TW201231437A - Anthracene derivative compounds for electronic applications - Google Patents

Abstract

This invention relates to electroactive compositions including anthracene derivative compounds. It also relates to electronic devices in which at least one active layer includes such a composition.

Description

201231437 • VI. Description of invention: , [Related application materials] The patent application in this patent is based on % USc §...(4) Recorded in Provisional Patent Application No. 61/424, No. 95, filed on December 17, 2002 Priority is hereby incorporated by reference in its entirety into this specification. TECHNICAL FIELD OF THE INVENTION The present invention relates to an electroactive composition comprising a hydrazine-derived compound. It is also an electronic device wherein at least the active layer comprises such a composition. [Prior Art]

Light-emitting organic electronic devices, such as light-emitting diodes that make up the display, are present in many different types of electronic devices. In all such devices, an organic electroactive layer is sandwiched between two electrical contact layers. At least one of the electrical contact layers is permeable to light such that light can pass through the electrical contact layer. When electrical power is applied through the electrical contact layer, the organic electroactive layer emits light via the <transmissive electrical contact layer. It is a matter of fact that S is an active material containing an electroluminescent layer of an organic electroluminescent compound as a host material. Simple organic molecules such as anthraquinone, anthraquinone derivatives and coumarin derivatives are known to exhibit electroluminescence. Semi-conductive conjugated polymers have also been used as electroluminescent components, such as those disclosed in U.S. Patent No. 5,247,190, U.S. Patent No. 5,408,109, the disclosure of which is incorporated herein by reference. However, there is still a need to continue to develop new materials for the electroactive layers of electronic devices. 201231437 SUMMARY OF THE INVENTION The present invention provides an electroactive composition comprising a barren ~ body and - electroluminescence (four),

Ar1 and Ar2 are the same or different, and are aryl groups. R1 to R8 are the same or different, and are selected from h, d:;, aryl, aryloxy, galvanic pits: R9 and R1G are The same or different, and is selected from the group consisting of H, 〇, and 矽; and, 'Meta

