Electroactive materials

Abstract

The invention relates to an electroactive material. Disclosed is an electroactive composition comprising (a) a host compound # imgabs0 # having the formula I and (b) a photoactive dopant. In formula I: R1 is D; a is an integer from 0 to 7; b is an integer from 0 to 8; c is an integer from 0 to 4; d is an integer from 0 to 7; and a + b + c + d = 5-26.

Description

[0001] This application is a divisional application of the Chinese patent application with the application date of June 26, 2017, application number "201780026822.9", and invention name "Electroactive Materials".

[0002] Benefit of prior application requirements

[0003] This application claims the benefit of U.S. Provisional Application No. 62 / 364,685, filed on July 20, 2016. Technical Field

[0004] The present disclosure relates to novel electroactive compounds. The present disclosure further relates to electronic devices having at least one layer comprising such electroactive compounds. Background Art

[0005] In organic electronic devices, such as the organic light-emitting diodes ("OLEDs") that make up OLED displays, one or more organic electroactive layers are sandwiched between two electrical contact layers. In an OLED, when a voltage is applied across these electrical contact layers, at least one of the organic electroactive layers emits light through the light-transmitting electrical contact layers.

[0006] It is well known to use organic electroluminescent compounds as the luminescent component in light-emitting diodes. Simple organic molecules, conjugated polymers, and organometallic complexes have been used. The luminescent material can be used alone or can be present in an electroactive host material.

[0007] Devices employing electroluminescent materials typically include one or more charge transport layers positioned between a photoactive (e.g., light-emitting) layer and a contact layer (hole-injecting contact layer). Devices may include two or more contact layers. A hole transport layer may be positioned between the photoactive layer and the hole-injecting contact layer. The hole-injecting contact layer may also be referred to as the anode. An electron transport layer may be positioned between the photoactive layer and the electron-injecting contact layer. The electron-injecting contact layer may also be referred to as the cathode.

[0008] There is a continuing need for electroactive materials for use in electronic devices. Summary of the Invention

[0009] Provided is a compound having formula I

[0010]

[0011] in:

[0012] R 1 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, germyl, deuterated alkyl, deuterated silyl, and deuterated germyl;

[0013] a is an integer from 0 to 7;

[0014] b is an integer from 0 to 8;

[0015] c is an integer from 0 to 4; and

[0016] d is an integer from 0 to 7.

[0017] Additionally provided is an electroactive composition comprising (a) a host compound having Formula I and (b) a photoactive dopant.

[0018] Additionally provided is an electronic device having at least one layer comprising a compound having any of Formula I.

[0019] Additionally provided is an electronic device having a photoactive layer comprising the electroactive composition.

[0020] The foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as defined in the appended claims. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] Embodiments are illustrated in the accompanying drawings to improve understanding of the concepts as presented herein.

[0022] Figure 1 Included is a diagram of one example of an organic electronic device including a compound described herein.

[0023] Figure 2 Included is a diagram of another example of an organic electronic device including a compound described herein.

[0024] It should be understood by those skilled in the art that the objects in the drawings are shown for simplicity and clarity and are not necessarily drawn to scale. For example, the sizes of some objects in the drawings may be exaggerated relative to other objects to help improve understanding of the embodiments. DETAILED DESCRIPTION

[0025] Provided is a compound having formula I, as described in detail below.

[0026] Additionally provided is an electroactive composition comprising (a) a host compound having Formula I and (b) a photoactive dopant, as described in detail below.

[0027] Additionally provided is an electronic device having at least one layer comprising a compound having any of Formula I.

[0028] Additionally provided is an electronic device having a photoactive layer comprising the electroactive composition.

[0029] Many aspects and embodiments have been described above and are exemplary only and non-limiting. After reading this specification, skilled artisans will appreciate that other aspects and embodiments are possible without departing from the scope of the invention.

[0030] Other features and benefits of any one or more embodiments will be apparent from the following detailed description and from the claims. The detailed description first presents definitions and clarifications of terms, followed by compounds of Formula I, electroactive compositions, electronic devices, and finally examples.

[0031] 1. Definition and clarification of terms

[0032] Before presenting details of the following embodiments, some terms are defined or clarified.

[0033] As used in the "Definition and Clarification of Terms", R, R' and R" and any other variables are generic names and may be the same as or different from those defined in the formula.

[0034] The term "alkyl" is intended to mean a group derived from an aliphatic hydrocarbon, and includes straight-chain, branched, or cyclic groups. A group "derived from" a compound means a group formed by removing one or more H or D. The term "branched alkyl" is intended to mean a group derived from an aliphatic hydrocarbon having at least one secondary or tertiary carbon. In some embodiments, the alkyl group has from 1 to 20 carbon atoms.

[0035] The term "aromatic compound" is intended to mean an organic compound comprising at least one unsaturated cyclic group having 4n+2 delocalized π electrons.

[0036] The term "aryl" is intended to mean a group derived from an aromatic compound having at least one point of attachment. The term includes groups having a single ring as well as groups having multiple rings that may be connected by a single bond or fused together. Hydrocarbyl aryls have only carbon atoms in the ring structure. Heteroaryls have at least one heteroatom in the ring structure. In some embodiments, hydrocarbyl aryls have 6-30 ring carbon atoms. In some embodiments, heteroaryls have 3-30 ring carbon atoms.

[0037] The term "alkoxy" is intended to mean the group -OR, where R is alkyl.

[0038] The term "aryloxy" is intended to mean the group -OR, where R is aryl.

[0039] Unless otherwise indicated, all groups may be substituted or unsubstituted. Optionally substituted groups, such as, but not limited to, alkyl or aryl, may be substituted by one or more substituents which may be the same or different. Suitable substituents include D, alkyl, aryl, nitro, cyano, -N(R')(R"), halogen, hydroxy, carboxyl, alkenyl, alkynyl, cycloalkyl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkoxycarbonyl, perfluoroalkyl, perfluoroalkoxy, arylalkyl, silyl, silyloxy, siloxane, thioalkoxy, -S(O)2-, -C(=O)-N(R')(R"), (R')(R")N-alkyl, (R')(R")N-alkoxyalkyl, (R')(R")N-alkylaryloxyalkyl, -S(O) s -aryl (where s=0-2), or -S(O) s - heteroaryl (where s = 0-2). Each R' and R" is independently an optionally substituted alkyl, cycloalkyl, or aryl group. R' and R", together with the nitrogen atom to which they are attached, may form a ring system in certain embodiments. The substituent may also be a crosslinking group. Any of the foregoing groups having available hydrogens may also be deuterated.

[0040] When referring to a layer, material, component, or structure, the term "charge transport" is intended to mean that such layer, material, component, or structure facilitates the migration of such charge through the thickness of such layer, material, component, or structure with relative efficiency and low charge loss. Hole transport materials favor positive charges; electron transport materials favor negative charges. Although light-emitting materials may also have some charge transport properties, the term "charge transport layer, material, component, or structure" is not intended to include layers, materials, components, or structures whose primary function is to emit light.

[0041] The term "compound" is intended to mean an uncharged substance composed of molecules further comprising atoms, wherein the atoms cannot be separated from their corresponding molecules by physical means without breaking the chemical bonds. The term is intended to include oligomers and polymers.

[0042] The term "deuterated" is intended to mean that at least one hydrogen ("H") has been replaced by deuterium ("D"). The term "deuterated analog" refers to a structural analog of a compound or group in which one or more available hydrogens have been replaced by deuterium. In a deuterated compound or deuterated analog, deuterium is present at at least 100 times the natural abundance level. The symbols shown below

[0043]

[0044] = deuterium substituted at any available position and the total number of deuterium substituents is from x to y. For example, the compounds shown below have 8-10 deuterium substituents at any available position.

[0045]

[0046] The term "dopant" is intended to mean a material within a layer comprising a host material that alters one or more electronic properties or one or more target wavelengths of radiation emitted, received, or filtered by the layer compared to the one or more electronic properties or one or more wavelengths of radiation emitted, received, or filtered by the layer in the absence of such material. The term "host material" is intended to mean a material in which a dopant is dispersed. The host material may or may not have one or more electronic properties or the ability to emit, receive, or filter radiation. In some embodiments, the host material is present at a higher concentration than the dopant.

[0047] The term "electroactive," when referring to a layer or material, is intended to mean a layer or material that electronically facilitates the operation of a device. Examples of electroactive materials include, but are not limited to, materials that conduct, inject, transport, or block electric charge, where the charge can be electrons or holes, or materials that emit radiation or exhibit a change in the concentration of electron-hole pairs upon receiving radiation. Examples of inactive materials include, but are not limited to, planarizing materials, insulating materials, and environmental barrier materials.

[0048] The prefix "fluoro" is intended to indicate that one or more hydrogens in the group have been replaced by fluorine.

[0049] The term "germyl" refers to the group R3Ge-, where R is the same or different at each occurrence and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl.

[0050] The prefix "hetero" indicates that one or more carbon atoms have been replaced by a different atom. In some embodiments, the heteroatom is O, N, S, or a combination thereof.

[0051] The term "liquid composition" is intended to mean a liquid medium in which a material is dissolved to form a solution, a liquid medium in which a material is dispersed to form a dispersion, or a liquid medium in which a material is suspended to form a suspension or emulsion.

[0052] The term "photoactive" refers to a material or layer that emits light when activated by an applied voltage (such as in a light emitting diode or chemical cell), emits light after absorbing a photon (such as in a down-converting phosphor device), or generates a signal in response to radiant energy with or without an applied bias (such as in a photodetector or photovoltaic cell).

[0053] The term "siloxane" refers to the group R3SiOR2Si-, where R is the same or different at each occurrence and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl. In some embodiments, one or more carbons in the R alkyl group are replaced by Si.

[0054] The term "silyloxy" refers to the group R3SiO-, where R is the same or different at each occurrence and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl.

[0055] The term "silyl" refers to a group R3Si-, wherein R is the same or different at each occurrence and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl. In some embodiments, one or more carbons in the R alkyl group are replaced by Si.

[0056] In structures in which a substituent bond passes through one or more rings as shown below,

[0057]

[0058] This means that the substituent R can be bonded at any available position on one or more rings.

[0059] When used to refer to layers in a device, the phrase "adjacent" does not necessarily mean that one layer is immediately next to another layer. On the other hand, the phrase "adjacent R groups" is used to refer to R groups that are immediately adjacent to each other in a chemical formula (i.e., R groups on atoms that are connected by a bond). Exemplary adjacent R groups are shown below:

[0060]

[0061] In this specification, unless otherwise expressly indicated or indicated to the contrary by the context of use, when an embodiment of the inventive subject matter is stated or described as comprising, including, containing, having, consisting of, or composed of certain features or elements, one or more features or elements in addition to those explicitly stated or described may also be present in that embodiment. An alternative embodiment of the disclosed inventive subject matter is described as consisting essentially of certain features or elements, in which embodiment features or elements that would materially change the principle of operation or distinguishing characteristics of the embodiment are absent. Another alternative embodiment of the described inventive subject matter is described as consisting of certain features or elements, in which embodiment, or in inescapable variations thereof, only the features or elements specifically stated or described are present.

[0062] In addition, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not to an exclusive "or." For example, condition A or B is satisfied by any one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0063] Furthermore, "a or an" is used to describe elements and components described herein. This is done for convenience only and to give a general sense of the scope of the invention. The description should be read to include one or at least one, and the singular also includes the plural unless it is obvious that it is intended otherwise.

[0064] Group numbers corresponding to columns within the Periodic Table of the Elements use the "New Notation" convention as found in the CRC Handbook of Chemistry and Physics, 81st Edition (2000-2001).

[0065] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which the present invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. Unless citing a specific paragraph, all publications, patent applications, patents and other references mentioned herein are combined by reference in their entirety. In the event of a conflict, this specification, including definitions, shall prevail. In addition, materials, methods and examples are illustrative only and are not intended to be restrictive.

[0066] To the extent not described herein, many details regarding specific materials, processing activities, and circuits are conventional and can be found in textbooks and other sources in the fields of organic light emitting diode displays, photodetectors, photovoltaics, and semiconductor components.

[0067] 2. Compounds having formula I

[0068] Provided is a compound having formula I

[0069]

[0070] in:

[0071] R 1 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, germyl, deuterated alkyl, deuterated silyl, and deuterated germyl;

[0072] a is an integer from 0 to 7;

[0073] b is an integer from 0 to 8;

[0074] c is an integer from 0 to 4; and

[0075] d is an integer from 0 to 7.

[0076] In some embodiments of Formula I, a=0.

[0077] In some embodiments of Formula I, a=1.

[0078] In some embodiments of Formula I, a=2.

[0079] In some embodiments of Formula I, a=3.

[0080] In some embodiments of Formula I, a=4.

[0081] In some embodiments of Formula I, a=5.

[0082] In some embodiments of Formula I, a=6.

[0083] In some embodiments of Formula I, a=7.

[0084] In some embodiments of Formula I, a>0.

[0085] In some embodiments of Formula I, b=0.

[0086] In some embodiments of Formula I, b=1.

[0087] In some embodiments of Formula I, b=2.

[0088] In some embodiments of Formula I, b=3.

[0089] In some embodiments of Formula I, b=4.

[0090] In some embodiments of Formula I, b=5.

[0091] In some embodiments of Formula I, b=6.

[0092] In some embodiments of Formula I, b=7.

[0093] In some embodiments of Formula I, b=8.

[0094] In some embodiments of Formula I, b>0.

[0095] In some embodiments of Formula I, c=0.

[0096] In some embodiments of Formula I, c=1.

[0097] In some embodiments of Formula I, c=2.

[0098] In some embodiments of Formula I, c=3.

[0099] In some embodiments of Formula I, c=4.

[0100] In some embodiments of Formula I, c>0.

[0101] In some embodiments of Formula I, d=0.

[0102] In some embodiments of Formula I, d=1.

[0103] In some embodiments of Formula I, d=2.

[0104] In some embodiments of Formula I, d=3.

[0105] In some embodiments of Formula I, d=4.

[0106] In some embodiments of Formula I, d=5.

[0107] In some embodiments of Formula I, d=6.

[0108] In some embodiments of Formula I, d=7.

[0109] In some embodiments of Formula I, d>0.

[0110] In some embodiments of Formula I, a=b=c=d=0.

[0111] In some embodiments of Formula I, a+b+c+d=1-26.

[0112] In some embodiments of Formula I, a+b+c+d=1-10.

[0113] In some embodiments of Formula I, a+b+c+d=1-4.

[0114] In some embodiments of Formula I, a+b+c+d=1-26 and R 1 =D.

[0115] In some embodiments of Formula I, a+b+c+d=5-26 and R 1 =D.

[0116] In some embodiments of Formula I, a+b+c+d=15-26 and R 1 =D.

