Novel compound and organic light-emitting device comprising same

Abstract

The present invention provides a novel compound and an organic-light emitting device comprising same, wherein the novel compound can be applied to at least one of an electron injection layer (EIL), an electron transport layer (ETL), a layer that simultaneously injects and transports electrons, a hole blocking layer (HBL), and an N-type charge generation layer (N-CGL).

Description

Novel compound and organic light-emitting device containing the same

[0001] The present invention relates to a novel compound and an organic light-emitting device containing the same.

[0002] The technology of organic light-emitting devices (or organic light-emitting diodes), which are one of the widely used flat panel display devices today, is rapidly advancing.

[0003] Generally, an organic light-emitting diode (OLED) comprises an organic thin film layer including a light-emitting layer formed between an anode (hole injection electrode) and a cathode (electron injection electrode), and emits light based on the principle that holes injected from the anode and electrons injected from the cathode pair up in the light-emitting layer and then annihilate each other.

[0004] More specifically, the organic light-emitting device is configured to include an organic thin film layer formed between an anode and a cathode, and the organic thin film layer may be configured to include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer sequentially stacked on the anode, wherein holes injected from the anode and electrons injected from the cathode combine in the light-emitting layer to form excitons, which become an unstable energy state (excited state) and then return to a stable ground state to emit light.

[0005] In the development of organic light-emitting diodes, high efficiency and long lifespan, as well as color purity, color stability under changes in current and voltage, and ease of fabrication are important; therefore, research and development are currently underway according to each method. As the demand for high-performance devices increases, there is a need to develop new materials capable of exhibiting superior performance.

[0006] The present invention aims to provide a novel compound that can be applied to one or more organic layers of an electron transport region, such as an electron injection layer (EIL), an electron transport layer (ETL), a layer that simultaneously injects and transports electrons, a hole blocking layer (HBL), and an N-type charge generation layer (N-CGL), and an organic light-emitting diode comprising the same.

[0007] Specifically, the present invention aims to provide a novel compound capable of realizing low voltage, high efficiency, and long lifespan of a device when applied to an organic layer of the electron transport region mentioned above, and an organic light-emitting device containing the same.

[0008] In particular, the present invention aims to provide a novel compound and an organic light-emitting diode containing the same, which, when applied to an N-type charge generation layer, can reduce the energy level difference with an adjacent layer (which may be an electron transport layer or a hole blocking layer), thereby maximizing the tunneling effect that allows electrons to move and improving electron injection capability, which is effective in improving driving voltage and lifespan.

[0009] The above tasks and additional tasks are described in detail below.

[0010] In order to solve the problem described above, the present invention, in one embodiment,

[0011] A compound represented by the following chemical formula 1 is provided.

[0012] <Chemical Formula 1>

[0013]

[0014] In the above chemical formula 1,

[0015] Ar1 to Ar3 are each independently substituted or unsubstituted C6 to C50 aryl groups, or substituted or unsubstituted C2 to C50 heteroaryl groups, wherein adjacent ones may or may not combine to form a substituted or unsubstituted ring.

[0016] L1 is each independently a directly bonded, substituted, or unsubstituted C6–C50 arylene group, or a substituted or unsubstituted C2–C50 heteroarylene group, and

[0017] R1 is each independently hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted C1–C30 alkyl group, substituted or unsubstituted C1–C30 alkenyl group, substituted or unsubstituted C1–C30 alkynyl group, substituted or unsubstituted C3–C30 cycloalkyl group, substituted or unsubstituted C1–C30 heterocycloalkyl group, substituted or unsubstituted C1–C30 alkoxy group, substituted or unsubstituted C1–C30 sulfide group, substituted or unsubstituted C6–C30 aryl group, substituted or unsubstituted C2–C30 heteroaryl group, substituted or unsubstituted C6–C30 aryloxy group, substituted or unsubstituted C2–C30 heteroaryloxy group, substituted or unsubstituted C1–C30 thio group, substituted or unsubstituted Selected from the group consisting of C1-C30 amine groups, substituted or unsubstituted C1-C30 silyl groups, and substituted or unsubstituted C1-C30 phosphine oxide groups, wherein adjacent groups may or may not combine to form a substituted or unsubstituted ring.

[0018] a is an integer from 0 to 7, and

[0019] b is an integer from 0 to 3.

[0020] In addition, in one embodiment of the present invention,

[0021] An organic light-emitting device containing the above novel compound is provided.

[0022] In addition, in one embodiment of the present invention,

[0023] The present invention provides an organic light-emitting device in which the above novel compound is applied to one or more layers among an electron injection layer (EIL), an electron transport layer (ETL), a layer that simultaneously injects and transports electrons, a hole blocking layer (HBL), and an N-type charge generation layer (N-CGL).

[0024] A novel compound according to one embodiment of the present invention is a compound comprising 1,10-phenanthroline and a substituent including silicon (Si), and can be applied to one of an electron injection layer, an electron transport layer, a layer that simultaneously injects and transports electrons, a hole blocking layer, and an N-type charge generation layer. In particular, when applied to an N-type charge generation layer, it can reduce the energy level difference with the adjacent layer (which may be an electron transport layer or a hole blocking layer), thereby maximizing the tunneling effect that allows electrons to move and improving electron injection capability, which is effective for improving the driving voltage and lifespan of the device.

[0025] In addition, the novel compound according to one embodiment of the present invention has excellent electron transport capability, so when applied to the organic layer of the electron transport region mentioned above, it is possible to realize an organic light-emitting diode with low voltage, high efficiency, and long lifespan.

[0026] The above effects and additional effects are described in detail below.

[0027] Before describing the present invention in detail below, it should be understood that the terms used in this specification are intended only to describe specific embodiments and are not intended to limit the scope of the invention, which is defined solely by the appended claims. Unless otherwise stated, all technical and scientific terms used in this specification have the same meaning as generally understood by those skilled in the art.

[0028] In describing the present invention, if it is determined that a detailed description of related known components or functions may obscure the essence of the invention, such detailed description is omitted.

[0029] In this specification, when a part is described as 'comprising' a certain component, it means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0030] In this specification, when a component is described as being 'on' another component, this includes not only cases where a component is in contact with another component, but also cases where another component exists between the two components.

[0031] In describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc., may be used. These terms are intended merely to distinguish the components from other components, and the nature, order, or sequence of the components is not limited by these terms. Where it is stated that a component is "connected," "combined," or "joined" to another component, it should be understood that the component may be directly connected or joined to the other component, but that another component may also be "connected," "combined," or "joined" between each component.

[0032] In this specification, examples of substituents are described below, but are not limited thereto.

[0033] In this specification, the term "substitution" means that a hydrogen atom bonded to an atom such as carbon or nitrogen of a compound is replaced by another substituent. The position where substitution occurs is not particularly limited and can be any position where substitution is possible, and when substitution occurs with two or more substituents, the substituents may be identical or different from each other.

[0034] In this specification, the term "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, nitro group, nitrile group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, sulfide group, aryloxy group, heteroaryloxy group, thio group, amine group, silyl group, phosphine oxide group, aryl group, and heteroaryl group, being substituted with a substituent in which two or more substituents selected from said group are connected, or having no substituents at all, and the selected substituents may or may not be combined with each other to form a ring. An example of a substituent in which two or more substituents are connected is a biphenyl group. That is, the biphenyl group corresponds to an aryl group, and simultaneously corresponds to a substituent in which two phenyl groups are connected, and simultaneously corresponds to an aryl group substituted with one phenyl group.

[0035] In this specification, the alkyl group may be a straight chain or a branched chain having 1 to 60 carbon atoms, and specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, Examples include isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto. Specifically, the number of carbon atoms in the alkyl group may be 1 to 30, and more specifically, 1 to 20.

