Materials for optoelectronic applications

Abstract

The invention relates to materials for optoelectronic applications. Compounds of Formula (I) are provided. Formulations comprising these compounds are also provided. Further provided are optoelectronic devices utilizing these compounds. # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to U.S. Provisional Application No. 63 / 508,408, filed on June 15, 2023, which is incorporated herein by reference in its entirety. Technical Field

[0003] The present disclosure relates generally to materials for optoelectronic applications. Background Art

[0004] Photoelectric devices rely on the optical and electronic properties of materials to electronically generate or detect electromagnetic radiation or generate electricity from environmental electromagnetic radiation. For a variety of reasons, photoelectric devices using organic materials have become increasingly popular. Many materials used to make such devices are relatively cheap, so organic photoelectric devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials (such as their flexibility) can make them more suitable for specific applications, such as manufacturing on flexible substrates. Examples of organic photoelectric devices include organic light emitting diodes / devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors.

[0005] Considerable attention has been paid to organic photovoltaics (OPVs) in recent years, as their flexibility, lightweight, non-toxic nature and translucency make them ideal for building-integrated and building-applied applications. Compared to commercial solar modules, which typically have a sunlight power conversion efficiency of PCE = 15-22%, organics have increased from 10% in 2016 to over 17% in 2019 for single-junction devices. Progress has been steadily advancing toward the single-junction thermodynamically limited efficiency of about 25%, with higher efficiencies possible for multi-junction cells. This rapid progress has been accelerated by the development of non-fullerene acceptors (NFAs).

[0006] All high-performance photovoltaic devices exhibit acceptable levels of reproducibility and long operating lifetimes, with the essential characteristic being that the materials they contain are of high purity. In crystalline Si photovoltaic cells, the chemical purity of Si is an important limiting factor in their performance. The introduction of external impurities can cause significant changes in conductivity by creating lattice strain or by forming interstitial and substitutional defects. As a result, precise control of the purity of the source materials is a common strategy to improve photovoltaic efficiency and reliability.

[0007] Compared with inorganic photovoltaics, understanding the impact of impurities on organic photovoltaics (OPV) has received little attention, despite the potential for impurities to have a profound impact on performance. In fact, molecular impurities remaining during the synthesis process or molecular impurities produced by decomposition during device operation can greatly affect the intrinsic optical and electrical properties of the original OPV material (Mateker, WR et al. Energy and Environmental Science (Energy Environ. Sci.) 6, 2529-2537 (2013); Salzman, RF et al. Organic Electronics (Org. Electron.) 6, 242-246 (2005); Tetreault et al., Organic Electronics. 92, 106091 (2021)). One example is the photoinduced dimerization product of the fullerene acceptor C60 during OPV operation, which reduces the exciton lifetime and diffusion length, resulting in a significant shortening of the device lifetime (Wang, N. et al., Solar Materials and Solar Cells (Sol. Energy Mater. Sol. Cells) 125, 170-175 (2014)). In addition to these changes, impurities can also destroy the crystalline order of molecular solids (Forrest, SR et al., Journal of Applied Physics (J. Appl. Phys.) 56, 543-551 (1984)), thereby reducing charge carrier mobility and cell power conversion efficiency (PCE). Therefore, contaminants in the source material must be removed very carefully and the material must be prevented from decomposing during device preparation and operation.

[0008] In recent years, ternary blended OPVs containing one donor and two acceptors or one acceptor and two donors have attracted great interest (Lu, L. et al., Nat. Photonics 8, 716-722 (2014); Gasparini, N. et al., Nat. Rev. Mater. 4, 229-242 (2019); Yu, R. et al., Adv. Energy Mater. 8, 1702814 (2018); Li, Y. et al., Journal of the American Chemical Society (J. Am. Chem. Soc.) 141, 18204-18210 (2019); Li, Y. et al., Adv. Mater. 30, 1804416 (2018)). Introducing a third molecular species in the bulk heterojunction (BHJ) layer can increase solar spectrum coverage, reduce energy losses, and significantly improve OPV efficiency compared to conventional binary module devices. In particular, the rapid development of acceptor (A)-donor (D)-acceptor (A) non-fullerene acceptors (NFAs) has enabled the PCE of ternary blended OPVs containing two NFAs and a polymer donor to approach 20% under 1 sun intensity and AM 1.5G illumination (Cui, Y. et al. Advanced Materials. 33, 2102420 (2021); Zuo, L. et al. Nature Nanotechnology (Nat. Nanotechnol.) 17, 53-60 (2022); Zhan, L. et al. Journal of Advanced Energy Materials. 12, 2201076 (2022); Hultmark, S. et al. Advanced Functional Materials (Adv. Funct. Mater.) 30, 2005462 (2020)). Summary of the invention

[0009] In one aspect, the present disclosure relates to compounds of formula (I):

[0010]

[0011] in:

[0012] D represents a linear ring system of three to twenty-five rings D'; wherein each ring D' is independently a monocyclic or polycyclic fused ring system; wherein each ring D' is a 5- to 10-membered carbocyclic or heterocyclic ring; wherein each ring D' is fused to an adjacent ring D' or bonded to an adjacent ring D' by a single bond; and wherein each ring D' is optionally substituted with one or more substituents R;

[0013] L is a divalent linking group covalently bonded to the terminal ring D' and A; and

[0014] A is an acceptor group selected from the group consisting of:

[0015]

[0016] Among them, Ar 1 is an aromatic ring or a heteroaromatic ring;

[0017] * indicates a bond with L;

[0018] R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

[0019] Any two adjacent substituents R are optionally joined to form a fused ring.

[0020] In another aspect, the present disclosure provides formulations comprising a compound of formula (I) as described herein.

[0021] In another aspect, the present disclosure provides an optoelectronic device comprising a compound of formula (I) as described herein. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] For a more complete understanding of the present disclosure, reference is made to the following detailed description and accompanying drawings, wherein like reference numerals may be used to refer to like elements throughout the drawings.

[0023] Figure 1 The proposed mechanism for the end-capping exchange reaction via the formation of an aldehyde intermediate is depicted.

[0024] Figure 2 The effect of the end-capping unit on the reactivity of the exchange process is depicted. On the left is the chemical structure of the studied molecule. On the right is a crude mixture of BTIC-4F and the studied molecule. 19 F{ 1 Comparison of H} NMR spectra. The mixture was obtained by stirring in chlorobenzene at 65°C for 24 hours. DETAILED DESCRIPTION

[0025] The present disclosure provides non-fullerene acceptors (NFAs) with good photostability and morphological stability. In some aspects, employing these NFAs in one or more device architectures improves the operating lifetime of OPV devices.

[0026] Various non-limiting examples of OPVs and compositions within various layers of the OPVs are described in more detail below.

[0027] definition

[0028] As used herein, the term "organic" includes polymeric materials and small molecule organic materials that can be used to make organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and a "small molecule" can actually be quite large. In some cases, a small molecule can include repeating units. For example, the use of a long chain alkyl group as a substituent does not remove a molecule from the "small molecule" category. Small molecules can also be incorporated into polymers, for example as side groups on a polymer backbone or as part of a backbone. Small molecules can also serve as a dendritic core portion, which is composed of a series of chemical shells built on the core portion. The dendritic core portion can be a fluorescent or phosphorescent small molecule emitter. Dendritic polymers can be "small molecules", and all dendritic polymers currently used in the field of optoelectronic devices are considered to be small molecules.

[0029] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. When a first layer is described as being "disposed above" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, there may be other layers between the first and second layers. For example, a cathode may be described as being "disposed above" an anode even if there are various organic layers between the cathode and the anode.

[0030] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0031] When the ligand is believed to directly contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "photosensitive." When the ligand is believed not to contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary," but the ancillary ligand may alter the properties of the photosensitive ligand.

[0032] As used herein, the terms "electrode" and "contact" may refer to a layer that provides a medium to deliver current to an external circuit or to provide a bias current or voltage to a device. For example, an electrode or contact may provide an interface between an active area of ​​an organic photosensitive optoelectronic device and a wire, lead, trace, or other member for transporting charge carriers to or from an external circuit. Examples of electrodes include anodes and cathodes, which may be used in a photosensitive optoelectronic device.

[0033] As used herein, the term "transparent" may refer to a material that allows at least 50% of incident electromagnetic radiation of the relevant wavelength to be transmitted therethrough. In a photosensitive optoelectronic device, it may be desirable to allow a maximum amount of ambient electromagnetic radiation from outside the device to enter the photoconductive active interior region. That is, the electromagnetic radiation must reach the photoconductive layer where it can be converted to electricity by absorption by the photoconductor. This generally requires that at least one of the electrical contacts or electrodes should minimize absorption and minimize reflection of the incident electromagnetic radiation. In some cases, such contacts should be transparent or at least translucent. In one embodiment, the transparent material may form at least a portion of the electrical contacts or electrodes.

[0034] As used herein, the term "semi-transparent" may refer to a material that allows some but less than 50% transmission of ambient electromagnetic radiation of relevant wavelengths. Where a transparent or semi-transparent electrode is used, the opposing electrode may be a reflective material so that light that has passed through the cell without being absorbed is reflected back through the cell.

[0035] As used and described herein, "layer" refers to a component or part of a device (e.g., an optoelectronic device) that is primarily defined by, for example, thickness relative to other adjacent layers and extends outwardly in length and width. It should be understood that the term "layer" is not necessarily limited to a single layer or sheet of material. In addition, it should be understood that the surfaces of certain layers, including interfaces of such layers with other materials or layers, may be imperfect, wherein the surfaces represent interpenetration, entanglement, or a tangled network with other materials or layers. Similarly, it should also be understood that a layer may be discontinuous, such that the continuity of the layer along the length and width may be disturbed or otherwise interrupted by other layers or materials.

[0036] As used herein, "photosensitive region" refers to a region of a device that absorbs electromagnetic radiation to generate excitons. Similarly, a layer is "photosensitive" if it absorbs electromagnetic radiation to generate excitons. The excitons can dissociate into electrons and holes to generate an electric current.

[0037] As used herein, the term "cathode buffer" is given its ordinary meaning in the art and generally refers to a material placed between the cathode and the photosensitive material. In general, the cathode buffer material helps to reduce the work function of the cathode interface. One of ordinary skill in the art will be able to select a suitable cathode buffer material with an appropriate work function for the methods and devices described herein.

[0038] As used herein, the term "anode buffer" is given its ordinary meaning in the art and generally refers to a material placed between the anode and the photosensitive material. In general, the anode buffer material helps to reduce the work function of the anode interface. One of ordinary skill in the art will be able to select a suitable anode buffer material with an appropriate work function for use in the methods and devices described herein.

[0039] As used herein, the terms "donor" and "acceptor" refer to the relative positions of the highest occupied molecular orbital ("HOMO") and lowest unoccupied molecular orbital ("LUMO") energy levels of two contacting but different organic materials. If the LUMO energy level of one material in contact with the other is lower, then the material is an acceptor. Otherwise it is a donor. In the absence of an external bias, it is energetically favorable for electrons at the donor-acceptor junction to move to the acceptor material, and for holes to move to the donor material.

[0040] As used herein, and as one skilled in the art would generally understand, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Because work functions are typically measured as negative numbers relative to the vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being farther in a downward direction from the vacuum level. Thus, the definition of HOMO and LUMO energy levels follows different rules than work functions.

[0041] As used herein, the term "band gap" (E g ) may refer to the energy difference between the HOMO and the LUMO. Band gaps are usually reported in electron volts (eV). Band gaps may be measured from UV-vis spectroscopy or cyclic voltammetry. A "low band gap" polymer may refer to a polymer with a band gap below 2 eV, for example, a polymer that absorbs light of wavelengths greater than 620 nm.

[0042] As used herein, the term "excitation binding energy" (E B ) may refer to the following formula: E B =(M + +M - )-(M*+M), where M + and M - are the total energies of the positively and negatively charged molecules, respectively; M* and M are the molecular energies of the first singlet state (S1) and the ground state, respectively. The exciton binding energy of the acceptor or donor molecule affects the energy shift required for efficient exciton dissociation. In some instances, the escape rate of holes increases with increasing HOMO shift. The exciton binding energy of the acceptor molecule, E B The decrease in leads to an increase in the hole escape rate for the same HOMO offset between the donor and acceptor molecules.

[0043] As used herein, “power conversion efficiency” (PCE) (η ρ ) can be expressed as:

[0044]

[0045] Where V OC is the open circuit voltage, FF is the fill factor, JSC is the short-circuit current, and P O is the input optical power.

[0046] As used herein, "spin coating" may refer to the process of solution depositing a layer or film of a material (i.e., coating material) on the surface of an adjacent substrate or material layer. The spin coating process may include applying a small amount of coating material to the center of a substrate, which is rotated at a low speed or not at all. The substrate is then rotated at a high speed so as to spread the coating material by centrifugal force. The rotation continues while the fluid rotates from the edge of the substrate until the desired film thickness is reached. The applied solvent is generally volatile and evaporates at the same time. Therefore, the higher the angular velocity of the rotation, the thinner the film. The thickness of the film also depends on the viscosity and concentration of the solution and solvent.

[0047] As used herein, and as will be generally understood by one skilled in the art, a first "highest occupied molecular orbital" (HOMO) or "lowest unoccupied molecular orbital" (LUMO) energy level is "greater than" or "higher than" a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potential (IP) is measured as negative energy relative to the vacuum energy level, a higher HOMO energy level corresponds to an IP with a smaller absolute value (less negative IP). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) with a smaller absolute value (less negative EA). On a conventional energy level diagram with the vacuum energy level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A "higher" HOMO or LUMO energy level appears to be closer to the top of this diagram than a "lower" HOMO or LUMO energy level.

[0048] As used herein, and as one skilled in the art would generally understand, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Because work functions are typically measured as negative numbers relative to the vacuum level, this means that a "higher" work function is more negative. On a conventional energy level diagram with the vacuum level at the top, a "higher" work function is illustrated as being farther in a downward direction from the vacuum level. Thus, the definition of HOMO and LUMO energy levels follows different rules than work functions.

[0049] The terms "halo," "halogen," and "halide" are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.

[0050] The term "pseudohalogen" refers to a polyatomic analog of a halogen whose chemical properties are similar to those of a true halogen, allowing it to replace the halogen in several classes of compounds. Exemplary pseudohalogens include, but are not limited to, nitrile, cyanide, isocyanide, cyanate, isocyanate, fulminate, thiocyanate, isothiocyanate, selenocyanate, tellurocyanate, azide, cobalt tetracarbonyl, trinitromethane, and tricyanomethanate groups.

[0051] The term "acyl" refers to a substituted carbonyl (C(O)-R s ).

[0052] The term "ester" refers to a substituted oxycarbonyl (-OC(O)-R s OR-C(O)-OR s ) group.

[0053] The term "ether" refers to -OR s Group.

[0054] The terms "thio" or "thioether" are used interchangeably and refer to -SR s Group.

[0055] The term "sulfinyl" refers to -S(O)-R s Group.

[0056] The term "sulfonyl" refers to -SO2-R s Group.

[0057] The term "phosphino" refers to -P(R s )3 groups, wherein each R s Can be the same or different.

[0058] The term "silyl" refers to -Si(R s )3 groups, wherein each R s Can be the same or different.

[0059] The term "boryl" refers to -B(R s )2 group or its Lewis adduct -B(Rs)3 group, wherein Rs may be the same or different.

[0060] In each of the above groups, R s R may be hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. s Selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0061] The term "alkyl" refers to and includes straight and branched alkyl groups. Preferably, the alkyl group is an alkyl group containing one to fifteen carbon atoms, and includes methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, etc. In addition, the alkyl group is optionally substituted.

[0062] The term "cycloalkyl" refers to and includes monocyclic, polycyclic and spiroalkyl groups. Preferred cycloalkyl groups are cycloalkyl groups containing 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. In addition, the cycloalkyl group is optionally substituted.

[0063] The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group in which at least one carbon atom is replaced by a heteroatom, respectively. Optionally, at least one heteroatom is selected from O, S, N, P, B, Si and Se, preferably O, S or N. In addition, the heteroalkyl or heterocycloalkyl group is optionally substituted.

