical product with improved buffer layer | |
| US4316041A (en) | Liquid crystal silanes | |
| CA2025054C (en) | Optical article for reflection modulation | |
| US4946235A (en) | Nonlinear optical waveguide device | |
| TW200563B (en) | Chromophore containing compounds for opto-electronic applications | |
| TWI526429B (en) | Dye compound, method of producing dipyrromethene metal complex compound, method of producing dye multimer, substituted pyrrole compound, colored curable composition, color filter, method of producing color filter, solid-state image sensor and liquid crys | |
| CN104761471A (en) | Liquid crystal aligning agent | |
| US6393190B1 (en) | Chromophores for polymeric thin films and optical waveguides and devices comprising the same | |
| EP0647874A1 (en) | Highly efficient nonlinear optical polyimides | |
| CN108885373A (en) | The polymer at the position containing the position for having the isocyanate group with isocyanate group and/or sealing endization and with photoreactivity and aligning agent for liquid crystal, liquid crystal orientation film and the liquid crystal of crosslinking agent indicate element | |
| CN103476873A (en) | Colored composition, colored cured film, color filter, method for producing color filter, liquid crystal display device, solid-state imaging element, and novel dipyrromethene-type metal complex compound or tautomer thereof | |
| CA2002865A1 (en) | Phthalimide compounds for forming amorphous layers by vacuum deposition | |
| EP0407523B1 (en) | Method of making an optical device having layers of low molecular weight organic material | |
| JPH0832760B2 (en) | Nonlinear optically active organic material and device containing elements made of this material | |
| US5200481A (en) | Tetraazaporphyrin monomers and polymers | |
| JP2000128983A (en) | Nonlinear optically active copolymer, and electro- optical or optical device containing the copolymer of this kind | |
| US5120610A (en) | Polymers having phthalocyanine units and their use as optically transparent films | |
| US5103060A (en) | Compounds which are ethylenically unsaturated in the terminal position, and the use thereof in nonlinear optics | |
| JPH05310655A (en) | Cyclobutenedione derivative containing polymerizable double bond its homo-or copolymer and nonlinear optical element using the same | |
| CN100439950C (en) | Two-phase film materials and method for making | |
| KR101163656B1 (en) | Diimmonium salt oligomer, preparation method and usage thereof | |
| US4496482A (en) | Liquid crystal silanes | |
| EP1290000A1 (en) | Novel chromophores for polymeric thin films and optical waveguides and devices comprising the same | |
| US5324827A (en) | Optionally oriented, monomeric and polymeric nonlinearly optically active materials and derivatives thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |