Polymers for Special Purposes

Abstract

The present invention relates to ring-opening metathesis polymerization (ROMP) reactions that produce polymers suitable for the electronics industry. In particular, the present invention provides low dielectric constant (D) polymers suitable for small, lightweight, high speed, and even high frequency transmission electronic products. k ) and low dielectric loss (D f Such polymers can be used in a variety of materials and composites in the printed circuit board (PCB) industry.

Description

Technical Field

[0001] Related Applications This application claims the benefit of U.S. Provisional Patent Application No. 62 / 740,443, filed Oct. 3, 2018, the contents of which are incorporated herein by reference.

[0002] The present invention relates to ring-opening metathesis polymerization (ROMP) reactions for making polymers suitable for the electronics industry. Specifically, the present invention relates to low dielectric constant (D k ) and low dielectric loss (D f ) in novel polymers having. Such polymers can be used in a variety of materials and composite materials in the printed circuit board (PCB) industry.

Background Art

[0003] Olefin metathesis has emerged as a unique and powerful transformation for interconverting olefinic hydrocarbons, which is due to the development of well-defined catalysts. See Grubbs, R, H. Handbook of Metathesis, (Wiley-VCH: Weinheim, Germany 2003). Olefin metathesis has become a valuable technique for rapidly and efficiently producing molecules that are difficult to make by other methods because of the very broad tolerance of substrates and functional groups. In particular, certain olefin metathesis catalysts of ruthenium and osmium, known as "Grubbs catalysts," have been found to be effective catalysts for olefin metathesis reactions such as cross-metathesis (CM), ring-closing metathesis (RCM), ring-opening metathesis (ROM), ring-opening cross-metathesis (ROCM), ring-opening metathesis polymerization (ROMP), and acyclic diene metathesis (ADMET) polymerization. By using such catalysts, the scope of olefin metathesis has been greatly expanded due to increased resistance to organic functionality against moisture and oxygen.

[0004] Polymers prepared by ROMP of cyclic olefins, especially norbornene-based polymers, are suitable for PCB prepregs (resin-impregnated glass cloth) and copper-clad laminates (CCL) due to their electrical properties.

[0005] Two major "components" of modern multilayer PCBs are CCL and prepregs. CCL is a primary structure with copper on a stable electrical insulating substrate, and copper wiring is obtained after lithography steps. It is made possible by prepregs to realize a multilayer PCB by integrally bonding the layers of CCL after processing steps such as photolithography, drilling, and copper plating. The prepreg serves a role similar to a "double-sided tape" that adhesively bonds the layers of CCL together, but it melts and flows during the high-temperature bonding step, adding the advantage of truly obtaining shape conformity. In fact, CCL is directly manufactured through the step of thermosetting prepregs and copper foils in a special press. The quality and effectiveness of electrical insulation between the copper wirings of a PCB depend on D k and D f . D k and D f are mainly contributed by polymers.

[0006] The inventors have discovered a series of low to medium molecular weight readily soluble polymers suitable for the manufacturing processes of PCB prepregs and CCL. These polymers were prepared using ROMP of special monomers and metal carbene olefin metathesis catalysts. This discovery was surprising and unexpected in view of the teachings of the art, as described and exemplified herein.

Summary of the Invention

[0007] The present invention provides polymers having improved dielectric constant (Dk) and dielectric loss (Df) compared to the prior art. Further aspects and advantages of the present invention include polymers having good processability, crosslinkability, and high glass transition temperature (Tg). These polymers may be suitably formulated in a varnish using a solvent or during a melt processing step to improve other properties such as adhesion to copper foil and coefficient of thermal expansion (CTE).

[0008] The process employed to manufacture the polymer is based on ring-opening metathesis polymerization using at least one metal carbene olefin metathesis catalyst in the presence of at least one functionalized monomer, at least one optional olefin, and at least one optional solvent. The polymer can be separated from unreacted catalyst and monomer.

[0009] The polymers of the present invention can be synthesized according to Synthetic Scheme 1. Scheme 1 [Chemical formula] Here,[[]]END]] "cat" represents a metal carbene olefin metathesis catalyst; z is 0, 1, 2, or 3; x and y are independently of each other molar fractions between 0 and 1, or equal to 0 or 1, R a is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted linear or branched C 2-24 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , -CN, -NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH2-(optionally substituted C 3-10cycloalkyl), optionally substituted C 5-24 aryl, -CH2-(optionally substituted C 5-24 aryl), optionally substituted C 3-10 cycloalkenyl, or -CH2-(optionally substituted C 3-8 cycloalkenyl); R b is H, optionally substituted straight or branched chain C 1-24 alkyl, optionally substituted straight or branched chain C 2-24 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , -CN, -NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH2-(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2-(optionally substituted C 5-24 aryl), optionally substituted C 3-8 cycloalkenyl, or -CH2-(optionally substituted C 3-8 cycloalkenyl); R c is H, optionally substituted straight or branched chain C 1-24 alkyl, optionally substituted straight or branched chain C 2-24 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH2-(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2-(optionally substituted C 5-24 aryl), optionally substituted C3-8 Cycloalkenyl, -CH2-(optionally substituted C 3-8 ycloalkenyl), -C(R h )(R i )COOR j 、-C(R h )(R i )C(O)H、-C(R h )(R i )C(O)R k 、-C(R h )(R i )CR l (OR m )(OR n )、-C(R h )(R i )C(O)NR o R p 、 or -C(R h )(R i )C(O)NR o OR n ; R d is H, optionally substituted straight-chain or branched-chain C 1-24 alkyl, optionally substituted straight-chain or branched-chain C 2-24 alkenyl, halogen, -C(O)R f 、-CH2-C(O)R f 、-OR g 、-CH2-OR g 、CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10 ycloalkyl, -CH2-(optionally substituted C 3-10 ycloalkyl), optionally substituted C 5-24 aryl, -CH2-(optionally substituted C 5-24 aryl), optionally substituted C 3-8 ycloalkenyl, -CH2-(optionally substituted C 3-8 ycloalkenyl), -C(R h )(R i )COOR j 、-C(R h )(R i )C(O)H、-C(R h )(Ri )C(O)R k 、 -C(R h )(R i )CR l (OR m )(OR n )、 -C(R h )(R i )C(O)NR o R p 、 or -C(R h )(R i )C(O)NR o OR n ; Each R s is independently, optionally substituted linear or branched C 1-24 alkyl, optionally substituted linear or branched C 2-24 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocyclic ring, -CH2-(optionally substituted heterocyclic ring), optionally substituted C 3-10 cycloalkyl, -CH2-(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2-(optionally substituted C 5-24 aryl), optionally substituted C 3-8 cycloalkenyl, -CH2-(optionally substituted C 3-8 cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), or -C(R h )(R i )C(O)NR o Rp ,-C(R h )(R i )C(O)NR o OR n and; t is 0, 1, 2, 3, 4, 5, or 6; R f is OH, OR k , NR g R h , optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R g is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, optionally substituted straight or branched chain C 2-6 alkenyl, -C(O)-(optionally substituted straight or branched chain C 2-6 alkenyl), or optionally substituted C 3-8 cycloalkenyl; R h is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R i is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R j is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R k is optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R l is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R m is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R n is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R o is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; and R p is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 Aryl, or optionally substituted C 3-8 Is cycloalkenyl.

Brief Description of the Drawings

[0010]

Figure 1

Modes for Carrying Out the Invention

[0011] Terms and Definitions Unless otherwise indicated, the present invention is not limited to specific reactants, reaction conditions, or the like, and thus may vary. It should also be understood that the terms used herein are for the purpose of describing particular embodiments and are not to be construed as limiting.

[0012] As used in the specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, what is meant by "a substituent" includes not only a single substituent but also two or more substituents and the like.

[0013] As used in this specification and the appended claims, the terms "for example," "as an example," "such as," or "including" are meant to introduce examples that further clarify a more general subject. Unless otherwise specified, these examples are provided only as an aid in understanding the invention and are not intended to limit it in any way.

[0014] In this specification and the following claims, multiple terms are referenced, and these terms are to be assumed to have the meanings described herein.

[0015] The term "alkyl" typically refers to a straight-chain or branched-chain saturated hydrocarbon group containing from 1 to 24 carbon atoms, preferably from 1 to 12 carbon atoms, more preferably from 1 to 6 carbon atoms: for example, methyl (Me), ethyl (Et), n-propyl (Pr or n-Pr), isopropyl (i-Pr), n-butyl (Bu or n-Bu), isobutyl (i-Bu), t-butyl (t-Bu), octyl (Oct), decyl, and the like.

[0016] The term "cycloalkyl" refers to a cyclic alkyl group, which can typically be monocyclic, bicyclic, or polycyclic and preferably has from 3 to 10, more preferably from 5 to 7 carbon atoms. Generally, cycloalkyl groups are cyclopentyl (Cp), cyclohexyl (Cy), or adamantyl.

[0017] The term "substituted alkyl" refers to alkyl substituted with one or more substituents, and the terms "heteroatom-containing alkyl" and "heteroalkyl" refer to alkyl in which at least one carbon atom is substituted with a heteroatom.

[0018] The term "alkylene" refers to a difunctional straight-chain or branched-chain alkyl group, where "alkyl" is as defined above.

[0019] The term "alkenyl" refers to a straight-chain or branched-chain hydrocarbon group containing from 2 to 24 carbon atoms and having at least one double bond, such as ethenyl, n-propenyl, iso-propenyl, n-butenyl, iso-butenyl, octenyl, decenyl, tetradecenyl, hexadecenyl, and the like. Preferred alkenyl groups herein contain from 2 to 12 carbon atoms, and more preferred alkenyl groups contain from 2 to 6 carbon atoms.

[0020] The term "substituted alkenyl" refers to an alkenyl substituted with one or more substituents, and the terms "heteroatom-containing alkenyl" and "heteroalkenyl" refer to an alkenyl in which at least one carbon atom is substituted with a heteroatom.

[0021] The term "cycloalkenyl" preferably refers to a cyclic alkenyl group having 3 to 8 carbon atoms.

[0022] The term "alkenylene" refers to a difunctional straight-chain or branched-chain one, where "alkenyl" is as defined above.

[0023] The term "alkynyl" refers to a straight-chain or branched-chain hydrocarbon group of 2 to 24 carbon atoms containing at least one triple bond, for example, ethynyl, n-propynyl, and the like. Preferred alkynyl groups herein contain 2 to 12 carbon atoms, and more preferred alkynyl groups contain 2 to 6 carbon atoms.

[0024] The term "substituted alkynyl" refers to an alkynyl substituted with one or more substituents, and the terms "heteroatom-containing alkynyl" and "heteroalkynyl" refer to an alkynyl in which at least one carbon atom is substituted with a heteroatom.

[0025] The term "alkynylene" refers to a difunctional straight-chain or branched alkynyl group, where "alkynyl" is as defined above.

[0026] The term "alkoxy" refers to an alkyl group bonded via a single terminal ether bond; that is, the "alkoxy" group may also be represented as -O-alkyl, where "alkyl" is as defined above. Similarly, "alkenyloxy" refers to an alkenyl group bonded via a single terminal ether bond, and "alkynyloxy" refers to an alkynyl group bonded via a single terminal ether bond.

[0027] The term "aryl", unless otherwise specified, refers to an aromatic substituent containing a single aromatic ring or multiple aromatic rings that are fused, directly linked, or indirectly linked (such that different aromatic rings are attached to a common group such as a methylene or ethylene moiety). Preferred aryl groups contain from 5 to 24 carbon atoms, and particularly preferred aryl groups contain from 6 to 10 carbon atoms. Exemplary aryl groups include one aromatic ring or two fused or linked aromatic rings, for example, phenyl (Ph), naphthyl, biphenyl, diphenyl ether, diphenylamine, benzophenone, phenanthryl, and the like.

[0028] The term "substituted aryl" refers to an aryl moiety substituted with one or more substituents, and the terms "heteroatom-containing aryl" and "heteroaryl" refer to an aryl substituent in which at least one carbon atom is substituted with a heteroatom, as will be described in more detail herein.

[0029] The term "aryloxy" refers to an aryl group bonded via a single terminal ether linkage, where "aryl" is as defined above. An "aryloxy" group may also be represented as -O-aryl, where aryl is as defined above. Preferred aryloxy groups contain from 5 to 24 carbon atoms, and particularly preferred aryloxy groups contain from 6 to 10 carbon atoms. Examples of aryloxy groups include, but are not limited to, phenoxy, o-halo-phenoxy, m-halo-phenoxy, p-halo-phenoxy, o-methoxy-phenoxy, m-methoxy-phenoxy, p-methoxy-phenoxy, 2,4-dimethoxy-phenoxy, 3,4,5-trimethoxy-phenoxy, and the like.

[0030] The term "alkaryl" refers to an aryl group having an alkyl substituent, and the term "aralkyl" refers to an alkyl group having an aryl substituent, where "aryl" and "alkyl" are as defined above. Preferred alkaryl and aralkyl groups contain from 6 to 24 carbon atoms, and particularly preferred alkaryl groups contain from 6 to 16 carbon atoms. Examples of alkaryl groups include, but are not limited to, p-methylphenyl, 2,4-dimethylphenyl, p-cyclohexylphenyl, 2,7-dimethylnaphthyl, 7-cyclooctylnaphthyl, 3-ethyl-cyclopenta-1,4-diene, and the like. Examples of aralkyl groups include, but are not limited to, benzyl, 2-phenyl-ethyl, 3-phenyl-propyl, 4-phenyl-butyl, 5-phenyl-pentyl, 4-phenylcyclohexyl, 4-benzylcyclohexyl, 4-phenylcyclohexylmethyl, 4-benzylcyclohexylmethyl, and the like.

[0031] The terms "alkaryloxy" and "aralkyloxy" refer to substituents of the chemical formula -OR where R is alkaryl or aralkyl, respectively, as defined herein.

[0032] The term "acyl" refers to a substituent having the chemical formula -(CO)-alkyl, -(CO)-aryl, -(CO)-aralkyl, -(CO)-alkaryl, -(CO)-alkenyl, or -(CO)-alkynyl, and the term "acyloxy" refers to a substituent having the chemical formula -O(CO)-alkyl, -O(CO)-aryl, -O(CO)-aralkyl, -O(CO)-alkaryl, -O(CO)-alkenyl, or -(CO)-alkynyl, where "alkyl", "aryl", "aralkyl", "alkaryl", "alkenyl", and "alkynyl" are as defined above. The acetoxy group (-O(CO)CH3, often abbreviated -OAc) is a common example of an acyloxy group.

[0033] The terms "cyclic" and "ring" refer to an alicyclic or aromatic group which may be substituted and / or may or may not contain heteroatoms, and which may be monocyclic, bicyclic, or polycyclic. The term "alicyclic" is used in its conventional meaning of referring to an aliphatic cyclic moiety, as contrasted with an aromatic cyclic moiety, and may be monocyclic, bicyclic, or polycyclic.

[0034] The term "polycyclic ring" refers to an alicyclic or aromatic group which may be substituted and / or may or may not contain heteroatoms, and which has at least two closed rings connected, fused, or linked via single bonds or bridges. Polycyclic rings include, but are not limited to, naphthyl, biphenyl, phenanthryl, and the like.

[0035] The term "spiro compound" refers to a compound having a twisted structure of two or more rings (ring systems), where two or three rings are connected by one common atom.

[0036] The terms "halo", "halogen", and "halide" are used in their conventional meaning of referring to a substituent of fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0037] "Hydrocarbyl" refers to a monovalent hydrocarbyl moiety containing from 1 to 24 carbon atoms, preferably from 1 to 12 carbon atoms, including straight-chain, branched-chain, cyclic, saturated, and unsaturated species, such as, for example, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and the like. "Substituted hydrocarbyl" refers to a hydrocarbyl substituted with one or more substituents.

[0038] "Hydrocarbylene" refers to a divalent hydrocarbyl moiety containing from 1 to 24 carbon atoms, preferably from 1 to 12 carbon atoms, including linear, branched, cyclic, saturated and unsaturated chemical species, and is formed by removing two hydrogens from a hydrocarbon. "Substituted hydrocarbylene" refers to a hydrocarbylene substituted with one or more substituents.

[0039] The term "heteroatom-containing" in "heteroatom-containing hydrocarbyl group" refers to a hydrocarbon molecule or a portion of a hydrocarbyl molecule in which one or more carbon atoms are substituted with atoms other than carbon, such as nitrogen, oxygen, sulfur, phosphorus, or silicon, typically nitrogen, oxygen, or sulfur. The terms "heteroatom-containing hydrocarbylene" and "heterohydrocarbylene" refer to a hydrocarbylene in which at least one carbon atom is substituted with a heteroatom. Similarly, the term "heteroalkyl" refers to an alkyl substituent containing a heteroatom, the term "heterocyclic" refers to a cyclic substituent containing a heteroatom, and the terms "heteroaryl" and "heteroaromatic" refer to "aryl" and "aromatic" substituents containing a heteroatom, respectively, etc. It is desirable to note that a "heterocyclic" group or compound may or may not be aromatic, and further, a "heterocycle" may be monocyclic, bicyclic, or polycyclic as described above with respect to the term "aryl". Examples of heteroalkyl groups include, but are not limited to, alkoxyaryl, alkylsulfanyl-substituted alkyl, N-alkylated aminoalkyl, and the like. Examples of heteroaryl substituents include, but are not limited to, pyrrolyl, pyrrolidinyl, pyridinyl, quinolinyl, indolyl, pyrimidinyl, imidazolyl, 1,2,4-triazolyl, tetrazolyl, etc. Examples of heteroatom-containing alicyclic groups include, but are not limited to, pyrrolidino, morpholino, piperazino, piperidino, etc.

[0040] In addition, if a particular group is permitted, the foregoing substituents may be further substituted with one or more additional substituents or with one or more hydrocarbyl moieties such as those specifically enumerated above. Similarly, the foregoing hydrocarbyl moieties may be further substituted with one or more substituents or with additional hydrocarbyl moieties such as those specifically enumerated above. Similarly, the foregoing hydrocarbylene moieties may be further substituted with one or more substituents or with the additional hydrocarbyl moieties mentioned above.

[0041] As implicitly referred to in some of the foregoing definitions, "substituted hydrocarbyl", "substituted alkyl", "substituted aryl", and "substituted" in like terms means that at least one hydrogen atom bonded to a carbon (or other) atom in a hydrocarbyl, alkyl, aryl, or other moiety is replaced with one or more non-hydrogen substituents. Examples of such substituents include halo, hydroxyl, sulfhydryl, C1-C 24 alkoxy, C2-C 24 alkenyloxy, C2-C 24 alkynyloxy, C5-C 24 aryloxy, C6-C 24 aralkyloxy, C6-C 24 alkaryloxy, acyl (C2-C 24 alkylcarbonyl (-CO-alkyl) and C6-C 24 arylcarbonyl (-CO-aryl) inclusive), acyloxy (-O-acyl where C2-C 24 alkylcarbonyloxy (-O-CO-alkyl) and C6-C 24 arylcarbonyloxy (-O-CO-aryl) inclusive), C2-C 24 alkoxycarbonyl (-(CO)-O-alkyl), C6-C 24 aryloxycarbonyl (-(CO)-O-aryl), halocarbonyl (-(CO)-X where X is halo), C2-C 24 alkylcarbonato (-O-(CO)-O-alkyl), C6-C 24Aryl carbonate (-O-(CO)-O-aryl), carboxylic acid (-COOH), carbamoyl (-(CO)-NH2), mono(C1-C 24 alkyl)-substituted carbamoyl (-(CO)-NH(C1-C 24 alkyl)), di(C1-C 24 alkyl)-substituted carbamoyl (-(CO)-N(C1-C 24 alkyl)2), mono(C1-C 24 haloalkyl)-substituted carbamoyl (-(CO)-NH(C1-C 24 haloalkyl)), di(C1-C 24 haloalkyl)-substituted carbamoyl (-(CO)-N(C1-C 24 haloalkyl)2), mono(C5-C 24 aryl)-substituted carbamoyl (-(CO)-NH-aryl), di(C5-C 24 aryl)-substituted carbamoyl (-(CO)-N(C5-C 24 aryl)2), N(C1-C 24 alkyl)(C5-C 24 aryl)-substituted carbamoyl (-(CO)-N(C1-C 24 alkyl)(C5-C 24 aryl)), thiocarbamoyl (-(CS)-NH2), mono(C1-C 24 alkyl)-substituted thiocarbamoyl (-(CS)-NH(C1-C 24 alkyl)), di(C1-C 24 alkyl)-substituted thiocarbamoyl (-(CS)-N(C1-C 24 alkyl)2), mono(C5-C 24 aryl) substituted thiocarbamoyl (-(CS)-NH-aryl), di(C5-C 24 aryl) substituted thiocarbamoyl (-(CS)-N(C5-C 24 aryl)2), N(C1-C 24 alkyl)(C5-C 24 aryl) substituted thiocarbamoyl (-(CS)-N(C1-C 24 alkyl)(C5-C 24Aryl)), carbamide (-NH-(CO)-NH2), cyano (-C≡N), cyanato (-O-C≡N), thiocyanato (-S-C≡N), isocyanate (-NCO), thioisocyanate (-NCS), formyl (-(CO)-H), thioformyl (-(CS)-H), amino (-NH2), mono (C1-C 24 alkyl)-substituted amino (-NH(C1-C 24 alkyl)), di (C1-C 24 alkyl)-substituted amino (-N(C1-C 24 alkyl)2), mono (C5-C 24 aryl)-substituted amino (-NH(C5-C 24 aryl)), di (C5-C 24 aryl) substituted amino (-N(C5-C 24 aryl)2), C2-C 24 alkylamide (-NH-(CO)-alkyl), C6-C 24 arylamide (-NH-(CO)-aryl), imino (-CRNH, where R is H, C1-C 24 alkyl, C5-C 24 aryl, C6-C 24 alkaryl, C6-C 24 aralkyl, etc., but not limited to these), C2-C 20 alkylimino (-CRN(alkyl), where R is H, C1-C 24 alkyl, C5-C 24 aryl, C6-C 24 alkaryl, C6-C 24 aralkyl, etc., but not limited to these), allylimino (-CRN(aryl), where R is H, C1-C 20 alkyl, C5-C 24 aryl, C6-C 24 alkaryl, C6-C 24 aralkyl, etc., but not limited to these), nitro (-NO2), nitroso (-NO), sulfo (-S(O)2OH), C1-C 24 alkylsulfanyl (-S-alkyl; also referred to as "alkylthio"), C5-C 24Aryl sulfanyl (-S-aryl; also referred to as "aryl thio"), C1-C 24 Alkyl sulfinyl (-(SO)-alkyl), C5-C 24 Aryl sulfinyl (-(SO)-aryl), C1-C 24 Alkyl sulfonyl (-(SO2)-alkyl), C1-C 24 Monoalkylaminosulfonyl (-(SO2)-N(H)alkyl), C1-C 24 Dialkylaminosulfonyl (-(SO2)-N(alkyl)2), C5-C 24 Aryl sulfonyl (-(SO2)-aryl), boryl (-(BH2)), borono (-(B(OH)2)), boranato (-(B(OR)2, where R includes, but is not limited to, alkyl or other hydrocarbyl), phosphono (-(P(O)(OH)2)), phospho (-(PO2)), phosphino (-(PH2)), silyl (-(SiR3, where R is H or hydrocarbyl), and silyloxy (-(O-silyl)); hydrocarbyl moiety C1-C 24 Alkyl (preferably C1-C 12 Alkyl, more preferably C1-C6 alkyl), C2-C 24 Alkenyl (preferably C2-C 12 Alkenyl, more preferably C2-C6 alkenyl), C2-C 24 Alkynyl (preferably C2-C 12 Alkynyl, more preferably C2-C6 alkynyl), C5-C 24 Aryl (preferably C6-C 10 Aryl), C6-C 24 Alkaryl (preferably C6-C 16 Alkaryl), or C6-C 24 Aralkyl (preferably C6-C 16 Aralkyl), etc., but are not limited thereto.

[0042] "Functionalized hydrocarbyl", "functionalized alkyl", "functionalized olefin", "functionalized cyclic olefin", and the like, "functionalized" means that at least one H atom bonded to a carbon (or other) atom in a hydrocarbyl, alkyl, olefin, cyclic olefin, or other moiety is replaced by one or more functional groups such as those described herein. The term "functional group" is meant to include any functional chemical species suitable for the uses described herein. In some cases, the terms "substituent" and "functional group" are used interchangeably.

[0043] "Optional" or "optionally" means that the circumstances described below may or may not occur, and as a result, the description includes examples where the circumstances occur and examples where they do not. For example, the phrase "optionally substituted" means that a non-hydrogen substituent may or may not be present on a given atom, and thus the description includes structures where a non-hydrogen substituent is present and structures where a non-hydrogen substituent is not present.

[0044] The term "nil" means absent or non-existent.

[0045] The term "sulfhydryl" represents a group of the chemical formula "-SH".

[0046] The term "hydroxyl" represents a group of the chemical formula "-OH".

[0047] The term "carbonyl" represents a group of the chemical formula "-C(O)-".

[0048] The term "ketone" is -C(O)R x and the like, represents an organic compound having a carbonyl group bonded to a carbon atom, where R x as defined above, can be alkyl, aryl, cycloalkyl, cycloalkenyl, or a heterocycle.

[0049] The term "ester" refers to an organic compound having a carbonyl group bonded to a carbon atom, such as -C(O)OR x where R x as defined above, can be alkyl, aryl, cycloalkyl, cycloalkenyl, or a heterocycle.

[0050] The term "amine" refers to a group of the chemical formula "-NR x R y " where R x and R y can be the same or, independently, can be H, alkyl, aryl, cycloalkyl, cycloalkenyl, or a heterocycle as defined above.

[0051] The term "carboxyl" refers to a group of the chemical formula "-C(O)O-".

[0052] The term "sulfonyl" refers to a group of the chemical formula "-SO2".

[0053] The term "sulfate" refers to a group of the chemical formula "-O-S(O)2-O-".

[0054] The term "sulfonate" refers to a group of the chemical formula "-S(O)2-O-".

[0055] The term "amide" refers to a group of the chemical formula "-C(O)NR x R y " where R x and R y can be the same or, independently, can be H, alkyl, aryl, cycloalkyl, cycloalkenyl, or a heterocycle as defined above.

[0056] The term "sulfamide" refers to a group of the chemical formula "-S(O)2NR x R y " where R x and R ymay be the same as, or independently, may be H, alkyl, aryl, cycloalkyl, cycloalkenyl, or heterocycle as defined above.

[0057] The term "sulfoxide" represents a group of the chemical formula "-S(O)-".

[0058] The term "phosphonic acid" represents a group of the chemical formula "-P(O)(OH)2".

[0059] The term "phosphoric acid" represents a group of the chemical formula "-OP(O)(OH)2".

[0060] The term "sulfonic acid" represents a group of the chemical formula "-S(O)2OH".

[0061] The chemical formula "H" represents a hydrogen atom.

[0062] The chemical formula "O" represents an oxygen atom.

[0063] The chemical formula "N" represents a nitrogen atom.

[0064] The chemical formula "S" represents a sulfur atom.

[0065] If the functional group interferes with the metal carbene olefin metathesis catalyst, the functional group may be protected, and any of the protecting groups commonly used in the art may be employed. For acceptable protecting groups, see, for example, Greene et al., Protective Groups in Organic Synthesis, 5th Ed. (New York: Wiley, 2014). Examples of protecting groups include acetals, cyclic acetals, boronate esters (boronates), cyclic boronate esters (cyclic boronates), carbonates, or the like. Examples of protecting groups include cyclic acetals or cyclic boronate esters.

[0066] The monomer of the present invention In one embodiment, the monomer of the present invention has the structure of chemical formula (I):

Chemical formula

[0067] In one embodiment, the monomer of the present invention has a structure of chemical formula (I), wherein: R ais H, a linear or branched C 1-12 alkyl, a linear or branched C 2-12 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, an optionally substituted heterocycle, -CH2-(an optionally substituted heterocycle), an optionally substituted C 5-7 cycloalkyl, -CH2-(an optionally substituted C 5-7 cycloalkyl), an optionally substituted C 6-10 aryl, -CH2-(an optionally substituted C 6-10 aryl), an optionally substituted C 5-7 cycloalkenyl, -CH2-(an optionally substituted C 5-7 cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , or -C(R h )(R i )C(O)NR o OR n ; Each R s is independently a linear or branched C 1-12 alkyl, a linear or branched C 2-12 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g, CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocyclic ring, -CH2-(optionally substituted heterocyclic ring), optionally substituted C 5-7 cycloalkyl, -CH2-(optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 cycloalkenyl, -CH2-(optionally substituted C 5-7 cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , or -C(R h )(R i )C(O)NR o OR n ; t is 0, 1, 2, 3, or 4; R f is OH, OR k , NR g R h , optionally substituted straight-chain or branched-chain C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocyclic ring, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R g is H, optionally substituted straight-chain or branched-chain C 1-12 alkyl, optionally substituted C 5-7Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, optionally substituted straight or branched chain C 2-6 Alkenyl, -C(O)-(optionally substituted C 6-10 Aryl), -C(O)-(optionally substituted straight or branched chain C 2-6 Alkenyl), or optionally substituted C 5-7 Cycloalkenyl; R h is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 Cycloalkenyl; R i is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 Cycloalkenyl; R j is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 Cycloalkenyl; R k is optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 Cycloalkenyl; R l is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R m is H, optionally substituted straight or branched chain C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R n is H, optionally substituted straight or branched chain C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R o is H, optionally substituted straight or branched chain C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; and R p is H, optionally substituted straight or branched chain C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl.

[0068] In one embodiment, the monomer of the present invention has a structure of chemical formula (I), wherein: R a is H, optionally substituted straight or branched chain C 1-6 alkyl, optionally substituted straight or branched chain C 2-6 alkenyl, halogen, -C(O)R f , -CH2-C(O)Rf 、 -OR g 、 -CH2-OR g 、 CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH2-(optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 cycloalkenyl, or -CH2-(optionally substituted C 5-7 cycloalkenyl); t is 0; R f is OH, OR k 、 NR g R h 、 optionally substituted straight or branched chain C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R g is H, optionally substituted straight or branched chain C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, optionally substituted straight or branched chain C 2-6 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted straight or branched chain C 2-6 alkenyl), or optionally substituted C 5-7 cycloalkenyl; and R h is H, optionally substituted straight or branched chain C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C5-7 is a cycloalkenyl; and R k is optionally substituted linear or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl.

[0069] In one embodiment, the monomer of the present invention has a structure of chemical formula (I), wherein: R a is [Chemical formula] and t = 0.

[0070] Non-limiting examples of the monomer of chemical formula (I) include: [Chemical formula] and the like.

[0071] In one embodiment, the monomer of the present invention has a structure of chemical formula (II): [Chemical formula] Wherein: R b is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted linear or branched C 2-24 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, optionally substituted spiro heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10Cycloalkyl, -CH2-(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2-(optionally substituted C 5-24 aryl), optionally substituted C 3-10 cycloalkenyl, -CH2-(optionally substituted C 3-8 cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , or -C(R h )(R i )C(O)NR o OR n ; Each R s is independently, optionally substituted straight-chain or branched-chain C 1-24 alkyl, optionally substituted straight-chain or branched-chain C 2-24 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, -CH2-(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, -CH2-(optionally substituted C 5-24 aryl), optionally substituted C 3-8 cycloalkenyl, -CH2-(optionally substituted C 3-8(Cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , or -C(R h )(R i )C(O)NR o OR n ; t is 0, 1, 2, 3, 4, 5, or 6; R f is OH, OR k , NR g R h , optionally substituted straight-chain or branched-chain C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R g is H, optionally substituted straight-chain or branched-chain C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, optionally substituted straight-chain or branched-chain C 2-6 alkenyl, -C(O)-(optionally substituted C 5-24 aryl), -C(O)-(optionally substituted straight-chain or branched-chain C 2-6 alkenyl), or optionally substituted C 3-8 cycloalkenyl; R h is H, optionally substituted straight-chain or branched-chain C 1-24Alkyl, optionally substituted C 3-10 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 Aryl, or optionally substituted C 3-8 Cycloalkenyl; R i is H, a straight-chain or branched-chain C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R j is H, a straight-chain or branched-chain C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R k is a straight-chain or branched-chain C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R l is H, a straight-chain or branched-chain C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R m is H, a straight-chain or branched-chain C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl; R nis H, a straight-chain or branched-chain C 1-24 alkyl, an optionally substituted C 3-10 cycloalkyl, an optionally substituted heterocycle, an optionally substituted C 5-24 aryl, or an optionally substituted C 3-8 cycloalkenyl; R o is H, a straight-chain or branched-chain C 1-24 alkyl, an optionally substituted C 3-10 cycloalkyl, an optionally substituted heterocycle, an optionally substituted C 5-24 aryl, or an optionally substituted C 3-8 cycloalkenyl; and R p is H, a straight-chain or branched-chain C 1-24 alkyl, an optionally substituted C 3-10 cycloalkyl, an optionally substituted heterocycle, an optionally substituted C 5-24 aryl, or an optionally substituted C 3-8 cycloalkenyl.

[0072] In one embodiment, the monomer of the present invention has the structure of Chemical Formula (II):

Chemical formula

[0073] In one embodiment, the monomer of the present invention has the structure of Chemical Formula (II), wherein: R b is H, a straight-chain or branched-chain C 1-12 alkyl, a straight-chain or branched-chain C 2-12 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g, CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocyclic ring, optionally substituted spiro heterocyclic ring, -CH2-(optionally substituted heterocyclic ring), optionally substituted C 5-7 cycloalkyl, -CH2-(optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 cycloalkenyl, -CH2-(optionally substituted C 5-7 cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , or -C(R h )(R i )C(O)NR o OR n ; Each R s is independently, optionally substituted straight-chain or branched-chain C 1-12 alkyl, optionally substituted straight-chain or branched-chain C 2-12 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocyclic ring, -CH2-(optionally substituted heterocyclic ring), optionally substituted C 5-7 cycloalkyl, -CH2-(optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10Aryl, -CH2-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 cycloalkenyl, -CH2-(optionally substituted C 5-7 cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , or -C(R h )(R i )C(O)NR o OR n ; t is 0, 1, 2, 3, or 4; R f is OH, OR k , NR g R h , optionally substituted linear or branched C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R g is H, optionally substituted linear or branched C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, optionally substituted linear or branched C 2-12 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted linear or branched C 2-12 alkenyl), or optionally substituted C5-7 is a cycloalkenyl; R h is H, a straight-chain or branched-chain C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocyclic ring optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R i is H, a straight-chain or branched-chain C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocyclic ring optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R j is H, a straight-chain or branched-chain C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocyclic ring optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R k is a straight-chain or branched-chain C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocyclic ring optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R l is H, a straight-chain or branched-chain C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocyclic ring optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R m is H, a straight-chain or branched-chain C 1-12 alkyl optionally substituted, a C 5-7Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R n is H, optionally substituted straight or branched chain C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R o is H, optionally substituted straight or branched chain C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; and R p is H, optionally substituted straight or branched chain C 1-12 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl.

[0074] In one embodiment, the monomer of the present invention has the structure of chemical formula (II), wherein: R b is H, optionally substituted straight or branched chain C 1-6 alkyl, optionally substituted straight or branched chain C 2-6 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted spiro heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH2-(optionally substituted C 5-7cycloalkyl), optionally substituted C 6-10 aryl, -CH2-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 cycloalkenyl, or -CH2-(optionally substituted C 5-7 cycloalkenyl); t is 0; R f is OH, OR k , NR g R h a linear or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R g is H, a linear or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, a linear or branched C 2-6 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted linear or branched C 2-6 alkenyl), or optionally substituted C 5-7 cycloalkenyl; R h is H, a linear or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; and R k is a linear or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C5-7 It is cycloalkenyl.