[0064] The term "alkenyl" refers to and includes straight and branched alkenyl groups. Alkenyl groups are essentially alkyl groups that include at least one carbon-carbon double bond in the alkyl chain. Cycloalkenyl groups are essentially cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalkyl ring. As used herein, the term "heteroalkenyl" refers to an alkenyl group in which at least one carbon atom is replaced by a heteroatom. Optionally, at least one heteroatom is selected from O, S, N, P, B, Si and Se, preferably O, S or N. Preferred alkenyl, cycloalkenyl or heteroalkenyl groups are those groups containing two to fifteen carbon atoms. In addition, alkenyl, cycloalkenyl or heteroalkenyl groups are optionally substituted.

[0065] The term "alkynyl" refers to and includes straight chain and branched chain alkynyl groups. Preferably, the alkynyl group is an alkynyl group containing two to fifteen carbon atoms. In addition, the alkynyl group is optionally substituted.

[0066] The terms "aralkyl" or "arylalkyl" are used interchangeably and refer to an alkyl group substituted with an aryl group. Additionally, the aralkyl group is optionally substituted.

[0067] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, at least one heteroatom is selected from O, S, N, P, B, Si and Se, preferably O, S or N. Heteroaromatic cyclic groups can be used interchangeably with heteroaryl. Preferably, hetero non-aromatic cyclic groups are groups containing 3 to 7 ring atoms including at least one heteroatom, and include cyclic amines, such as morpholino, piperidino, pyrrolidino, etc., and cyclic ethers / thioethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, etc. In addition, heterocyclic groups can be optionally substituted.

[0068] The term "aryl" refers to and includes monocyclic aromatic hydrocarbons and polycyclic aromatic ring systems. Polycyclics may have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), wherein at least one ring is an aromatic hydrocarbon, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocycle and / or heteroaryl. Preferably, the aryl is an aryl containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Particularly preferred are aryls with six carbons, ten carbons or twelve carbons. Suitable aryls include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthren, phenanthrene, fluorene, pyrene, lettuce, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl is optionally substituted.

[0069] The term "heteroaryl" refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems having at least one heteroatom. Heteroatoms include, but are not limited to, O, S, N, P, B, Si and Se. In many cases, O, S or N are preferred heteroatoms. Monocyclic heteroaromatic systems are preferably monocyclic rings with 5 or 6 ring atoms, and the rings may have one to six heteroatoms. Heteropolycyclic ring systems may have two or more rings in which two carbons are shared by two adjacent rings (the rings are "fused"), wherein at least one ring is a heteroaryl, for example, the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocycle and / or heteroaryl. Heteropolycyclic aromatic ring systems may have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferably, heteroaryl is a heteroaryl containing three to thirty carbon atoms, preferably three to twenty carbon atoms, and more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridyl indole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline , quinoxaline, naphthyridine, phthalazine, pteridine, dibenzopyran (xanthene), acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazine and its aza analogs. In addition, heteroaryl is optionally substituted.

[0070] Among the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine and benzimidazole groups and their respective corresponding aza analogs are of particular interest.

[0071] As used herein, the terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclyl, aryl and heteroaryl are independently unsubstituted or substituted with one or more common substituents.

[0072] In many cases, the universal substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0073] In some cases, preferred universal substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.

[0074] In some cases, preferred universal substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silane, aryl, heteroaryl, thio, and combinations thereof.

[0075] In other cases, more preferred universal substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

[0076] The terms "substituted" and "substituted" refer to the bonding of a substituent other than H to the relevant position, such as carbon or nitrogen. For example, when R 1 When it represents a single substitution, then one R 1 must not be H (i.e. substituted). Similarly, when R 1 When it indicates disubstituted, the two R 1 must not be H. Similarly, when R 1 When there is no substitution, R 1 For example, it can be hydrogen with available valences of the ring atoms, such as the carbon atoms of benzene and the nitrogen atoms in pyrrole, or simply represent nothing for ring atoms with fully saturated valences, such as the nitrogen atoms in pyridine. The maximum number of substitutions possible in the ring structure will depend on the total number of available valences in the ring atoms.

[0077] As used herein, "combinations thereof" means that one or more members of the applicable list are combined to form known or chemically stable arrangements that can be envisioned by a person of ordinary skill in the art from the applicable list. For example, alkyl and deuterium can be combined to form partially or completely deuterated alkyl; halogen and alkyl can be combined to form halogenated alkyl substituents; and halogen, alkyl and aryl can be combined to form halogenated aralkyl. In one case, the term substitution includes a combination of two to four of the listed groups. In another case, the term substitution includes a combination of two to three groups. In yet another case, the term substitution includes a combination of two groups. Preferred combinations of substituents are substituents containing up to fifty atoms that are not hydrogen or deuterium, or substituents including up to forty atoms that are not hydrogen or deuterium, or substituents including up to thirty atoms that are not hydrogen or deuterium. In many cases, preferred combinations of substituents will include up to twenty atoms that are not hydrogen or deuterium.

[0078] The "aza" designations in the fragments described herein, i.e., azadibenzofuran, azadibenzothiophene, etc., mean that one or more CH groups in the corresponding aromatic ring can be replaced by a nitrogen atom, for example and without any limitation, azatriphenylene encompasses dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed by the term as set forth herein.