[0036] In the present specification, the alkenyl group may be a straight chain or a branched chain having 2 to 60 carbon atoms, and specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, a styrenyl group, etc. Specifically, the number of carbon atoms in the alkenyl group can be 2 to 30, and more specifically, 2 to 20.

[0037] In the present specification, the alkynyl group may be a straight chain or a branched chain having 2 to 60 carbon atoms. Specifically, the number of carbon atoms in the alkynyl group may be 2 to 30, and more specifically, 2 to 20.

[0038] In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain having 1 to 60 carbon atoms, and specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto. Specifically, the number of carbon atoms of the alkoxy group may be 1 to 30, and more specifically, 1 to 20.

[0039] In the present specification, the cycloalkyl group may be a single or polycyclic group having 3 to 60 carbon atoms, and specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc. Specifically, the number of carbon atoms of the cycloalkyl group may be 3 to 30, and more specifically, 3 to 20.

[0040] In the present specification, the heterocycloalkyl group comprises one or more non-carbon atoms, i.e., heteroatoms, and specifically may be a cycloalkyl group comprising one or more heteroatoms selected from the group consisting of O, N, S, and Se, and may be a monocyclic or polycyclic group having 2 to 60 carbon atoms. Specifically, the number of carbon atoms of the heterocycloalkyl group may be 2 to 30, and more specifically 2 to 20.

[0041] In the present specification, the sulfide group may include S and may have 1 to 60 carbon atoms. Specific examples include, but are not limited to, alkyl sulfide groups such as dimethyl sulfide, aryl sulfide groups such as diphenyl sulfide, and heteroaryl sulfide groups substituted with heteroaryl groups. Specifically, the number of carbon atoms of the sulfide group may be 1 to 30, and more specifically, 1 to 20.

[0042] In this specification, the aryloxy group may be a substituent comprising O, wherein the O atom is directly connected as a radical, and may have 6 to 60 carbon atoms. Specific examples of oxygen groups substituted with an aryl group include, but are not limited to, phenoxy groups, naphthoxy groups, and biphenoxy groups. The heteroaryloxy group may be an oxygen group substituted with a heteroaryl group, and may have 2 to 60 carbon atoms. Specifically, the number of carbon atoms of the aryloxy group may be 6 to 30, and more specifically, 6 to 20.

[0043] In the present specification, the thio group may include S and may have 1 to 60 carbon atoms. Specific examples include alkyl thio groups such as methyl thio group, ethyl thio group, butyl thio group, pentyl thio group, and hexyl thio group; aryl thio groups such as phenyl thio group and naphthyl thio group; and heteroaryl thio groups substituted with heteroaryl groups, but are not limited thereto. Specifically, the number of carbon atoms of the thio group may be 1 to 30, and more specifically, 1 to 20.

[0044] In the present specification, the silyl group may be a substituent comprising Si, in which the Si atom is directly connected as a radical, and may have 1 to 60 carbon atoms. Specific examples include alkylsilyl groups such as trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl; arylsilyl groups such as triphenylsilyl, diphenylsilyl, and phenylsilyl; and heteroarylsilyl groups substituted with heteroaryl groups, but are not limited thereto. Specifically, the number of carbon atoms of the silyl group may be 1 to 30, and more specifically, 1 to 20.

[0045] In the present specification, the phosphine oxide group comprises P=O and may have 1 to 60 carbon atoms. Specific examples include, but are not limited to, alkylphosphine oxide groups such as dimethylphosphine oxide, arylphosphine oxide groups such as diphenylphosphine oxide and dinaphthylphosphine oxide, and heteroarylphosphine oxide groups substituted with heteroaryl groups. Specifically, the number of carbon atoms of the phosphine oxide group may be 1 to 30, and more specifically, 1 to 20.

[0046] In this specification, the aryl group may be monocyclic or polycyclic having 6 to 60 carbon atoms. Specific examples of monocyclic aryl groups may include, but are not limited to, phenyl groups, biphenyl groups, terphenyl groups, etc. Specific examples of polycyclic aryl groups may include, but are not limited to, naphthyl groups, anthracenyl groups, phenanthrenyl groups, triphenylenyl groups, pyrenyl groups, fluorenyl groups, etc. Specifically, the number of carbon atoms in the aryl group may be 6 to 50, and more specifically, 6 to 30.

[0047] In the present specification, the heteroaryl group comprises one or more atoms that are not carbon, i.e., heteroatoms, and specifically may comprise one or more heteroatoms selected from the group consisting of O, N, S and Se, and may be a single ring or a polycyclic group having 2 to 60 carbon atoms. Specific examples include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, triazolyl group, acrridinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, pyridoindolyl group, benzothienopyrimidyl group, indenocarbazolyl group, isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, Dibenzothiophenyl group, benzofuranyl group, phenanthridinyl group, phenanthrolinyl group, isooxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group are included, but are not limited thereto. Specifically, the number of carbon atoms in the heteroaryl group may be 2 to 50, and more specifically, 2 to 30.

[0048] In the present specification, the amine group may be selected from the group consisting of -NH2, alkylamine group, N-alkylarylamine group, arylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group, and heteroarylamine group.

[0049] In this specification, an arylene group refers to a divalent aryl group having two bonding sites to an aryl group, and a heteroarylene group also refers to a divalent heteroaryl group having two bonding sites to a heteroaryl group. Except that they are each divalent groups, the descriptions of the arylene and heteroaryl groups described above may apply.

[0050] In the chemical formulas or structural formulas within this specification, * or indicates the joint location.

[0051] In this specification, the same symbols within a single chemical formula or structural formula may be the same or different from each other.

[0052] In the present specification, when ranges such as "C2 to C50" or "0 to 7" are described, they may be reduced to various ranges within the described ranges even without special description, and are deemed to be described in the present specification. For example, C2 to C50 is deemed to describe various reduced ranges such as C5 to C50, C6 to C30, C6 to C20, C6 to C15, C6 to C10, and C12 to C30, in addition to C2 to C50. Accordingly, the description of numerical ranges in the present specification may be reduced and corrected later.

[0053] Throughout this specification, the term "interaction with a dopant" may mean that an organic compound in an N-type charge generation layer coordinates with a dopant including an alkali metal, an alkaline earth metal, a rare earth metal, or a lanthanum metal, and according to one embodiment, may include the organic compound and the dopant combining to form a gap state.

[0054] Throughout this specification, the term "organic light-emitting element" may refer to an organic light-emitting diode and a panel including the same, or an electronic device including a panel and a circuit. Here, for example, the electronic device may include, but is not limited to, display devices, lighting devices, solar cells, portable or mobile terminals (e.g., smartphones, tablets, PDAs, electronic dictionaries, PMPs, etc.), navigation terminals, game consoles, various TVs, various computer monitors, etc., and may be any type of device that includes the aforementioned component(s).

[0055]

[0056] The present invention will be described in detail below.

[0057] The present invention relates to a novel compound and an organic light-emitting device containing the same.

[0058] As a specific example of the compound of the present invention, a compound represented by the following chemical formula 1 may be cited.

[0059] <Chemical Formula 1>

[0060]

[0061] In the above chemical formula 1,

[0062] Ar1 to Ar3 are each independently substituted or unsubstituted C6 to C50 aryl groups, or substituted or unsubstituted C2 to C50 heteroaryl groups, wherein adjacent ones may or may not combine to form a substituted or unsubstituted ring.

[0063] L1 is each independently a directly bonded, substituted, or unsubstituted C6–C50 arylene group, or a substituted or unsubstituted C2–C50 heteroarylene group, and

[0064] R1 is each independently hydrogen, deuterium, halogen group, cyano group, nitro group, nitrile group, substituted or unsubstituted C1–C30 alkyl group, substituted or unsubstituted C1–C30 alkenyl group, substituted or unsubstituted C1–C30 alkynyl group, substituted or unsubstituted C3–C30 cycloalkyl group, substituted or unsubstituted C1–C30 heterocycloalkyl group, substituted or unsubstituted C1–C30 alkoxy group, substituted or unsubstituted C1–C30 sulfide group, substituted or unsubstituted C6–C30 aryl group, substituted or unsubstituted C2–C30 heteroaryl group, substituted or unsubstituted C6–C30 aryloxy group, substituted or unsubstituted C2–C30 heteroaryloxy group, substituted or unsubstituted C1–C30 thio group, substituted or unsubstituted Selected from the group consisting of C1-C30 amine groups, substituted or unsubstituted C1-C30 silyl groups, and substituted or unsubstituted C1-C30 phosphine oxide groups, wherein adjacent groups may or may not combine to form a substituted or unsubstituted ring.

[0065] a is an integer from 0 to 7, and

[0066] b can be an integer from 0 to 3.

[0067] The novel compound of the present invention is a compound comprising 1,10-phenanthroline and a substituent containing silicon (Si). Specifically, it is characterized by 1) a substituent containing silicon is bonded to a position immediately adjacent to the nitrogen (N) of 1,10-phenanthroline, and 2) a linker connecting 1,10-phenanthroline and silicon includes naphthylene, wherein the naphthylene is located immediately adjacent to the silicon. That is, it has a structure in which silicon and naphthylene are directly connected.

[0068] According to one embodiment, Ar1 to Ar3 may each be an independently substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group, and adjacent ones may combine with each other to form a substituted or unsubstituted ring. Specifically, Ar1 to Ar3 may each be an independently substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C2 to C10 heteroaryl group, and adjacent ones may combine with each other to form a substituted or unsubstituted ring. More specifically, Ar1 to Ar3 may each be an independently substituted or unsubstituted C6 to C10 aryl group, and adjacent ones may combine with each other to form a substituted or unsubstituted ring. As a specific example, Ar1 to Ar3 may each be an independently substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, and adjacent ones may combine with each other to form a substituted or unsubstituted ring.

[0069] According to one embodiment, L1 may each independently be a directly bonded, substituted, or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group. Specifically, L1 may each independently be a directly bonded, substituted, or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C2-C20 heteroarylene group, and more specifically, may be a directly bonded, substituted, or unsubstituted C6-C10 arylene group or a substituted or unsubstituted C2-C10 heteroarylene group.As a specific example, L1 is each independently a directly bonded, substituted or unsubstituted phenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted biphenylene group, substituted or unsubstituted terphenylene group, substituted or unsubstituted phenanthrenylene group, substituted or unsubstituted anthracenylene group, substituted or unsubstituted chrysenylene group, substituted or unsubstituted benzophenanthrenylene group, substituted or unsubstituted benzoanthracenylene group, substituted or unsubstituted pyrenylene group, substituted or unsubstituted diphenylfluorenylene group, substituted or unsubstituted dimethylfluorenylene group, substituted or unsubstituted spirobifluorenylene group, substituted or unsubstituted pyridinylene group, substituted or unsubstituted pyrimidinylene group, substituted or unsubstituted pyrazinylene group, substituted or unsubstituted pyridazinylene group, substituted or unsubstituted trizinylene group, substituted or unsubstituted quinolinylene group, substituted or unsubstituted isoquinolinylene group, substituted or unsubstituted quinazolilene group, substituted or unsubstituted quinoxalilene group, substituted or unsubstituted phthalazinilene group, substituted or unsubstituted cinnolinylene group, substituted or unsubstituted 1,5-naphthiridinylene group, substituted or unsubstituted 1,6-naphthiridinylene group, substituted or unsubstituted 1,7-naphthiridinylene group, substituted or unsubstituted 1,8-naphthiridinylene group, substituted or unsubstituted 2,5-naphthiridinylene group, substituted or unsubstituted 2,6-naphthiridinylene group, substituted or unsubstituted 2,7-naphthiridinylene group, substituted or unsubstituted dibenzofuranylene group, substituted or unsubstituted dibenzothiophenylene group, substituted or unsubstituted benzoxazolilene group, substituted or unsubstituted It may be a benzothiazolylene group or a substituted or unsubstituted benzimidazolilene group, and more specific examples may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group or a substituted or unsubstituted pyridinylene group, but are not particularly limited thereto.