[0075] In one embodiment, the monomer of the present invention has the structure of Chemical Formula (II), where: R b is

Chemical Formula

[0076] Non-limiting examples of the monomer of Chemical Formula (II) include:

Chemical Formula

[0077] In one embodiment, the monomer of the present invention has the structure of Chemical Formula (III):

Chemical Formula

[0078] In one embodiment, the monomer of the present invention has the structure of Chemical Formula (III), where z is 1 or 2.

[0079] In one embodiment, the monomer of the present invention has the structure of Chemical Formula (III), where z is 2.

[0080] Non-limiting examples of the monomer of Chemical Formula (III) include:

Chemical Formula

[0081] In one embodiment, the olefins of the present invention have the structure of Chemical Formula (IV):

Chemical Formula

[0082] In one embodiment, the olefins of the present invention have the structure of chemical formula (IV), wherein: R c is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted straight or branched chain C 2-12 Alkenyl, halogen, -C(O)R f , -CH2-C(O)Rf , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocyclic ring, -CH2-(optionally substituted heterocyclic ring), optionally substituted C 5-7 cycloalkyl, -CH2-(optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 cycloalkenyl, -CH2-(optionally substituted C 5-7 cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , or -C(R h )(R i )C(O)NR o OR n ; R d is H, optionally substituted straight-chain or branched-chain C 1-12 alkyl, optionally substituted straight-chain or branched-chain C 2-12 alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocyclic ring, -CH2-(optionally substituted heterocyclic ring), optionally substituted C 5-7 cycloalkyl, -CH2-(optionally substituted C 5-7cycloalkyl), optionally substituted C 6-10 Aryl, -CH-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 Cycloalkenyl, -CH-(optionally substituted C 5-7 cycloalkenyl), -C(R h )(R i )COOR j , -C(R h )(R i )C(O)H, -C(R h )(R i )C(O)R k , -C(R h )(R i )CR l (OR m )(OR n ), -C(R h )(R i )C(O)NR o R p , or -C(R h )(R i )C(O)NR o OR n and; R f OH, OR k , N.R. g R h , optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 is cycloalkenyl; R g is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, optionally substituted straight or branched chain C 2-6 alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted straight or branched chain C 2-6 alkenyl), or optionally substituted C5-7 is a cycloalkenyl; R h is H, a linear or branched C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocycle optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R i is H, a linear or branched C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocycle optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R j is H, a linear or branched C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocycle optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R k is a linear or branched C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocycle optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R l is H, a linear or branched C 1-12 alkyl optionally substituted, a C 5-7 cycloalkyl optionally substituted, a heterocycle optionally substituted, a C 6-10 aryl optionally substituted, or a C 5-7 cycloalkenyl; R m is H, a linear or branched C 1-12 alkyl optionally substituted, a C 5-7Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 Cycloalkenyl; R n is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 Cycloalkenyl; R o is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 Cycloalkenyl; and R p is H, optionally substituted straight or branched chain C 1-12 Alkyl, optionally substituted C 5-7 Cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 Aryl, or optionally substituted C 5-7 Cycloalkenyl.

[0083] In one embodiment, the olefins of the present invention have the structure of chemical formula (IV), wherein: R c is H, optionally substituted straight or branched chain C 1-6 Alkyl, optionally substituted straight or branched chain C 2-6 Alkenyl, halogen, -C(O)R f , -CH2-C(O)R f , -OR g , -CH2-OR g , CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 5-7 Cycloalkyl, -CH2-(optionally substituted C 5-7cycloalkyl), optionally substituted C 6-10 aryl, -CH2-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 cycloalkenyl, or -CH2-(optionally substituted C 5-7 cycloalkenyl); R d is H, optionally substituted straight or branched C 1-6 alkyl, optionally substituted straight or branched C 2-6 alkenyl, halogen, -C(O)R f -CH2-C(O)R f -OR g -CH2-OR g CN, NO2, -CF3, -P(O)(OH)2, -OP(O)(OH)2, optionally substituted heterocycle, -CH2-(optionally substituted heterocycle), optionally substituted C 5-7 cycloalkyl, -CH2-(optionally substituted C 5-7 cycloalkyl), optionally substituted C 6-10 aryl, -CH2-(optionally substituted C 6-10 aryl), optionally substituted C 5-7 cycloalkenyl, or -CH2-(optionally substituted C 5-7 cycloalkenyl); R f is OH, OR k NR g R h optionally substituted straight or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; R g is H, optionally substituted straight or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, optionally substituted straight or branched C 2-6Alkenyl, -C(O)-(optionally substituted C 6-10 aryl), -C(O)-(optionally substituted linear or branched C 2-6 alkenyl), or optionally substituted C 5-7 cycloalkenyl; R h is H, optionally substituted linear or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl; and R k is optionally substituted linear or branched C 1-6 alkyl, optionally substituted C 5-7 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 5-7 cycloalkenyl.

[0084] In one embodiment, the olefin of the present invention has the structure of chemical formula (IV), wherein: R c is H,

Chemical formula

Chemical formula

[0085] Non-limiting examples of the monomers of chemical formula (IV) include:

Chemical formula

[0086] It is well known to those skilled in the art that the bicyclic and polycyclic olefins disclosed herein may consist of various structural isomers and / or stereoisomers, and that any and all of them are suitable for use in the present invention. Unless otherwise specified, any reference herein to such bicyclic and polycyclic olefins includes any and all mixtures of such structural isomers and / or stereoisomers.

[0087] Thus, examples of monomers include dicyclopentadiene; tricyclopentadiene, tetracyclopentadiene; norbornene; 5-methyl-2-norbornene; 5-ethyl-2-norbornene; 5-isobutyl-2-norbornene; 5,6-dimethyl-2-norbornene; 5-phenylnorbornene; 5-benzylnorbornene; 5-acetylnorbornene; 5-methoxycarbonylnorbornene; 5-ethoxycarbonyl-1-norbornene; 5-methyl-5-methoxy-carbonylnorbornene; 5-cyanonorbornene; 5,5,6-trimethyl-2-norbornene; cyclohexenylnorbornene; endo, exo-5,6-dimethoxynorbornene; endo, endo-5,6-dimethoxycarbonylnorbornene; endo, exo-5-6-dimethoxycarbonylnorbornene; endo, endo-5,6-dimethoxycarbonylnorbornene; 2,3-dimethoxynorbornene; norbornadiene; tricycloundecene; tetracyclododecene; 8-methyltetracyclododecene; 8-ethyl-tetracyclododecene; 8-methoxycarbonyltetracyclododecene; 8-methyl-8-tetracyclo-dodecene; 8-cyanotetracyclododecene; C2-C 12 Hydrocarbyl-substituted norbornenes, such as 5-butyl-2-norbornene; 5-hexyl-2-norbornene; 5-octyl-2-norbornene; 5-decyl-2-norbornene; 5-dodecyl-2-norbornene; 5-vinyl-2-norbornene; 5-ethylidene-2-norbornene; 5-isopropenyl-2-norbornene; 5-propenyl-2-norbornene; and 5-butenyl-2-norbornene, and the like; and C2-C 12Hydrocarbyl-substituted tetracyclododecenes such as, but not limited to, 5-butyl-2-tetracyclododecene, 5-hexyl-2-tetracyclododecene, 5-octyl-2-tetracyclododecene, 5-decyl-2-tetracyclododecene, 5-dodecyl-2-tetracyclododecene, 5-vinyl-2-tetracyclododecene, 5-ethylidene-2-tetracyclododecene, 5-isopropenyl-2-tetracyclododecene, 5-propenyl-2-tetracyclododecene, and 5-butenyl-2-tetracyclododecene. Metal carbene olefin metathesis catalyst

[0088] A metal carbene olefin metathesis catalyst suitable for ring-opening of the monomers of the present invention has the general structure of chemical formula (1):

Chemical formula

[0089] In one embodiment, the moiety

Chemical formula

Chemical formula

[0090] In one embodiment, L 1 and L 2 are independently selected from phosphine, sulfonated phosphine, phosphite, phosphinite, phosphonite, arsine, stibine, ether (including cyclic ethers), amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, substituted pyridine, imidazole, substituted imidazole, pyrazine, substituted pyrazine, and thioether. Exemplary ligands are trisubstituted phosphines. Preferred trisubstituted phosphines have the chemical formula PR H1 R H2 R H3 wherein R H1 , R H2 and R H3 are each independently optionally substituted: C 6-10 aryl, C1-C 10 alkyl, or C 3-10 cycloalkyl. In the most preferred embodiment, L 1 and L 2It is independently selected from the group consisting of trimethylphosphine (PMe3), triethylphosphine (PEt3), tri-n-butylphosphine (PBu3), tri(ortho-tolyl)phosphine (P-o-tolyl3), tri-tert-butylphosphine (P-tert-Bu3), tricyclopentylphosphine (PCp3), tricyclohexylphosphine (PCy3), triisopropylphosphine (P-i-Pr3), trioctylphosphine (POct3), triisobutylphosphine, (P-i-Bu3), triphenylphosphine (PPh3), tri(pentafluorophenyl)phosphine (P(C6F5)3), methyldiphenylphosphine (PMePh2), dimethylphenylphosphine (PMe2Ph), and diethylphenylphosphine (PEt2Ph).

[0091] In one embodiment, L 1 is [Chemical formula] wherein X and Y are independently C, CR 3a , N, O, S, or P; only one of X or Y can be C or CR 3a ; typically, X and Y are independently N; Q 1 , Q 2 , R 3 , R 3a , and R 4 are independently optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl; generally Q 1 , Q 2 , R 3 , R 3a , and R 4 are optionally substituted hydrocarbylene, optionally substituted heteroatom-containing hydrocarbylene, or are optionally attached to X or Y via a linker such as -(CO)-; typically, Q 1 , Q 2 , R 3 , R 3a , and R 4is directly bonded to X or Y; and when X is O or S, p is 0, when X is N, P, or CR 3a p is 1, and when X is C, p is 2; when Y is O or S, q is 0, when Y is N, P, or CR 3a q is 1, and when X is C, q is 2.

[0092] In one embodiment, L 1 is

Chemical Structure

[0093] In one embodiment, L 1 is

Chemical Formula

[0094] In one embodiment, L 2 is [Chemical formula] wherein: R a2 is hydrogen, optionally substituted hydrocarbyl, or optionally substituted heteroatom-containing hydrocarbyl; generally R a2 is optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, or optionally substituted C5-C 24 aryl; typically R a2 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, cyclohexyl, or phenyl; and R b2 is hydrogen, optionally substituted hydrocarbyl, or optionally substituted heteroatom-containing hydrocarbyl; generally R b2 is optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, or optionally substituted C5-C 24 aryl; typically R b2 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, cyclohexyl, or phenyl; or R a2 and R b2 are joined to form a 5- or 6-membered heterocycle together with a sulfoxide group [-S(O)-].

[0095] In one embodiment, L 2 is [Chemical formula] and in the formula: R is optionally substituted hydrocarbyl or optionally substituted heteroatom-containing hydrocarbyl; generally R is optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, or optionally substituted C5-C 24 aryl; typically R is methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, or phenyl.

[0096] In one embodiment, L 2 is [Chemical formula] and in the formula: R 1p , R 2p , and R 3p are each independently optionally substituted C6-C 10 aryl, optionally substituted C1-C 10 alkyl, or optionally substituted C3-C 10 cycloalkyl. R 8p , R 9p , and R 10p are each independently optionally substituted C6-C 10 aryl, optionally substituted C1-C 10 alkyl, or optionally substituted C3-C 10 cycloalkyl.

[0097] In one embodiment, L 2 is [Chemical formula] and in the formula: R a3 is optionally substituted hydrocarbyl or optionally substituted heteroatom-containing hydrocarbyl; generally R a3is optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, or optionally substituted C5-C 24 aryl; typically R a3 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, cyclohexyl, benzyl, or phenyl; R b3 is optionally substituted hydrocarbyl, or optionally substituted heteroatom-containing hydrocarbyl; generally R b3 is optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, or optionally substituted C5-C 24 aryl; typically R b3 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, cyclohexyl, benzyl, or phenyl; or R a3 and R b3 can form a 5-, 6-, or 7-membered heterocyclic ring with the nitrogen atom to which they are attached; R c3 is optionally substituted hydrocarbyl, or optionally substituted heteroatom-containing hydrocarbyl; generally R c3 is optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, or optionally substituted C5-C 24 aryl; typically R c3 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, cyclohexyl, benzyl, or phenyl; R d3 is optionally substituted hydrocarbyl, or optionally substituted heteroatom-containing hydrocarbyl; generally R d3 is optionally substituted C1-C 10 alkyl, optionally substituted C3-C 10 cycloalkyl, optionally substituted C5-C 24is aryl; typically R d3 is methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, cyclohexyl, benzyl, or phenyl; or R c3 and R d3 can form a 5-, 6-, or 7-membered heterocyclic ring with the nitrogen atom to which they are attached; or R b3 and R c3 can combine to form a 5-, 6-, or 7-membered heterocyclic ring with the nitrogen atom to which they are linked.

