Vinylsilane compound and organic light emitting device including the same

Abstract

Disclosed are a vinylsilane compound represented by Formula 1, an organic light emitting device including an organic layer containing the compound, and a flat panel display apparatus: Formula 1 wherein A, R1, R2, Ar1, Ar2, n, and m are defined in the specification.

Description

[0001] This application is a divisional application of a patent application with the application date of January 4, 2013, the application number of 201310002140.8, and the title of "Vinyl silane compound and organic light emitting device comprising the same". TECHNICAL FIELD

[0002] The present application relates to a vinyl silane compound represented by Formula 1 and an organic light emitting device comprising the same. BACKGROUND

[0003] An organic light emitting device is a self-emission type display device having a wide viewing angle, high contrast ratio, and short response time. Due to these characteristics, the organic light emitting device has attracted considerable attention. Such an organic light emitting device can be broadly classified into an inorganic light emitting device including an emission layer containing an inorganic compound and an organic light emitting device including an emission layer containing an organic compound. In particular, the organic light emitting device has higher luminance, lower driving voltage, and shorter response time than the inorganic light emitting device, and is capable of presenting multicolor display. Therefore, much research has been conducted on such an organic light emitting device.

[0004] Generally, the organic light emitting device has a stacked structure including an anode, a cathode, and an organic emission layer between the anode and the cathode. However, a hole injection layer and / or a hole transport layer can be stacked between the anode and the organic emission layer, and / or an electron transport layer can be stacked between the organic emission layer and the cathode. In other words, the organic light emitting device can have a stacked structure of anode / hole transport layer / organic emission layer / cathode or anode / hole transport layer / organic emission layer / electron transport layer / cathode.

[0005] As a material for forming the organic emission layer, anthracene derivatives have been widely used. In terms of color purity of emitted blue light, light emitted from most of the known light emitting materials is blue-green rather than deep blue. In addition, when the light emitting material is used in the organic light emitting device, most of the organic light emitting devices do not have a long enough half-life, and thus are not commercially viable. SUMMARY

[0006] Embodiments of the present application provide a novel vinyl silane compound having improved electrical characteristics, charge transport ability, and light emitting ability.

[0007] Embodiments of the present application provide an organic light emitting device comprising the vinyl silane compound.

[0008] Embodiments of the present application provide a flat panel display apparatus comprising the organic light emitting device.

[0009] According to embodiments of the present application, a vinyl silane compound is represented by the following Formula 1:

[0010] Formula 1

[0011]

[0012] In Formula 1, each A is independently a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C5-C 60 alkenyl, a substituted or unsubstituted C5-C 60 aryl, or a substituted or unsubstituted C3-C 60 heteroaryl. R1and R2are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C 60 alkyl, a substituted or unsubstituted C3-C 60 cycloalkyl, a substituted or unsubstituted C5-C 60 aryl, or a substituted or unsubstituted C3-C 60 heteroaryl. B can be a divalent linking group, and can be a substituted or unsubstituted C1-C 60 alkylene, a substituted or unsubstituted C5-C 60 arylene, or a substituted or unsubstituted C3-C 60 heteroarylene. Ar1and Ar2are each independently a substituted or unsubstituted C5-C 60 aryl, a substituted or unsubstituted C3-C 60 heteroaryl, or a substituted or unsubstituted C6-C 60 condensed polycyclic group. Ar1and Ar2are optionally linked to form a ring, n is an integer from 0 to 3, m is an integer from 1 to 4, and n+m = 4.

[0013] In some embodiments, each A can be independently a substituted or unsubstituted C1-C 30 alkyl, a substituted or unsubstituted C5-C 30 aryl, or a substituted or unsubstituted C3-C 30 heteroaryl.

[0014] In some embodiments, R1and R2may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C 30 alkyl, a substituted or unsubstituted C3-C 30 cycloalkyl, a substituted or unsubstituted C5-C 30 aryl, or a substituted or unsubstituted C3-C 30 heteroaryl.

[0015] In some embodiments, B can be a divalent linking group, and can be a substituted or unsubstituted C5-C 30 arylene, or a substituted or unsubstituted C3-C 30 heteroarylene.

[0016] In some embodiments, Ar1and Ar2may each independently be a substituted or unsubstituted C5-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, or substituted or unsubstituted C6-C 30 condensed polycyclic group.

[0017] In some embodiments, in the above Formula 1, R1and R2may each independently be a hydrogen atom or a deuterium atom.

[0018] In some embodiments, in the above Formula 1, A can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 20 alkyl, or any one of the following Formulae 2a to 2d:

[0019]

[0020] In Formulae 2a to 2d, each of Y1, Y2, and Y3may independently be a linking group represented by -N=, -N(R 20 )-, or -C(R 21 )=. Each of Z1, Z2, R 20 , and R 21 may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C 20 alkyl, a substituted or unsubstituted C5-C 20 aryl, a substituted or unsubstituted C3-C 20 heteroaryl, a substituted or unsubstituted C6-C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group. p can be an integer of 1 to 12. * can indicate a bonding site.

[0021] In the above Formula 1, each of Ar1and Ar2may independently be any one of compounds represented by the following Formulae 3a to 3f:

[0022]

[0023] In the above Formulae 3a to 3f, Q1may be a linking group represented by -C(R 30 )(R 31 )-, -N(R 32 )-, -S-, or -O-. Each of Y1, Y2, and Y3may be a linking group independently represented by -O-, -N=, -N(R 20 )-, or -C(R 21 )=. Each of Z1, Z2, Z3, R 20 , R 21 , R30 R 31 and R 32 Each of these can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C atom. 20 Alkyl, substituted or unsubstituted C5-C 20 Aryl, substituted or unsubstituted C3-C 20 heteroaryl, substituted or unsubstituted C6-C 20 Condensed polycyclic groups, halogen atoms, cyano groups, nitro groups, hydroxyl groups, or carboxyl groups. p can be an integer from 1 to 12. r can be an integer from 0 to 5. * can indicate the binding site.

[0024] In some embodiments, in Formula 1 above, B can be a linker represented by any one of Formulas 4a to 4i below, or a linker obtained by linking two or more groups represented by Formulas 4a to 4i below:

[0025]

[0026] In equations 4a to 4i above, Q1 can be derived from -C(R) 30 (R) 31 )-、-N(R 32 The linker bases are represented by -, -S, or -O. Each of Y1, Y2, and Y3 can independently be -O-, -N=, or -N(R). 20 - or -C(R) 21 = represents the linking basis. Z1, R 20 R 21 R 30 R 31 and R 32 Each of these can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C atom. 20 Alkyl, substituted or unsubstituted C5-C 20 Aryl, substituted or unsubstituted C3-C 20 heteroaryl, substituted or unsubstituted C6-C 20 Condensed polycyclic groups, halogen atoms, cyano groups, nitro groups, hydroxyl groups, or carboxyl groups. p can be an integer from 1 to 12. * can indicate the binding site.

[0027] In some embodiments, the vinylsilane compound represented by Formula 1 above can be any one of the following compounds:

[0028]

[0029]

[0030]

[0031]

[0032]

[0033] According to another embodiment of the present application, an organic light emitting device includes a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes the vinylsilane compound.

[0034] The organic layer can be an emission layer, and the vinylsilane compound can be used as a host for a fluorescent or phosphorescent device.

[0035] The organic layer can be an emission layer, and the vinylsilane compound can be used as a fluorescent dopant.

[0036] The organic layer can include a hole injection layer, a hole transport layer, or a functional layer having a hole injection and a hole transport ability.

[0037] The organic light emitting device can include an emission layer, a hole injection layer, a hole transport layer, or a functional layer having a hole injection and a hole transport ability, and the emission layer, the hole injection layer, the hole transport layer, or the functional layer having a hole injection and a hole transport ability can include the vinylsilane compound, and the emission layer can include an anthracene compound.

[0038] The organic light emitting device can include an emission layer, a hole injection layer, a hole transport layer, or a functional layer having a hole injection and a hole transport ability, and the emission layer, the hole injection layer, the hole transport layer, or the functional layer having a hole injection and a hole transport ability can include the vinylsilane compound, and the emission layer can include an arylamine compound.

[0039] The organic light emitting device can include an emission layer, a hole injection layer, a hole transport layer, or a functional layer having a hole injection and a hole transport ability, and the emission layer, the hole injection layer, the hole transport layer, or the functional layer having a hole injection and a hole transport ability can include the vinylsilane compound, and the emission layer can include a styryl compound.

[0040] The organic light emitting device can include an emission layer, a hole injection layer, a hole transport layer, or a functional layer having a hole injection or a hole transport ability, and the hole injection layer, the hole transport layer, or the functional layer having a hole injection or a hole transport ability can include the vinylsilane compound, and any one of a red layer, a green layer, and a white layer of the emission layer can include a phosphorescent compound.

[0041] The hole injection layer, the hole transport layer, or the functional layer having a hole injection and a hole transport ability can include a charge generation material.

[0042] The charge-generating material may include p-dopers, which may include quinone derivatives, metal oxides, or cyano-containing compounds.

[0043] The organic layer may include an electron transport layer, which may include electron transport organic compounds and metal complexes.

[0044] The organic layer can be formed using a wet process utilizing the vinylsilane compound.

[0045] According to another embodiment of the present invention, a flat panel display device may include the organic light-emitting device, wherein a first electrode of the organic light-emitting device may be electrically connected to the source electrode or drain electrode of a thin-film transistor. Attached Figure Description

[0046] The above and other features and advantages of the invention will become more apparent from the following detailed description taken in conjunction with the accompanying drawings, in which:

[0047] Figure 1 This is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention. Detailed Implementation

[0048] As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. When a statement such as “at least one of…” follows a series of elements, it modifies the entire series of elements, rather than individual elements within the series.

[0049] Anthracene derivatives are known as materials for organic emitting layers. For example, organic light-emitting devices made using phenyl anthracene dimers or trimers are known. However, because two or three oligomers of anthracene are conjugated, such organic light-emitting devices have narrow band gaps and low blue light color purity.

[0050] Furthermore, such compounds are highly susceptible to oxidation, potentially leading to impurities that necessitate purification. To overcome these drawbacks, organic light-emitting devices have been introduced using anthracene compounds (including anthracene compounds with naphthalene substitution at the 1 and 9 positions) or diphenylanthracene compounds (including diphenylanthracene compounds with aryl substitution at the meta position). However, these organic light-emitting devices exhibit relatively low luminous efficiency.

[0051] Naphthalene-substituted monoanthracene derivatives can also be used to manufacture organic light-emitting devices. However, these devices have low luminous efficiency (approximately 1 cd / A), making them unsuitable for practical use. Alternatively, phenylanthracene compounds containing aryl substituents at the meta position can be used to manufacture organic light-emitting devices. Such compounds exhibit good heat resistance but suffer from an unsatisfactory low luminous efficiency of approximately 2 cd / A.

[0052] Furthermore, it has been reported that luminescent materials can be doped to improve the luminous efficiency of the emitter layer (EML). In this case, anthracene compounds as described above are used as the host, and styrene-based or stilbene-based compounds are used as dopants. The luminous efficiency of the EML is improved when blue fluorescent dopants with arylamine groups added to the ends of the styrene-based compounds are used. However, in terms of the color purity of the emitted blue light, the light emitted from most of these luminescent materials is bluish-green rather than deep blue. Additionally, when these luminescent materials are used in organic light-emitting devices, most organic light-emitting devices do not have a sufficiently long half-life, making them commercially unfeasible.

[0053] The invention will now be described more fully with reference to the accompanying drawings, in which exemplary embodiments of the invention are shown.

[0054] In some embodiments of the present invention, a vinylsilane compound is represented by the following formula 1.

[0055] Formula 1

[0056]

[0057] In Equation 1 above, each A can be independently either substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C5-C 60 aryl or substituted or unsubstituted C3-C 60 Heteroaryl. Each of R1 and R2 can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C atom. 60 Alkyl, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 aryl or substituted or unsubstituted C3-C 60 Heteroaryl. B can be a divalent linker and can be substituted or unsubstituted C1-C. 60 Alkylene, substituted or unsubstituted C5-C 60 aryl or substituted or unsubstituted C3-C 60Hybrid aryl. Each of Ar1 and Ar2 can be independently substituted or unsubstituted C5-C. 60 Aryl, substituted or unsubstituted C3-C 60 Heteroaryl or substituted or unsubstituted C6-C 60 Condensed polycyclic basis. Ar1 and Ar2 can be optionally linked to form a ring, n can be an integer from 0 to 3, m can be an integer from 1 to 4, and n + m = 4.

[0058] The compounds described above according to embodiments of the present invention can be used as luminescent materials, hole transport materials, or hole injection materials in organic light-emitting devices. Compounds containing vinylsilanes in their molecular structure (e.g., the compounds described above) exhibit improved luminescent efficiency due to the introduction of amine groups into the molecular structure. Furthermore, when these compounds are used as blue fluorescent dopants, high-purity blue light can be obtained. These compounds possess enhanced hole transport capabilities and can therefore be used as hole injection or hole transport materials. Various substituents can be introduced into the molecule, thereby improving thermal properties (Tg, Tm). Additionally, the state of the film in the thin-film state is improved, thereby increasing resistance to high-temperature atmospheres and improving resistance to Joule heat generated between organic layers and between the organic layer and the metal electrode. Furthermore, organic light-emitting devices manufactured using the vinylsilane compounds described above exhibit high durability during storage and operation.

[0059] The substituents of the compounds described above will be described in more detail.

[0060] According to an embodiment of the present invention, in Formula 1 above, each A can independently be a substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C5-C 30 aryl or substituted or unsubstituted C3-C 30 Heteroaryl. Each of R1 and R2 can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C atom. 30 Alkyl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C5-C 30 aryl or substituted or unsubstituted C3-C 30 Heteroaryl. B can be a divalent linker and can be substituted or unsubstituted C5-C. 30 aryl or substituted or unsubstituted C3-C 30 Hybrid aryl. Each of Ar1 and Ar2 can be independently substituted or unsubstituted C5-C. 30 Aryl, substituted or unsubstituted C3-C 30 Heteroaryl or substituted or unsubstituted C6-C 30 Condensation polycyclic groups.

[0061] According to an embodiment of the present invention, in Formula 1 above, each of R1 and R2 can be independently a hydrogen atom or a deuterium atom.

[0062] According to another embodiment of the present invention, in Formula 1 above, each A can independently be any one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C. 20 Alkyl groups or one of the compounds represented by formulas 2a to 2d below:

[0063]

[0064] In equations 2a to 2d above, each of Y1, Y2, and Y3 can be independently represented by -N = , -N(R 20 - or -C(R) 21 = represents the linking base. Z1, Z2, R 20 and R 21 Each of these can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C atom. 20 Alkyl, substituted or unsubstituted C5-C 20 Aryl, substituted or unsubstituted C3-C 20 heteroaryl, substituted or unsubstituted C6-C 20 Condensed polycyclic groups, halogen atoms, cyano groups, nitro groups, hydroxyl groups, or carboxyl groups. p can be an integer from 1 to 12. * Indicates the binding site.

[0065] In some embodiments, in Formula 1 above, each of Ar1 and Ar2 can independently be any one of the compounds represented by Formulas 3a to 3f below:

[0066]

[0067] In equations 3a to 3f above, Q1 can be derived from -C(R) 30 (R) 31 )-、-N(R 32 The linking bases are represented by -, -S, or -O. Each of Y1, Y2, and Y3 can be independently represented by -O-, -N=, or -N(R). 20 - or -C(R) 21 The connection base is represented by ) = Z1, Z2, Z3, R. 20 R 21 R 30 R 31 and R 32 Each of these can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C atom. 20 Alkyl, substituted or unsubstituted C5-C20 Aryl, substituted or unsubstituted C3-C 20 heteroaryl, substituted or unsubstituted C6-C 20 Condensed polycyclic groups, halogen atoms, cyano groups, nitro groups, hydroxyl groups, or carboxyl groups. p can be an integer from 1 to 12. r can be an integer from 0 to 5. * Indicates the binding site.

[0068] According to another embodiment of the present invention, in Formula 1 above, B can be a linking group represented by one of Formulas 4a to 4i, or it can be a linking group obtained by linking at least two of the groups represented by Formulas 4a to 4i:

[0069]

[0070] In equations 4a to 4i above, Q1 can be derived from -C(R) 30 (R) 31 )-、-N(R 32 The linking bases are represented by -, -S, or -O. Each of Y1, Y2, and Y3 can be independently represented by -O-, -N=, or -N(R). 20 - or -C(R) 21 = represents the linking basis. Z1, R 20 R 21 R 30 R 31 and R 32 Each of these can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C atom. 20 Alkyl, substituted or unsubstituted C5-C 20 Aryl, substituted or unsubstituted C3-C 20 heteroaryl, substituted or unsubstituted C6-C 20 Condensed polycyclic groups, halogen atoms, cyano groups, nitro groups, hydroxyl groups, or carboxyl groups. p can be an integer from 1 to 12. * Indicates the binding site.

[0071] The substituents described herein will now be described in detail below. In this regard, the number of carbons in the substituents is given for illustrative purposes only and does not limit the characteristics of the substituents.

[0072] Unreplaced C1-C 60 Alkyl groups can be straight-chain or branched. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, and dodecyl. Substitution of C1-C 60 Examples of alkyl groups include unsubstituted C1-C. 60At least one hydrogen atom in the alkyl group is surrounded by a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, or a C1-C1 group. 10 Alkyl, C1-C 10 Alkoxy, C2-C 10 alkenyl, C2-C 10 alkynyl group, C6-C 16 Aryl or C4-C 16 Any group substituted with a heteroaryl group.

[0073] Unreplaced C2-C 60 Alkenyl refers to an unsaturated alkyl group having at least one carbon-carbon double bond in the middle or at the end of an alkyl group. Examples of alkenyl groups include, but are not limited to, vinyl, propenyl, butenyl, etc. Substituted C2-C 60 Examples of alkenyl groups include unsubstituted C2-C. 60 Any group in which at least one hydrogen atom in the alkenyl group is replaced by one of the substituents described above in conjunction with the alkyl group.

[0074] Unreplaced C2-C 60 An alkynyl group refers to an alkyl group having at least one carbon-carbon triple bond in the middle or at the end of an alkyl group. Unsubstituted C2-C 20 Examples of alkynyl groups include, but are not limited to, ethynyl, propynyl, phenylethynyl, naphthylethynyl, isopropylethynyl, tert-butylethynyl, diphenylethynyl, etc. Substituted C2-C 60 Examples of alkynyl groups include unsubstituted C2-C. 60 Any group in which at least one hydrogen atom of the alkynyl group is replaced by one of the substituents described above in conjunction with the alkyl group.

[0075] Unreplaced C3-C 60 cycloalkyl refers to C3-C 60 Cyclic alkyl groups. Substituted C3-C 60 Cycloalkyl groups are unsubstituted C3-C 60 At least one hydrogen atom in the cycloalkyl group is bonded to C1-C above. 60 An alkyl group is any group substituted by one of the substituents in a substituent group.

[0076] Unreplaced C1-C 60 An alkoxy group is a group having the structure -OA, where A is an unsubstituted C1-C group as described above. 60 Alkyl group. Unsubstituted C1-C 60 Non-limiting examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, and pentoxy. Substituted C1-C 60 The alkoxy group is an unsubstituted C1-C 60Any group in which at least one hydrogen atom in the alkoxy group is replaced by one of the substituents described above in conjunction with the alkyl group.

[0077] Unreplaced C5-C 60 Aryl refers to a carbocyclic aromatic system containing at least one ring. At least two rings can be fused together or linked together by a single bond. The term "aryl" refers to aromatic systems such as phenyl, naphthyl, or anthracene. Substitution of C5-C 60 The aryl group is an unsubstituted C5-C. 60 At least one hydrogen atom in the aryl group is bonded to an unsubstituted C1-C atom above. 60 An alkyl group is any group substituted by one of the substituents in a substituent group.

[0078] Substituted or unsubstituted C5-C 60 Examples of aryl groups include, but are not limited to, phenyl, C1-C 10 Alkylphenyl (e.g., ethylphenyl), halophenyl (e.g., o-fluorophenyl, m-fluorophenyl, or p-fluorophenyl, dichlorophenyl), cyanophenyl, dicyanophenyl, trifluoromethoxyphenyl, biphenyl, halobiphenyl, cyanobiphenyl, C1-C 10 Alkyl biphenyl, C1-C 10 Alkoxybiphenyl, o-tolyl, m-tolyl and p-tolyl, o-isopropylphenyl, m-isopropylphenyl or p-isopropylphenyl alkyl, phenoxyphenyl, (α,α-xylene)phenyl, (N,N'-dimethyl)aminophenyl, (N,N'-diphenyl)aminophenyl, cyclopentadienyl, indenyl, naphthyl, halonaphthyl (e.g., fluoronaphthyl), C1-C 10 Alkyl naphthyl (e.g., methylnaphthyl), C1-C 10 Alkoxynaphthyl (e.g., methoxynaphthyl), cyanonathyl, anthracene, chamomilecycloyl, heptatenyl, acenaphthyl, perinaphthyl, fluorenyl, anthraquinoneyl, methylanthrayl, phenanthrene, benzo[a]phenanthreneyl, pyrene, yl, ethyl- The compounds include methyl, styryl, peryl, chloroperyl, pentylene, pentylphenyl, tetraphenyl, hexaphenyl, pentylphenyl, rubidinyl, styryl, trinaphthyl, heptaphenyl, pentylphenyl, pinanthryl, and ovolene.

[0079] Unreplaced C3-C 60 Heteroaryl groups include aryl groups selected from one, two, or three heteroatoms of N, O, P, and S. At least two rings may be fused together or linked together by a single bond. Unsubstituted C4-C 60Examples of heteroaryl groups include pyrazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyridinyl, pyrimidinyl, triazinyl, carbazoleyl, indolyl, quinolinyl, isoquinolinyl, and dibenzothiopheneyl. Substituted C3-C 60 heteroaryl groups are unsubstituted C3-C 60 At least one hydrogen atom in the heteroaryl group is bonded to an unsubstituted C1-C atom above. 60 An alkyl group is any group substituted by one of the substituents in a substituent group.

[0080] Unreplaced C5-C 60 The aryloxy group is represented by -OA1, where A1 can be C5-C6. 60 Aryl. An example of an aryl group is a phenoxy group. Substituted C5-C 60 The aryl group is an unsubstituted C5-C. 60 At least one hydrogen atom in the aryloxy group is bonded to an unsubstituted C1-C atom above. 60 An alkyl group is any group substituted by one of the substituents in a substituent group.

[0081] Unreplaced C5-C 60 The arylthio group is represented by -SA1, where A1 can be C5-C6. 60 Aryl. Non-limiting examples of arylthio groups include phenylthio and naphthio. Substituted C5-C 60 The arylthio group is an unsubstituted C5-C. 60 At least one hydrogen atom in the arylthio group is bonded to an unsubstituted C1-C atom above. 60 An alkyl group is any group substituted by one of the substituents in a substituent group.

[0082] Unreplaced C6-C 60 A condensed polycyclic group refers to a substituent comprising at least two rings (including at least one aromatic ring and at least one non-aromatic ring fused together), or a substituent having an unsaturated group in the ring but not a conjugated structure. (C6-C) 60 The difference between condensed polycyclic aromatic hydrocarbons and aryl and heteroaryl aromatic hydrocarbons is that they contain non-aromatic components.

[0083] Non-limiting examples of vinylsilane compounds represented by Formula 1 include compounds 1 to 71 represented by the formulas listed below. However, heterocyclic compounds of Formula 1 are not limited to these compounds.

[0084] An organic light-emitting device according to an embodiment of the present invention includes: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes the vinylsilane compound.

[0085] The organic layer may include at least one of the following: hole injection layer (HIL), hole transport layer (HTL), functional layer with hole injection and hole transport capabilities (hereinafter referred to as H-functional layer), buffer layer, electron blocking layer (EBL), emitter layer (EML), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), and functional layer with electron transport and electron injection capabilities (hereinafter referred to as E-functional layer).

[0086] As used herein, the term "organic layer" refers to a single layer and / or multiple layers located between the first and second electrodes of an organic light-emitting device.

[0087] The organic layer may include an EML, which may include the vinyl silane compound. Optionally, the organic layer may include at least one of a HIL, an HTL, and an H-functional layer having hole injection and hole transport capabilities, wherein at least one of the HIL, HTL, and H-functional layer may include the vinyl silane compound.

[0088] Vinylsilanes included in the EML can be used as fluorescent dopants. For example, the vinylsilane compound can be used as a blue fluorescent dopant for emitting blue light. Alternatively, vinylsilanes included in the EML can be used as fluorescent or phosphorescent dopants for emitting red, green, or blue light.

[0089] Figure 1 This is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention. (Refer to...) Figure 1 The structure of an organic light-emitting device and the method for manufacturing an organic light-emitting device are described.

[0090] The substrate (not shown) can be any substrate commonly used in organic light-emitting devices and may include, for example, a glass substrate or a transparent plastic substrate that has good mechanical strength, thermal stability, transparency, surface planarity, ease of handling and water resistance.

[0091] The first electrode can be formed by applying a first electrode material onto a substrate through vapor deposition or sputtering. When the first electrode is an anode, the first electrode material can be selected from materials with high work function, allowing holes to be easily injected into the first electrode. The first electrode can be a reflective electrode or a transparent electrode. Examples of first electrode materials can include transparent materials with good conductivity, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). Alternatively, the first electrode material can be magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. When using these materials, the first electrode can be a reflective electrode.

[0092] The first electrode can have a single-layer structure or a multilayer structure comprising two or more layers. For example, the first electrode can have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0093] An organic layer can be deposited on the first electrode.

[0094] Organic layers may include HIL, HTL, buffer layer (not shown), EML, ETL, EIL, etc.

[0095] HIL can be formed on the first electrode by any of a variety of methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, etc.).

[0096] When using vacuum deposition to form high-intensity lithium-ion batteries (HILs), the deposition conditions can be varied depending on the material used to form the HIL and the HIL's structure and thermal properties. For example, deposition conditions can include, but are not limited to, deposition temperatures ranging from approximately 100°C to approximately 500°C, and approximately 10... -8 To about 10 -3 The vacuum pressure of Tor and approximately up to approximately The deposition rate.

[0097] When spin coating is used to form HIL, the coating conditions can be varied depending on the material used to form the HIL and the structure and thermal properties of the HIL. For example, coating conditions may include, but are not limited to, a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C, wherein residual solvent after coating can be removed at said temperature.

[0098] HILs can be formed from any material commonly used to form HILs. Non-limiting examples of materials that can be used to form HILs include N,N′-diphenyl-N,N′-di-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine (DNTPD), phthalocyanine compounds such as copper phthalocyanine, 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), TDATA, 2-TNATA, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), or polyaniline / poly(4-styrenesulfonate) (PANI / PSS).

[0099]

[0100] HIL can have approximately up to approximately The thickness, for example, has approximately up to approximately The thickness of the HIL. When the thickness of the HIL is within these ranges, the HIL can have good hole injection characteristics without significantly increasing the driving voltage.

[0101] HTLs can then be formed on HILs by any of a variety of methods (e.g., vacuum deposition, spin coating, casting, LB deposition, etc.). When using vacuum deposition or spin coating to form HTLs, although the deposition or coating conditions may vary depending on the material used to form the HTLs, the deposition or coating conditions may be similar to those used to form HILs.

[0102] HTLs can be formed from vinyl silane compounds according to embodiments of the invention or from any material commonly used to form HTLs. Non-limiting examples of such HTL materials include N,N′-bis(3-tolyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), N,N′-bis(1-naphthyl)-N,N′-diphenylbenzidine (NPB), etc.

[0103]

[0104] HTL can have approximately To about The thickness, for example, has approximately To about The thickness of the HTL. When the thickness of the HTL is within these ranges, the HTL can have good hole transport characteristics without significantly increasing the driving voltage.

[0105] The H-functional layer (i.e., the layer with hole injection and hole transport capabilities) may include at least one of the aforementioned materials for forming the HIL and at least one of the materials for forming the HTL. The H-functional layer may have approximately up to approximately The thickness, for example, has approximately up to approximately The thickness of the H-functional layer. When the thickness of the H-functional layer is within these ranges, the H-functional layer can have good hole injection and transport characteristics without significantly increasing the driving voltage.

[0106] In some embodiments, at least one of HIL, HTL, and H-functional layers may include at least one compound represented by Formula 300 below and a compound represented by Formula 350 below:

[0107] Formula 300

[0108]

[0109] Formula 350

[0110]

[0111] In Equations 300 and 350 above, Ar 11 Ar 12 Ar 21 and Ar 22 Each of them can be independently substituted or unsubstituted C5-C. 60 Aspartic acid. Ar 11 Ar 12 Ar 21 and Ar 22 Same as Ar1 and Ar2 defined above.

[0112] In Equation 300 above, each of e and f can be an integer from 0 to 5, or 0, 1, or 2. For example, e can be 1 and f can be 0, but the invention is not limited thereto.

[0113] In equations 300 and 350 above, R 51 To R 58 R 61 To R 69 R 71 and R 72 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, or a substituted or unsubstituted C1-C group. 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkyl, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Aryl, substituted or unsubstituted C5-C 60 Aryloxy group or substituted or unsubstituted C5-C 60 Arylthioyl group. For example, R 51 To R 58 R 61 To R 69 R 71 and R 72Each of these can independently be any one of the following: hydrogen atom; deuterium atom; halogen atom; hydroxyl group; cyano group; nitro group; amino group; amidine group; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; C1-C 10 Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.); C1-C 10 Alkyl group (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.); C1-C substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphate group or a salt thereof. 10 Alkyl or C1-C 10 alkoxy; phenyl; naphthyl; anthracene; fluorenyl; pyrene; or a deuterium atom, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidoyl group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl or C1-C 10 The alkoxy group may be substituted with at least one of the following: phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene, but is not limited thereto.

[0114] In equation 300 above, R 59 It can be any of the following: phenyl; naphthyl; anthracene; biphenyl; pyridyl; or a C1-C atom or salt thereof, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amido group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, or a substituted or unsubstituted C1-C atom. 20 Alkyl or substituted or unsubstituted C1-C 20 At least one substituted phenyl, naphthyl, anthraceneyl, biphenyl or pyridyl group of alkoxy groups.

[0115] According to embodiments of the present invention, the compound represented by formula 300 above can be represented by formula 300A below, but is not limited thereto:

[0116] Type 300A

[0117]

[0118] In Equation 300A above, R 51 R 60 R 61 and R 59 As described above.

[0119] For example, at least one of HIL, HTL, and H-functional layers may include at least one of compounds 301 to 320 below, but is not limited thereto:

[0120]

[0121]

[0122] In addition to known hole injection materials, known hole transport materials, and / or materials with hole injection and hole transport capabilities, at least one of the hole injection layer, hole transport layer, and H-functional layer may also include a charge generation material for improving the layer conductivity.

[0123] Charge-generating materials may include, for example, p-dopers. P-dopers may include, but are not limited to, any of quinone derivatives, metal oxides, and cyano-containing compounds. Non-limiting examples of p-dopers include: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-CTNQ), etc.; metal oxides, such as tungsten oxide, molybdenum oxide, etc.; and cyano-containing compounds, such as compound 200 below.

[0124]

[0125]

[0126] When the HIL, HTL, or H-functional layer also includes a charge-generating material, the charge-generating material may be uniformly dispersed in the layer or non-uniformly distributed in the layer, but is not limited thereto.

[0127] A buffer layer can be disposed between the EML and at least one of the hole injection layer, hole transport layer, and H-functional layer. The buffer layer compensates for the optical resonant distance according to the wavelength of light emitted from the EML, thereby increasing the luminous efficiency. The buffer layer can include any known hole injection material or any known hole transport material. Optionally, the buffer layer can include the same material as any one of the HIL, HTL, and H-functional layers formed beneath the buffer layer.

[0128] EML can then be formed on HTL, H-functional layers, or buffer layers by vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) deposition. When forming EML by vacuum deposition or spin coating, the deposition and coating conditions can vary depending on the material used to form the EML, but can be similar to those used to form HIL.

[0129] EML may include vinylsilane compounds according to embodiments of the present invention.

[0130] In addition to the vinylsilane compound, the EML may also include a body.

[0131] Non-limiting examples of the main components include Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), TCTA, 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-bis-2-naphthylanthracene (TBADN), E3 and stilbeneyl aryl compounds (DSA), dmCBP (see formula below) and compounds 501 to 509 below:

[0132]

[0133]

[0134]

[0135] Alternatively, the host may be an anthracene compound represented by the following formula 400:

[0136] Formula 400

[0137]

[0138] In Equation 400 above, Ar 111 and Ar 112 Each of them can be independently substituted or unsubstituted C5-C. 60 Aspartic acid. Ar 113 To Ar 116 Each of them can be independently substituted or unsubstituted C1-C. 10 Alkyl, or substituted or unsubstituted C5-C 60 Aryl. Each of g, h, i, and j can be an integer from 0 to 4 independently.

[0139] For example, in Equation 400 above, Ar 111 and Ar 112 Each of them can be independently: phenylene; naphthylene; phenanthrene; or pyrene; or phenylene, naphthylene, phenanthrene, fluorene, or pyrene by at least one of phenyl, naphthyl, or anthracene, but is not limited thereto.

[0140] In Equation 400 above, each of g, h, i, and j can be 0, 1, or 2 independently.

[0141] In Equation 400 above, Ar 113 To Ar 116 Each of them can independently be any one of the following: a C1-C substituted with at least one of phenyl, naphthyl, or anthracene. 10Alkyl; phenyl; naphthyl; anthracene; pyrene; phenanthrene; fluorenyl; deuterium atom, halogen atom, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyl, C1-C 60 At least one of the following substituted phenyl, naphthyl, anthraceneyl, pyreneyl, phenanthryl, or fluorenyl groups: alkoxy, phenyl, naphthyl, anthraceneyl, pyreneyl, phenanthryl, or fluorenyl groups; or But it is not limited to this.

[0142] For example, the anthracene compound represented by formula 400 above can be one of, but is not limited to, the following compounds:

[0143]

[0144]

[0145] Alternatively, the host may be an anthracene compound represented by the following formula 401:

[0146] Formula 401

[0147]

[0148] In Equation 401 above, Ar 122 To Ar 125 Ar of Equation 400 as defined above 113 same.

[0149] In Equation 401, Ar 126 and Ar 127 Each of them can be independently C1-C 10 Alkyl (e.g., methyl, ethyl, or propyl).

[0150] In Equation 401 above, each of k and l can be an integer from 0 to 4 independently. For example, each of k and l can be 0, 1, or 2 independently.

[0151] For example, the anthracene compound represented by formula 401 above can be any of the following compounds, but is not limited to:

[0152]

[0153] When the organic light-emitting device is a full-color organic light-emitting device, the EML can be patterned to include a red EML, a green EML, and a blue EML. In this case, the blue EML may include a vinylsilane compound as a blue fluorescent dopant, as described above.

[0154] At least one of the red, green, and blue fluorescent layers may include the following dopant (ppy = phenylpyridine).

[0155] Non-limiting examples of blue dopants may include the following compounds:

[0156]

[0157]

[0158] Non-limiting examples of blue dopants may include, but are not limited to, the following compounds:

[0159]

[0160]

[0161] Non-limiting examples of green dopants may include the following compounds:

[0162]

[0163] Non-limiting examples of dopants included in EMLs can include the following Pt complexes:

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Non-limiting examples of dopants included in EMLs may include the following Os complexes:

[0170]

[0171] Typically, when an EML includes a body and a dopant, the amount of dopant can range from about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the body, but is not limited thereto.

[0172] EML can have approximately up to approximately The thickness, for example, has approximately up to approximately The thickness of the EML. When the thickness of the EML is within these ranges, the EML can have good light-emitting characteristics without significantly increasing the driving voltage.

[0173] The ETL is then formed on the EML by any of various methods (e.g., by vacuum deposition, spin coating, casting, etc.). When forming the ETL by vacuum deposition or spin coating, the conditions can vary depending on the material used to form the ETL, but can be substantially the same as those used to form the HIL. The ETL can include any known electron transport material that facilitates the stable transport of electrons injected from the electron injection electrode (i.e., the cathode). Non-limiting examples of electron transport materials can include quinoline derivatives, specifically tris(8-hydroxyquinoline)aluminum (Alq3), TAZ, Balq, bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), ADN, compound 201 below, or compound 202 below.

[0174]

[0175]

[0176] ETL can have approximately up to approximately The thickness, for example, has approximately up to approximately The thickness of the ETL. When the thickness of the ETL is within these ranges, the ETL can have good electronic transport characteristics without significantly increasing the driving voltage.

[0177] In addition to known electron transport organic compounds, ETL can also include metal-containing materials.

[0178] Metal-containing materials may include Li complexes. Non-limiting examples of Li complexes may include lithium hydroxyquinoline (LiQ) or the following compound 203:

[0179] Compound 203

[0180]

[0181] EIL can be formed on ETL and can be formed from, but is not limited to, materials that facilitate electron injection from the cathode.

[0182] EIL can be formed from any known material used to form the EIL layer (e.g., LiF, NaCl, CsF, Li2O, BaO, etc.). The deposition conditions can vary depending on the material used to form the EIL, but can be essentially the same as those used to form HIL.

[0183] EIL can have approximately up to approximately The thickness, for example, has approximately up to approximately The thickness of the EIL. When the thickness of the EIL is within these ranges, the EIL can have good electron injection characteristics without significantly increasing the driving voltage.

[0184] A second electrode is disposed on the organic layer. The second electrode can be a cathode serving as an electron injection electrode. In this case, the material used to form the second electrode can include metals, alloys, or conductive compounds (materials with low work function) or mixtures thereof. Non-limiting examples of such materials include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The material can be used to form a thin film to prepare the second electrode as a transparent electrode. To fabricate a top-emitting organic light-emitting device, a transparent cathode formed from a transparent material such as ITO or IZO can be used as the second electrode.