R" is the same or different from R12 and is selected from the group consisting of H, D thiol and aryl groups, and the condition is that at least one of R11 and π is an aryl group, and Ar2, R11 and At least one of R12 is a naphthyl group. [Embodiment] The various aspects and embodiments disclosed herein are illustrative and not restrictive. After reading this manual, those skilled in the art will be able to make one of the examples in accordance with the following detailed description and application scope without departing from the scope of the invention. Other features and benefits of the various embodiments are added. The detailed description of the case first proposes the definition and clarification of the term, and = the electroactive composition, the electronic device, and finally the example.缉 1 · Definitions and clarification of terms Before describing the details of the following examples, some terms are defined or clarified. The term "aliphatic ring" as used herein means a cyclic group having no delocalized pi electrons. In certain embodiments, the aliphatic ring is not unsaturated. In some embodiments, the containing ring has a double bond or a bond. ~ The term "alkoxy" refers to a R0 group in which R is an alkyl group. The term "alkyl group" means a group derived from an aliphatic hydrocarbon having a point of attachment, and the alkyl group includes a linear group, a branched group and a cyclic group. The term is meant to include miscellaneous groups. The term "hydrocarbon compound" refers to an alkyl group having no heteroatoms. The term "deuterated alkyl" is one having at least one hydrocarbon alkyl group which may be substituted with D. In certain embodiments, the alkyl group has from 1 to 20 carbon atoms. The term "branched alkyl" refers to a alkyl group having at least one secondary carbon or tertiary interrupted. The term "secondary alkyl group" refers to a branched alkyl group having one secondary carbon atom. The term "tertiary alkyl" refers to a branched alkyl group having one tertiary carbon atom. In some embodiments, the carboxy group is bonded via a secondary or tertiary carbon. 201231437 surgery s. "Aryl" means a group derived from an aromatic cigarette having a point of attachment. The term "aromatic compound" means an organic compound containing at least one unsaturated cyclic group having a non-localized π electron. The term is intended to include heteroaryl groups. The term "hydrocarbon aryl" means an aromatic compound having no hetero atom in the ring. The term "aryl" includes a radical having a single ring and a group having a polycyclic ring bonded by a single bond or fused together. The term "deuterated aryl" refers to an aryl group having at least one direct linkage to an aryl group which may be substituted with D. The term "extended aryl" means a group derived from an aromatic hydrocarbon having two points of attachment. In certain embodiments, an aryl group has from 3 to 60 carbon atoms. The term "aryloxy" refers to an RO- group in which R is an aryl group. The term "blue luminescent material" or "blue dopant" means a material capable of emitting radiation having a maximum emission amplitude in the range of about 4 〇〇 〇 48 。. The same 'blue emission color' means the color multiplication of the maximum in the wavelength range of about 400-480 nm. The uncharged substance f, which consists of molecules, which are composed of atoms in which the atoms cannot be physically separated. When the phrase "adjacent to" is used to refer to a layer in a layer, the phrase "adjacent to" does not necessarily mean that the layer is immediately adjacent to another layer. On the other hand, the phrase "adjacent R groups" is used to mean R groups adjacent to each other in the -chemical formula. In other words, adjacent lines are located on a few atoms adjacent to each other by a bond. The term "speaking" means that at least one Η has been replaced by D. The atmosphere is at least twice as natural and abundant. The "gasification congener" of the compound 有 has the same structure as the compound X |, but is substituted with at least one D. 6 201231437 The term "dopant" means a material located in a layer comprising a host material that changes the electrical properties of the layer in which the material is not present or the wavelength of the emitted, received or filtered radiation. The electronic properties of the layer or the wavelength of the target radiation emitted, received or filtered. When the term "electroactive" refers to a layer or material, the term "electrically active" means a layer or material that exhibits electronic or electrical light-emitting properties. In an electronic device, an electroactive material electrically contributes to the operation of the device. Examples of electroactive materials include, but are not limited to, materials that conduct, inject, transport, or interrupt electrical charges, where the charge can be electrons or holes, and include materials that emit radiation when exposed to radiation or exhibit changes in concentration of electron-hole pairs. . Examples of inactive materials include, but are not limited to, planarizing materials, insulating materials, and environmental insulating materials. The electric double reward Tueiectroiuminesw is called c," you mean that a material is emitted from a material in response to a current passing through the material. "Electr〇 luminescent" means an electroluminescence material. The term "emission maximum" refers to the highest center of gravity of a transmitted beam. The maximum value of the emission has - corresponding; wave ^. The term "green hair" or "green" means that it can emit radiation (4), and its emission is in the range of __(10) long. Similarly, "green emission color" means a color having a maximum wavelength in the range of about 480-560 nm. , ', the beginning of the word "het (10)" different atoms replace the carbon atom? In some embodiments, different atomic systems n, 〇 or ^ = "host material" means a dopant added The material may or may not have electronic properties or the ability to emit, receive or pulsate 201231437. In some embodiments, the bulk material is present in a thicker sound. "Film" is used interchangeably and refers to the coating of the desired area. The slang is not limited by size. This area can be as small as an entire device - or with a _ specific Wei area (eg, actual, not) 'Or with - single reading - small. Layers and films can be formed by any one of the knowing techniques 'including vapor deposition, liquid deposition (continuous and continuous technology) and heat transfer. Continuous deposition techniques include but not Limited to spin coating, gravure coating, curtain coating, dip coating, slot die coating, spray coating and nozzle coating. The continuous deposition techniques include, but are not limited to, inkjet printing, gravure printing and Screen printing. S-the term "organic electronic device" or sometimes only "Electronic device" means a device comprising one or more organic semiconductor layers or semiconductor materials 4. The term "silyl" refers to the group R3Si_, wherein R is Η, D, Cl-; Alkyl), fluoroalkyl or aryl. In certain embodiments, one or more carbons of the 'R alkyl group are replaced by a ruthenium. In some embodiments, the thiol group The group is (hexyl) 2Si(CH3)CH2CH2Si(CH3)2- and [CF3(CF2)6CH2CH2]2Si(CH3)-. Unless otherwise indicated, all groups may be substituted or unsubstituted. In some embodiments, the substituent is selected from the group consisting of d, -, decyl, alkoxy, erythro, aryl, aryloxy, cyano, and NR2, wherein R is alkyl or Aryl. All technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the invention belongs, unless otherwise defined, although similar or equivalent to the methods and materials described herein. Used to practice or test the invention', but suitable methods and materials are described below. All publications, patent applications, patents, and other publications are hereby incorporated by reference in their entirety in the entirety in the the the the the the the the The examples are merely illustrative and are not intended to be limiting. The full text is used throughout the International Union of Pure and Applied Chemistry (IUPAC) numbering system, where the families from the Periodic Table of the Elements are numbered 1-18 from left to right ( CRC Handbook of Chemistry and Physics, 81st edition, 2000. In this specification, unless explicitly stated or indicated to be inconsistent with the context, the subject matter of the subject matter is described or disclosed as including, containing, containing, having, One or more of the features or elements may be present in one or more of the features or elements of the embodiment in addition to those explicitly recited or disclosed. The other embodiments of the present invention are described as being mainly composed of certain features or elements, and there are no features or parts that would substantially alter the operating principles or distinctive features of the embodiments. Still another embodiment of the subject matter described herein is described as being comprised of certain features or elements, and in this embodiment or its non-substantial variations, there are only those features or elements that are explicitly pointed out or described. In addition, unless expressly stated to the contrary, "or" means an inclusive "or" rather than an exclusive "or". For example, any of the following conditions satisfy the condition Α or B: Α is true (or exists) and B is pseudo (or non-existent), A is pseudo (or non-existent) and b is true (or exists) , and both A and B are true (or exist). 201231437 Again, the use of "a" or "an" is used to describe the elements and components described herein. This is done merely for convenience' and provides a general sense of the scope of the invention. This description should be understood to include one or at least one, and the singular also includes the plural. 2. Electroactive Composition The electroactive composition described herein comprises a ruthenium derivative having the formula I and an electroluminescent material. In certain embodiments, the electroactive composition comprises primarily a host material having Formula I and one or more electroluminescent dopants. In certain embodiments, the electroactive layer comprises primarily a first host material having Formula I, a second host material, and an electroluminescent dopant. Examples of second host materials include, but are not limited to, [chrysenes], phenanthrenes, triphenylenes, phenanthrolines, naphthalenes, anthracenes, quinoline (quinolines), isoquinolines, quinine [mouth + 咢] • #* (quinoxalines), phenyl benzopyridines, benzodifurans and metal quinoline complexes (metal Quinolinate complexes) The amount of dopant present in the electroactive composition is generally from 3 to 20% by weight based on the total weight of the composition; in certain embodiments, from 5 to 15% by weight. When the second host is included, the ratio of the first body to the second body of Formula I is typically in the range of 1:20 to 20:1; in some embodiments, 5:15 to 15:5. In certain embodiments, the first primary 201231437 bulk material of Formula I comprises at least 50% by weight of the total body material; in certain embodiments, at least 70% by weight. a. 蒽 derivative body

The anthracene derivative host material has the formula I

Ar1 and Ar2 are the same or different and are aryl groups; R1 to R8 are the same or different and are selected from the group consisting of ruthenium, D, alkyl, alkoxy, aryl, aryloxy, fluorenyl and oxime a group consisting of alkane; R9 and R1G are the same or different, and are selected from the group consisting of H, D, alkyl, and fluorenyl; and R11 and R12 are the same or different, and are selected from H, D. And a group consisting of an alkyl group, a decyl group and an aryl group, with the proviso that at least one of R11 and R12 is an aryl group, and at least one of Ar2, R11 and R12 is a naphthyl group. In certain embodiments of Formula I, Ar1 is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthracenyl, phenylnaphthyl, naphthylphenyl, oxime analogs thereof, and groups having formula II The group consisting of:

Wherein: R16 and R17 are the same or different and are selected from the group consisting of H, D and Cu alkyl; R18 is the same or different at each occurrence, and is selected from H, D, alkyl, alkane a group consisting of an oxy group, a decane group and a fluorenyl group, or an adjacent group of R16 groups may be bonded together to form an aromatic ring; and R19 is selected from the group consisting of H, D, an alkyl group, a fluorenyl group and an aryl group. Groups; and m are the same or different at each occurrence and are integers from 1 to 6. In certain embodiments of Formula I, Ar1 is selected from the group consisting of phenyl, naphthyl, phenylenenaphthyl, n-phenylphenyl, its analogs, and groups having formula m, wherein The formula m is:

201231437 Embodiment: The definition of R16SR, m as above. In some 'm' is an integer from 1 to 3. In certain embodiments of Formulas II and III, at least one of Rule 16 and at least one is an alkyl group. In certain embodiments, both the ruthenium and Rn are methyl groups. , or in style! In certain embodiments, Afl is a heteroaryl group. In a second embodiment, the heteroaryl group is selected from the group consisting of biting, benzo biting, Si benzo, and W.

Ar is phenyl, naphthyl or its oxime. In certain embodiments of formula I, an analog is obtained. In certain embodiments of Formula I, the scales 1 to 118 are selected from the group consisting of Η & In certain embodiments of Formula I, at least one of Ri to R8 is selected from the group consisting of a hospital base, a hospitaloxy group, a silk, an aryloxy group, a charcoal group, and the remainder of R to R8 is selected from the group consisting of D. In certain embodiments, r2 is selected from the group consisting of an alkyl group, a 'base group, an aryl group, an aryloxy group, a money house, and a Shiheji. In certain embodiments, R2 is selected from the group consisting of alkyl and aryl.

In certain embodiments of Formula I, Ruler 9 and Ri(R) are selected from the group consisting of H, D, and C1-5 alkyl groups. In certain embodiments, R9 and r1〇 are Η or D. , R and R towel at least - are aryl groups. In some embodiments, the aryl group is selected from the group consisting of stupid, naphthyl, phenanthryl, anthracenyl and their deuterated analogs. In certain embodiments of formula I, Ar2 is naphthyl or substituted t-base and R-R is a strepyl or substituted phenyl. In certain embodiments of 201231437, Ar2 is phenyl or substituted phenyl, and one of Rn and R is naphthyl or substituted naphthyl. In certain embodiments, the substituted naphthyl and substituted phenyl groups may be further substituted with a deuterated phenyl, naphthyl, alkyl or fluorenyl group. In certain embodiments of Formula I, 'may be any combination of the following: (i) ^r1 is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthracenyl, phenyl-naphthyl, naphthylphenyl, and fluorene a group of analogs, groups of formula II and groups of formula, or Arl is a heteroaryl group selected from furan, benzofuran, diphenyl hydrazine a group consisting of furan, pyrene, benzopyran and diphenylpyran; (ii) R1 to R8 are selected from hydrazine and D, or at least one of R1 to R8 is selected from alkyl, alkoxy a base, an aryl group, an aryloxy group, a decyl alkane and a fluorenyl group, and the remainder of R1 to R8 is selected from the group consisting of hydrazine and 0; (1) and 1^ are selected from the group consisting of H, D& C15 alkyl; Iv) at least one of Rn and W is selected from the group consisting of phenyl, decyl, phenanthryl, fluorenyl and their oximation analogs; (v) Ar2 is naphthyl or taken from Tecino and Ru And Rn is a phenyl group or a substituted base group, or fluorene is a phenyl group or a substituted phenyl group and one of r11 is a naphthyl group or a substituted naphthyl group. In some actual closures, the m-producing compounds described herein are at least deuterated. This means that at least 50% of H is replaced by D. In certain embodiments, the compound is at least (10) devaluated; in some embodiments, at least 70% is singulated; in some embodiments, at least 8% is singulated; in some embodiments, at least 9G %Kb In certain embodiments, the compound is 100% deuterated. Some non-limiting examples of compounds of formula I are as follows: 201231437

Compound HI

Compound H2

Compound H3

15 201231437 Compound H4

Compound H5

Compound H6

The anthracene derivative compound can be prepared by known coupling and substitution reactions. Such reactions are well known and widely found in the literature. Examples of references include: Yamamoto, Progress in Polymer Science, Vol. 17, p 1153 (1992); Colon et al., Journal of Polymer Science, Part A, Polymer chemistry Edition, Vol. 28, p. 201231437 . 367 (1990) U.S. Patent No. 5,962,631, and PCT Application WO 00/53565; T. Ishiyama et al., J. Org. Chem. * 1995 60, 7508-7510; M. Murata et al., J. Org. Chem. 1997 62, 6458-6459; M. Murata et al., J. Org. Chem. 2000 65, 164-168; L. Zhu, et al., J. Org. Chem. 2003 68, 3729-3732; Stille, JK Angew. Chem. Int. Ed. Engl. 1986, 25, 508; Kumada, M. Pure. Appl. Chem. 1980, 52, 669; Negishi, E. Acc. Chem. Res. 1982, 15, 340 Hartwig, J., Synlett 2006, No. 9, pp. 1283-1294; Hartwig, J., Nature 455, No. 18, pp. 314-322. The preparation of the deuterated compound can be made in a similar manner using a deuterated precursor material, or more commonly a Lewis acid/D exchange catalyst such as tri-aluminum or ethyl aluminide or such as CF3COOD, DC1 The non-deuterated compound is treated with an emulsifying solvent such as toluene (d6-benzene) in the presence of an acid. The deuteration reaction is also described in the related application published as WO 2011/053334. The compounds described herein can be formed into a film using liquid deposition techniques. This is further illustrated in these examples. Alternatively, it can be formed into a film by a vapor deposition technique. b. Electroluminescent material The dopant is an electroluminescent material which is capable of electroluminescence with a maximum emission between 380 and 750 nm. In some embodiments, the dopant has an emission color of red, green, or blue. In some embodiments, the emission color of the dopant is green or blue. 201231437 Electroluminescent ("EL") materials that can be used as dopants in the electroactive layer include, but are not limited to, small molecule organic fluorescent compounds, fluorescent and phosphorescent metal complexes, co-light polymers', and mixtures thereof. Examples of fluorescent compounds include, but are not limited to, [#+快] (chrysenes), pyrenes, perylenes, rubrenes, coumarins, anthracenes, and the like. A thiadiazoles, a derivative of the above, and a mixture of the foregoing. Examples of metal complexes include, but are not limited to, metal chelated oxinoid compounds. Examples of conjugated polymers include, but are not limited to, poly(phenylenevinylenes), polyfluorenes, poly (spirobifluorenes), polythiophenes. , poly(p-phenylenes), copolymers thereof and mixtures thereof. Examples of red luminescent materials include, but are not limited to, periflanthenes, fluoranthenes, and perylenes. Red luminescent materials are disclosed in, for example, U.S. Patent No. 6,875, 524, issued to U.S. Pat. Examples of green luminescent materials include, but are not limited to, diaminoanthracenes and polyphenylenevinylene polymers. The green luminescent material is disclosed in, for example, the published PCT application WO 2007/021117. Examples of blue luminescent materials include, but are not limited to, diarylanthracenes, diaminochrysenes, diaminopyrenes, and polyfluorene polymers. Blue luminescent materials are disclosed in, for example, U.S. Patent No. 6,875, 524, issued to U.S. Pat. In certain embodiments, the dopant is an organic compound. In some embodiments, the dopant is selected from the group consisting of a non-polymer spiral dimer compound and a fluoranthene compound. In certain embodiments, the dopant is a compound having an arylamine group. In certain embodiments, the electroactive dopant is selected from the group consisting of:

Wherein: A is the same or different at each occurrence, and is an aromatic group having 3 to 60 carbon atoms; Q' is a single bond or an aromatic group having 3 to 60 carbon atoms; q is an integer from 1 to 6, respectively. 19 201231437 In certain embodiments of the above formula, at least one of A and Q in each formula has at least three fused rings. In certain embodiments, p and q are equal to one. In certain embodiments, the Q is a Styry(R) or styrylphenyl group. In certain embodiments, Q' is an aromatic group having at least two fused rings. In certain embodiments, the 'Q system is selected from the group consisting of naphthalene, anthracene, chrysene, pyrene, tetracene, mouth + mountain, mouth + star 】 (xanthene), perylene, coumarin, rh〇damine, quinacridone and rubrene. In certain embodiments, the A is selected from the group consisting of phenyl, biphenyl, tolyl (10)y, naphthy(na), naphthylphenyl, and anthracenyl. The group that makes up. In certain embodiments, the dopant has the formula:

Wherein: γ is the same or different at each occurrence, and is an aromatic group having 3 to 60 carbon atoms; a Q group is a group, a divalent triphenylamine residue group or a single bond. 20 201231437 In certain embodiments, the dopant is a poly aryl acene. In certain embodiments, the dopant is an asymmetric aryl acene. In certain embodiments, the dopant is a derivative having the formula IV:

Wherein: R2() is the same or different at each occurrence, and is selected from the group consisting of D, alkyl, alkoxy and aryl, wherein adjacent R1G groups can be grouped together to form a 5 or 6 member aliphatic rings;

Ar2 to Ar5 are the same or different and are selected from the group consisting of an aryl group and a deuterated aryl group; d is the same or different at each occurrence, and is an integer from 0 to 4; In an embodiment, the dopant is a [-+ fast] derivative having the formula V: 21 201231437

Wherein: R21 is the same or different at each occurrence, and is selected from the group consisting of D, alkyl, alkoxy, aryl, fluoro, cyano, nitro, and S02R, wherein R is alkyl Or a perfluoroalkyl group, wherein adjacent R21 groups may be joined together to form a 5- or 6-membered aliphatic ring;

Ar2 to Ar5 are the same or different and are selected from the group consisting of aryl hydrazines; and e is the same or different at each occurrence, and is an integer from 0 to 5. Some non-limiting examples of green dopants are the compounds D1 to D7 shown below. D1:

22 201231437 D2:

D3:

23 201231437 D4:

D5:

24 201231437 D6:

D7:

Some non-limiting examples of blue dopants are compounds D8 through D14 as shown below. 25 201231437

D9:

DIO:

26 201231437

Dll: D21 D12:

27 201231437 D13:

D14:

In certain embodiments, the electroluminescent dopant is selected from the group consisting of an amine substituted [w + +] (chrysenes) and an amine substituted oxime. The compositions described herein can be formed into a film using liquid deposition techniques. 28 201231437 3. An electronic device in which an electronic device can benefit from the use of one or more layers of compounds described herein includes, but is not limited to, (1) devices that convert electrical energy into radiation (eg, light-emitting diodes, light-emitting diodes) A polar body display, a illuminating illuminator, or a diode laser), (2) a device that detects signals via an electronic program (such as a photodetector, a photoconductive battery, a photoresist, an optical switch, a photonic crystal, a phototube, an IR detector) a device (3) a device that converts light radiation into electrical energy (eg, a photovoltaic device or a solar cell), and (4) a device in which one or more of the electronic components includes one or more organic semiconductor layers (eg, thin film electricity) Crystal or diode). The compounds of the invention are typically used in applications such as oxygen sensitive detectors and luminescence indicators for biological detection. An aspect of an organic electronic device structure is shown in FIG. The device 100 has a first electrical contact layer, an anode layer U and a second electrical contact layer, a cathode layer 16A, and an electroactive layer 14 therebetween. A hole injection layer 12A may be adjacent to the anode. Adjacent to the hole injection layer may be a hole transport layer comprising a hole transport material adjacent to the cathode. The electron transport layer 150 may comprise an electron transport material. The device may use one or more additional hole injection or hole transport layers (not shown) in close proximity to the anode 110 and/or one or more additional electron injecting or electron transport layers (not shown) in close proximity to the cathode 160. Layers 120 through 150 are individually and collectively referred to as active layers. In one embodiment, the different layers have a thickness range as follows: The anode 110 is 500-5000 A, in one embodiment ι〇〇〇_2〇〇〇A; $'the same as the main entry layer 12〇 is 50-2000 A, in one embodiment 200-1000' hole transport layer 130 is 50-2000 A, in one embodiment 29 201231437 200-1000 A; electroactive layer 140 is 10-2000 A, in one embodiment 100-1000 A; electron transport layer 150 is 50-2000 A, in one embodiment 100-1000 A; cathode 160 is 200-10000 a, in one embodiment 300- 5,000 people. The relative thickness of each layer can affect the position of the electron-hole recombination zone in the device and thus the emission spectrum of the device. The desired ratio of layer thickness will depend on the exact nature of the material used. Depending on the application of the device 100, the electroactive layer 14 can be a light-emitting layer (for example, in a light-emitting diode or a light-emitting electrochemical cell) activated by an applied voltage, or one with or without one A layer of material that responds to radiate energy and generate a signal (eg, in a light sniffer) under external bias. Examples of photodetectors include photoconductive cells, photoresistors, light control switches, optoelectronic crystals, photocells, and photovoltaic cells. These terms are described in Johns Markus's "Electronics and Nucleonics Dictionary" on pages 470 and 476. Page (McGraw-Hill, Inc., 1966). The new electroactive composition described herein can be a layer of 14 Å. In some embodiments, the devices have additional layers to aid in processing or to improve functionality. a. The image quality part of the electroactive layer color display is evaluated in the color gamut, which is the number of colors that can be produced by mixing the red, green and blue (RGB) three primary color sub-pixels with different relative intensities. The color gamut depends on the emission wavelength energy. And the width of the primary color. Ideally, the maximum emission of the RGB sub-pixels is 700, 520, and 460 nm, respectively, and the width is 1-2 nm. In fact, the width is usually 30 201231437 dozens of nanometers. In organic light-emitting diode (OLED) displays, blue emitters are inherently too broad and rarely meet the National Television Standards Board (NTSC) CIE (x, y) = (0.15, 0.06) standard. As described herein, CIE (x, y) is the X and y color coordinates according to C.I.E. Chroma (Commission Internationale de L'Eclairage, 1931). The OLED blue can be sharpened to the standard by filtering and/or adding a microcavity structure to the device. However, both methods increase the cost, and the latter affects another important image quality parameter, that is, the viewing angle. Another problem with today's technology is that dark blue OLEDs have poor quantum performance due to the difficulty in limiting/capturing charge on wide-gap emitters. The best-performing blue OLEDs in terms of color, performance and longevity, with quantum efficiencies exceeding 5%' can provide thousands of hours of high illumination. However, the intrinsic illuminating color is generally not superior to CIE(x, y)~(0.14, 0.12). A dopant having a larger HOMO-LUMO bandwidth can improve the color to CIE (x, y) ~ (0.14, 〇.1 〇). However, the band gap between the host and the dopant is almost the same. Although good host radiation can thus be produced with a quantum efficiency < 5%, it still does not meet the NTSC standard. There is therefore a need for a darker blue OLED that is capable of meeting the NTSC standard and having a quantum efficiency of 5%. In certain embodiments, the ruthenium compound described herein has a wide bandgap. This is caused by the conjugated decomposition of adjacent naphthyl and aryl groups. The host compound is suitable as a deep blue chromonic dopant in the electroactive layer 140. The body can also be used for other dopants that emit color. / In certain embodiments, the electroactive layer comprises predominantly a host material of the formula and one or more electroluminescent dopants. In certain embodiments, the electroactive layer comprises primarily a first host material of Formula I, a second host material 31 201231437 material, and an electroluminescent dopant. Examples of second host materials include, but are not limited to, [chrysenes], phenanthrenes, triphenylenes, phenanthrolines, naphthalenes, anthracenes, 喧1 # (quinolines), isoquinolines, quinoxalines, phenylpyridines, benzodifurans, and metal quinolinate complexes. The amount of dopant present in the electroactive composition is generally from 3 to 20% by weight based on the total weight of the composition; in some embodiments, from 5 to 15% by weight. When the second body is included, the ratio of the first body to the second body of Formula I is approximately in the range of 1:20 to 20:1; in some embodiments, it is 5:15 to 15:5. In certain embodiments, the first host material of Formula I comprises at least 50% by weight of the total host material; in certain embodiments, at least 70% by weight. In certain embodiments the 'second host material has the formula VI:

among them:

Ar6 is the same or different at each occurrence and is an aryl group; Q is selected from the group consisting of polyatomic aryl groups to 32 201231437

T is selected from the group consisting of (CR,) a, SiR2, s, S02, PR, p0, p〇, BR, and R; 1 R is the same or different at each occurrence, and is selected from an alkyl group a group consisting of aryl groups; soil R' is the same or different at each occurrence, and is selected from the group consisting of ruthenium and osmium; & a is an integer from 1 to 6; and η is 〇 to An integer of 6. While η may have a value from 〇 to 6, it will be understood that for some Q groups the value of 'η is limited by the chemistry of the group. In the embodiment, η is 0 or 1. ' ^ In certain embodiments of Formula VI, the adjacent Αγ* group binds to form a ring, such as a carbazole. In the formula VI, "contiguous" means that the Ar group is bonded to the same N. In certain embodiments, the Ar6 system is independently selected from the group consisting of phenyl, biphenyl, terphenyi, quaterphenyl, naphthyl, phenanthryl a group consisting of naphthylphenyl and phenanthrylphenyl. Analogs higher than biphenyl (having 5-10 benzene rings) can also be used. 33 201231437 In some real _, at least "6 has at least one substituted soil. The substituents are in order to change the carcass: characteristics." Some implementations, the substituents enhance the body ^, processability. In some implementations, the substituents increase solubility and/or increase the host T g. In some embodiments, the substituents are selected from the group consisting of D, a group, and an alkoxy group. a group consisting of a group, a oxane, and combinations thereof. In certain embodiments, Q is an aryl group having at least two fused rings. In certain embodiments, Q has 3_5. Aromatic fused rings. In certain embodiments, the Q system is selected from the group consisting of [#+快], phenanthrene, terphenyl, phenanthroline, naphthalene, anthracene, quinoline, and isoquinoline. Other layers of the device layer in the device may be made of any known material for such a layer. The anode 110 is an electrode that is particularly effective for injecting positive charge carriers. Made of materials, mixed metals, alloys, metal oxides or mixed metal oxides, or they may be electrically conductive a suitable polymer or a mixture thereof. Suitable metals include Group 11 metals, Group 4 to 6 metals, and Group 8 to 10 transition metals. If the anode is light transmissive, Groups 12, 13 and A mixed metal oxide of a Group 14 metal such as indium tin oxide. The anode 110 may also include an organic material such as polyaniline, which is described in "Flexible light-emitting diodes made from soluble conducting polymer" Nature, Vol. 357, 477 to 479 pages (June 11, 1992). At least one of the anodes 34 201231437 and the cathode is desirably at least partially translucent to facilitate viewing of the generated light. The hole injection layer 120 includes a hole injection material and may have one or more functions within an organic electronic device including, but not limited to, planarization of its underlying layer, charge transport and/or charge injection characteristics, Removal of impurities such as oxygen or metal ions and other functions that contribute to the performance of the organic electronic device. The hole injection material can be a polymer, a polymer or a small molecule. It can be vapor deposited or deposited from a liquid in the form of a solution, dispersion, suspension, emulsion, colloidal mixture or other composition. The hole injection layer may be formed of a polymeric material such as polyaniline (PANI) or polyethylene oxydioxide (PEDOT), which is often doped with a protonic acid. The protic acid may be, for example, polystyrenesulfonic acid, poly(2-acrylamido-2-methyl-1-propionic acid) (poly (2-acrylamido-2-methyl-) L-propanesulfonic acid)) A similar. The hole injection layer may include a charge transport compound and the like, such as copper phthalocyanine and tetrathiafulvalene-tetracyanoquinodimethane (TFF-TCNQ). In some embodiments the hole injection layer comprises at least one electrically conductive polymer and at least one fluorinated acid polymer. Such materials are described in, for example, U.S. Patent Application Serial Nos. 2004-0102577, 2004-0127637, and 2005/205860. In certain embodiments, the hole transport layer 130 comprises a novel deuterated compound of formula I. Layer 130 Other hole transmission materials are shown, for example, in 35 201231437

Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition, Vol. 18, p 837-860, 1996, Y. Wang. Both the hole transporting molecule and the hole transporting polymer can be used. Commonly used hole transport molecules are: Ν, Ν·-diphenyl Ν, Ν'-bis(3_mercaptophenyl)-[1, fluorene-biphenyl]-4,4'-diamine ( N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[l,r-biphenyl]-4,4'-diamine,TPD), 1,1_bis[(di-4-methylphenyl) 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane, TAPC), N,N'-bis(4-methylphenyl)-fluorene, Ν'- Bis(4-ethylphenyl)-[1,Γ-(3,3'-dimethyl)biphenyl]-4,4'-diamine (N,N'-bis(4-methylphenyl)-N , N'-bis(4-ethylphenyl)-[l,r-(3,3'-dimethyl)biphenyl]-4,4'-diamine, ETPD), 肆(3-methylphenyl)-N,N , N', N'-2,5-phenylenediamine (tetrakis-(3_methylphenyl)-N,N,N',N'-2,5-phenylenediami ne, PDA), a-benzene-4-oxime, a-phenyl-4-N,N-diphenylaminostyrene (TPS), p-(diethylamino)benzaldehyde diphenylhydrazone (DEH), triphenylamine (p-(diethylamino)benzaldehyde diphenylhydrazone, DEH) Triphenylamine, ΤΡΑ), bis[4-(N,N-diethylamine)-2-mercaptobenzene](4-methylphenyl)methane (bis[4-(N,N-diethylamino)-2-methylphenyl] (4-methylphe Nyl)methane, MPMP), 1-phenyl-3-[p-(diethylamine)styrene]-5-[p-(diethylamino)phenyl]oxazoline (l-phenyl-3-[p -(diethylamino)styryl]-5-[p-(diethylamino) phenyl] pyrazoline, PPR or DEASP), 1,2-anti-bis(9H-咔sa-9-yl)cyclobutane (l,2-trans- Bis(9H-carbazol-9-yl)cyclobutane, DCZB), Ν,Ν,Ν·,Ν'-肆(4-methylphenyl)-(1,Γ-biphenyl)-4,-diamine 36 201231437 (N,N,N'5N'-tetrakis(4-methylphenyl)-(l,r-biphenyl)-4,4'-diamine, TTB), Ν,Ν,-bis(naphthalen-1-yl)- N,N,-bis-(phenyl)benzidine (N,N'-bis(naphthalen-l-yl)-N,N'-bis_(phenyl)benzidine, α-ΝΡΒ) and porphyrinic compounds Such as copper offering green. Commonly used hole transporting polymers are polyvinyl carbazole, (benzyl)-polydecane and polyaniline. It is also possible to obtain a hole transporting polymer by doping the above-mentioned hole transporting molecules into a polymer such as polystyrene and polycarbonate. In some cases, triarylamine polymers, especially triarylamine-co-polymers, are used. In some cases, the polymers and the copolymers are crosslinkable. An example of a crosslinkable hole transporting polymer can be referred to, for example, U.S. Patent Application Publication No. 2005-0184287 and the disclosure of PCT Application No. WO 2005/052027. In some embodiments, the § hai hole transport layer is doped with a p-type dopant (p_d〇pant), such as tetrafluorotetracyanoquinodimethane and 茈3,4,9 ,10-tetracarboxylic-3,4,9,10-dianhydride (perylene-3,4,9,l-tetracarboxylic-3,4,9,10-dianhydride) ° In certain embodiments, the electron Transport layer 150 includes the new deuterated compound of formula I. Other examples of electron transporting materials that can be used for the layer 15 include metal chelate oxinoid compounds such as tris(8-glycolin) (Alq3); bis(2-methyl-8.hydroxyquinoline) (p-phenylphenol)aluminum (m) (BA1Q); and azaleaf compound such as 2-(4-diphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD) And 3_(4_diphenyl)_4_phenyl_5_(4_tert-butylphenyl H,2,4-tris-sodium (TAZ), and 1,3,5-tris(phenyl-2-benzene) And imidazole) benzene (TPBI); quinoxaline derivatives such as 2,3-bis(4-fluorophenyl)quinoxaline; phenanthroline derivatives such as 9, 〇-diphenyl phenanthroline (DPA) and 2 , 9-Dimethyl-4,7-diphenyl_11〇-phenanthroline (DDpA); and mixtures thereof. The electron transmission 37 201231437 The transport layer can also be b-type doped _,, heterogeneous layer! 5G can And (4) in the electron wheel and as = resist layer = energy to avoid exciton quenching between the layer interfaces. Compared with t and t this layer enhances electron mobility and reduces exciton quenching. σ The cathode 160 is a pair of notes A particularly effective electrode. The cathode can be metal or non-metal with a work function of == sub. The material used for the cathode can be metal (such as u, Cs), group 2 (soil test) metal, genus, package Including rare earth itin and lanthanide and (10). It is possible to use a mixture of m钡, magnesium, and a combination of an organic layer and a cathode layer to deposit an L1#cm substance such as LiF, csF or Li2〇 to lower the operating voltage. It is known that there may be other layers in the organic electronic device. For example, there may be a layer between the anode m and the hole injection layer 12 (not to control the amount of positive charge injected, and / Or provide band-gap matching, or as a protective layer. Layers well known in the art, for example, copper, nitrous oxide, fluorite, decane or ultra-thin metal such as Pt Alternatively, some or all of the anode layer no, the active layer 120, 130, 14〇, 15〇 or the cathode layer 16 may be surface treated to increase the charge carrier transport efficiency. It is preferred to provide a device having high electroluminescence efficiency by balancing the positive and negative charge green in the emissive layer. It should be understood that 'each-functional layer may be composed of more than one layer. It can be prepared by various techniques. The device, the techniques comprising arranging gas on a suitable substrate (4) Other layers such as glass, plastic and metal substrates can be used, for example, hot steaming, chemical vapor 38 201231437 deposition and similar conventional vapor deposition techniques. Alternatively, conventional coatings or Printing Technology 'Applying an organic layer from a suitably sprayed solution or dispersion, including but not limited to, spin coating, dip coating, roll-to-roll _-t〇-r〇ii) technology, inkjet printing, screen printing Printing, gravure printing and the like. The invention also relates to an electronic device comprising at least one active layer between two electrical contact layers, wherein at least one active layer of the device comprises a deuterated sigma of formula 1. Devices often have additional hole transport layers and electron transport layers. In order to achieve a high efficiency, the highest occupied molecular orbital (HOMO) of the led' hole transport material must match the work function of the anode and the lowest unoccupied molecular orbital of the electron transport material (lowest un-occupied molecular Orbita Bu LUMO) must match the work function of the cathode. The chemical compatibility and sublimation temperatures of these materials are also important considerations when selecting electron and hole transport materials. It will be appreciated that the efficiency of the device made from the ruthenium compound described herein can be further improved by optimizing the other layers in the device. For example, a more efficient cathode such as Ca, Ba or LiF can be used. It is also possible to use a substrate for fabrication and a novel hole transport material, which causes a reduction in operating power or an increase in quantum efficiency. Additional layers can be added to modify the energy levels of the various layers and contribute to electroluminescence. The compounds of the present invention are often fluorescent and photoluminescent and can be used in applications other than OLEDs, such as oxygen sensitive indicators and as fluorescent indicators in biometric assays. The following examples are intended to illustrate the invention, but not to limit the features and advantages. All percentages used in the examples are by weight: not otherwise indicated, otherwise it should be noted that it is not necessary to perform an action, as described in the specific description or example and in addition to the description =作;:部: may not be required, the external 'listed actions are == and 'this technology has the general scope of the patent, the scope of the invention, the scope of the invention, does not deviate from the following application, this specification and diagram It is to be understood that such modifications are intended to be included in the scope of the present invention. The invention has been described with respect to the benefits of the particular embodiments, other advantages and solutions. However, benefits, advantages, problem resolutions, and any features that make these benefits, advantages, or problem solutions more prominent are not to be construed as critical, necessary, or essential features of any or all patent applications. It will be understood that some of the features of the various embodiments described herein may be combined in a separate embodiment for the purpose of clarity. Conversely, various features described herein in the single embodiment may be provided separately or in any sub-combination. Further, the relevant numerical values described in the <RTI ID=0.0> </ RTI> ranges include each and every value within the range. 40 201231437 [Simplified Description of the Drawings] The embodiments are described in the accompanying drawings to improve the understanding of the concepts presented herein. Figure 1 includes an illustration of an example of an organic electronic device. Those skilled in the art should understand that the objects in the drawings are illustrated for the purpose of simplicity and clarity and are not necessarily to scale. For example, in these figures, the dimensions of some of the items may be exaggerated relative to other items to facilitate an understanding of the embodiments. [Main component symbol description] 100. .. device 110. .. anode layer 120.. hole injection layer 130.. hole transmission layer 140. . . electroactive layer 150. .. electron transport layer 160. .Cathode layer 41