[0070] According to one embodiment, R1 may each independently be a deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C10 aryl group, or a substituted or unsubstituted C2-C10 heteroaryl group, specifically may be one of a deuterium, a methyl group, an ethyl group, a t-butyl group, a phenyl group, a deuterium-substituted phenyl group, a naphthyl group, a biphenyl group, and a pyridine group, and more specifically may be a phenyl group, but is not particularly limited thereto. According to one embodiment, when adjacent R1s are bonded to form a ring, they may form a substituted or unsubstituted benzene or a substituted or unsubstituted naphthyl, but are not particularly limited thereto.

[0071] According to one embodiment, when Ar1, Ar2, Ar3, L1, and R1 are substituted in the above chemical formulas, the substituents that can be substituted may be selected from the group consisting of deuterium, halogen group, cyano group, fluorine group (-F), -CF3, C1-C30 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group, and if a substituent is specifically defined, it shall be followed accordingly. As a specific example, when substituted, the substituent may be one or more of deuterium, halogen group, cyano group, fluorine group (-F), -CF3, methyl group, ethyl group, t-butyl group, phenyl group, naphthyl group, biphenyl group, and pyridine group, but is not specifically limited thereto.

[0072] According to one embodiment, a may specifically be an integer from 0 to 3, and more specifically 0 or 1, but is not particularly limited thereto.

[0073] According to one embodiment, b may specifically be an integer from 0 to 2, and more specifically 0 or 1, but is not particularly limited thereto.

[0074] As a specific example compound of the present invention, the above chemical formula 1 may be represented by the following chemical formula 2 or chemical formula 3.

[0075] <Chemical Formula 2>

[0076]

[0077] <Chemical Formula 3>

[0078]

[0079] In the above chemical formulas 2 and 3,

[0080] The above L1, R1, a, and b are identical to the definitions of Chemical Formula 1, and

[0081] R2 is each independently selected from the group consisting of hydrogen, deuterium, halogen group, cyano group, fluorine group (-F), -CF3, C1-C10 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group, and

[0082] c is an integer from 0 to 5, each independently, and

[0083] d can be an integer from 0 to 4, each independently.

[0084] The above formula 2 is a case where Ar1 to Ar3 in formula 1 are substituted or unsubstituted phenyl groups, and the above formula 3 is a case where Ar1 in formula 1 is a substituted or unsubstituted phenyl group, and adjacent Ar2 and Ar3 are bonded to each other to form a substituted or unsubstituted condensed ring structure in the form of fluorene.

[0085] In the above chemical formulas 2 and 3, c and d can each be independently 0 or 1, and when 1, R2 can each be independently one of a cyano group, a fluorine group (-F) and -CF3, specifically a cyano group. When such electron-withdrawing substituents are introduced, it can be effective in improving the efficiency of organic light-emitting devices.

[0086] According to one embodiment, in the above formula 2, c may be all 0 or only one may be 1, and R2 may be a cyano group.

[0087] According to one embodiment, in the above formula 3, c and d may both be 0 or either one may be 1, and R2 may be a cyano group.