[0079] As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be easily prepared using methods known in the art. For example, U.S. Patent No. 8,557,400, Patent Publication No. WO 2006 / 095951 and U.S. Patent Application Publication No. US2011 / 0037057 (all of which are incorporated herein by reference in their entirety) describe the preparation of organometallic complexes substituted with deuterium. Also refer to Ming Yan et al., "Tetrahedron", 2015, 71, 1425-30 and Atzrodt et al., "Angew. Chem. Int. Ed." (Review) 2007, 46, 7744-65, which are incorporated herein by reference in their entirety, which respectively describe the deuteration of methylene hydrogen in benzylamine and the effective way to replace aromatic ring hydrogen with deuterium.

[0080] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or attaching fragments are considered equivalent.

[0081] In some cases, a pair of adjacent substituents may be optionally joined or fused to form a ring. Preferred rings are five-membered, six-membered or seven-membered carbocyclic or heterocyclic rings, including the following two cases: a portion of the ring formed by the substituent pair is saturated and a portion of the ring formed by the substituent pair is unsaturated. As used herein, "adjacent" means that the two substituents involved can be immediately adjacent to each other on the same ring or on two adjacent rings with two closest available substitutable positions (such as the 2,2' position in biphenyl or the 1,8 position in naphthalene), as long as they can form a stable fused ring system.

[0082] Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For organic layers, preferred methods include thermal evaporation, inkjet (e.g., as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entirety), organic vapor phase deposition (OVPD) (e.g., as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety), and deposition by organic vapor jet printing (OVJP) (e.g., as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety). Other suitable deposition methods include spin coating and other solution-based processes. Solution-based processes are preferably performed in a nitrogen or inert atmosphere. For other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding (as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entirety), and patterning associated with some of the deposition methods such as inkjet and organic vapor jet printing (OVJP). Other methods may also be used. The material to be deposited may be modified to make it compatible with a specific deposition method. For example, substituents such as alkyl and aryl groups, which may be branched or unbranched and preferably contain at least 3 carbons, may be used in small molecules to enhance their ability to withstand solution processing. Substituents having 20 or more carbons may be used, and 3-20 carbons are a preferred range. The solution processability of materials having asymmetric structures may be better than that of materials having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendritic polymer substituents may be used to enhance the ability of small molecules to withstand solution processing.

[0083] The device manufactured according to the embodiment of the present disclosure may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrode and the organic layer from exposure to harmful substances in the environment including moisture, steam and / or gas, etc. The barrier layer can be deposited on the substrate, above the electrode, under the substrate, or next to the substrate, electrode, or on any other part (including the edge) of the device. The barrier layer may include a single layer or multiple layers. The barrier layer can be formed by various known chemical vapor deposition techniques, and may include a composition having a single phase and a composition having multiple phases. Any suitable material or material combination can be used for the barrier layer. The barrier layer may include an inorganic compound or an organic compound or both. The preferred barrier layer includes a mixture of a polymeric material and a non-polymeric material, as described in U.S. Patent No. 7,968,146, PCT Patent Application No. PCT / US2007 / 023098 and No. PCT / US2009 / 042829, which are incorporated herein by reference in their entirety. In order to be considered a "mixture", the aforementioned polymeric material and non-polymeric material constituting the barrier layer should be deposited under the same reaction conditions and / or deposited simultaneously. The weight ratio of polymeric material to non-polymeric material can be in the range of 95:5 to 5:95. The polymeric material and non-polymeric material can be produced from the same precursor material. In one example, the mixture of polymeric material and non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

[0084] The device manufactured according to the embodiments of the present disclosure may be incorporated into a variety of electronic component modules (or units) that may be incorporated into a variety of electronic products or intermediate components.

[0085] The materials and structures described herein can be applied to devices other than organic solar cells. For example, other optoelectronic devices such as organic electroluminescent devices (OLEDs) and organic photodetectors can use the materials and structures. More generally, organic devices such as organic transistors can employ the materials and structures.

[0086] According to one aspect, the present disclosure relates to compounds of formula (I):

[0087]

[0088] in:

[0089] D represents a linear ring system of three to twenty-five rings D'; wherein each ring D' is independently a monocyclic or polycyclic fused ring system; wherein each ring D' is a 5- to 10-membered carbocyclic or heterocyclic ring; wherein each ring D' is fused to an adjacent ring D' or bonded to an adjacent ring D' by a single bond; and wherein each ring D' is optionally substituted with one or more substituents R;

[0090] Each L is independently a divalent linking group covalently bonded to the terminal ring D' and A; and

[0091] Each A is independently an acceptor group selected from the group consisting of:

[0092]

[0093] Each Ar 1 are independently aromatic or heteroaromatic;

[0094] * indicates a bond with L;

[0095] R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

[0096] Any two adjacent substituents R are optionally joined to form a fused ring.

[0097] In one embodiment, the divalent linking group L promotes the binding between the linear ring system D and the acceptor group A. In one embodiment, each divalent linking group L is independently selected from the group consisting of aromatic rings, heteroaromatic rings, cyclic olefins, cyclic heteroolefins, and alkynes. In one embodiment, the divalent linking group L is not 1,2-cyclopentene. In one embodiment, one divalent linking group L is not 1,2-cyclopentene. In one embodiment, no divalent linking group L is not a single bond. In one embodiment, one divalent linking group L is not a single bond.

[0098] In one embodiment, each L is independently selected from the group consisting of:

[0099]

[0100] where * represents the bond to the linear ring system D;

[0101] # indicates the bond with A;

[0102] Z is NR, C(R)2, O, S, Se or Te;

[0103] Ar 2 and Ar 3 Each is an aromatic ring or a heteroaromatic ring;

[0104] q is 0 and Ar 2 or Ar 3 An integer between the maximum possible substitution on ; and

[0105] R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two adjacent R are optionally joined to form a ring.