[0117] In some embodiments of Formula I, a+b+c+d=20-26 and R 1 =D.

[0118] In some embodiments of Formula I, a+b+c+d=26 and R 1 =D.

[0119] In some embodiments of Formula I, at least one of ad is non-zero, and at least one R 1 =D.

[0120] In some embodiments of Formula I, a>0 and at least one R 1 =D.

[0121] In some embodiments of Formula I, b>0 and at least one R 1 =D.

[0122] In some embodiments of Formula I, c>0 and at least one R 1 =D.

[0123] In some embodiments of Formula I, d>0 and at least one R 1 =D.

[0124] In some embodiments of Formula I, at least one of ad is non-zero, and at least one R 1 = an alkyl or deuterated alkyl group having 1-6 carbons; in some embodiments, 1-4 carbons.

[0125] In some embodiments of Formula I, at least one of ad is non-zero, and at least one R 1 =trimethylsilyl or a deuterated analog thereof.

[0126] In some embodiments of Formula I, at least one of ad is non-zero, and at least one R 1 =trimethylgermyl or its deuterated analog.

[0127] Positions on the compound can be labeled as follows:

[0128]

[0129] In some embodiments of Formula I, a>0 and at least one R 1 =D. In some embodiments, at least one R 1 =D and is present in at least one of positions 1-7.

[0130] In some embodiments of Formula I, a>0 and at least one R 1 is an alkyl or deuterated alkyl group having 1 to 6 carbon atoms. In some embodiments, at least one R 1 is an alkyl group or a deuterated alkyl group and is present in at least one of positions 2, 3, 4, and 5.

[0131] In some embodiments of Formula I, a>0 and at least one R 1 is trimethylsilyl or deuterated trimethylsilyl. In some embodiments, at least one R 1 is a trimethylsilyl group or a deuterated trimethylsilyl group and is present at at least one of positions 2, 3, 4, and 5.

[0132] In some embodiments of Formula I, a>0 and at least one R1 is trimethylgermyl or deuterated trimethylgermyl. In some embodiments, at least one R 1 is trimethylgermyl or deuterated trimethylgermyl and is present in at least one of positions 2, 3, 4, and 5.

[0133] In some embodiments of Formula I, b>0 and at least one R 1 =D. In some embodiments, at least one R 1 =D and is present in at least one of positions 8-15.

[0134] In some embodiments of Formula I, b>0 and at least one R 1 is an alkyl or deuterated alkyl group having 1 to 6 carbon atoms. In some embodiments, at least one R 1 is an alkyl group or a deuterated alkyl group and is present in at least one of positions 9, 10, 13, and 14.

[0135] In some embodiments of Formula I, b>0 and at least one R 1 is trimethylsilyl or deuterated trimethylsilyl. In some embodiments, at least one R 1 is a trimethylsilyl group or a deuterated trimethylsilyl group and is present at at least one of positions 9, 10, 13, and 14.

[0136] In some embodiments of Formula I, b>0 and at least one R 1 is trimethylgermyl or deuterated trimethylgermyl. In some embodiments, at least one R 1 is trimethylgermyl or deuterated trimethylgermyl and is present at at least one of positions 9, 10, 13, and 14.

[0137] In some embodiments of Formula I, c>0 and at least one R 1 =D. In some embodiments, at least one R 1 =D and is present in at least one of positions 16-19.

[0138] In some embodiments of Formula I, d>0 and at least one R 1 =D. In some embodiments, at least one R 1 =D and is present in at least one of positions 20-26.

[0139] In some embodiments of Formula I, d>0 and at least one R 1 is an alkyl or deuterated alkyl group having 1 to 6 carbon atoms. In some embodiments, at least one R 1 is an alkyl group or a deuterated alkyl group and is present in at least one of positions 20, 23, 24, 25, and 26.

[0140] In some embodiments of Formula I, d>0 and at least one R 1 is trimethylsilyl or deuterated trimethylsilyl. In some embodiments, at least one R 1 is a trimethylsilyl group or a deuterated trimethylsilyl group and is present at at least one of positions 20, 23, 24, 25, and 26.

[0141] In some embodiments of Formula I, d>0 and at least one R 1 is trimethylgermyl or deuterated trimethylgermyl. In some embodiments, at least one R 1 is trimethylgermyl or deuterated trimethylgermyl and is present at at least one of positions 20, 23, 24, 25, and 26.

[0142] In some embodiments of Formula I, a=1 and R 1 Present in one of positions 2, 3, 4, and 5.

[0143] In some embodiments of Formula I, b=1 and R 1 Present at one of positions 9, 10, 13, and 14.

[0144] In some embodiments of Formula I, d=1 and R 1 Present at one of positions 20, 23, 24, 25, and 26.

[0145] In some embodiments of Formula I, at least one of ad is non-zero; and at least one R 1 is alkyl or deuterated alkyl and is present in at least one of positions 2, 3, 4, 5, 9, 10, 13, 14, 20, 23, 24, 25, and 26.

[0146] In some embodiments of Formula I, at least one of ad is non-zero; and at least one R 1 is trimethylsilyl or deuterated trimethylsilyl and is present in at least one of positions 2, 3, 4, 5, 9, 10, 13, 14, 20, 23, 24, 25, and 26.

[0147] In some embodiments of Formula I, at least one of ad is non-zero; and at least one R 1 is trimethylgermyl or deuterated trimethylgermyl and is present in at least one of positions 2, 3, 4, 5, 9, 10, 13, 14, 20, 23, 24, 25, and 26.

[0148] In some embodiments of Formula I, at least one of ad is non-zero; and at least one R 1is selected from the group consisting of alkyl, trimethylsilyl, trimethylgermyl, and deuterated analogs thereof, and is present at at least one of positions 2, 3, 4, 5, 9, 10, 13, 14, 20, 23, 24, 25, and 26.

[0149] Any of the above embodiments of Formula I may be combined with one or more of the other embodiments, as long as they are not mutually exclusive. For example, an embodiment in which a=1 may be combined with an embodiment in which at least one R 1 is an embodiment of an alkyl group and wherein b=1 and at least one R 1 is a combination of embodiments of D. The same is true for the other non-mutually exclusive embodiments discussed above. Those skilled in the art will understand which embodiments are mutually exclusive and will therefore readily be able to determine the combinations of embodiments contemplated for this application.

[0150] Compounds of formula I can be made using any technique that will produce a CC bond. A variety of such techniques are known, such as Suzuki, Yamamoto, and Stille couplings, and metal-catalyzed and oxidative direct arylations.

[0151] Deuterated compounds can be prepared in a similar manner using deuterated precursor materials, or more typically by treating the undeuterated compound with a deuterated solvent (such as benzene-d6) in the presence of a Bronsted acid H / D exchange catalyst (such as trifluoromethanesulfonic acid) or a Lewis acid H / D exchange catalyst (such as aluminum trichloride or ethylaluminum dichloride).

[0152] Exemplary preparations are given in the Examples.

[0153] Some non-limiting examples of compounds having Formula I are shown below.

[0154] Compound 1

[0155]

[0156] Compound 2

[0157]

[0158] Compound 3

[0159]

[0160] Compound 4

[0161]

[0162] Compound 5

[0163]

[0164] Compound 6

[0165]

[0166] Compound 7

[0167]

[0168] Compound 8

[0169]

[0170] Compound 9

[0171]

[0172] Compound 10

[0173]

[0174] The compound can be formed into a layer for an electronic device. The term "layer" is used interchangeably with the term "film" and refers to a coating covering a desired area. The term is not limited by size. The area can be as large as the entire device, or as small as a specific functional area such as an actual visual display, or as small as a single sub-pixel. Layers and films can be formed by any conventional deposition technique, including vapor deposition, liquid deposition (continuous and discontinuous techniques) and thermal transfer. Continuous liquid deposition techniques include, but are not limited to, spin coating, gravure coating, curtain coating, dip coating, slot die coating, spray coating, and continuous nozzle coating. Discontinuous liquid deposition techniques include, but are not limited to, inkjet printing, gravure printing and screen printing.