[0098] In another embodiment, a metal carbene olefin metathesis catalyst suitable for ring-opening of the monomers of the present invention has the general structure of Chemical Formula (2):

Chemical formula

[0099] In some embodiments, the metal carbene olefin metathesis catalysts used in the present invention have the general structure:

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0100] The preferred metal carbene olefin metathesis catalyst used in the present invention has the chemical formula:

Chem.

[0101] The most preferred metal carbene olefin metathesis catalyst used in the present invention has the chemical formula:

Chem.

[0102] It will be understood that the amount of catalyst used in the reaction (i.e., "catalyst loading") depends on various factors such as the identity of the reactants employed and the reaction conditions. Thus, it is understood that the catalyst loading can be optimally and independently selected for each reaction. However, generally the catalyst will be present in an amount in the range from low values such as about 0.1 ppm, 1 ppm, or 5 ppm to high values such as about 10 ppm, 15 ppm, 25 ppm, 50 ppm, 100 ppm, 200 ppm, 500 ppm, or 1000 ppm relative to the amount of olefinic substrate.

[0103] The catalyst will generally be present in an amount in the range from low values such as about 0.00001 mol%, 0.0001 mol%, or 0.0005 mol% to high values such as about 0.001 mol%, 0.0015 mol%, 0.0025 mol%, 0.005 mol%, 0.01 mol%, 0.02 mol%, 0.05 mol%, or 0.1 mol% relative to the amount of olefinic substrate.

[0104] When expressed as the molar ratio of olefin to catalyst (the "olefin to catalyst ratio"), the loading will generally be present in an amount in the range from low values such as about 10,000,000:1, 1,000,000:1, 500,000:1, or 200,00:1 to high values such as about 100,000:1, 60,000:1, 50,000:1, 45,000:1, 40,000:1, 30,000:1, 20,000:1, 10,000:1, 5,000:1, or 1,000:1.

[0105] Embodiments of the present invention The polymer of the present invention can be synthesized according to Scheme 1, and at least one monomer of chemical formulas (I), (II), and (III), and optionally at least one olefin of formula (IV) can be subjected to a ring-opening metathesis reaction in the presence of at least one metal carbene olefin metathesis catalyst. The at least one metal carbene olefin metathesis catalyst can have the structure of chemical formula (1), chemical formula (2), or a mixture thereof.

[0106] In one embodiment, the present invention provides a polymer having a dielectric constant D at 1 to 100 GHz, a dielectric loss D at 1 to 100 GHz, and D < 0.01, which is synthesized by a ring-opening metathesis reaction comprising at least one monomer of chemical formulas (I), (II), and (III), optionally an olefin of chemical formula (IV), and at least one metal carbene olefin metathesis catalyst. k <3, and a dielectric loss D at 1 to 100 GHz f <0.01, and

Chemical formula

[0107] In one embodiment, the polymer of the present invention has a Dk of 2.42, 2.44, 2.46, 2.47, 2.5 at 10 GHz and a Df of 0.017, 0.006, 0.004, 0.0033, 0.0008, 0.0009 at 10 GHz.

[0108] In one embodiment, the present invention provides a polymer having a dielectric constant D at 1 to 100 GHz and a dielectric loss D at 1 to 100 GHz, which is synthesized by a ring-opening metathesis reaction comprising at least one monomer of chemical formulas (I), (II), and (III), optionally an olefin of chemical formula (IV), and at least one metal carbene olefin metathesis catalyst. k <3, and having a dielectric loss D f <0.01.

Chemical formula

[0109] In one embodiment, the present invention provides a polymer having a dielectric constant D k <3 and a dielectric loss D f <0.01 at 1 to 100 GHz, wherein: at least one monomer of formula (I) is

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0110] The expression "ring-opening metathesis reaction involving at least one monomer of formula (I), (II), and (III), and optionally an olefin of formula (IV)" means the following. The ring-opening metathesis reaction involves either at least one of each monomer of formula (I), (II), and (III), and optionally at least one olefin of formula (IV), or the ring-opening metathesis reaction means it includes any combination of two or three of at least one monomer of formula (I), (II), or (III), and optionally the olefin of formula (IV).

[0111] The polymers of the present invention can be synthesized by a ring-opening metathesis reaction involving at least one monomer of formula (I), (II), and (III), optionally at least one olefin of formula (IV), and at least one metal carbene olefin metathesis catalyst.

[0112] Also, the polymers of the present invention can also be synthesized by a ring-opening metathesis reaction involving at least one monomer of formula (I), at least one monomer of formula (II), and at least one metal carbene olefin metathesis catalyst.

[0113] Also, the polymers of the present invention can also be synthesized by a ring-opening metathesis reaction involving at least one monomer of formula (I), at least one monomer of formula (II), and at least one metal carbene olefin metathesis catalyst, where at least one monomer of formula (I) is

Chemical formula

Chemical formula

[0114] The polymer of the present invention can also be synthesized by a ring-opening metathesis reaction including at least one monomer of chemical formula (I), at least one monomer of chemical formula (II), optionally at least one olefin of chemical formula (IV), and at least one metal carbene olefin metathesis catalyst.

[0115] The polymer of the present invention can also be synthesized by a ring-opening metathesis reaction including at least one monomer of chemical formula (I), at least one monomer of chemical formula (II), optionally at least one olefin of chemical formula (IV), and at least one metal carbene olefin metathesis catalyst, wherein at least one monomer of chemical formula (I) is

Chem.

Chem.

Chem.

[0116] The polymer of the present invention can also be synthesized by a ring-opening metathesis reaction including at least one monomer of chemical formula (I), at least one monomer of chemical formula (II), at least one monomer of chemical formula (III), and at least one metal carbene olefin metathesis catalyst.

[0117] The polymer of the present invention can also be synthesized by a ring-opening metathesis reaction comprising at least one monomer of chemical formula (I), at least one monomer of chemical formula (II), at least one monomer of chemical formula (III), and at least one metal carbene olefin metathesis catalyst; wherein at least one monomer of chemical formula (I) is

Chemical formula

Chemical formula

Chemical formula

[0118] The polymer of the present invention can also be synthesized by a ring-opening metathesis reaction comprising at least one monomer of chemical formula (II), at least one monomer of chemical formula (III), optionally at least one olefin of chemical formula (IV), and at least one metal carbene olefin metathesis catalyst.

[0119] The polymer of the present invention can also be synthesized by a ring-opening metathesis reaction comprising at least one monomer of chemical formula (II), at least one monomer of chemical formula (III), optionally at least one olefin of chemical formula (IV), and at least one metal olefin metathesis catalyst, where:

Chemical formula

Chemical formula

[0120] The polymer of the present invention can also be synthesized by a ring-opening metathesis reaction including at least one monomer of formula (I), at least one monomer of formula (III), and at least one metal carbene olefin metathesis catalyst.

[0121] The polymer of the present invention can also be synthesized by a ring-opening metathesis reaction including at least one monomer of formula (I), at least one monomer of formula (III), and at least one metal carbene olefin metathesis catalyst, and at least one monomer of formula (I) is [Chemical formula] and; and at least one monomer of formula (III) is [Chemical formula] is.

[0122] In one embodiment, at least one metal carbene olefin metathesis catalyst can be any of the metal carbene olefin metathesis catalysts described herein and can have a structure of chemical formula (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23), (24), or (25).

[0123] In one embodiment, at least one metal carbene olefin metathesis catalyst has a structure of chemical formula (22), (23), (24), or (25).

[0124] In one embodiment, a preferred at least one metal carbene olefin metathesis catalyst is a ruthenium olefin metathesis catalyst.

[0125] Chemical formulas (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), (I), (II), (III), and (IV) are as defined herein.

[0126] The polymer of the present invention can be further reacted with additives. These additives can be: antioxidants, peroxides, silica, flame retardants, reinforcing materials, light stabilizers, dyes, elastomers, fillers. Some additives such as antioxidants can be used to prevent the thermal oxidation of the polymer; Lewis acids or Bronsted acids can be used and can be used to coordinate with functional groups that retard the polymerization reaction.

[0127] The polymers of the present invention can also be crosslinked, for example, at high temperatures and optionally in the presence of free radical initiators such as organic peroxides or other curing agents. For example, diamines, triamines, polyamines, polycarboxylic acids, anhydrides and polyanhydrides, polythiols, and cationic initiators such as Lewis acids

[0128] Application Examples Those skilled in the art will understand that the polymers of the present invention can be used in various types of applications, such as prepregs, fiber composite laminates, solvent-based coatings, melt-extruded parts, films, and liquid compounds. Non-limiting examples of prepregs and laminates include rigid printed circuit boards, metal-clad printed circuit boards, flexible printed circuit boards, hybrid (e.g., rigid-flex) printed circuit boards, heat dissipation countermeasures, IC substrate cores, redomes, unidirectional carbon fiber or glass fiber prepreg tapes, electrical insulation composites, etc. Non-limiting examples of films include adhesives for FPCs, build-up layers of IC substrates, redistribution layers, die attach films, heat dissipation countermeasures, underfills, encapsulants, etc. Non-limiting examples of liquid compounds include underfills, potting materials, encapsulants, die attach adhesives, photopatterning, mold compounds, wafer bonding, solder masks, heat dissipation countermeasures, conductive pastes, inks, etc. The polymers of the present invention can further be hydrogenated to form polymer materials with a low degree of unsaturated carbon-carbon bonds.

[0129] Experiments The following examples are for illustrative purposes and are intended, and should be desirably construed, not to limit the present invention in any way. Those skilled in the art will understand that variations and modifications of the following examples can be made without departing from the spirit or scope of the present invention.

[0130] While every effort has been made to ensure accuracy with respect to the numerical values used (e.g., amounts, temperatures, etc.), some experimental errors and deviations are desirably taken into account. Unless otherwise indicated, temperatures are in degrees Celsius (°C) and pressures are at or near atmospheric pressure.

[0131] Unless otherwise noted, all glassware was dried in an oven and reactions were carried out under ambient conditions. Unless otherwise noted, all solvents and reagents were purchased from commercial suppliers and used as received.

[0132] The number-average molecular weight (Mn) and weight-average molecular weight (Mw) of the polymers were measured by GPC / SEC. The polydispersity index, PDI = Mw / Mn, was calculated. Gel permeation chromatography (GPC) / size exclusion chromatography (SEC) data were collected using two Agilent PLgel MIXED-B 300×7.5 mm columns with 10 μm beads, connected to an Agilent 1260 series pump, a Wyatt 18-angle DAWN HELEOS light scattering detector, and an Optilab rEX differential refractive index detector. The mobile phase was THF and the flow rate was 1 mL / min.

[0133] In these examples, any of the metal carbene olefin metathesis catalysts described herein can be used. Some of the monomers were synthesized according to known literature procedures.

[0134] General GC method conditions: Column: Agilent 122-5032E DB-5 (30 m × 250 μm × 0.25 μm), or equivalent. (5% phenylmethylsiloxane). Injection temperature, 280 °C, detector temperature, 310 °C, oven temperature, start temperature, 50 °C, hold time, 0.5 min. Ramp rate is 20 °C / min to 210 °C, ramp time is 5 °C / min to 240 °C, ramp time is 20 °C / min to 280 °C, hold time 2.5 min; mode = split 20.0:1.0, split flow rate = 20.0 mL / min Pressure = 12.05 psi; Total flow = 23.6 mL / min; Constant flow carrier gas = Helium @ 23.5 mL / min.

