Optical material and articles formed therefrom

An optical material comprising:

• an oligomer or polymer material comprising structural repeating units represented by any of the formulas selected from:
• wherein the oligomer or polymer material is formed by curing a polymerizable composition;
• wherein, in the selected formula, R and R′, R1 and R2, or R3 and R4 are independently selected from the group consisting of C1-C15 alkyl, C2-C15 alkenyl, halo-(C1-C15 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C15 alkyl), aryl-(C1-C15 alkyl), heteroaryl or heteroaryl-(C1-C15 alkyl), or alkoxy-(C1-C15 alkyl), each of which may be optionally substituted by C1-C15 alkyl, halo-(C1-C15 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C15 alkyl), aryl, aryl-(C1-C15 alkyl), heteroaryl, C1-C15 alkoxy, C1-C15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester;
• or
• wherein, in the selected formula, R and R′, R1 and R2, or R3 and R4 are taken together with the atoms to which they are bound to form a 5-7 membered heterocyclic ring which may be optionally substituted by C1-C15 alkyl, halo-(C1-C15 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C15 alkyl), aryl, aryl-(C1-C15 alkyl), heteroaryl, C1-C15 alkoxy, C1-C15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester;
• and
• wherein the optical material has a low absorbance, or substantially no absorbance, of wavelengths in one or more of the spectral regions including the vacuum ultraviolet region (below 200 nm), the ultraviolet region (180 nm to 360 nm), the visible region (380 nm to 720 nm), the near infrared region (750 nm to 2,500 nm), the infrared region (2,500 nm to 10,000 nm), the far infrared region (10,000 nm or more) and the terahertz region (about 0.1 to 10 THz).

An optical material comprising:

• a polymerizable material comprising a formula selected from:
• wherein, in the selected formula, R and R′, R1 and R2, R3 and R4, and R5 and R6 are independently selected from the group consisting of C1-C5 alkyl, C2-C15 alkenyl, halo-(C1-C5 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C5 alkyl), aryl-(C1-C5 alkyl), heteroaryl or heteroaryl-(C1-C5 alkyl), or alkoxy-(C is alkyl), each of which may be optionally substituted by C1-C5 alkyl, halo-(C1-C5 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl- (C1-C5 alkyl), aryl, aryl-(C1-C5 alkyl), heteroaryl, C1-C5 alkoxy, C1-C5 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester;
• or
• wherein, in the selected formula, R and R′, R1 and R2, or R3 and R4 are taken together with the atoms to which they are bound to form a 5-7 membered heterocyclic ring which may be optionally substituted by C1-C5 alkyl, halo-(C1-C5 alkyl), C3-C6 cycloalkyl, halo-(C3-C6 cycloalkyl), heterocyclyl, heterocyclyl-(C1-C5 alkyl), aryl, aryl-(C1-C5 alkyl), heteroaryl, C1-C15 alkoxy, C1-C5 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, or ester;
• or
• wherein, in the selected formula, -[A]- represents —(CRARB)n—, —(CRARB)n—O(C═O)—(CH2)1-15—(C═O)O—(CRARB)n—, —(CH2)n-[CY]-(CH2), a polybutadienyl linking group, a polyethylene glycol linking group, a polyether linking group, a polyurethane linking group, an epoxy linking group, a polyacrylic linking group, or a polycarbonate linking group;
• wherein each instance of RA or RB is independently H, C1-C15 alkyl, C2-C15 alkenyl, or a moiety represented by the formula:
• wherein -L- is a linking group selected from the group consisting of alkylene, alkenylene, haloalkylene, cycloalkylene, cycloalkylene, heterocyclylene, heterocyclyl alkylene, aryl-alkylene, heteroarylene or heteroaryl-(alkylene), or alkoxy-(alkylene), each of which may be optionally branched and each of which may be optionally substituted by alkyl, haloalkyl, cycloalkyl, halo cycloalkyl, heterocyclyl, heterocyclyl- (alkyl), aryl, aryl-(alkyl), heteroaryl, C1-C15 alkoxy, C1-C15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, ester, each of which can be optionally branched;
• R3 is independently selected from the group defined in R6 above;
• and
• R4 is alkyl, alkenyl, haloalkyl, cycloalkyl, halo cycloalkyl, heterocyclyl, heterocyclyl alkyl), aryl-(alkyl), heteroaryl or heteroaryl- (alkyl), or alkoxy-(alkyl), each of which may be optionally branched and each of which can be optionally substituted by alkyl, haloalkyl, cycloalkyl, halo cycloalkyl, heterocyclyl, heterocyclyl-(alkyl), aryl, aryl-(alkyl), heteroaryl, C1-C15 alkoxy, C1-C15 alkylthio, hydroxyl, nitro, azido, cyano, acyloxy, carboxy, ester, each of which may be optionally branched;
• -[CY]- represents an alkyl, alkenyl, haloalkyl, cycloalkyl, halo cycloalkyl, heterocyclyl, heterocyclyl alkyl), aryl-(alkyl), heteroaryl or heteroaryl-(alkyl), or alkoxy - (alkyl) group
• n is an integer from 1 to 25;
• m is an integer from 1 to 25;
• each instance of Q represents —O— or a direct bond;
• and
• wherein the polymerizable composition has a refractive index between 1.40 and 1.50 when measured at 25° C. in a liquid state, prior to curing.