[0185] At this point, we have already referred to Figure 1 Organic light-emitting devices have been described, but the present invention is not limited thereto.

[0186] When the EML includes phosphorescent dopants, the HBL can be formed between the HTL and the EML, or between the H-functional layer and the EML, by vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, etc., thereby preventing the diffusion of triplet excitons or holes into the ETL. When forming the HBL by vacuum deposition or spin coating, the conditions can be varied depending on the material used to form the HBL, but can be substantially the same as those used to form the HIL. In this case, the HBL can be formed from any material commonly used to form the HBL. Non-limiting examples of such HBL materials include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives. For example, the HBL can be formed from BCP as shown below.

[0187]

[0188] HBL can have a range of approximately up to approximately The thickness, for example, has a range of approximately up to approximately The thickness of the HBL. When the thickness of the HBL is within these ranges, the HBL can have good hole blocking characteristics without significantly increasing the driving voltage.

[0189] According to embodiments of the present invention, organic light-emitting devices can be included in various types of flat panel display devices, such as passive matrix organic light-emitting display devices or active matrix organic light-emitting display devices. Specifically, when the organic light-emitting device is included in an active matrix organic light-emitting display device containing thin-film transistors, the first electrode on the substrate can be used as a pixel electrode and can be electrically connected to the source electrode or drain electrode of the thin-film transistor. Furthermore, the organic light-emitting device can also be included in a flat panel display device with a double-sided screen.

[0190] The organic layer of the organic light-emitting device according to embodiments of the present invention can be formed by vapor deposition using compounds according to embodiments of the present invention, or by wet coating using compounds prepared in solution.

[0191] In the following description, organic light-emitting devices will be illustrated with reference to synthetic examples and examples. However, these examples are given for illustrative purposes only and are not intended to limit the scope of the invention.

[0192] Synthesis Example

[0193] Synthesis of compound 11

[0194]

[0195] 2.85 g (10.0 mmol) of 9,9-dimethylfluorene-2-ylaniline, 4.23 g (15.0 mmol) of 1-bromo-4-iodobenzene, 0.18 g (0.2 mmol) of Pd2(dba)3, 0.04 g (0.2 mmol) of P(tBu)3, and 1.44 g (15.0 mmol) of NaOtBu were dissolved in 30 mL of toluene and stirred at 80 °C for 4 hours. After the reaction was complete, the reaction product was cooled to room temperature, 40 mL of water was added to the product, and the product was extracted three times with 50 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 3.30 g of intermediate I-1 (yield: 75%).

[0196] 3.0 g (6.8 mmol) of intermediate I-1, 1.95 g (6.8 mmol) of triphenylvinylsilane, 0.16 g (0.17 mmol) of Pd2(dba)3, 1.14 mL (8.16 mmol) of Et3N, and 0.16 g (0.68 mmol) of tris(2-furanyl)phosphine (TFP) were dissolved in 40 mL of THF and stirred at 50 °C for 6 hours. After the reaction was complete, the product was cooled to room temperature, 40 mL of water was added, and the product was extracted three times with 50 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 3.60 g of compound 11 (yield: 82%). 1 The obtained compound was confirmed by 1H NMR and MS / FAB.

[0197] C 47 H 39 NSi: Calculated value 645.29, measured value 645.30

[0198] Synthesis of compound 36

[0199]

[0200] 7.66 g (20.0 mmol) of 9-bromo-10-(naphth-1-yl)-anthracene was dissolved in 30 mL of THF, and then 8.8 mL (22.0 mmol) of n-BuLi (2.5 M in hexane) was slowly added dropwise at -78 °C. The solution was stirred at the same temperature, -78 °C, for 1 hour, and then 3.89 g (30 mmol) of dichlorodimethylsilane was slowly added dropwise. After the reaction was complete, the reaction solution was stirred at -78 °C for 1 hour, and then further stirred at room temperature for 1 hour. The reaction solution was dried and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 5.56 g of intermediate I-2 (yield: 70%).

[0201] 5 g (12.6 mmol) of intermediate I-2 was dissolved in 40 mL of THF, and 2.48 g (18.9 mmol) of vinyl magnesium bromide was slowly added dropwise at -40 °C. The resulting solution was stirred at 0 °C for 2 hours. After the reaction was complete, 40 mL of water was added to the reaction solution, and the solution was extracted three times with 50 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to obtain 3.57 g of intermediate I-3 (yield: 73%).

[0202] 3.20 g (8.24 mmol) of intermediate I-3, 3.63 g (8.24 mmol) of 7-bromo-9,9-dimethyl-9-H-(fluoren-2-yl)-diphenylamine, 0.20 g (0.21 mmol) of Pd2(dba)3, 1.38 mL (9.89 mmol) of Et3N, and 0.19 g (0.82 mmol) of tris-2-furanylphosphine (TFP) were dissolved in 50 mL of THF, and the mixture was stirred at 50 °C for 7 hours. After the reaction was complete, the product was cooled to room temperature, 50 mL of water was added, and the product was extracted three times with 50 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 4.62 g of compound 36 (yield: 75%). 1 The obtained compound was confirmed by 1H NMR and MS / FAB. 55 H 45 NSi: Calculated value 747.33, measured value 747.31

[0203] Synthesis of compound 37

[0204]

[0205] 2.85 g (10.0 mmol) of 9,9-dimethylfluorene-2-yl-aniline, 5.28 g (15.0 mmol) of 2,7-dibromo-9,9-dimethyl-9-H-fluorene, 0.18 g (0.2 mmol) of Pd2(dba)3, 0.04 g (0.2 mmol) of P(tBu)3, and 1.44 g (15.0 mmol) of NaOtBu were dissolved in 40 mL of toluene and stirred at 80 °C for 4 hours. After the reaction was complete, the reaction product was cooled to room temperature, 40 mL of water was added to the product, and the product was extracted three times with 50 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 3.90 g of intermediate I-4 (yield: 70%).

[0206] 3.4 g (6.1 mmol) of intermediate I-4, 1.75 g (6.1 mmol) of triphenylvinylsilane, 0.14 g (0.15 mmol) of Pd2(dba)3, 1.02 mL (7.32 mmol) of Et3N, and 0.14 g (0.61 mmol) of tri-2-furanylphosphine (TFP) were dissolved in 40 mL of THF, and the mixture was stirred at 50 °C for 6 hours. After the reaction was complete, the product was cooled to room temperature, 40 mL of water was added, and the product was extracted three times with 50 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to obtain 3.63 g of intermediate I-5 (yield: 78%).

[0207] 3.05 g (4.0 mmol) of intermediate I-5, 0.115 g (0.12 mmol) of [(Ph3)P]3Ru(CO)(Cl)Htris(triphenylphosphine)carbonylruthenium(II) hydrochloride, and 0.72 mL (40.0 mmol) of D2O were dissolved in 50 mL of 1,4-dioxane and stirred at 80 °C for 12 hours. After the reaction was complete, the product was cooled to room temperature, the solvent was removed, and the product was extracted three times with 40 mL of water and 40 mL of dichloromethane. The organic layer was collected, dried with magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 2.66 g of compound 37 (yield: 87%). 1 The obtained compound was confirmed by 1H NMR and MS / FAB.

[0208] C 56 H 45 D2NSi: Calculated value is 763.36, measured value is 763.35

[0209] Synthesis of compound 64

[0210]

[0211] 2.50 g (8.50 mmol) of 2-hydroxy-7-bromo-9,9-dimethyl-9-H-fluorene, 2.43 g (8.50 mmol) of triphenylvinylsilane, 0.19 g (0.21 mmol) of Pd2(dba)3, 1.43 mL (10.2 mmol) of Et3N, and 0.20 g (0.85 mmol) of tri-2-furanylphosphine (TFP) were dissolved in 60 mL of THF and stirred at 50 °C for 6 hours. After the reaction was complete, the product was cooled to room temperature, 40 mL of water was added, and the product was extracted three times with 60 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 3.36 g of intermediate I-6 (yield: 80%).

[0212] 3.0 g (6.0 mmol) of intermediate I-6 was dissolved in 30 mL of CH₂Cl₂ and 2.52 mL (18.0 mmol) of NEt₃, and 2.54 g (9.0 mmol) of Tf₂O was slowly added dropwise at 0 °C. The resulting solution was stirred at room temperature for 2 hours. After the reaction was complete, the reaction product was cooled to room temperature, 40 mL of water was added to the product, and the product was extracted three times with 50 mL of dichloromethane. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to obtain 3.31 g of intermediate I-7 (yield: 88%).

[0213] 3.13 g (5.0 mmol) of intermediate I-7, 1.04 g (5.0 mmol) of diphenyl-(4-vinyl-phenyl)-amine, 0.056 g (0.25 mmol) of Pd(OAc)2, 0.76 g (0.25 mmol) of P(p-toly)3, and 1.019 g (10.0 mmol) of Et3N were dissolved in 40 mL of dimethylacetamide (DMAc) and stirred at 100 °C for 4 hours. After the reaction was complete, the product was cooled to room temperature, 40 mL of water was added, and the product was extracted three times with 50 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 2.66 g of compound 63 (yield: 71%). 1 The obtained compound was confirmed by 1H NMR and MS / FAB.

[0214] C 55 H 45 NSi: Calculated value 747.33, measured value 747.32

[0215] Synthesis of compound 68

[0216]

[0217] 0.79 g (7.06 mmol) of dimethyldivinylsilane, 5.28 g (14.1 mmol) of (6-bromo-naphth-2-yl)-diphenylamine, 0.16 g (0.18 mmol) of Pd2(dba)3, 1.19 mL (8.47 mmol) of Et3N, and 0.17 g (0.71 mmol) of tris-2-furanylphosphine (TFP) were dissolved in 50 mL of THF and stirred at 50 °C for 7 hours. After the reaction was complete, the product was cooled to room temperature, 50 mL of water was added, and the product was extracted three times with 60 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 3.36 g of compound 68 (yield: 68%). 1 The obtained compound was confirmed by 1H NMR and MS / FAB.

[0218] C 50 H 42 N2Si: Calculated value 698.31, measured value 698.32

[0219] Synthesis of compound 70

[0220]

[0221] 2.02 g (9.56 mmol) of trichlorophenylsilane was dissolved in 50 mL of THF, and 3.76 g (28.7 mmol) of vinyl magnesium bromide was slowly added dropwise at -40 °C. The resulting solution was stirred at 0 °C for 3 hours. After the reaction was complete, 30 mL of water was added to the reaction product, and the product was extracted three times with 30 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 1.21 g of intermediate I-8 (yield: 68%).

[0222] 1.0 g (5.38 mmol) of intermediate I-8, 5.23 g (16.1 mmol) of (4-bromo-phenyl)-diphenylamine, 0.12 g (0.13 mmol) of Pd2(dba)3, 0.91 mL (6.46 mmol) of Et3N, and 0.31 g (0.54 mmol) of tris-2-furanylphosphine (TFP) were dissolved in 60 mL of THF and stirred at 50 °C for 9 hours. After the reaction was complete, the product was cooled to room temperature, 60 mL of water was added to the product, and the product was extracted three times with 60 mL of diethyl ether. The organic layer was collected, dried over magnesium sulfate, and the solvent was evaporated. The residue was separated and purified by silica gel column chromatography to give 3.20 g of compound 70 (yield: 65%). 1 The obtained compound was confirmed by 1H NMR and MS / FAB.

[0223] C 66 H 53 N3Si: Calculated value 915.40, measured value 915.42

[0224] The MS / FAB and synthesis of the compounds reported in the above synthesis examples will now be described. 1 H NMR data and the equivalent of the corresponding intermediate prepared in the synthesis example above.

[0225] Compound 1: C 38 H 31 NSi FAB / MS

[0226] The calculated value is 529.22, and the measured value is 529.24.

[0227] 1 H NMR(CDCl3,400MHz)7.54-7.52(m,6H),7.35-7.32(m,6H),7.26-7.21(m,6H) ,7.18-7.11(m,5H),7.07-7.04(m,2H),6.98-6.93(t,2H),6.83-6.81(m,4H)

[0228] Compound 5: C 38 H 29 F2NSi FAB / MS

[0229] The calculated value is 565.20, and the measured value is 565.23.

[0230] 1H NMR(CDCl3,400MHz)7.54-7.52(m,6H),7.35-7.32(m,6H),7.26-7.21(m,6H) ,7.18-7.11(m,5H),7.07-7.04(m,2H),6.98-6.93(t,2H),6.83-6.81(m,4H)

[0231] Compound 8: C 39 H 30 N2Si FAB / MS

[0232] The calculated value is 554.22, and the measured value is 554.20.

[0233] 1 H NMR(CDCl3,400MHz)7.55-7.53(m,6H),7.39-7.32(m,6H),7.28-7.22(m,6H),7.08 -7.01(m,4H),6.95-6.92(m,2H),6.88-6.85(m,2H),6.67(t,2H),6.56-6.52(m,2H)

[0234] Compound 11: C 47 H 39 NSi FAB / MS

[0235] The calculated value is 645.29, and the measured value is 645.30.

[0236] 1 H NMR(CDCl3,400MHz)7.77(d,1H),7.57-7.54(m,7H),7.37-7.31(m,7H),7.30-7.21(m,6H),7.13 -7.01(m,5H),6.97-6.95(m,2H),6.87-6.81(m,2H),6.75(d,1H),6.62-6.59(m,2H),1.62(s,6H)

[0237] Compound 12: C 50 H 38 N2Si FAB / MS

[0238] The calculated value is 694.28, and the measured value is 694.29.

[0239] 1H NMR(CDCl3,400MHz)8.21(d,1H),7.56-7.48(m,10H),7.41(d,1H),7.39-7.31(m,8H),7 .30-7.21(m,9H),7.12-7.08(m,3H),6.99-6.96(m,3H),6.76(t,1H),6.63-6.60(m,2H)

[0240] Compound 14: C 47 H 46 N2Si FAB / MS

[0241] The calculated value is 666.34, and the measured value is 666.32.

[0242] 1 H NMR(CDCl3,400MHz)8.23(d,1H),7.86-7.81(m,2H),7.62(d,1H),7.55-7.50(m,4H),7.45-7.42(m,2H),7.40-7.28(m,6H),7.17- 7.12(m,2H),7.02(d,1H),6.98-6.93(m,3H),6.84(d,1H),6.72(d,1H),6.56-6.51(m,1H),1.61(s,6H),0.93(t,9H),0.57(q,6H)

[0243] Compound 15: C 52 H 41 NSi FAB / MS

[0244] The calculated value is 707.30, and the measured value is 707.33.

[0245] 1 H NMR(CDCl3,400MHz)7.85-7.80(m,3H),7.73-7.69(m,2H),7.67(d,1H),7.66(d,1H),7.61-7.58(m,2H),7.53(d,1H),7.50-7.43(m,3H) ,7.41-7.27(m,10H),7.15-7.10(m,4H),7.03(t,1H),6.98(d,1H),6.81-6.78(m,2H),6.76-6.65(m,2H),6.50-6.48(m,2H),0.40(s,6H)

[0246] Compound 17: C 48 H 37 NSi FAB / MS

[0247] The calculated value is 655.27, and the measured value is 655.26.

[0248] 1 H NMR(CDCl3,400MHz)8.16(d,1H),7.86(d,1H),7.60-7.56(m,6H),7.52-7.45(m,8H),7.37-7.32(m,6H) ,7.29-7.20(m,6H),7.12-7.07(m,2H),7.00-6.94(m,3H),6.88(d,1H),6.81(t,1H),6.74-6.71(m,2H)

[0249] Compound 19: C 43 H 34 N2Si FAB / MS

[0250] The calculated value is 606.25, and the measured value is 606.27.

[0251] 1 H NMR(CDCl3,400MHz)8.22(d,1H),7.63-7.61(m,2H),7.58-7.53(m,6H),7.48-7.42(m,5H),7.39-7.35 (m,6H),7.32-7.23(m,7H),7.05-7.01(m,2H),6.93-6.90(m,1H),6.84-6.81(m,2H),6.76-6.72(m,2H)

[0252] Compound 22: C 44 H 33 NSi FAB / MS

[0253] The calculated value is 603.24, and the measured value is 603.23.

[0254] 1 H NMR(CDCl3,400MHz)8.11(d,2H),7.60-7.53(m,10H),7.48-7.46(m,2H),7.44-7. 41(m,2H),7.37-7.35(m,10H),7.31-7.26(m,5H),7.21-7.17(m,1H),7.07(d,1H)

[0255] Compound 25: C 56 H 42 FNSi FAB / MS

[0256] The calculated value is 775.31, and the measured value is 775.33.

[0257] 1 H NMR(CDCl3,400MHz)7.73-7.69(m,2H),7.66-7.61(m,3H),7.56-7.47(m,12H),7.45-7.40(m,8H),7.36-7 .31(m,6H),7.29-7.24(m,2H),7.20-7.05(m,4H),6.96-6.90(m,2H),6.83-6.78(m,1H),6.63-6.59(m,2H)

[0258] Compound 26: C 44 H 30 D5NSi FAB / MS

[0259] The calculated value is 610.28, and the measured value is 610.30.

[0260] 1 H NMR(CDCl3,400MHz)7,56-7.52(m,6H),7.51-7.47(m,2H),7.46-7.44(m,4H),7.36-7.33(m,6H) ,7.27-7.20(m,4H),7.13-7.08(m,2H),6.95-6.89(m,3H),6.77-6.72(m,1H),6.61-6.58(m,2H)

[0261] Compound 30: C 49 H 38 N2Si FAB / MS

[0262] The calculated value is 682.28, and the measured value is 682.31.

[0263] 1 H NMR(CDCl3,400MHz)8.87(d,1H),8.68-8.64(m,1H),7.86-7.82(m,1H),7.56-7.48(m,8H),7.46-7.40(m,5H),7.38-7.33(m,6H),7.28 -7.24(m,3H),7.20-7.15(m,3H),7.09-7.04(m,3H),6.89(d,1H),6.72(t,1H),6.66-6.62(m,2H),6.46-6.43(m,2H),6.40-6.37(m,1H)

[0264] Compound 32: C 53 H 43 NSi FAB / MS

[0265] The calculated value is 721.32, and the measured value is 721.30.

[0266] 1 H NMR(CDCl3,400MHz)7.74(d,1H),7.67-7.60(m,4H),7.56-7.48(m,7H),7.46-7.38(m,5H),7.37-7.31(m,5H),7.28 -7.22(m,4H),7.09-7.04(m,2H),6.92-6.85(m,4H),6.79(t,1H),6.73-6.69(m,2H),6.56-6.52(m,2H),1.72(s,6H)

[0267] Compound 36: C 55 H 45 NSi FAB / MS

[0268] The calculated value is 747.33, and the measured value is 747.31.

[0269] 1 H NMR(CDCl3,400MHz)8.08(d,2H),7.83(d,1H),7.78(d,2H),7.74-7.69(m,3H),7.65-7.60(m,2H),7.54-7.51(m,2H),7.48-7.42(m, 2H),7.37-7.33(m,2H),7.18-7.10(m,6H),7.02(t,1H),6.88-6.79(m,5H),6.70(d,1H),6.58-6.53(m,4H),1.65(s,6H),0.63(s,6H)

[0270] Compound 37: C 56 H 45 D2NSi FAB / MS

[0271] The calculated value is 763.36, and the measured value is 763.35.