[0135] FTIR (Fourier Transform Infrared) analysis was determined on a Thermoscientific Nicolet iS 10 FTIR equipped with an ATR crystal using Omnic 9 software; Crystal type Diamond with ZnSe lens; pH range 1 - 14. Background was collected with respect to the surface of the IR crystal (FTIR sensor), then 50 mg of polymer powder was added to completely cover the crystal and 32 scans were taken for data collection.

[0136] The following abbreviations were used in the examples: Mn [kDa] Number average molecular weight in kDa Mw [kDa] Weight average molecular weight in kDa PDI Polydispersity index Tg (°C) Glass transition temperature in °C IPA iso - Propanol MeOH Methanol TGA Thermogravimetric analysis DMSO Dimethyl sulfoxide NaOH Sodium hydroxide K2CO3 Potassium carbonate TBA - I Tetrabutylammonium iodide TBA - HSO4 Tetrabutylammonium hydrogen sulfate TPP Triphenylphosphine BHT Butylated hydroxytoluene THF Tetrahydrofuran MEK Methyl ethyl ketone CDCl3 Deuterated chloroform C6D6 Deuterated benzene DI water Deionized water DCPD Dicyclopentadiene DCM Dichloromethane DSC Differential scanning calorimeter

[0137] Table 1 shows non-limiting examples of monomers and reagents used in the synthesis of the polymers of the present invention: [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Examples]

[0138] [Chemical formula]

[0139] Into a 1 L flask equipped with a magnetic stir bar, bicyclo[2.2.1]hept-5-en-2-methanol, 2-methanesulfonate [CAS 86646-41-5] (55 g, 271.91 mmol), 2-(1-propenyl)phenol [CAS 6380-21-8] (40 g, 298.12 mmol), potassium carbonate (10 g, 72.35 mmol), and DMSO (300 mL) were added. The flask was placed under a nitrogen atmosphere and heated overnight to 85 °C. The reaction mixture was cooled to room temperature and extracted with hexanes and washed with water (3 times, 500 mL each). The organic layer was washed with a 10% wt / wt aqueous NaOH solution (200 mL) to remove excess phenol and then washed with water (200 mL). The organic layer was dried over sodium sulfate and filtered through a plug of silica gel. Removal of the solvent under high vacuum gave 40.56 g of the desired product. A mixture of endo- and exo-isomers was obtained. 11H NMR (400 MHz, CDCl3) δ 0.60 - 0.65 (m, 1H), 1.24 - 1.37 (m, 2H), 1.47 (d, J = 8.0 Hz, 1H), 1.42 (dd, J = 1.8 Hz, J = 7.4 Hz, 3H), 1.89 - 1.93 (m, 1H), 2.55 - 2.63 (m, 1H), 2.84 (br s, 0.7H), 2.88 (br s, 0.3H), 3.05 (br s, 1H), 3.52 (t, J = 9.2 Hz, 1H), 3.75 (dd, J = 6.6 Hz, J = 9.0 Hz, 1H), 3.86 (t, J = 9.0 Hz, 0.3H), 4.05 (dd, J = 6.2 Hz, J = 9.2 Hz, 0.3H), 5.78 - 5.87 (m, 1H), 5.95 (dd, J = 3.0 Hz, J = 5.8 Hz, 0.7H), 6.10 (dd, J = 3.0 Hz, J = 5.8 Hz, 0.3H), 6.15 (dd, J = 3.0 Hz, J = 5.8 Hz, 1H), 6.60 (d, J = 11.6 Hz, 1H), 6.82 (t, J = 8.0 Hz, 1H), 6.91 (quint, J = 6.9 Hz, 1H), 7.18 (t, J = 8.0 Hz, 1H), 7.28 (d, J = 7.2 Hz, 1H).

Example

[0140]

Chem.

[0141] An aqueous solution of NaOH (564 g, 50% wt / wt) was placed in a three-necked round-bottom flask equipped with a magnetic stir bar, and then diluted with ice (400 g). 2-Hydroxymethyl-5-norbornene [CAS 95-12-5] (300 g, 2.416 mol) was added, and stirring was started. TBA-I (120 g, 324.88 mmol) and TBA-HSO4 (18 g, 53.01 mmol) were added, and this biphasic mixture was heated to 55 °C. Methallyl chloride (350 g, 3.865 mol) was added dropwise over 1 hour using an addition funnel. The reaction mixture was stirred at 55 °C overnight. The mixture was cooled to room temperature and transferred to a separatory funnel. The aqueous layer was removed, and the organic layer was washed with DI water 3× (500 mL each). The organic layer was decanted into a container and dried over sodium sulfate. This mixture was transferred to a 1 L round-bottom flask. A magnetic stir bar, a vigreux column, a distillation bridge, and a condenser were attached to the flask. The pot temperature was heated to 90 °C, and the cut was monitored by GC at a high vacuum of 60 mTorr. By distillation, 320 g of the desired product was obtained. A mixture of endo- and exo-isomers was obtained. 1 H NMR (400 MHz, C6D6) δ 0.40 - 0.45 (m, 1H), 0.99 - 1.04 (m, 0.2H), 1.07 (d, J = 7.6 Hz, 0.8H), 1.14 - 1.22 (m, 0.4H), 1.32 - 1.34 (m, 0.2H), 1.42 (dd, J = 2.0 Hz, J = 8.4 Hz, 0.8H), 1.61 - 1.68 (m, 3H), 1.74 - 1.79 (m, 0.2H), 2.29 - 2.37 (m, 0.8H), 2.58 (br s, 0.8H), 2.62 (br s, 0.2H), 2.79 (br s, 0.2H), 2.94 - 2.96 (m, 1.2H), 3.03 - 3.06 (m, 0.8H), 3.12 - 3.17 (m, 0.2H), 3.25 - 3.29 (m, 0.2H) 3.66 - 3.75 (m, 2H), 4.83 (br s, 1H), 5.02 (br s, 1H), 5.90 - 5.95 (m, 1H), 5.96 - 6.03 (m, 1H).

Example

[0142]

Chem.

[0143] Into a 2 L three-necked flask equipped with a magnetic stir bar, a thermocouple well, and a condenser, DCPD (443 g, 3.351 mol) and 2-allylphenol [CAS 1745-81-9] (449.63 g, 3.351 mol) were placed. The flask was placed under a nitrogen atmosphere and heated to an internal temperature of 170 °C over 2 days. After cooling the reaction mixture to room temperature, a Vigreux column, a distillation bridge, and a condenser were attached to the flask. The pot temperature was heated to 170 °C and the cut was monitored by GC with a high vacuum of 60 mTorr. By distillation, 67.11 g of the desired product was obtained. A mixture of endo- and exo-isomers was obtained. 1 H NMR (400 MHz, CDCl3) δ 0.63 - 0.67 (m, 1H), 1.19 - 1.37 (m, 2H), 1.55 (d, J = 8.8 Hz, 0.5H), 1.78 - 1.86 (m, 1H), 2.05 (quint, J = 2.1 Hz, 0.5H), 2.33 - 2.54 (m, 2H), 2.63 - 2.79 (m, 2H), 6.02 (br s, 0.5H), 6.09 - 6.11 (m, 0.75H), 6.17 - 6.20 (m, 0.75H), 6.73 - 6.78 (m, 1H), 6.81 - 6.84 (m, 1H), 6.97 - 7.03 (m, 1H), 7.06 - 7.12 (m, 1H), 8.10 (br s, 1H).

Example

[0144] General procedure for synthesizing the polymer of the present invention A 1 L three-neck round-bottom flask equipped with a thermocouple well and a rare-earth magnetic stir bar was charged with a solvent (85% by mass) and sparged with argon for 15 minutes. Non-limiting examples of the solvent include toluene, DCM, THF, cyclohexanone, and cyclopentanone. A metal carbene olefin metathesis catalyst was added to the flask and stirring was initiated at room temperature (23 °C). A solution of the monomer and olefin and an optional solvent were placed in an addition funnel, sparged with argon for 15 minutes, and then slowly added to the stirred catalyst solution. The monomer solution was added at a rate of 1 mL / min. In some cases, an increase in the internal temperature of several degrees Celsius was observed, followed by a return to room temperature. The reaction was monitored by GC and the consumption of the monomer was confirmed. The reaction time took several hours to overnight.

[0145] Once the reaction was complete, the reaction mixture was diluted with a large amount of antisolvent while stirring vigorously, and an antioxidant was further added. The solvent / antisolvent ratio was 1 / 6. Non-limiting examples of the antisolvent are: acetone, IPA, MeOH, hexanes, ethanol, heptanes, MEK, or mixtures thereof. A polymer suspension was formed and stirred for 1 hour, followed by filtration through a fritted glass funnel and washing with 500 mL of antisolvent. The resulting polymer was dried in a vacuum oven under N2: 2 hours at 25 - 30 °C and 12 hours at 40 - 45 °C. After the oven was cooled to room temperature, the polymer powder was removed. TGA was performed to determine whether the polymer was dry.

[0146] The polymers made according to the general procedure described in the experiment of Example 4 are listed in Table 2. The numbers below the structures represent the ratios in moles.

Table 2-1

Table 2-2

Table 2-3

Table 2-4

Table 2-5

Table 2-6

Example

[0147] Preparation of Bulk Cast Polymer To enable measurement of Dk / Df, a bulk cast polymer was prepared. The mold part was constructed between aluminum plates having a 1 / 8-inch thick cavity. A liquid monomer sample was prepared in the ratio specified by the reaction scheme. Further additives such as antioxidants, inhibitors, and peroxides were added to the reaction mixture. The reaction mixture was then degassed while stirring at room temperature, and a catalyst was added followed by further degassing. The catalyzed and degassed reaction mixture was poured into a room-temperature mold and placed in an oven preheated to 40°C. After 10 minutes at 40°C, the oven temperature was raised to 225°C and cured for 2 hours. The cured part was removed from the mold, machined into the desired shape to obtain test pieces, and sent to CCN (Connected Community Networks, Inc) for dielectric measurement. The thermal properties were measured internally by DSC. The data are shown in Table 3.

Table 3-1

Table 3-2

Example

[0148] Procedure for the Synthesis of Polymer 26 Into a 12 L three-necked round-bottom flask equipped with a thermocouple well and a rare earth magnetic stir bar, isopropanol (7 L) was added, and then this was sparged with argon for 15 minutes. C627 (0.11 g) and Irganox (3.0 g) were added to the flask, and the solution was continuously purged with argon for 5 minutes. PhNB (300 g), DNB (61.960 g), and NB-MMA (33.876 g) were placed in a 1 L Erlenmeyer flask, mixed, and sparged with argon. The contents were transferred to a 1 L addition funnel, and then the funnel was connected to the flask. The system was evacuated and refilled with argon three times. The mixture in the addition funnel was added dropwise to the isopropanol solution. As the addition continued, a white polymer solid precipitated from the solution. The addition took 3 to 4 hours. The final temperature in the flask reached 30 °C. This solid was separated with a frit funnel and washed with isopropanol. This solid was further dried in a vacuum oven at 30 °C for 16 hours. Yield: 328 g. The data are shown in Table 4. [Table 4]

[0149] Procedure for the Characterization of the Crosslinking of Polymer 26 Polymer 26 was dissolved in toluene together with Luperox 101 organic peroxide (1 wt% based on the polymer weight). The solvent was evaporated to obtain a dry solid, which was molded into a 25 mm disk for parallel plate viscoelastic measurements. Using a TA Discovery HR-3 rheometer, the disk was heated from 60 °C to 200 °C at 5 °C per minute under oscillatory shear, and the complex viscosity was measured as a function of temperature. See Figure 1. Those skilled in the art will recognize that the behavior in Figure 1 is a typical example of a linear polymer in the B stage, where after undergoing a heat-induced melt flow with a decrease in viscosity as the temperature rises, the curve reaches a minimum due to the crosslinking reaction and the viscosity rapidly increases to reach gelation or crosslinking.