[0175] In some embodiments, the novel compounds having Formula I are useful as hole transport materials in devices.

[0176] In some embodiments, the novel compounds having Formula I are electroluminescent and are useful as emissive materials in devices.

[0177] In some embodiments, the novel compounds having Formula I are useful as hosts for electroluminescent materials.

[0178] In some embodiments, the novel compounds having Formula I are useful as electron transport materials in devices.

[0179] 3. Electroactive Compositions

[0180] The electroactive composition comprises (a) a host compound having Formula I and (b) a photoactive dopant.

[0181] The host compound of formula I is described in detail above.

[0182] Electroluminescent ("EL") materials that can be used as dopants in electroactive compositions include, but are not limited to, small molecule organic light-emitting compounds, light-emitting metal complexes, conjugated polymers, and mixtures thereof. Examples of small molecule light-emitting organic compounds include, but are not limited to Pyrene, perylene, rubrene, coumarin, anthracene, stilbene, thiadiazole, benzofluorene, naphthofuran, derivatives thereof, deuterated analogs thereof, and mixtures thereof. Examples of metal complexes include, but are not limited to, metal chelate oxinoid compounds and cyclometallated complexes of metals such as iridium and platinum. Examples of conjugated polymers include, but are not limited to, poly(phenylene vinylene), polyfluorene, poly(spirobifluorene), polythiophene, poly(p-phenylene), copolymers thereof, deuterated analogs thereof, and mixtures thereof.

[0183] In some embodiments, the dopant is deuterated.

[0184] In some embodiments, the dopant is a small organic light-emitting compound.

[0185] In some embodiments, the dopant is selected from the group consisting of a non-polymeric spirobifluorene compound, a fluoranthene compound, a substituted derivative thereof, and a deuterated analog thereof.

[0186] In some embodiments, the dopant is a compound having an arylamine group. In some embodiments, the dopant has the following formula II or formula III:

[0187]

[0188] in:

[0189] A is the same or different at each occurrence and is a hydrocarbon aryl or heteroaryl group having from 3 to 60 ring carbon atoms;

[0190] Q' is a hydrocarbon aryl or heteroaryl group having from 3 to 60 ring carbon atoms;

[0191] p and q are independently integers from 1-6.

[0192] In some embodiments of the above formulas, Q' in each formula has at least 3 fused rings.

[0193] In some embodiments of Formula II and Formula III, p and q are equal to 1.

[0194] In some embodiments of Formula II and Formula III, Q' is styryl or styrylphenyl.

[0195] In some embodiments of Formula II and Formula III, Q' is an aromatic group having at least two fused rings. In some embodiments, Q' is derived from a compound selected from the group consisting of naphthalene, anthracene, Pyrene, tetracene, xanthene, perylene, coumarin, rhodamine, quinacridone, rubrene, phenanthrene, benzofluorene, naphthofuran, naphthodifuran, naphthotrifuran, naphthotetrafuran, substituted derivatives thereof, and deuterated analogs thereof.

[0196] In some embodiments of Formula II and Formula III, Q' is derived from a compound selected from the group consisting of anthracene, Pyrene, benzofluorene, naphthofuran, naphthodifuran, substituted derivatives thereof, and deuterated analogs thereof.

[0197] In some embodiments of Formula II and Formula III, A is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, anthracenyl, substituted derivatives thereof, and deuterated analogs thereof.

[0198] In some embodiments, the dopant has the formula:

[0199]

[0200] in:

[0201] Y is the same or different at each occurrence and is an aromatic group having 3 to 60 carbon atoms;

[0202] Q" is an aromatic group, a divalent triphenylamine residue, or a single bond.

[0203] In some embodiments, the dopant is an aryl acene. In some embodiments, the dopant is an asymmetric aryl acene.

[0204] In some embodiments, the dopant is blue-emitting. The term "blue-emitting" is intended to refer to a material capable of emitting radiation having an emission maximum at a wavelength in the range of about 400-500 nm. In some embodiments, the emission maximum is at a wavelength in the range of about 445-490 nm.

[0205] In some embodiments, the dopant has a photoluminescence y-coordinate according to the CIE color scale (Commission Internationale de L'Eclairage, 1931) of less than 0.15; in some embodiments, less than 0.10; and in some embodiments, less than 0.090.

[0206] In some embodiments, the dopant has Formula III, wherein p=q=1 and Q' is derived from a compound selected from the group consisting of anthracene, Pyrene, benzofluorene, naphthofuran, naphthodifuran, substituted derivatives thereof, and deuterated analogs thereof.

[0207] In some embodiments, the weight ratio of the dopant to the host compound having Formula I is in the range of 2:98 to 50:50; in some embodiments, 3:97 to 30:70; in some embodiments, 5:95 to 20:80.

[0208] In some embodiments, unexpectedly and surprisingly, devices comprising the novel electroactive compositions described herein have increased lifetimes relative to similar anthracene host compounds. In some embodiments, devices comprising the novel electroactive compositions comprising non-deuterated compounds (having Formula I) have lifetimes that are approximately the same as similar deuterated anthracene host compounds.

[0209] In some embodiments, unexpectedly and surprisingly, devices comprising the novel electroactive compositions described herein have increased efficiency relative to similar anthracene host compounds.

[0210] 4. Electronic devices

[0211] Organic electronic devices that can benefit from having one or more layers comprising at least one compound as described herein include, but are not limited to: (1) devices that convert electrical energy into radiation (e.g., light emitting diodes, light emitting diode displays, lighting devices, light sources, or diode lasers), (2) devices that detect signals electronically (e.g., photodetectors, photoconductive cells, photoresistors, photorelays, phototransistors, phototubes, IR detectors, biosensors), (3) devices that convert radiation into electrical energy (e.g., photovoltaic devices or solar cells), (4) devices that convert light of one wavelength into light of a longer wavelength (e.g., down-converting phosphor devices); and (5) devices that include one or more electronic components comprising one or more organic semiconductor layers (e.g., transistors or diodes). Other uses of the compositions according to the present invention include coating materials for memory storage devices, antistatic films, biosensors, electrochromic devices, solid electrolytic capacitors, energy storage devices (such as rechargeable batteries), and electromagnetic shielding applications.

[0212] Figure 1A diagram of an organic electronic device structure including the new compositions described herein is shown in . Device 100 has a first electrical contact layer, an anode layer 110 and a second electrical contact layer, a cathode layer 160, and a photoactive layer 140 therebetween. Additional layers may optionally be present. Adjacent to the anode may be a hole injection layer 120, sometimes referred to as a buffer layer. Adjacent to the hole injection layer may be a hole transport layer 130 comprising a hole transport material. Adjacent to the cathode may be an electron transport layer 150 comprising an electron transport material. As an option, the device may utilize one or more additional hole injection layers or hole transport layers (not shown) adjacent to the anode 110 and / or one or more additional electron injection layers or electron transport layers (not shown) adjacent to the cathode 160. Layers 120 to 150 are individually and collectively referred to as organic active layers.