[0106] In one embodiment, D comprises three rings D', four rings D', five rings D', six rings D', seven rings D', eight rings D', nine rings D', ten rings D', eleven rings D', twelve rings D', thirteen rings D', fourteen rings D', fifteen rings D', sixteen rings D', seventeen rings D', eighteen rings D', nineteen rings D', twenty rings D', twenty-one rings D', twenty-two rings D', twenty-three rings D', twenty-four rings D' or twenty-five rings D'.

[0107] In one embodiment, each ring D' is independently selected from the group consisting of:

[0108]

[0109] wherein each X is independently selected from the group consisting of oxygen, carbon, hydrogen, sulfur, selenium, and nitrogen; and

[0110] wherein each ring D' is optionally substituted with one or more substituents R.

[0111] In one embodiment, each Ar 1 Independently selected from the group consisting of:

[0112]

[0113]

[0114] Where R 1 To R 8 Each independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0115] In one embodiment, R 1 To R 8 When it occurs at least once, it represents a halogen.

[0116] In one embodiment, Ar 2 and Ar 3Each is independently selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, triazole, thiazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, benzoxazole, benzothiophene, benzothiazole, benzoselenophene, indene, indole, benzimidazole, carbazole, dibenzofuran, dibenzothiophene, quinoxaline, phthalazine, phenanthridine, phenanthridine and fluorene.

[0117] In one embodiment, the compound is represented by formula (II):

[0118]

[0119] in:

[0120] m is an integer between 0 and 10;

[0121] n is an integer between 0 and 10;

[0122] D 1 , each D 2 and each D 3 Fused or covalently bonded to an adjacent ring

[0123] D 1 , D 2 and D 3 Each is independently a monocyclic or polycyclic condensed ring system, wherein each ring of the monocyclic or polycyclic condensed ring system is a 5- to 10-membered carbocyclic or heterocyclic ring; wherein D 1 , D 2 and D 3 Each is optionally further substituted with one or more substituents R; and

[0124] R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two adjacent substituents R are optionally joined to form a fused ring.

[0125] In one embodiment, D 1 Represented by one of the following structures:

[0126]

[0127] in:

[0128] Each X is independently selected from the group consisting of oxygen, carbon, hydrogen, sulfur, selenium and nitrogen;

[0129] p is an integer between 0 and 10;

[0130] Where D 4 is a monocyclic or polycyclic condensed ring system, wherein each ring of the monocyclic or polycyclic condensed ring system is a 5- to 10-membered carbocyclic or heterocyclic ring; wherein D 4 is optionally further substituted with one or more substituents R; and

[0131] Where D 1 Optionally substituted with one or more R substituents.

[0132] In one embodiment, D 2 Select from the group consisting of:

[0133]

[0134] wherein R at each occurrence independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two groups R are optionally taken together to form a ring.

[0135] In one embodiment, D 3 Select from the group consisting of:

[0136]

[0137] wherein p is an integer between 0 and 2; and

[0138] R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two groups R are optionally taken together to form a ring.

[0139] In one embodiment, the compound is represented by formula (III), formula (IV), formula (V), formula (VI), formula (VII) or formula (VIII);

[0140]

[0141]

[0142] in

[0143] X is selected from the group consisting of oxygen, carbon, hydrogen, sulfur, selenium and nitrogen.

[0144] In one embodiment, the compound is represented by one of the following formulae:

[0145]

[0146] According to another aspect, a formulation comprising a compound described herein is also disclosed.

[0147] Organic photovoltaic cells

[0148] In one aspect, the present disclosure relates to an OPV device comprising a compound of the present disclosure.In one embodiment, the OPV device comprises an anode; a cathode; and an active material disposed between the anode and the cathode, wherein the active material comprises an acceptor and a donor.

[0149] In one embodiment, the OPV device comprises a single junction organic photovoltaic device. In one embodiment, the OPV device comprises two electrodes having an anode and a cathode in a superimposed relationship, at least one donor composition and at least one acceptor composition, wherein the donor-acceptor material or active layer is disposed between the two electrodes. In one embodiment, one or more intermediate layers may be disposed between the anode and the active layer. Alternatively or additionally, one or more intermediate layers may be disposed between the active layer and the cathode.

[0150] In one embodiment, the anode comprises a conductive oxide, a thin metal layer, or a conductive polymer. In one embodiment, the anode comprises a conductive metal oxide. Exemplary conductive metal oxides include, but are not limited to, indium tin oxide (ITO), tin oxide (TO), gallium indium tin oxide (GITO), zinc oxide (ZO), and zinc indium tin oxide (ZITO). In one embodiment, the anode comprises a metal layer. Exemplary metals for the metal layer include, but are not limited to, Ag, Au, Pd, Pt, Ti, V, Zn, Sn, Al, Co, Ni, Cu, Cr, and combinations thereof. In one embodiment, the metal layer comprises a thin metal layer. In one embodiment, the anode 102 comprises a conductive polymer. Exemplary conductive polymers include, but are not limited to, polyaniline (PANI) or 3,4-polyethylenedioxythiophene: polystyrene sulfonate (PEDOT:PSS). In one embodiment, the thickness of the anode is between about 0.1nm-100nm. In one embodiment, the thickness of the anode is between about 1-10nm. In one embodiment, the thickness of the anode is between about 0.1-10nm. In one embodiment, the thickness of the anode is between about 10-100nm. In one embodiment, the anode comprises a transparent or semi-transparent conductive material.