Claims (1)

201231437 VII. Application scope of the patent: 1. An electroactive assembly wire comprising - a host material and an electrical material, wherein the anthracene derivative has the formula I Wherein: Ar1 and Ar2 are the same or different and are an aryl group; R1 to R8 are the same or different and are selected from the group consisting of ruthenium, D, alkyl, alkoxy, aryl, aryloxy, fluorene And R9 and R10 are the same or different, and are selected from the group consisting of H, D, alkyl and sulfhydryl; and R11 and R12 are the same or different, and It is selected from the group consisting of ruthenium, D, alkyl, fluorenyl and aryl groups, with the proviso that at least one of R11 and R12 is an aryl group, and at least one of Ar2, R11 and R12 is a naphthyl group. 2. The composition according to claim 1, wherein Ar] is selected from the group consisting of phenyl, naphthyl, phenanthryl, anthracenyl, phenylnaphthyl, naphthylphenyl, oxime analog thereof, and having the formula 11 a group consisting of groups of which II is: 42 201231437 Wherein: R16 and R17 are the same or different and are selected from the group consisting of ruthenium, D and a basal group; R18 is the same or different at each occurrence, and is selected from H, D, alkyl' a group consisting of an alkoxy group, a decane group and a fluorenyl group, or an adjacent group of R16 groups may be bonded together to form an aromatic ring; R19 is selected from the group consisting of H, D, alkyl, anthracenyl and aryl. a group consisting of; and m is the same or different at each occurrence and is an integer of six. 3. The composition according to claim 1 or 2, wherein R1 to r8 are selected from H and 4. The composition according to claim i or 2, wherein at least one of ... to ... is selected from a hospital base The other ones of the alkoxy group, the aryl group, and the aryloxy group R1 to R8 are selected from the group consisting of m sigma and sylvestre, and the composition is as described in the above-mentioned composition, wherein r^r1. Select a group consisting of free, D, and C. The composition of any one of clauses 5 to 5, wherein at least one of the ruler 11 and at least one selected from the group consisting of a phenyl group, a naphthyl group, a phenanthryl group, an anthracenyl group, and a deuterated analog thereof Group. The composition according to any one of claims 1 to 6, wherein the sulphate is a naphthyl group or a substituted naphthyl group, and one of Rn and Ri2 is a phenyl group or a substituted phenyl group. The composition according to any one of claims 6 to 6, wherein Ar2 is a phenyl group or a substituted phenyl group, and one of R11 and R12 is a naphthyl group or a substituted naphthyl group. 9. The composition of claim 3, wherein the electroluminescent dopant is selected from the group consisting of an amine group substituted with a chrysenes and an amine substituted. 10. An organic electronic device comprising an anode, a cathode and an electroactive layer therebetween, wherein the electroactive layer comprises the electroactive composition of claim 1. U. — a derivative of a compound having the formula I 44 201231437 Wherein: Ar1 and Ar2 are the same or different and are an aryl group; R1 to R8 are the same or different and are selected from the group consisting of H, D, alkyl, alkoxy, aryl, aryloxy, fluorene a group consisting of a base and a oxane; R9 and R1G are the same or different, and are selected from the group consisting of ruthenium, D, alkyl, and Shishiji; and R11 and R12 are the same or different, and are Selecting a group consisting of ruthenium, D, alkyl, decyl and aryl, with the proviso that at least one of R11 and R12 is an aryl group, and at least one of Ar2, R11 and R12 is a naphthyl group, and Wherein the compound is at least 50% deuterated. 45