[0213] In some embodiments, to achieve full color, the light emitting layer is pixelated, with each different color having a sub-pixel unit. Figure 2 . The device 200 has an anode 110, a hole injection layer 120, a hole transport layer 130, a photoactive layer 140, an electron transport layer 150, and a cathode 160. The photoactive layer is divided into sub-pixels 141, 142, 143, which are repeated across the layer. In some embodiments, these sub-pixels represent red, blue, and green emission. Although Figure 2 Three different sub-pixel units are depicted in FIG, but two or more sub-pixel units may be used.

[0214] Here we will refer to Figure 1 These different layers are discussed further below. However, this discussion also applies to Figure 2 and other configurations.

[0215] In some embodiments, the different layers have the following thickness ranges: anode 110, In some embodiments, hole injection layer 120, In some embodiments, hole transport layer 130, In some embodiments, Photoactive layer 140, In some embodiments, electron transport layer 150, In some embodiments, cathode 160, In some embodiments, The desired ratio of layer thicknesses will depend on the exact nature of the materials used.

[0216] One or more of the novel compounds of Formula I described herein may be present in one or more electroactive layers of a device.

[0217] In some embodiments, the novel compound having Formula I can be used as a hole transport material in layer 130 .

[0218] In some embodiments, the novel compound having Formula I can be used as a photoactive material in layer 140. In some embodiments, the novel compound having Formula I is present as a photoactive dopant material in one or more host materials.

[0219] In some embodiments, the novel composition comprising a compound having Formula I and a dopant is used as the photoactive layer 140 .

[0220] In some embodiments, an organic electronic device includes an anode, a cathode, and at least one organic active layer therebetween, wherein the organic active layer comprises a compound having Formula I.

[0221] In some embodiments, an organic electronic device includes an anode, a cathode, and a photoactive layer therebetween, wherein the photoactive layer includes a composition comprising a compound having Formula I and a dopant.

[0222] In some embodiments, the organic electronic device includes an anode, a cathode, and a photoactive layer therebetween, and further includes an additional organic active layer comprising a compound having Formula I. In some embodiments, the additional organic active layer is a hole transport layer.

[0223] The anode 110 is an electrode that is particularly effective for injecting positive charge carriers. It can be made of a material comprising, for example, a metal, a mixed metal, an alloy, a metal oxide, or a mixed metal oxide, or it can be a conductive polymer, and mixtures thereof. Suitable metals include Group 11 metals, metals in Groups 4, 5, and 6, and transition metals from Groups 8-10. If the anode is to be light-transmitting, mixed metal oxides of Groups 12, 13, and 14 metals, such as indium tin oxide, are generally used. The anode can also comprise an organic material such as polyaniline, as described in "Flexible light-emitting diodes made from soluble conducting polymer," Nature, Vol. 357, pp. 477-479 (June 11, 1992). At least one of the anode and cathode should be at least partially transparent to allow the generated light to be observed.

[0224] The optional hole injection layer 120 includes a hole injection material. The term "hole injection layer" or "hole injection material" is intended to refer to a conductive or semiconductive material and may have one or more functions in an organic electronic device, including but not limited to planarization of underlying layers, charge transport and / or charge injection properties, removal of impurities such as oxygen or metal ions, and other aspects that benefit or improve the performance of the organic electronic device. The hole injection material can be a polymer, oligomer, or small molecule and can be in the form of a solution, dispersion, suspension, emulsion, colloidal mixture, or other composition.

[0225] Hole injection layer 120 can be formed by polymeric materials, such as polyaniline (PANI) or polyethylenedioxythiophene (PEDOT), and the polymeric materials are usually doped with protonic acid. Protonic acid can be, for example, poly(styrene sulfonic acid), poly(2-acrylamide-2-methyl-1-propanesulfonic acid) etc. Hole injection layer 120 can include charge transfer compounds etc., such as copper phthalocyanine and tetrathiafulvalene-tetracyanoquinodimethane system (TTF-TCNQ). In certain embodiments, hole injection layer 120 is made of a dispersion of conductive polymer and colloid-formed polymeric acid. Such materials have been described in, for example, the U.S. patent applications 2004-0102577, 2004-0127637 and 2005-0205860 announced.

[0226] Layer 130 includes a hole transport material.

[0227] In some embodiments, layer 130 includes a compound having Formula I. In some embodiments, layer 130 includes only a compound having Formula I, with no additional materials present that would substantially alter the operating principle or distinguishing characteristics of the layer.

[0228] In some embodiments, layer 130 includes other hole transport materials. Examples of hole transport materials for hole transport layers are summarized in, for example, Y. Wang, Kirk-Othmer Encyclopedia of Chemical Technology, 4th edition, volume 18, pages 837-860, 1996. Both hole transport small molecules and polymers can be used. Commonly used hole transport molecules include, but are not limited to: 4,4',4"-tris(N,N-diphenyl-amino)-triphenylamine (TDATA); 4,4',4"-tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine (MTDATA); N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine (TPD); 4,4'-bis( Carbazol-9-yl) biphenyl (CBP); 1,3-bis(carbazol-9-yl)benzene (mCP); 1,1-bis[(di-4-methylphenylamino)phenyl]cyclohexane (TAPC); N,N'-bis(4-methylphenyl)-N,N'-bis(4-ethylphenyl)-[1,1'-(3,3'-dimethyl)biphenyl]-4,4'-diamine (ETPD); tetrakis-(3-methylphenyl)-N,N, N',N'-2,5-phenylenediamine (PDA); α-phenyl-4-N,N-diphenylaminostyrene (TPS); p-(diethylamino)benzaldehyde diphenylhydrazone (DEH); triphenylamine (TPA); bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane (MPMP); 1-phenyl-3-[p-(diethylamino)phenyl]-5-[p-(diphenyl)phenyl]- [ethylamino)phenyl]pyrazoline (PPR or DEASP); 1,2-trans-bis(9H-carbazol-9-yl)cyclobutane (DCZB); N,N,N',N'-tetrakis(4-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TTB); N,N'-bis(naphthalen-1-yl)-N,N'-bis-(phenyl)benzidine (α-NPB); and porphyrin compounds such as copper phthalocyanine. Commonly used hole transport polymers include, but are not limited to, polyvinylcarbazole, (phenylmethyl)polysilane, poly(dioxythiophene), polyaniline, and polypyrrole. It is also possible to obtain hole transport polymers by incorporating hole transport molecules such as those mentioned above into polymers such as polystyrene and polycarbonate. In some cases, triarylamine polymers are used, especially triarylamine-fluorene copolymers. In some cases, the polymers and copolymers are crosslinkable. Examples of crosslinkable hole transport polymers can be found, for example, in published US patent application 2005-0184287 and published PCT application WO 2005 / 052027.In some embodiments, the hole transport layer is doped with a p-type dopant, such as tetrafluorotetracyanoquinodimethane and perylene-3,4,9,10-tetracarboxy-3,4,9,10-dianhydride.

[0229] Depending on the application of the device, the photoactive layer 140 can be a light-emitting layer that is activated by an applied voltage (e.g., in a light-emitting diode or a light-emitting electrochemical cell), a layer of material that absorbs light and emits light having a longer wavelength (e.g., in a down-converting phosphor device), or a layer of material that responds to radiant energy and generates a signal with or without an applied bias (such as in a photodetector or photovoltaic device).