Claims

1. A polymer synthesized by a ring-opening metathesis reaction comprising at least one monomer of chemical formula (I), at least one monomer of chemical formula (II), at least one monomer of chemical formula (III), optionally an olefin of chemical formula (IV), and at least one metal carbene olefin metathesis catalyst, having a dielectric constant D at 1 to 100 GHz ｋ < 3, and a dielectric loss D at 1 to 100 GHz ｆ < 0.01, wherein 【Chemical Formula 1-1】 In the formula: z is 0, 1, 2, or 3; R ａ is H, a straight-chain or branched-chain C １－２４ alkyl, a straight-chain or branched-chain C ２－２４ alkenyl, halogen, -C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , CN, NO ２ , -CF ３ , -P(O)(OH) ２ , -OP(O)(OH) ２ , an optionally substituted heterocyclic ring, -CH ２ -(optionally substituted heterocyclic ring), an optionally substituted C ３－１０ cycloalkyl, -CH ２ -(optionally substituted C ３－１０ cycloalkyl), an optionally substituted C ５－２４ aryl, -CH ２ -(optionally substituted C ５－２４ aryl), an optionally substituted C ３－８ cycloalkenyl, -CH ２ -(optionally substituted C ３－８ cycloalkenyl), or 【Chemical Formula 1-2】 and; R ｂ is H, a straight-chain or branched-chain C １－２４ alkyl, a linear or branched C optionally substituted ２－２４ alkenyl, halogen, -C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , NO₂, -CF ３ , -P(O)(OH) ２ , -OP(O)(OH) ２ , an optionally substituted heterocyclic ring, -CH ２ -(an optionally substituted heterocyclic ring), an optionally substituted C ３－１０ cycloalkyl, -CH ２ -(an optionally substituted C ３－１０ cycloalkyl), an optionally substituted C ５－２４ aryl, -CH ２ -(an optionally substituted C ５－２４ aryl), an optionally substituted C ３－８ cycloalkenyl, -CH ２ -(an optionally substituted C ３－８ cycloalkenyl), or [Chemical Formula 1-3] and; R ｃ is H, a linear or branched C optionally substituted １－２４ alkyl, a linear or branched C optionally substituted ２－２４ alkenyl, halogen, -C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , CN, NO ２ , -CF ３ , -P(O)(OH) ２ , -OP(O)(OH) ２ , an optionally substituted heterocyclic ring, -CH ２ -(an optionally substituted heterocyclic ring), an optionally substituted C ３－８１０ cycloalkyl, -CH ２ -(an optionally substituted C ３－１０ cycloalkyl), an optionally substituted C ５－２４ Aryl, -CH ２ -(optionally substituted C ５－２４ aryl), optionally substituted C ３－８ cycloalkenyl, -CH ２ -(optionally substituted C ３－８ cycloalkenyl), -C(R ｈ )(R ｉ COOR ｊ , -C(R ｈ )(R ｉ )(C(O)H, -C(R ｈ )(R ｉ )(C(O)R ｋ , -C(R ｈ )(R ｉ )(CR ｌ (OR ｍ )(OR ｎ ), -C(R ｈ )(R ｉ )(C(O)NR ｏ R ４２ , -C(R ｈ )(R ｉ )(C(O)NR ｏ OR ｎ , or R ｄ can combine with to form a polycyclic ring; R ｄ is H, optionally substituted linear or branched C １－２４ alkyl, optionally substituted linear or branched C ２－２４ alkenyl, halogen, -C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , CN, NO ２ , -CF ３ , -P(O)(OH) ２ , -OP(O)(OH) ２ , optionally substituted heterocyclic ring, -CH ２ -(optionally substituted heterocyclic ring), optionally substituted C ３－１０ cycloalkyl, -CH ２ -(optionally substituted C ３－１０ cycloalkyl), optionally substituted C ５－２４ aryl, -CH ２ -(optionally substituted C ５－２４ aryl), optionally substituted C ３－８ cycloalkenyl, -CH ２ -(optionally substituted C ３－８ cycloalkenyl), -C(R ｈ )(R ｉ )COOR ｊ 、-C(R ｈ )(R ｉ )C(O)H, -C(R ｈ )(R ｉ )C(O)R ｋ 、-C(R ｈ )(R ｉ )CR ｌ (OR ｍ )(OR ｎ ), -C(R ｈ )(R ｉ )C(O)NR ｏ R ｐ 、-C(R ｈ )(R ｉ )C(O)NR ｏ OR ｎ 、or R ｃ can combine to form a polycyclic ring; Each R ｓ is independently, optionally substituted straight-chain or branched-chain C １－２４ alkyl, optionally substituted straight-chain or branched-chain C ２－２４ alkenyl, halogen, -C(O)R ｆ 、-CH ２ -C(O)R ｆ 、-OR ｇ 、-CH ２ -OR ｇ 、CN, NO ２ 、-CF ３ 、-P(O)(OH) ２ 、-OP(O)(OH) ２ 、optionally substituted heterocyclic ring, -CH ２ -(optionally substituted heterocyclic ring), optionally substituted C ３－１０ cycloalkyl, -CH ２ -(optionally substituted C ３－１０ cycloalkyl), optionally substituted C ５－２４ aryl, -CH ２-(optionally substituted C ５－２４ aryl), optionally substituted C ３－８ cycloalkenyl, -CH ２ -(optionally substituted C ３－８ cycloalkenyl), -C(R ｈ )(R ｉ )COOR ｊ , -C(R ｈ )(R ｉ )C(O)H, -C(R ｈ )(R ｉ )C(O)R ｋ , -C(R ｈ )(R ｉ )CR ｌ (OR ｍ )(OR ｎ ), -C(R ｈ )(R ｉ )C(O)NR ｏ R ｐ , or -C(R ｈ )(R ｉ )C(O)NR ｏ OR ｎ ; t is 0, 1, 2, 3, 4, 5, or 6; R ｆ is OH, OR ｋ , NR ｇ R ｈ , optionally substituted straight or branched C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ｇ is H, optionally substituted straight or branched C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, substituted C ５－２４ aryl, optionally substituted straight or branched C ２－６ alkenyl, -C(O)-(optionally substituted straight or branched C ２－６ alkenyl), or optionally substituted C ３－８ cycloalkenyl; R ｈ is H, a linear or branched C １－２４ alkyl optionally substituted with, a C ３－１０ cycloalkyl optionally substituted with, a heterocycle optionally substituted with, a C ５－２４ aryl, or a C ３－８ cycloalkenyl optionally substituted with; R ｉ is H, a linear or branched C １－２４ alkyl optionally substituted with, a C ３－１０ cycloalkyl optionally substituted with, a heterocycle optionally substituted with, a C ５－２４ aryl, or a C ３－８ cycloalkenyl optionally substituted with; R ｊ is H, a linear or branched C １－２４ alkyl optionally substituted with, a C ３－１０ cycloalkyl optionally substituted with, a heterocycle optionally substituted with, a C ５－２４ aryl, or a C ３－８ cycloalkenyl optionally substituted with; R ｋ is a linear or branched C １－２４ alkyl optionally substituted with, a C ３－１０ cycloalkyl optionally substituted with, a heterocycle optionally substituted with, a C ５－２４ aryl, or a C ３－８ cycloalkenyl optionally substituted with; R ｌ is H, a linear or branched C １－２４ alkyl optionally substituted with, a C ３－１０ cycloalkyl optionally substituted with, a heterocycle optionally substituted with, a C ５－２４ aryl, or a C ３－８ cycloalkenyl optionally substituted with; R ｍ is H, a linear or branched C １－２４ alkyl optionally substituted with, a C ３－１０ cycloalkyl optionally substituted with, a heterocycle optionally substituted with, a C ５－２４Aryl, or optionally substituted C ３－８ is cycloalkenyl; R ｎ is H, optionally substituted linear or branched C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl; R ｏ is H, optionally substituted linear or branched C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl; and R ｐ is H, optionally substituted linear or branched C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl polymer, provided that the at least one metal carbene olefin metathesis catalyst has the structure of formula (1), the structure of formula (2), or the structures of formula (1) and formula (2), the structure of formula (1) is as follows: 【Chemical formula 1-4】 wherein: M is ruthenium; L １ 、L ２ 、and L ３ are each independently a neutral electron donating ligand; n is 0 or 1; m is 0, 1, or 2; k is 0 or 1; X １ and X ２is independently an anionic ligand; R １ and R ２ are independently hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl; or, R １ and R ２ are joined to form one or more cyclic groups; and / or the structure of the chemical formula (2) is as follows: : 【Chemical Formula 1-5】 wherein: L １ is independently a neutral electron-donating ligand; X １ and X ２ are independently anionic ligands; W is O, halogen, NR ３３ , or S; R １９ is H, optionally substituted C １－２４ alkyl, -C(R ３４ )(R ３５ )COOR ３６ , -C(R ３４ )(R ３５ )C(O)H, -C(R ３４ )(R ３５ )C(O)R ３７ , -C(R ３４ )(R ３５ )CR ３８ (OR ３９ )(OR ４０ ), -C(R ３４ )(R ３５ )C(O)NR ４１ R ４２ , -C(R ３４ )(R ３５ )C(O)NR ４１ OR ４０ , -C(O)R ２５ , optionally substituted heterocycle, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ cycloalkenyl, or W is NR ３３In the case where it is, R １９ is R ３３ and can combine to form an optionally substituted heterocyclic ring. When W is halogen, R １９ is nil; R ２０ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocycle, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ cycloalkenyl, or R ２１ and can combine to form a polycyclic ring; R ２１ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocycle, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ cycloalkenyl, or R ２０ and can combine, or R ２２ and can combine to form a polycyclic ring; R ２２ is H, optionally substituted C １－２４Alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ cycloalkenyl, or R ２１ is combined with, or R ２３ is combined with to form a polycyclic ring; R ２３ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ cycloalkenyl, or R ２２ is combined with to form a polycyclic ring; R ２４ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ 、 -OP(O)(OH) ２ 、 -SR ３１ 、 optionally substituted heterocyclic ring, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ cycloalkenyl; R ２５ is OH, OR ３０ 、 NR ２７ R ２８ 、 optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocyclic ring, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ２６ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocyclic ring, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ２７ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocyclic ring, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ２８ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocyclic ring, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ２９ is H, optionally substituted C １－２４ alkyl, OR ２６ 、 -NR ２７ R ２８ 、 optionally substituted heterocyclic ring, optionally substituted C ３－１０Cycloalkyl, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ３０ is optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ３１ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ３３ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ３４ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ３５ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; R ３６ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ３７ is optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ３８ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ３９ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ４０ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ４１ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ４２ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ cycloalkenyl; and x is 1 or 2.