[0272] 1 H NMR(CDCl3,400MHz)7.79-7.72(m,2H),7.67-7.65(m,1H),7.60(t,1H),7.56-7.52(m,7H),7.37-7.31(m,8H),7.28-7.26( m,3H),7.13-7.05(m,4H),7.00-6.96(m,2H),6.92-6.87(m,1H),6.74(d,1H),6.69(d,1H),6.52-6.47(m,2H),1.60(s,12H)

[0273] Compound 39: C 59 H 46 FNSi FAB / MS

[0274] The calculated value is 815.34, and the measured value is 815.33.

[0275] 1 H NMR(CDCl3,400MHz)7.73-7.69(m,2H),7.66-7.59(m,6H),7.56-7.50(m,11H),7.44-7.38(m,2H),7.36-7.32(m,6H),7.28 -7.25(m,3H),7.19(d,1H),7.12(d,1H),7.08-7.03(m,2H),6.94-6.87(m,3H),6.81(d,1H),6.76-6.73(m,2H),1.69(s,6H)

[0276] Compound 44: C 48 H 37 NSi FAB / MS

[0277] The calculated value is 655.27, and the measured value is 655.25.

[0278] 1 H NMR(CDCl3,400MHz)7.67-7.61(m,3H),7.58-7.52(m,8H),7.51-7.45(m,2H),7.39-7.32(m,7H),7. 29-7.25(m,3H),7.18(d,1H),7.06-7.01(m,5H),6.92-6.86(m,2H),6.79(t,2H),6.72-6.68(m,4H)

[0279] Compound 47: C 54 H 39 NSi FAB / MS

[0280] The calculated value is 729.29, and the measured value is 729.31.

[0281] 1H NMR(CDCl3,400MHz)8.52(d,1H),8.16(d,1H),8.06-8.02(m,2H),7.99(d,1H),7.90(d,1H),7.75-7.73(m,2H),7.59-7.48 (m,9H),7.36-7.32(m,6H),7.27-7.22(m,3H),7.08-7.03(m,5H),6.97-6.93(m,2H),6.82-6.78(m,2H),6.69-6.66(m,4H)

[0282] Compound 52: C 55 H 46 N2Si FAB / MS

[0283] The calculated value is 762.34, and the measured value is 762.33.

[0284] 1 H NMR(CDCl3,400MHz)8.47-8.45(m,1H),7.78-7.76(m,2H),7.62-7.54(m,9H),7.38-7.3 1(m,9H),7.29-7.24(m,4H),7.16-7.08(m,5H),7.02(d,2H),6.97(d,2H),1.62(s,12H)

[0285] Compound 54: C 44 H 33 NOSi FAB / MS

[0286] The calculated value is 619.23, and the measured value is 619.25.

[0287] 1 H NMR(CDCl3,400MHz)7.99(d,1H),7.93(d,1H),7.58-7.57(m,1H),7.55-7.49(m,7H),7.36-7.31(m, 6H),7.30-7.24(m,5H),7.09-7.04(m,4H),6.99(d,1H),6.88(d,1H),6.75(t,2H),6.69-6.65(m,4H)

[0288] Compound 57: C 50 H 38 N2Si FAB / MS

[0289] The calculated value is 694.28, and the measured value is 694.27.

[0290] 1H NMR(CDCl3,400MHz)8.25(d,1H),7.89-7.87(m,1H),7.56-7.50(m,7H),7.42-7.31(m,9H),7.28-7.23 (m,5H),7.16-7.11(m,2H),7.09-7.03(m,5H),6.95-6.91(m,2H),6.86-6.82(m,2H),6.75-6.71(m,4H)

[0291] Compound 58: C 49 H 37 N3Si FAB / MS

[0292] The calculated value is 695.28, and the measured value is 695.29.

[0293] 1 H NMR(CDCl3,400MHz)8.62-8.60(m,1H),8.50(d,1H),7.92(d,1H),7.79-7.76(m,1H),7.70(d,1H),7.59-7.48(m, 8H),7.43-7.33(m,8H),7.29-7.20(m,5H),7.10-7.04(m,5H),6.95(d,1H),6.90-6.86(m,2H),6.79-6.74(m,4H)

[0294] Compound 60: C 44 H 33 NSSi FAB / MS

[0295] The calculated value is 635.21, and the measured value is 635.19.

[0296] 1 H NMR(CDCl3,400MHz)8.17-8.15(m,1H),7.90(d,1H),7.77(d,1H),7.72(d,1H),7.56-7.52(m,6H),7.45(d,1H),7.36-7.32 (m,6H),7.28-7.24(m,3H),7.11-7.04(m,4H),6.98(d,1H),6.85(d,1H),6.77(d,1H),6.67-6.63(m,2H),6.55-6.51(m,4H)

[0297] Compound 62: C 50 H 39 NSi FAB / MS

[0298] The calculated value is 681.29, and the measured value is 681.32.

[0299] 1 H NMR(CDCl3,400MHz)8.12(d,1H),7.98(d,1H),7.82-7.77(m,3H),7.66(d,1H),7.56-7.52(m,6H),7.48-7.44(m,2H),7 .36-7.32(m,6H),7.29-7.24(m,4H),7.19(d,2H),7.08-7.03(m,4H),6.93(d,1H),6.83-6.76(m,4H),6.69-6.65(m,4H)

[0300] Compound 64: C 55 H 45 NSi FAB / MS

[0301] The calculated value is 747.33, and the measured value is 747.36.

[0302] 1 H NMR(CDCl3,400MHz)7.70(d,1H),7.68-7.66(m,1H),7.63(d,1H),7.56-7.52(m,6H),7.50-7.49(m,1H),7.48-7.44(m,2H),7.43-7. 39(m,2H),7.36-7.31(m,6H),7.29-7.24(m,4H),7.19(d,1H),7.08-7.03(m,5H),6.96-6.92(m,5H),6.85-6.80(m,4H),1.62(s,6H)

[0303] Compound 65: C 58 H 47 NSi2FAB / MS

[0304] The calculated value is 813.32, and the measured value is 813.30.

[0305] 1 H NMR(CDCl3,400MHz)7.56-7.54(m,6H),7.53-7.51(m,6H),7.36-7.35(m,3H),7.34-7.33(m,6H),7.32-7. 31(m,4H),7.28-7.22(m,11H),7.08-7.01(m,4H),6.96-6.93(m,4H),6.81-6.77(m,1H),6.70-6.66(m,2H)

[0306] Compound 68: C 50 H42 N2Si FAB / MS

[0307] The calculated value is 698.31, and the measured value is 698.32.

[0308] 1 H NMR(CDCl3,400MHz)7.73(d,2H),7.70-7.65(m,3H),7.64-7.61(m,5H),7.09-7.02(m,10H ),6.98-6.97(m,2H),6.86-6.80(m,3H),6.77-6.73(m,4H),6.67-6.63(m,7H),0.25(s,6H)

[0309] Compound 70: C 66 H 53 N3Si FAB / MS

[0310] The calculated value is 915.40, and the measured value is 915.42.

[0311] 1 H NMR(CDCl3,400MHz)7.616-7.57(m,3H),7.54-7.52(m,2H),7.44-7.38(m,8H),7.33-7.28(m,1H),7.08-7. 04(m,10H),7.03-7.02(m,4H),7.00-6.97(m,1H),6.88-6.83(m,6H),6.79-6.74(m,6H),6.65-6.61(m,12H)

[0312] Compound 71: C 80 H 64 N4Si FAB / MS

[0313] The calculated value is 1108.49, and the measured value is 1108.50.

[0314] 1 H NMR(CDCl3,400MHz)7.51-7.47(m,8H),7.16-7.14(m,2H),7.12-7.10(m,2H),7 .09-7.03(m,16H),6.93-6.90(m,10H),6.87-6.79(m,10H),6.72-6.67(m,16H)

[0315] Example 1

[0316] As the anode, 15Ω / cm 2 The ITO glass substrate was cut to a size of 50mm × 50mm × 0.7mm, and ultrasonically cleaned in isopropanol and pure water for 5 minutes each, followed by UV and ozone cleaning for 30 minutes. The ITO glass substrate was then mounted on a vacuum depositor.

[0317] 2-TNATA was deposited on an ITO glass substrate to form a thickness of [missing information]. HIL, and then vacuum deposit compound 11 on HIL to form a thickness of HTL. 9,10-bis(naphthyl-2-yl)anthracene (ADN) as the blue fluorescent host and 4,4'-bis[4-(diphenylamino)styryl]biphenyl (DPAVBi) as the blue fluorescent dopant were co-deposited on the HTL at a weight ratio of 98:2 to form a thickness of [missing information]. The EML is then deposited. Alq3 is then deposited on the EML to form a layer with a thickness of [thickness value missing]. The ETL is used to deposit LiF (alkali metal halide) to form a thickness of [thickness value missing]. EIL was deposited, and Al was vacuum deposited on the EIL to form a thickness of [missing information]. The second electrode (cathode) (LiF / Al electrode) is used to complete the manufacturing of the OLED.

[0318]

[0319] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 6.19V, 2,245cd / m 2 High brightness, luminous efficacy of 4.49 cd / A, and at 100 mA / cm² 2 The next half-life is 253 hours.

[0320] Example 2

[0321] The OLED was prepared in the same manner as in Example 1, except that compound 12 was used instead of compound 11 to form HTL.