[0230] In some embodiments, the photoactive layer includes a compound having Formula I as a photoactive material. In some embodiments, the photoactive layer further includes a host material. Examples of host materials include, but are not limited to Phenanthrene, triphenylene, phenanthroline, triazine, naphthalene, anthracene, quinoline, isoquinoline, quinoxaline, phenylpyridine, carbazole, indolocarbazole, indoloindole, furan, benzofuran, dibenzofuran, benzodifuran, naphthofuran, naphthodifuran, metal quinoline complexes, substituted derivatives thereof, deuterated analogs thereof, and combinations thereof. In some embodiments, the host material is deuterated.

[0231] In some embodiments, the photoactive layer includes as a host material a compound having Formula I and a photoactive dopant. The photoactive dopant can be an organic electroluminescent ("EL") material, as described in detail above.

[0232] In some embodiments, the photoactive layer further comprises a second host material. Examples of the second host material include, but are not limited to, Phenanthrene, triphenylene, phenanthroline, triazine, naphthalene, anthracene, quinoline, isoquinoline, quinoxaline, phenylpyridine, carbazole, indolocarbazole, indoloindole, furan, benzofuran, dibenzofuran, benzodifuran, naphthofuran, naphthodifuran, metal quinoline complexes, substituted derivatives thereof, and deuterated analogs thereof.

[0233] In some embodiments, the second host is selected from the group consisting of triphenylene, carbazole, indolocarbazole, indoloindole, furan, benzofuran, dibenzofuran, naphthodifuran, substituted derivatives thereof, and deuterated analogs thereof.

[0234] In some embodiments, the weight ratio of the host material having Formula I to the second host material is in the range of 10:1 to 1:10; in some embodiments, 3:1 to 1:3.

[0235] In some embodiments, the photoactive layer 140 includes a photoactive dopant and a host material having Formula I.

[0236] In some embodiments, the photoactive layer 140 includes only a photoactive dopant and a host material having Formula I, with no additional materials present that would substantially alter the operating principle or distinctive properties of the layer.

[0237] In some embodiments, the photoactive layer 140 includes a photoactive dopant, a host material having Formula I, and a second host material.

[0238] In some embodiments, the photoactive layer 140 includes only a photoactive dopant, a first host material having Formula I, and a second host material, with no additional materials present that would substantially alter the working principle or distinguishing characteristics of the layer.

[0239] The weight ratio of dopant to total host material is in the range of 2:98 to 50:50; in some embodiments, 3:97 to 30:70; in some embodiments, 5:95 to 20:80.

[0240] Optional layer 150 may simultaneously function to facilitate electron transport and also act as a confinement layer to prevent exciton quenching at the layer interface. Preferably, this layer promotes electron mobility and reduces exciton quenching.

[0241] In some embodiments, layer 150 includes other electron transport materials. Examples of electron transport materials that can be used in optional electron transport layer 150 include metal chelated oxine compounds, including metal quinolate derivatives such as tris (8-hydroxyquinoline) aluminum (AlQ), bis (2-methyl-8-hydroxyquinoline) (p-phenylphenol) aluminum (BAlq), tetrakis (8-hydroxyquinoline) hafnium (HfQ) and tetrakis (8-hydroxyquinoline) zirconium (ZrQ); and azole compounds such as 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3,4- oxadiazole (P BD), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ) and 1,3,5-tris(phenyl-2-benzimidazole)benzene (TPBI); quinoxaline derivatives such as 2,3-bis(4-fluorophenyl)quinoxaline; phenanthroline such as 4,7-diphenyl-1,10-phenanthroline (DPA) and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (DDPA); triazine; fullerene; and mixtures thereof. In some embodiments, the electron transport material is selected from the group consisting of metal quinolates and phenanthroline derivatives. In some embodiments, the electron transport layer further comprises an n-type dopant. N-type dopant materials are well known. N-type dopants include, but are not limited to, Group 1 and Group 2 metals; Group 1 and Group 2 metal salts such as LiF, CsF, and Cs2CO3; Group 1 and Group 2 metal organic compounds such as lithium quinolate; and molecular n-type dopants such as leuco dyes, metal complexes such as W2(hpp)4 (wherein hpp = 1,3,4,6,7,8-hexahydro-2H-pyrimido-[1,2-a]-pyrimidine) and cobaltocene, tetrathianaphthene, bis(ethylenedithio)tetrathiafulvalene, heterocyclic groups or divalent groups, and dimers, oligomers, polymers, dispiro compounds, and polycyclic compounds of heterocyclic groups or divalent groups.

[0242] An optional electron injection layer may be deposited over the electron transport layer. Examples of electron injection materials include, but are not limited to, organometallic compounds containing Li, LiF, Li2O, lithium quinolate, organometallic compounds containing Cs, CsF, Cs2O, and Cs2CO3. This layer may react with the underlying electron transport layer, the overlying cathode, or both. When an electron injection layer is present, the amount of material deposited is typically in the range of In some embodiments,

[0243] The cathode 160 is an electrode that is particularly effective for injecting electrons or negative charge carriers. The cathode can be any metal or non-metal having a work function lower than that of the anode. The material for the cathode can be selected from the alkali metals of Group 1 (e.g., Li, Cs), Group 2 (alkaline earth) metals, Group 12 metals, including rare earth elements and lanthanides, and actinides. Materials such as aluminum, indium, calcium, barium, samarium, and magnesium, as well as combinations thereof, can be used.

[0244] It is known to have other layers in organic electronic devices. For example, there may be a layer (not shown) between the anode 110 and the hole injection layer 120 to control the amount of positive charge injected and / or to provide band gap matching of the layer, or to serve as a protective layer. Layers known in the art, such as ultra-thin layers of copper phthalocyanine, silicon oxynitride, fluorocarbons, silanes, or metals such as Pt, may be used. Alternatively, some or all of the anode layer 110, active layers 120, 130, 140, and 150, or cathode layer 160 may be surface treated to increase the charge carrier transport efficiency. The choice of material for each component layer is preferably determined by balancing the positive and negative charges in the emitter layer to provide a device with high electroluminescent efficiency.

[0245] It should be understood that each functional layer may be composed of more than one layer.

[0246] The device layer can be formed by any deposition technique or combination of techniques, including vapor deposition, liquid deposition, and thermal transfer. Substrates such as glass, plastic, and metal can be used. Conventional vapor deposition techniques such as thermal evaporation, chemical vapor deposition, and the like can be used. The organic layer can be applied from a solution or dispersion in a suitable solvent using conventional coating or printing techniques, including but not limited to spin coating, dip coating, roll-to-roll technology, inkjet printing, continuous nozzle printing, screen printing, gravure printing, and the like.

[0247] For liquid deposition methods, one skilled in the art can readily determine the appropriate solvent for a particular compound or related class of compounds.

[0248] In some embodiments, the hole transport layer is formed by liquid deposition of a hole transport material and any additional materials in a liquid medium. In some embodiments, the liquid medium comprises one or more organic solvents. In some embodiments, the organic solvent is an aromatic solvent. In some embodiments, the organic liquid is selected from chloroform, dichloromethane, chlorobenzene, dichlorobenzene, toluene, xylene, mesitylene, anisole, N-methyl-2-pyrrolidone, tetralin, 1-methoxynaphthalene, cyclohexylbenzene, and mixtures thereof. The hole transport material may be present in the liquid medium at a concentration of 0.2% to 5% (w / v); in some embodiments, 0.4% to 3% (w / v).