2. R ａ is H, optionally substituted straight or branched chain C １－６ alkyl, optionally substituted straight or branched chain C ２－６ alkenyl, halogen, -C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , CN, NO ２ , -CF ３ , -P(O)(OH) ２ , -OP(O)(OH) ２ , optionally substituted heterocycle, -CH ２ -(optionally substituted heterocycle), optionally substituted C ５－７ cycloalkyl, -CH ２ -(optionally substituted C ５－７ cycloalkyl), optionally substituted C ６－１０ aryl, -CH ２ -(optionally substituted C ６－１０ aryl), optionally substituted C ３－８ cycloalkenyl, -CH ２ -(optionally substituted C ３－８ cycloalkenyl), or 【Chemical Formula 1-6】 and; R ｂ is H, optionally substituted straight or branched chain C １－６ alkyl, optionally substituted straight or branched chain C ２－６ alkenyl, halogen, -C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , -CH ２ -OR ｇ , -NO₂, -CF ３, -P(O)(OH) ２ , -OP(O)(OH) ２ , an optionally substituted heterocyclic ring, -CH ２ -(an optionally substituted heterocyclic ring), an optionally substituted C ５－７ cycloalkyl, -CH ２ -(an optionally substituted C ５－７ cycloalkyl), an optionally substituted C ６－１０ aryl, -CH ２ -(an optionally substituted C ６－１０ aryl), an optionally substituted C ３－８ cycloalkenyl, -CH ２ -(an optionally substituted C ３－８ cycloalkenyl), or [Chemical Formula 1-7] and; t is 0; R ｆ is OH, OR ｋ , NR ｇ R ｈ , an optionally substituted straight-chain or branched-chain C １－６ alkyl, an optionally substituted C ５－７ cycloalkyl, an optionally substituted heterocyclic ring, an optionally substituted C ６－１０ aryl, or an optionally substituted C ３－８ cycloalkenyl; R ｇ is H, an optionally substituted C １－６ alkyl, an optionally substituted C ５－７ cycloalkyl, an optionally substituted heterocyclic ring, a substituted C ６－１０ aryl, an optionally substituted straight-chain or branched-chain C ２－６ alkenyl, -C(O)-(an optionally substituted straight-chain or branched-chain C ２－６ alkenyl), or an optionally substituted C ３－８ cycloalkenyl; R ｈ is H, an optionally substituted straight-chain or branched-chain C １－６ alkyl, an optionally substituted C ５－７ cycloalkyl, an optionally substituted heterocyclic ring, an optionally substituted C ６－１０Aryl, or optionally substituted C ３－８ is cycloalkenyl; R ｋ is optionally substituted linear or branched C １－６ alkyl, optionally substituted C ５－７ is cycloalkyl, optionally substituted heterocycle, optionally substituted C ６－１０ is aryl, or optionally substituted C ３－８ is cycloalkenyl; z is 2; R ｃ is H, optionally substituted linear or branched C １－６ alkyl, optionally substituted linear or branched C ２－６ alkenyl, halogen, -C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , CN, NO ２ , -CF ３ , -P(O)(OH) ２ , -OP(O)(OH) ２ , optionally substituted heterocycle, -CH ２ -(optionally substituted heterocycle), optionally substituted C ５－７ is cycloalkyl, -CH ２ -(optionally substituted C ５－７ is cycloalkyl), optionally substituted C ６－１０ is aryl, -CH ２ -(optionally substituted C ６－１０ is aryl), optionally substituted C ３－８ is cycloalkenyl, or -CH ２ -(optionally substituted C ３－８ is cycloalkenyl); and R ｄ is H, optionally substituted linear or branched C １－６ alkyl, optionally substituted linear or branched C ２－６ alkenyl, halogen, -C(O)R ｆ , -CH ２ -C(O)R ｆ , -OR ｇ , CN, NO ２ , -CF ３ , -P(O)(OH) ２ , -OP(O)(OH) ２ , an optionally substituted heterocyclic ring, -CH ２ -(an optionally substituted heterocyclic ring), an optionally substituted C ５－７ cycloalkyl, -CH ２ -(an optionally substituted C ５－７ cycloalkyl), an optionally substituted C ５－２４ aryl, -CH ２ -(an optionally substituted C ６－１０ aryl), an optionally substituted C ３－８ cycloalkenyl, or -CH ２ -(an optionally substituted C ３－８ cycloalkenyl), the polymer according to claim 1.

3. R ａ is an optionally substituted straight-chain or branched-chain C ２－２４ alkenyl, an optionally substituted straight-chain or branched-chain C １－２４ alkyl, or an optionally substituted C ５－２４ aryl; z is 2; R ｂ is an optionally substituted straight-chain or branched-chain C １－２４ alkyl, -CH ２ -OR ｇ , -CH ２ -(an optionally substituted heterocyclic ring), -C(O)R ｆ , an optionally substituted heterocyclic ring, an optionally substituted spiro heterocyclic ring, -CH ２ -(an optionally substituted C ５－２４ aryl), or -CH ２ -OR ｇ ; R ｇ is H, an optionally substituted straight-chain or branched-chain C １－２４ alkyl, -C(O)-(an optionally substituted straight-chain or branched-chain C ２－６ alkenyl), or a substituted C ５－２４ aryl; R ｆ is OH; R ｃis H; and R ｄ is a linear or branched C １－２４ alkyl, optionally substituted, or -CH ２ -(optionally substituted heterocycle), the polymer according to claim 1.

4. At least one monomer of chemical formula (I) has the following structure: R ａ is 【Chemical Formula 2】 is; and t = 0; at least one monomer of chemical formula (II) has the following structure: R ｂ is 【Chemical Formula 3-1】 【Chemical Formula 3-2】 is; and t = 0; at least one monomer of chemical formula (III) has a structure where z is 1 or 2; and at least one olefin of chemical formula (IV) has the following structure: R ｃ is H, 【Chemical Formula 4】 is; and R ｄ is 【Chemical Formula 5】 is, the polymer according to claim 1.

5. At least one monomer of chemical formula (I) is 【Chemical Formula 6】 is; At least one monomer of chemical formula (II) is 【Chemical Formula 7-1】 【Chemical Formula 7-2】 is; At least one monomer of chemical formula (III) is 【Chemical Formula 8】 is; At least one olefin of chemical formula (IV) is [Chemical Formula 9] the polymer according to claim 1, which is

6. At least one monomer of chemical formula (I) is [Chemical Formula 10] as follows; At least one monomer of chemical formula (II) is [Chemical Formula 11] as follows; At least one monomer of chemical formula (III) is [Chemical Formula 12] as follows; At least one olefin of chemical formula (IV) is [Chemical Formula 13] the polymer according to claim 1, which is

7. L of chemical formulas (1) and (2) １ is [Chemical Formula 16] as follows, wherein: X and Y are each independently C, CR ３ａ , N, O, S, or P; Q １ , Q ２ , R ３ , R ３ａ , and R ４ are each independently hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl; when X is O or S, p is 0; when X is N, P, or CR ３ａ , p is 1; when X is C, p is 2; and when Y is O or S, q is 0; when Y is N, P, or CR ３ａ , q is 1; when X is C, q is 2, the polymer according to any one of claims 1 to 6.

8. L of Chemical Formulas (1) and (2) １ is 【Chemical Formula 17】 and in the formula: Q is a two-atom bond having the structure -[CR １１ R １２ ] ｓ -[CR １３ R １４ ] ｔ - or -[CR １１ =CR １３ ], and R １１ R １２ R １３ and R １４ are independently hydrogen, optionally substituted hydrocarbyl, or optionally substituted heteroatom-containing hydrocarbyl; s and t are independently 1 or 2; or R １１ R １２ R １３ and R １４ Any two of which may be optionally joined to form an optionally substituted saturated or unsaturated polycyclic ring structure, the polymer according to any one of claims 1 to 6.

9. L of Chemical Formulas (1) and (2) １ is 【Chemical Formula 18】 and in the formula: Z is N or CR ３２ ; R １ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ -OR ２６ CN, -NR ２７ R ２８ NO ２ -CF ３ -S(O) ｘ R ２９ -P(O)(OH) ２ -OP(O)(OH) ２ 、 -SR ３１ 、 optionally substituted heterocyclic ring, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ cycloalkenyl, or R ２ can combine with to form a spiro compound, or R ３ combine with, or R ４ combine with to form a polycyclic ring; R ２ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ 、 -OR ２６ 、 CN, -NR ２７ R ２８ 、 NO ２ 、 -CF ３ 、 -S(O) ｘ R ２９ 、 -P(O)(OH) ２ 、 -OP(O)(OH) ２ 、 -SR ３１ 、 optionally substituted heterocyclic ring, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ cycloalkenyl, or R １ can combine with to form a spiro compound, or R ３ combine with, or R ４ combine with to form a polycyclic ring; R ３ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ 、 -OR ２６ 、 CN, -NR ２７ R ２８ 、 NO ２ 、 -CF ３ 、 -S(O) ｘ R ２９ 、 -P(O)(OH) ２ 、 -OP(O)(OH) ２ 、 -SR ３１ 、 optionally substituted heterocyclic ring, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４ Aryl, optionally substituted C ３－８ is cycloalkenyl, or R ２ combines with, or R １ combines with to form a polycyclic ring, or R ４ combines with to form a spiro compound; R ４ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ is cycloalkenyl, or R ３ combines with to form a spiro compound, or R ２ combines with, or R １ combines with to form a polycyclic ring; R ５ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ is a cycloalkenyl or R ６ can combine with to form an optionally substituted polycyclic ring; R ６ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocyclic ring, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ is a cycloalkenyl or R ５ can combine with or R ７ to form an optionally substituted polycyclic ring; R ７ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocyclic ring, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ is a cycloalkenyl or R ６ can combine with or R ８ to form an optionally substituted polycyclic ring; R ８ is H, optionally substituted C １－２４Alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ cycloalkenyl, or R ７ combines with, or R ９ combines with to form an optionally substituted polycyclic ring; R ９ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , optionally substituted heterocycle, optionally substituted C ３－１０ cycloalkyl, optionally substituted C ５－２４ aryl, optionally substituted C ３－８ cycloalkenyl, or R ８ combines with to form an optionally substituted polycyclic ring; R １０ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９, -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocyclic ring, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ cycloalkenyl, or R １１ combines with to form an optionally substituted polycyclic ring; R １１ is H, an optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocyclic ring, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ cycloalkenyl, or R １０ combines with, or R １２ combines with to form an optionally substituted polycyclic ring; R １２ is H, an optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocyclic ring, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ is a cycloalkenyl or R １１ is combined with or R １３ is combined with to form an optionally substituted polycyclic ring; R １３ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocyclic ring, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ cycloalkenyl or R １４ is combined with or R １２ is combined with to form an optionally substituted polycyclic ring; R １４ is H, optionally substituted C １－２４ alkyl, halogen, -C(O)R ２５ , -OR ２６ , CN, -NR ２７ R ２８ , NO ２ , -CF ３ , -S(O) ｘ R ２９ , -P(O)(OH) ２ , -OP(O)(OH) ２ , -SR ３１ , an optionally substituted heterocyclic ring, an optionally substituted C ３－１０ cycloalkyl, an optionally substituted C ５－２４ aryl, an optionally substituted C ３－８ cycloalkenyl or R １３ is combined with to form a polycyclic ring; R ３２ is H, optionally substituted C １－２４Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ２５ is OH, OR ３０ , NR ２７ R ２８ , optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ２６ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ２７ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ２８ is H, optionally substituted C １－２４ Alkyl, optionally substituted C ３－１０ Cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ Aryl, or optionally substituted C ３－８ Cycloalkenyl; R ２９ is H, optionally substituted C １－２４ Alkyl, OR ２６ , -NR ２７ R ２８ , optionally substituted heterocycle, optionally substituted C ３－１０ Cycloalkyl, optionally substituted C ５－２４Aryl, or optionally substituted C ３－８ is cycloalkenyl; R ３０ is optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl; R ３１ is H, optionally substituted C １－２４ alkyl, optionally substituted C ３－１０ cycloalkyl, optionally substituted heterocycle, optionally substituted C ５－２４ aryl, or optionally substituted C ３－８ is cycloalkenyl; and x is 1 or 2, the polymer according to any one of claims 1 to 6.

10. The ring-opening metathesis reaction is at least one monomer of formula (I), at least one monomer of formula (II), at least one monomer of formula (III), the metal carbene olefin metathesis catalyst of formula (1), the metal carbene olefin metathesis catalyst of formula (2), or a combination of the metal carbene olefin metathesis catalyst of formula (1) and the metal carbene olefin metathesis catalyst of formula (2), and at least one metal carbene olefin metathesis catalyst, the polymer according to any one of claims 1 to 9.

11. The polymer according to any one of claims 1 to 9, wherein the ring-opening metathesis reaction comprises at least one monomer of chemical formula (I), at least one monomer of chemical formula (II), at least one monomer of chemical formula (III), at least one olefin of chemical formula (IV), and at least one metal carbene olefin metathesis catalyst of chemical formula (1), a metal carbene olefin metathesis catalyst of chemical formula (2), or a combination of a metal carbene olefin metathesis catalyst of chemical formula (1) and a metal carbene olefin metathesis catalyst of chemical formula (2).

12. at least one monomer of chemical formula (II) is 【Chemical formula 19】 The polymer according to any one of claims 1 to 11, which is or a combination thereof.

13. at least one monomer of formula (II) is 5-octyl-2-norbornene, 5-ethylidene-2-norbornene, or a mixture thereof; at least one monomer of formula (III) is dicyclopentadiene, tricyclopentadiene, or a mixture thereof, The polymer according to any one of claims 1 to 11.

14. An article of manufacture comprising the polymer according to any one of claims 1 to 13.

15. The article of manufacture according to claim 14, selected from the group consisting of prepregs, fiber composite laminates, coatings using solvents, melt-extruded parts, films, and liquid compounds.

16. The article of manufacture according to claim 15, which is a prepreg.

17. The polymer according to any one of claims 1 to 13, wherein the polymer is crosslinked optionally in the presence of a free radical initiator, a cationic initiator, other curing agents, or a mixture thereof.

Images