[0151] In one embodiment, the cathode comprises a conductive oxide, a metal layer, or a conductive polymer. Exemplary conductive oxides, metal layers, and conductive polymers are described elsewhere herein. In one embodiment, the cathode comprises a thin metal layer. In one embodiment, the cathode comprises a metal or a metal alloy. In one embodiment, the cathode may comprise Ca, Al, Mg, Ti, W, Ag, Au, or another suitable metal or alloy thereof. In one embodiment, the thickness of the cathode is between about 0.1-100 nm. In one embodiment, the thickness of the cathode is between about 1-10 nm. In one embodiment, the thickness of the cathode is between about 0.1-10 nm. In one embodiment, the thickness of the cathode is between about 10-100 nm. In one embodiment, the cathode comprises a transparent or translucent conductive material.

[0152] In one embodiment, the OPV device may include one or more charge collection / transport interlayers disposed between the electrode and the active region or layer. In one embodiment, the OPV device includes one or more interlayers. In one embodiment, the interlayers include metal oxides. Exemplary metal oxides include, but are not limited to, MoO3, MoO x , V2O5, ZnO and TiO2. In one embodiment, the first intermediate layer has the same composition as the second intermediate layer. In one embodiment, the first intermediate layer and the second intermediate layer have different compositions. In one embodiment, the thickness of the intermediate layers is independently between about 0.1-100nm. In one embodiment, the thickness of the intermediate layers is independently between about 1-10nm. In one embodiment, the thickness of the intermediate layers is independently between about 0.1-10nm. In one embodiment, the thickness of the intermediate layers is independently between about 10-100nm.

[0153] In one embodiment, the device comprises various layers of a tandem or multi-junction photovoltaic device. In one embodiment, the OPV device comprises two electrodes having an anode and 204 in a superimposed relationship, at least one donor composition and at least one acceptor composition, disposed in multiple active layers or regions between the two electrodes. Other active layers or regions may also be present. In one embodiment, the anode and cathode each independently comprise a conductive oxide, a thin metal layer, or a conductive polymer. Exemplary conductive oxides, metal layers, and conductive polymers are described elsewhere herein.

[0154] In one embodiment, the OPV device comprises one or more intermediate layers disposed between the anode and the first active layer. Alternatively or additionally, at least one intermediate layer may be disposed between the second active layer and the cathode. In one embodiment, the OPV device comprises one or more intermediate layers disposed between the first active layer and the second active layer. In one embodiment, the OPV device comprises a first intermediate layer. In one embodiment, the OPV device comprises a second intermediate layer. In one embodiment, the OPV device comprises a third intermediate layer. In one embodiment, the OPV device comprises first and second intermediate layers. In one embodiment, the OPV device comprises a first and third intermediate layer. In one embodiment, the OPV device comprises a second and third intermediate layer. In one embodiment, the OPV device comprises a first, second, and third intermediate layer. In one embodiment, the first, second, and / or third intermediate layer comprises a metal oxide. Exemplary metal oxides are described elsewhere herein.

[0155] Experimental Examples

[0156] The highest efficiency organic photovoltaic (OPV) cells to date have achieved efficiencies approaching 20%. In addition, OPVs have demonstrated extraordinary stability over hundreds or even thousands of years. However, the highest efficiency solar cells (although not necessarily the longest lived) contain polymer donors and solution-deposited non-fullerene acceptors, compared to a power conversion efficiency (PCE) of only 11% for all-vacuum-deposited OPVs. This is in stark contrast to the extremely successful, more than $50 billion organic LED (OLED) industry, which is dominated entirely by vacuum-deposited materials and structures. The primary reason for the adoption of vacuum-deposited materials in OLEDs is the ability to purify source materials for high performance, reliability, and reproducibility. To fully exploit the manufacturing infrastructure and deep expertise available for OLEDs, OPVs based on vapor-deposited materials must ultimately achieve efficiencies comparable to or even exceeding those of OPVs using solution-processed materials. While donors compatible with efficient vacuum deposition have been achieved, similarly deposited acceptors have not yet been developed. Here, we disclose a series of vacuum-deposited NFA materials with absorption in the range up to 1000 nm and good chemical stability. This is critical to improving the reproducibility and reliability of vacuum-deposited OPVs.

[0157] In a recent study, it was found that the acceptor-donor-acceptor (ADA) type non-fullerene acceptor (NFA) for high-efficiency OPV cells undergoes a dissociation reaction during thermal evaporation, producing excessive reaction products ( Figure 1 The vinyl group connecting D and A can dissociate, and the reactivity of the dissociation is closely related to the polarizability of the C=C double bond ( Figure 2). A series of vacuum deposited NFA materials are disclosed here, which have an absorption range of up to 1000nm and good chemical stability. This is crucial to improving the reproducibility and reliability of vacuum deposited OPV.

[0158] The first strategy is to distribute the charge at the C located in the vinyl bond by inserting a second conjugated acceptor such as benzothiadiazole.

[0159] An alternative strategy also proposed for this procedure is to use double bond cyclization by bridging the acceptor moiety to the thiophene chain. This may slightly blue-shift the absorption, which can be offset by extending the thiophene backbone.

[0160] One final strategy is to replace the vinyl group with a triple-bonded alkynyl group. All three approaches distribute the electron density located at the b-carbon site on the vinyl bond across several bonds, presumably making the overall structure stable enough to allow thermal evaporation while not tampering with the basic ada structure that has led to such efficient OPVs over the past few years.