[0249] In some embodiments, the photoactive layer is formed by liquid deposition of the photoactive material and any host material in a liquid medium. Suitable classes of solvents that can be used as the liquid medium include, but are not limited to, aliphatic hydrocarbons (such as decane, hexadecane, and decahydronaphthalene), halogenated hydrocarbons (such as dichloromethane, chloroform, chlorobenzene, trifluorotoluene, and perfluoroheptane), aromatic hydrocarbons (such as unsubstituted and alkyl- and alkoxy-substituted benzene, toluene, and xylene), aromatic ethers (such as anisole, dibenzyl ether, and fluorinated derivatives), heteroaromatic compounds (such as pyridine), polar solvents (such as tetrahydrofuran, dimethylacetamide, N-methylpyrrolidone, and nitriles such as acetonitrile), esters (such as ethyl acetate, propylene carbonate, methyl benzoate, and phosphates such as tributyl phosphate), alcohols and glycols (such as isopropyl alcohol and ethylene glycol), glycol ethers and derivatives (such as propylene glycol methyl ether and propylene glycol methyl ether acetate), ketones (such as cyclopentanone and diisobutyl ketone), and mixtures thereof.

[0250] In some embodiments, the device is fabricated by vapor deposition of all layers.

[0251] In some embodiments, the device is made by liquid deposition of the hole injection layer, hole transport layer, and photoactive layer, and vapor deposition of the anode, electron transport layer, electron injection layer, and cathode.

[0252] It will be appreciated that the efficiency of devices made from the novel compositions described herein can be further improved by optimizing other layers in the device. For example, more efficient cathodes such as Ca, Ba, or LiF can be used. Formed substrates and novel hole transport materials that result in reduced operating voltage or increased quantum efficiency are also applicable. Additional layers can also be added to customize the energy levels of the various layers and enhance electroluminescence.

[0253] In some embodiments, the device has the following structure in order: anode, hole injection layer, hole transport layer, photoactive layer, electron transport layer, electron injection layer, cathode.

[0254] Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, suitable methods and materials are described below. In addition, the materials, methods, and examples are illustrative only and are not intended to be limiting. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety.

[0255] Examples

[0256] The concepts described herein will be further described in the following examples, which do not limit the scope of the invention described in the claims.

[0257] Synthesis Example 1

[0258] This example illustrates the preparation of the compound of Formula I (Compound 1).

[0259] This compound can be prepared according to the following scheme:

[0260]

[0261] Here, Pd / P represents a palladium catalyst combined with a phosphine compound, and Δ represents heating.

[0262] Equimolar amounts of materials 1 and 2 can be dissolved in toluene. 4 mol equivalents of 2M Na2CO3 solution can be added thereto, and the solution is bubbled with argon for 30 min. 0.05 mol equivalents of Pd(PPh3)4 can be added thereto, and the mixture is stirred at 90°C for 6 h. After cooling, the reaction mixture can be filtered and concentrated to obtain material 3.

[0263] Material 3 can be brominated with Br2 in dichloromethane to obtain material 4.

[0264] Equimolar amounts of materials 4 and 5 can be dissolved in toluene. 4 mol equivalents of 2M Na2CO3 solution can be added thereto, and the solution is bubbled with argon for 30 min. 0.05 mol equivalents of Pd(PPh3)4 can be added thereto, and the mixture is stirred at 90°C for 6 h. After cooling, the reaction mixture can be filtered and concentrated to obtain compound 1. Compound 1 can be purified by column chromatography.

[0265] Synthesis Example 2

[0266] This example illustrates the preparation of a compound of Formula I (Compound 2).

[0267] This compound can be prepared according to the following scheme:

[0268]

[0269] Under nitrogen atmosphere, 4 mol equivalents of AlCl can be added to 10 mol equivalents of compound 1 from synthesis example 1 dissolved in perdeuterobenzene (perdeuterobenzene). The resulting mixture can be stirred at room temperature for 6 hours, after which D o (50 mL) can be added. The layer can be separated, and the organic layer is dried and concentrated to obtain compound 2. The crude product can be purified by column chromatography.

[0270] Comparative Synthesis Example A

[0271] Comparative Compound A can be produced in a similar manner to Synthesis Example 1, as shown in the following scheme.

[0272]

[0273] Comparative Synthesis Example B

[0274] Comparative Compound B can be produced in a similar manner to Synthesis Example 2, as shown in the following scheme.

[0275]

[0276] Device Examples

[0277] (1) Materials

[0278] Comparative Compound B has the structure shown above.

[0279] Dopant D-1 is bis(diarylamino)benzofluorene. Such materials have been described, for example, in US Pat. No. 8,465,848.

[0280] ET-1 is an arylphosphine oxide.

[0281] ET-2 is lithium quinolate.

[0282] HIJ-1 is a hole injection material made of an aqueous dispersion of a conductive polymer and a polymeric fluorinated sulfonic acid.

[0283] HIJ-2 is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile.

[0284] HTM-1 is an arylamino-phenanthrene.

[0285] NPD is N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine

[0286] (2) Device manufacturing

[0287] OLED devices were manufactured using a combination of solution processing and thermal evaporation techniques. Patterned indium tin oxide (ITO)-coated glass substrates from Thin Film Devices, Inc. were used. These ITO substrates were based on Corning 1737 glass coated with ITO having a sheet resistance of 30 ohms / square and a transmittance of 80%. The patterned ITO substrates were ultrasonically cleaned in an aqueous detergent solution and rinsed with distilled water. The patterned ITO was subsequently ultrasonically cleaned in acetone, rinsed with isopropyl alcohol, and dried in a stream of nitrogen.

[0288] Before the device is about to be manufactured, the ITO substrate of cleaning, patterning is treated with ultraviolet ozone for 10 minutes.After cooling, immediately on the ITO surface, the aqueous dispersion of HIJ-1 is spin-coated and heated to remove solvent, to form a short circuit reduction layer (" SRL ").Then the workpiece is placed in a vacuum chamber.Then suitable mask is used to be deposited in sequence by thermal evaporation by hole injection material, the first hole transport material, the second hole transport material, photoactive and host materials, electron transport material, electron injection material and Al cathode, to form hole injection layer (" HIL "), one or more hole transport layers (" HTL "), photoactive layer or emissive layer (" EML "), electron transport layer (" ETL ") and electron injection layer (" EIL "), subsequently forming cathode.By chamber exhaust, and use glass cover, desiccant and UV curable epoxy to encapsulate these devices.

[0289] (3) Device characterization

[0290] OLED devices are characterized by measuring their (1) current-voltage (IV) curve, (2) electroluminescence radiation versus voltage, and (3) electroluminescence spectrum versus voltage. All three measurements are performed simultaneously and are computer controlled. The current efficiency of the device at a certain voltage is determined by dividing the electroluminescence radiation of the LED by the current density required to operate the device. The unit is cd / A. The power efficiency is the current efficiency divided by the operating voltage. The unit is lm / W. Color coordinates are determined using a Minolta CS-100 colorimeter or a Photoresearch PR-705 colorimeter.

[0291] Device Examples 1-3

[0292] These examples illustrate the performance of devices having a photoactive layer comprising the novel compounds of Formula I as host material.

[0293] The device has the following structure, in order (all percentages are by weight, based on the total weight of the layers):

[0294] glass substrate

[0295] Anode: ITO (50nm)

[0296] SRL:HIJ-1(100nm)

[0297] HIL: HIJ-2 (7nm)

[0298] HTL1:NPD(90nm)

[0299] HTL2:HTM-1(20nm)

[0300] EML: Host and dopant D-1 (25 nm) as shown in Table 1

[0301] ETL: ET-1:ET-2 (1:1 weight ratio) (26.2nm)

[0302] EIL: ET-2 (3.5nm)

[0303] Cathode: Al (100nm)

[0304] The results are given in Table 1.