[0322] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 6.33V, 2,107 cd / m 2 High brightness, luminous efficacy of 4.21 cd / A, and at 100 mA / cm² 2 The next half-life is 210 hours.

[0323] Example 3

[0324] The OLED was prepared in the same manner as in Example 1, except that compound 17 was used instead of compound 11 to form HTL.

[0325] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 6.15V, 2,263cd / m 2 High brightness, luminous efficacy of 4.53 cd / A, and at 100 mA / cm² 2 The next 240 hours of half life.

[0326] Example 4

[0327] The OLED was prepared in the same manner as in Example 1, except that compound 68 was used instead of compound 11 to form the HTL.

[0328] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 6.26V, 2,197cd / m 2 High brightness, luminous efficacy of 4.39 cd / A, and at 100 mA / cm² 2 The next 166 hours of half life.

[0329] Example 5

[0330] The OLED was prepared in the same manner as in Example 1, except that compound 70 was used instead of compound 11 to form the HTL.

[0331] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 6.56V, 2,086cd / m 2 High brightness, luminous efficacy of 4.17 cd / A, and at 100 mA / cm² 2 Half-life at 153.

[0332] Example 6

[0333] As the anode, 15Ω / cm 2 The ITO glass substrate was cut to a size of 50mm × 50mm × 0.7mm, and ultrasonically cleaned in isopropanol and pure water for 5 minutes each, followed by UV and ozone cleaning for 30 minutes. The ITO glass substrate was then mounted on a vacuum depositor.

[0334] 2-TNATA was deposited on an ITO glass substrate to form a thickness of [missing information]. HIL, and vacuum deposited 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) on HIL to form a thickness of HTL. 9,10-di-naphthyl-2-yl-anthracene (AND) as the blue fluorescent host and compound 11 as the blue fluorescent dopant were co-deposited on the HTL at a weight ratio of 98:2 to form a thickness of [missing information]. The EML is then deposited. Alq3 is then deposited on the EML to form a layer with a thickness of [thickness value missing]. The ETL is used to deposit LiF (alkali metal halide) to form a thickness of [thickness value missing]. EIL was deposited, and Al was vacuum deposited on the EIL to form a thickness of [missing information]. The second electrode (cathode) (LiF / Al electrode) is used to complete the manufacturing of the OLED.

[0335] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 7.06V, 2,524cd / m 2 High brightness, luminous efficacy of 5.04 cd / A, and at 100 mA / cm² 2 The next 162 hours of half life.

[0336] Example 7

[0337] The OLED was prepared in the same manner as in Example 6, except that compound 37 was used instead of compound 11 to form the EML.

[0338] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 7.13V, 3,312 cd / m 2 High brightness, luminous efficacy of 6.62 cd / A, and at 100 mA / cm² 2 The next 177 hours of half life.

[0339] Example 8

[0340] The OLED was prepared in the same manner as in Example 6, except that compound 39 was used instead of compound 11 to form the EML.

[0341] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 7.29V, 3,382cd / m 2 High brightness, luminous efficacy of 6.76 cd / A, and at 100 mA / cm² 2 The next 173 hours of half life.

[0342] Example 9

[0343] The OLED was prepared in the same manner as in Example 6, except that compound 47 was used instead of compound 11 to form the EML.

[0344] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 7.28V, 3,526cd / m 2 High brightness, luminous efficacy of 7.04 cd / A, and at 100 mA / cm² 2 The next 181 hours of half life.

[0345] Example 10

[0346] The OLED was prepared in the same manner as in Example 6, except that compound 64 was used instead of compound 11 to form the EML.

[0347] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 7.25V, 3,464cd / m 2 High brightness, luminous efficacy of 6.93 cd / A, and at 100 mA / cm² 2 The next 205 hours of half life.

[0348] Example 11

[0349] The OLEDs were prepared in the same manner as in Example 1 or Example 6, except that compound 17 was used instead of NPB to form the HTL and compound 47 was used instead of DPAVBi to form the EML.

[0350] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 6.11V, 3,608cd / m 2 High brightness, luminous efficacy of 7.22 cd / A, and at 100 mA / cm² 2 The half-life is 356 hours.

[0351] Example 12

[0352] The OLEDs were prepared in the same manner as in Example 1 or Example 6, except that compound 17 was used instead of NPB to form the HTL and compound 64 was used instead of DPAVBi to form the EML.

[0353] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 6.13V, 3,634cd / m 2High brightness, luminous efficacy of 7.27 cd / A, and at 100 mA / cm² 2 The half-life is 341 hours.

[0354] Comparative Example 1

[0355] The OLED was prepared in the same manner as in Example 1, except that 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was used to form the HTL instead of compound 11.

[0356] The OLED has a power of 50mA / cm 2 Current density, drive voltage of 7.35V, 2,065cd / m 2 High brightness, luminous efficacy of 4.13 cd / A, and at 100 mA / cm² 2 The next 145 hours of half life.

[0357] When compound 1 according to embodiments of the present invention is used to form the HTL, similar or improved IVL characteristics can be achieved compared to when NPB is used to form the HTL. Specifically, a significantly extended lifetime can be obtained using the HTL of compound 1. The IVL and lifetime characteristics of the OLEDs of Examples 1 to 5 and Comparative Example 1 are shown in Table 1 below.

[0358] Table 1

[0359]

[0360] Furthermore, it can be confirmed that when the compound represented by Formula 1 is used as a dopant in the EML, the resulting OLED exhibits improved efficiency and extended lifetime compared to OLEDs using DPAVBi as the blue fluorescent dopant. Moreover, in Examples 11 and 12, where the compound of Formula 1 is used to form the HTL and EML, the resulting OLEDs can exhibit improved driving voltage and extended lifetime. The IVL and lifetime characteristics of the OLEDs of Examples 6 to 12 and Comparative Example 1 are shown in Tables 2 and 3 below.

[0361] Table 2

[0362]

[0363] Table 3

[0364]

[0365]

[0366] As described above, the novel vinylsilane compounds according to one or more embodiments of the present invention possess excellent emission characteristics and charge transport capabilities, and therefore can be used as electron injection / transport materials for fluorescent and phosphorescent devices of most colors (e.g., red, green, blue, and white fluorescent and phosphorescent devices), and can be used as luminescent materials for green, blue, or white fluorescent devices. Therefore, organic light-emitting devices with high efficiency, low driving voltage, high brightness, and long lifetime can be manufactured using the vinylsilane compounds.

[0367] Although the invention has been shown and described with reference to specific exemplary embodiments, those skilled in the art will understand that various changes may be made to the described embodiments without departing from the spirit and scope of the invention as defined by the claims.

Claims

1. An organic light-emitting device, the organic light-emitting device comprising: First electrode; Second electrode; as well as An organic layer is located between the first electrode and the second electrode. The organic layer includes: an emission layer; and a hole injection layer, a hole transport layer, or a functional layer having both hole injection and hole transport capabilities. The emission layer comprises a vinylsilane compound represented by Formula 1. Wherein, the vinylsilane compound in the emission layer is a fluorescent dopant, and The hole transport layer comprises a vinyl silane compound represented by Formula 1: Formula 1 ， in: Each A is independently represented by equation 2a: In equation 2a: Z1 can be a hydrogen atom, a deuterium atom, a halogen atom, or a cyano group independently; p is an integer from 1 to 12; and It is a combination position. Each of R1 and R2 is independently either a hydrogen atom or a deuterium atom. B is a linking group obtained by connecting two groups represented by formulas 4a, 4c, 4h and 4i: Among them, in equations 4a, 4c, 4h and 4i, Q1 is derived from -C(R) 30 (R) 31 )- indicates the linker base; Each of Y1, Y2, and Y3 is independently determined by -C(R 21 = represents the linking base; Z1.R 21 R 30 and R 31 Each of these atoms is independently a hydrogen atom, a deuterium atom, or a C1-C atom. 20 Alkyl, halogen atom, or cyano group; p is an integer from 1 to 12; and Indicator bit, Each of Ar1 and Ar2 is independently a group represented by any one of formulas 3b and 3c: Among them, in equations 3b and 3c, Z1 can be independently a hydrogen atom, a deuterium atom, or a C1-C atom. 20 Alkyl, phenyl, halogen atom or cyano group; p is an integer from 1 to 12; and Indicator bit, n is 3. m is 1.

2. The organic light-emitting device according to claim 1, wherein, The compound represented by Equation 1 is a compound represented by one of the following formulas: 。 3. The organic light-emitting device according to claim 1, in, The emitter layer also includes anthracene compounds.

4. The organic light-emitting device according to claim 1, in, The emission layer also includes arylamine compounds.

5. The organic light-emitting device according to claim 1, in, The emission layer also includes styrene-based compounds.

6. The organic light-emitting device according to claim 1, in, The red, green, or white layer of the emitting layer includes a phosphorescent compound.

7. The organic light-emitting device according to claim 6, wherein, Hole injection layer, hole transport layer, or functional layer with both hole injection and hole transport capabilities include charge generation materials.

8. The organic light-emitting device according to claim 7, wherein, The charge-generating material includes a p-doped agent. The p-dopant includes quinone derivatives, metal oxides, or cyano-containing compounds.

9. The organic light-emitting device according to claim 1, wherein, The organic layer also includes an electron transport layer. The electron transport layer comprises an electron transport organic compound and a metal complex.

10. The organic light-emitting device according to claim 1, wherein, The organic layer is formed using a wet process with the vinyl silane compound according to claim 1.

11. A flat panel display device, the flat panel display device comprising the organic light-emitting device according to claim 1, wherein, The first electrode of the organic light-emitting device is electrically connected to the source electrode or drain electrode of the thin-film transistor.

Images