[0161] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present disclosure. For example, many materials and structures described herein can be replaced by other materials and structures without departing from the spirit of the present disclosure. Therefore, the disclosed compounds of the present invention can include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that the various theories about why the embodiments work are not intended to be restrictive.

Claims

1. A compound having a structure represented by formula (I): in: D represents a linear ring system of three to twenty-five rings D'; wherein each ring D' is independently a monocyclic or polycyclic fused ring system; wherein each ring D' is a 5- to 10-membered carbocyclic or heterocyclic ring; wherein each ring D' is fused to an adjacent ring D' or bonded to an adjacent ring D' by a single bond; and wherein each ring D' is optionally substituted with one or more substituents R; Each L is independently a divalent linking group covalently bonded to the terminal ring D' and A; and Each A is independently an acceptor group selected from the group consisting of: Each Ar 1 are independently aromatic or heteroaromatic; * indicates a bond with L; R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; and Any two adjacent substituents R are optionally joined to form a fused ring.

2. The compound of claim 1, wherein each L is independently selected from the group consisting of an aromatic ring, a heteroaromatic ring, a cyclic olefin, a cyclic heteroolefin, and an alkyne; wherein each L is optionally substituted with one or more substituents R.

3. The compound of claim 1, wherein each L is independently selected from the group consisting of: where * represents the bond to the linear ring system D; # indicates the bond with A; Z is NR, C(R)2, O, S, Se or Te; Ar 2 and Ar 3 Each is an aromatic ring or a heteroaromatic ring; q is 0 and Ar 2 or Ar 3 An integer between the maximum possible substitution on ; and R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two adjacent R are optionally joined to form a ring. The compound according to claim 1 , wherein D comprises six rings D′, seven rings D′ or eight rings D′.

5. The compound according to claim 1, wherein each ring D' is independently selected from the group consisting of: wherein each X is independently selected from the group consisting of oxygen, carbon, hydrogen, sulfur, selenium, and nitrogen; and wherein each ring D' is optionally substituted with one or more substituents R.

6. The compound according to claim 1, wherein each Ar 1 Independently selected from the group consisting of: Where R 1 To R 8 Each independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.

7. The compound according to claim 6, wherein R 1 To R 8 At least one of represents a halogen.

8. The compound according to claim 1, wherein the compound is represented by formula (II): in: m is an integer between 0 and 10; n is an integer between 0 and 10; D 1 , each D 2 and each D 3 Fused or covalently bonded to an adjacent ring D 1 , D 2 and D 3 Each is independently a monocyclic or polycyclic condensed ring system, wherein each ring of the monocyclic or polycyclic condensed ring system is a 5- to 10-membered carbocyclic or heterocyclic ring; wherein D 1 , D 2 and D 3 Each is optionally further substituted with one or more substituents R; and R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two adjacent substituents R are optionally joined to form a fused ring.

9. The compound according to claim 7, wherein D 1 Represented by one of the following structures: in: Each X is independently selected from the group consisting of oxygen, carbon, hydrogen, sulfur, selenium and nitrogen; p is an integer between 0 and 10; Where D 4 is a monocyclic or polycyclic condensed ring system, wherein each ring of the monocyclic or polycyclic condensed ring system is a 5- to 10-membered carbocyclic or heterocyclic ring; wherein D 4 is optionally further substituted with one or more substituents R; and Where D 1 Optionally substituted with one or more R substituents.

10. The compound according to claim 8, wherein D 2 Select from the group consisting of: wherein R at each occurrence independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two groups R are optionally taken together to form a ring.

11. The compound according to claim 8, wherein D 3 Select from the group consisting of: wherein p is an integer between 0 and 2; and R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two groups R are optionally taken together to form a ring.

12. The compound according to claim 8, wherein the compound is represented by formula (III), formula (IV), formula (V), formula (VI), formula (VII) or formula (VIII); in X is selected from the group consisting of oxygen, carbon, hydrogen, sulfur, selenium and nitrogen.

13. The compound according to claim 8, wherein the compound is represented by one of the following formulae:

14. The compound according to claim 8, wherein the compound is represented by one of the following formulae:

15. The compound according to claim 8, wherein the compound is represented by one of the following formulae:

16. A photoelectric device comprising a compound represented by formula (I): in: D represents a linear ring system of three to twenty-five rings D'; wherein each ring D' is independently a monocyclic or polycyclic fused ring system; wherein each ring D' is a 5- to 10-membered carbocyclic or heterocyclic ring; wherein each ring D' is fused to an adjacent ring D' or bonded to an adjacent ring D' by a single bond; and wherein each ring D' is optionally substituted with one or more substituents R; Each L is independently a divalent linking group covalently bonded to the terminal ring D' and A; and Each A is independently an acceptor group selected from the group consisting of: Each Ar 1 are independently aromatic or heteroaromatic; * indicates a bond with L; R, at each occurrence, independently represents hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; and Any two adjacent substituents R are optionally joined to form a fused ring.

17. The optoelectronic device of claim 16, wherein the optoelectronic device is selected from the group consisting of an organic light emitting device (OLED), an organic phototransistor, an organic photovoltaic cell, and an organic photodetector.

18. The optoelectronic device of claim 16, wherein the optoelectronic device is a photovoltaic cell.

19. A consumer product comprising the optoelectronic device of claim 16.

20. A formulation comprising the compound of claim 1.

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