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US 7,714,099 B2Granted
Luminescent compositions and their uses
AssigneesHitachi Chemical Company, Ltd., Sumation Co., Ltd.
InventorsYoshii Morishita, Satoyuki Nomura, Yoshihiro Tsuda, Seiji Tai, Matthew L. Marrocco, III, Farshad J. Motamedi, Li-Sheng Wang, Yongchao Liang
Life of this patent
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Abstract
High quantum yield luminescent monomers, oligomers, and polymers, comprising benzotriazole repeating units and derivatives thereof have been discovered and utilized in optical devices and components therefor, including electroluminescent devices, light emitting devices, photoluminescent devices, organic light emitting diodes (OLEDs), OLED displays, sensors, and the like.
Claims84
A polymer or oligomer comprising:
- (a) at least one type of a constitutional repeating unit of the general formula selected from the group consisting of Formula I and Formula II, represented below, said constitutional repeating unit having a benzotriazole type group, either as part of the main chain or as a side chain
- b) at least one type of a constitutional repeating unit of the general formula represented below by Formula III in the amount of 75 mol % or less:
- wherein
- R is H, D, alkyl, alkaryl, heteroalkyl, aryl, aralkyl, heteroaryl, alkyl ketone, aryl ketone, alkylester, arylester, amide, carboxylic acid, phenol, 2-hydroxyphenyl, 2-alkoxyphenyl, 2-aryloxyphenyl, substituted 2-hydroxyphenyl, substituted 2-alkoxyphenyl, substituted 2-aryloxyphenyl, fluoroalkyl, or fluoroaryl;
- A1 is C, when said benzotriazole type group is linked at A1, or A1 is CH, CR1, or N, when said benzotriazole type group is not linked at A1;
- A2 is C, when said benzotriazole type group is linked at A2, or A2 is CH, CR2, or N, when said benzotriazole type group is not linked at A2;
- A3 is C, when said benzotriazole type group is linked at A3, or A3 is CH, CR3, or N, when said benzotriazole type group is not linked at A3;
- A4 is CH, CR4, or N, when said benzotriazole type group is not linked at A4, or A4 is C, when said benzotriazole type group is linked at A4;
- J is a trivalent moiety selected from the group consisting of 1,2,4-phenylenetriyl and >CR6CR7R8—;
- G is nil or is selected from the group consisting of —Ar—, —O—, —S—, —NR1—, CR2R3—, —CR1R2CR3R4—, N═CR1—, CR1═CR2—, —N═N—, —(CO)—, C3 to C30 alkyldiyl, and C3 to C30 heteroalkyldiyl;
- Q is selected from the group consisting of —Ar—, —O—, —S—, —NR1—, —OCR1R2—, —CR1R2—, —OCR1R2CR3R4—, —CR1R2CR3R4—, —N═CR1—, —CR1═N—, —CR1═CR2—, —N═N—, and —(CO)—, —BR1—, SiR1R2—, —(CO)—O—, —O—(CO)—, —NR1—(CO)—, and —(CO)—NR1—, C3 to C30 alkyldiyl, and C3 to C30 heteroalkyldiyl;
- R1, R2, R3, R4 are each independently selected from the group consisting of H, D, —NR6R7, halide, alkoxy, aryloxy, alkyl, alkaryl, heteroalkyl, aryl, aralkyl, heteroaryl, alkyl ketone, aryl ketone, alkylester, arylester, amide, carboxylic acid, phenol, alkylphenol, fluoroalkyl, fluoroaryl, alkyleneoxy, polyalkylene oxy, polyalkylene, linear or dendritic;
- and any two of adjacent R1, R2, R3 or R4 are optionally bridging, or taken together with the two carbons to which each is respectively attached may form an aromatic ring selected from the group consisting of unsubstituted or substituted benzene, naphthalene, anthracene, thiophene, pyridine, bipyridine, pyrazine, pyrimidine, oxadiazole, thiadiazole, and benzofuran;
- R6, R7, and R8 are each independently substituted or unsubstituted alkyl or aryl;
- and any two of adjacent R6, R7, R8, are optionally bridging;
- and
- Ar is unsubstituted or substituted, single or multiple ring, fused or non-fused aromatic or heteroaromatic.
14 more elements
A process of preparing a polymer or oligomer comprising:
- (a) admixing
- (i) at least one compound selected from the group consisting of Formula VIII, Formula IX, and Formula X, represented below
- (ii) optionally, at least one compound of the general formula represented below by Formula XI:
- wherein
- R is H, D, alkyl, alkaryl, heteroalkyl, aryl, aralkyl, heteroaryl, alkyl ketone, aryl ketone, alkylester, arylester, amide, carboxylic acid, phenol, 2-hydroxyphenyl, 2-alkoxyphenyl, 2-aryloxyphenyl, substituted 2-hydroxyphenyl, substituted 2-alkoxyphenyl, substituted 2-aryloxyphenyl, fluoroalkyl, or fluoroaryl;
- A5 is CH, CR1, or N;
- A6 is CH, CR2, or N;
- A7 is CH, CR3, or N;
- A8 is CH, CR4, or N;
- R1, R2, R3, R4 are each independently selected from the group consisting of H, D, —NR6R7, halide, alkoxy, aryloxy, alkyl, alkaryl, heteroalkyl, aryl, aralkyl, heteroaryl, alkyl ketone, aryl ketone, alkylester, arylester, amide, carboxylic acid, phenol, alkylphenol, fluoroalkyl, fluoroaryl, alkyleneoxy, polyalkylene oxy, polyalkylene, linear or dendritic;
- and any two of adjacent R1, R2, R3 or R4 are optionally bridging, or taken together with the two carbons to which each is respectively attached may form an aromatic ring selected from the group consisting of unsubstituted or substituted benzene, naphthalene, anthracene, thiophene, pyridine, bipyridine, pyrazine, pyrimidine, oxadiazole, thiadiazole, and benzofuran;
- Q is selected from the group consisting of —Ar—, —O—, —S—, —NR1—, —OCR1R2—, —CR1R2—, —OCR1R2CR3R4—, —CR1R2CR3R4—, —N═CR1—, —CR1═N—, —CR1═CR2—, —N═N—, and —(CO)—, —BR1—, SiR1R2—, —(CO)—O—, —O—(CO)—, —NR1—(CO)—, and —(CO)—NR1—, C3 to C30 alkyldiyl, and C3 to C30 heteroalkyldiyl;
- R6 and R7 are each independently substituted or unsubstituted alkyl or aryl;
- and
- R6 and R7 are optionally bridging;
- Ar is unsubstituted or substituted, single or multiple ring, fused or non-fused aromatic or heteroaromatic;
- and
- R10 and R10′ are each independently a group or groups capable of participating in aryl to aryl and/or aryl to alkyl coupling reaction;
- and
- (b) adding a polymerization catalyst and optional co-reactants into the mixture to cause:
- (i) polymerization to form a carbon to carbon bond linking at least one compound selected from the group consisting of Formula VIII, Formula IX, and Formula X with at least one other compound selected from the group consisting of Formula VIII, Formula IX, and Formula X;
- and/or
- (ii) polymerization to form a carbon to carbon bond linking at least one compound selected from the group consisting of Formula VIII, Formula IX, and Formula X with at least one compound of Formula XI.
20 more elements
Dependencies are inferred from the claim text.