[0305] Table 1. Device results

[0306] Examples main body ratio CE EQE CIEx CIE V T80 1 Compound 1 20:1 9.8 12.1 0.142 0.087 5.6 1050 2 Compound 1 13:1 10.2 12.1 0.140 0.093 5.6 1120 3 Compound 1 32:1 10.0 12.3 0.141 0.089 5.6 800

[0307] All data are based on 1000 nits unless otherwise stated. Ratio is the host:dopant weight ratio; CE is the current efficiency in cd / A; EQE = external quantum efficiency in percent; CIEx and CIEy refer to the x and y color coordinates according to the CIE chromaticity scale (International Commission on Illumination, 1931); V is at 15 mA / cm 2 The voltage under T80 is 16.5mA / cm 2 The time in hours for the device to reach 80% of the initial luminance at the current density and 50C.

[0308] Device Examples 4-6 and Comparative Example A

[0309] These examples illustrate the performance of devices having a photoactive layer comprising the novel compounds of Formula I as host material.

[0310] These devices have the same structure as in Device Examples 1-3, except for the entities and ratios given in Table 2.

[0311] The results are given in Table 2.

[0312] Table 2. Device results

[0313] Examples main body ratio CE EQE CIEx CIE V T80 A B 20:1 10.3 12.1 0.140 0.095 5.6 1400 4 Compound 2 20:1 10.5 12.3 0.140 0.096 5.6 2100 5 Compound 2 13:1 10.2 11.8 0.139 0.098 5.5 1900 6 Compound 2 32:1 10.1 12.3 0.141 0.090 5.6 1570

[0314] All data are based on 1000 nits unless otherwise stated. Ratio is the host:dopant weight ratio; CE is the current efficiency in cd / A; EQE = external quantum efficiency in percent; CIEx and CIEy refer to the x and y color coordinates according to the CIE chromaticity scale (International Commission on Illumination, 1931); V is at 15 mA / cm 2 The voltage under T80 is 16.5mA / cm 2 The time in hours for the device to reach 80% of the initial luminance at the current density and 50C.

[0315] It should be noted that not all of the activities described above in the general description or examples are required, that a portion of a specific activity may not be required, and that one or more other activities may be performed in addition to those described. Furthermore, the order in which the activities are listed is not necessarily the order in which they should be performed.

[0316] In the foregoing description, the concepts have been described with reference to specific embodiments. However, those skilled in the art will appreciate that various modifications and changes may be made without departing from the scope of the present invention as set forth in the following claims. Accordingly, the specification and drawings are to be regarded in an illustrative rather than a restrictive sense, and all such modifications are intended to be included within the scope of the present invention.

[0317] Benefits, other advantages, and solutions to problems have been described above with respect to specific embodiments. However, no benefit, advantage, solution to a problem, or any feature or features that may cause or make apparent any benefit, advantage, or solution, is to be construed as a key, required, or essential feature of any or all of the claims.

[0318] It is to be understood that, for the sake of clarity, certain features described herein in the context of separate embodiments may also be provided in a single embodiment in combination. Conversely, for the sake of brevity, the various features described in the context of a single embodiment may also be provided individually or in any sub-combination. The use of numerical values within the various ranges specified herein is expressed as approximate values, just as the minimum and maximum values within the ranges are both preceded by the word "about". In this way, slight variations above or below the ranges may be used to obtain results substantially the same as the values within these ranges. Moreover, the disclosure of these ranges is also intended to be a continuous range of each value included between the minimum and maximum averages, including fractional values that may be generated when some components of a value are mixed with components of different values. In addition, when disclosing wider and narrower ranges, it is within the expectations of the present invention to match the minimum value from one range with the maximum value from another range, and vice versa.

[0319] The present invention includes the following embodiments:

[0320] Embodiment 1. An electroactive composition comprising (a) a host compound having formula I

[0321] in:

[0322] R 1 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, silyl, germyl, deuterated alkyl, deuterated silyl, and deuterated germyl;

[0323] a is an integer from 0 to 7;

[0324] b is an integer from 0 to 8;

[0325] c is an integer from 0 to 4; and

[0326] d is an integer from 0 to 7;

[0327] and (b) a photoactive dopant.

[0328] 2. The composition of embodiment 1, wherein at least one of ad is non-zero and at least one R 1 =D.

[0329] 3. The composition according to embodiment 1, wherein a+b+c+d=1-26 and R 1 =D.

[0330] 4. The composition according to embodiment 1, wherein a+b+c+d=15-26 and R 1 =D.

[0331] 5. The composition of embodiment 1, wherein the position on the compound of formula I is marked

[0332]

[0333] And further, wherein at least one of ad is non-zero; and at least one R 1 is selected from the group consisting of alkyl, trimethylsilyl, trimethylgermyl, and deuterated analogs thereof, and is present at at least one of positions 2, 3, 4, 5, 9, 10, 13, 14, 20, 23, 24, 25, and 26.

[0334] 6. The composition of embodiment 1, wherein the dopant has formula II or formula III

[0335]

[0336] in:

[0337] A is the same or different at each occurrence and is a hydrocarbon aryl or heteroaryl group having from 3 to 60 ring carbon atoms;

[0338] Q' is a hydrocarbon aryl or heteroaryl group having from 3 to 60 ring carbon atoms;

[0339] p and q are independently integers from 1-6.

[0340] 7. The composition of embodiment 6, wherein Q' is derived from a compound selected from the group consisting of anthracene, Pyrene, benzofluorene, naphthofuran, naphthodifuran, substituted derivatives thereof, and deuterated analogs thereof.

[0341] 8. An organic electronic device comprising an anode, a cathode, and a photoactive layer interposed therebetween, wherein the photoactive layer comprises the composition according to embodiment 1.

[0342] 9. An organic electronic device comprising an anode, a cathode, and a photoactive layer interposed therebetween, wherein the photoactive layer comprises the composition according to embodiment 3.

[0343] 10. An organic electronic device comprising an anode, a cathode, and a photoactive layer therebetween, wherein the photoactive layer comprises the composition according to embodiment 5.

Claims

1. An electroactive composition comprising (a) a host compound having formula I in: R 1 is D; a is an integer from 0 to 7; b is an integer from 0 to 8; c is an integer from 0 to 4; d is an integer from 0 to 7; and a+b+c+d=5-26; and (b) a photoactive dopant.

2. The composition according to claim 1, wherein a=7, b=8, c=4 and d=7; a=7, b=8, c=0 and d=0; a=0, b=8, c=4 and d=7; or a=0, b=8, c=0 and d=0.

3. The composition according to claim 1, wherein The host compound has the formula and (b) a photoactive dopant.

4. The composition according to claim 1, wherein The dopant has formula II or formula III in: A is the same or different at each occurrence and is a hydrocarbon aryl or heteroaryl group having from 3 to 60 ring carbon atoms; Q' is a hydrocarbon aryl or heteroaryl group having from 3 to 60 ring carbon atoms; p and q are independently integers from 1-6.

5. The composition according to claim 4, wherein Q' is derived from a compound selected from the group consisting of anthracene, Pyrene, benzofluorene, naphthofuran, naphthodifuran, substituted derivatives thereof, and deuterated analogs thereof.

6. An organic electronic device comprising an anode, a cathode and a photoactive layer therebetween, wherein: The photoactive layer comprises the composition of claim 1 .

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