[0088] Meanwhile, in the above chemical formulas 1 to 3, a can be 0 or 1, and when it is 1, R1 can be a phenyl group, and the bonding position can be 2, 4, or 7, specifically when the silicon-containing substituent is located at position 9 based on 1,10-phenanthrin, and specifically can be 2.

[0089] Based on the above, the above chemical formula 1 can be represented by the following chemical formula 2-1 or 3-1.

[0090] <Chemical Formula 2-1>

[0091]

[0092] <Chemical Formula 3-1>

[0093]

[0094] In the above chemical formulas 2-1 and 3-1, L1 and b are the same as defined in chemical formula 1, and

[0095] R1 is independently a hydrogen or a phenyl group, and

[0096] R2 can each independently be hydrogen or a cyano group.

[0097] In the above chemical formulas 2-1 and 3-1, one or more of R1 may be phenyl groups, specifically, only one of them may be a phenyl group. When a phenyl group is substituted on 1,10-phenanthroline in this way, stability is improved, which can be effective in improving lifespan.

[0098] In the above chemical formulas 2-1 and 3-1, one or more of R2 may be cyano groups, specifically, only one of them may be a cyano group. When a cyano group is substituted on a silicon-containing substituent in this way, it can be effective for improving efficiency.

[0099] In the above chemical formulas 1 to 3, the naphthylene linker may specifically be one of the following structural formulas N-1 to N-10. More specifically, the naphthylene linker may be one of N-1 to N-4, and even more specifically, may be N-1 or N-3, but is not particularly limited thereto.

[0100]

[0101] In the above structural formulas N-1 to N-10, one of the two bonding positions "*" is a position bonded to L1, and the other is a position bonded to silicon (Si).

[0102] The compound represented by the above chemical formula 1 may be selected from the group consisting of the following compounds 1 to 196. The following compounds are merely examples for explaining the present invention and are not limited thereto:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] The novel compound according to the present invention is applicable to a charge generation layer (CGL) in a tandem device, particularly to an N-type charge generation layer (n-CGL), and can exhibit effects such as increased efficiency, reduced driving voltage, and long lifespan of the device. Meanwhile, it is not limited to this and can also be applied to organic layers such as an electron injection layer (EIL), an electron transport layer (ETL), a layer that simultaneously injects and transports electrons, and a hole blocking layer (HBL), where a compound with excellent electron mobility must be applied.

[0111] The present invention comprises an organic light-emitting device comprising a first electrode and a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to Formula 1. The organic layer comprising the compound may be an electron injection layer, an electron transport layer, a layer that simultaneously injects and transports electrons, a hole blocking layer, or a charge generating layer.

[0112] In addition, the present invention includes a tandem organic light-emitting device comprising a first electrode and a second electrode, a plurality of light-emitting parts located between the first electrode and the second electrode, and a charge-generating layer located at one or more places among two adjacent light-emitting parts, wherein one or more of the charge-generating layers comprises an N-type charge-generating layer comprising a compound represented by Chemical Formula 1.

[0113] The organic light-emitting diode and tandem organic light-emitting diode according to the present invention will be described in more detail below.

[0114] An organic light-emitting device has an organic layer located between a first electrode and a second electrode. The organic layer may be composed of one or more organic layers, and specifically, it may be composed of one or more layers selected from among known organic layers constituting a light-emitting part, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0115] The hole injection layer (HIL) is a layer that injects holes from the electrode, and as a hole injection material, a compound that has the ability to transport holes, has an excellent hole injection effect on the anode, the emitting layer, or the emitting material, prevents the movement of excitons generated in the emitting layer to the electron injection layer or the electron injection material, and also has excellent thin film formation ability is preferred.

[0116] The hole transport layer (HTL) is a layer that receives holes from the hole injection layer and transports the holes to the emissive layer. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emissive layer, and a material with high mobility for holes is suitable.

[0117] The light-emitting material used in the emissive layer (EML) is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. The emissive layer may include a host material and a dopant material.

[0118] The electron transport layer (ETL) is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As an electron transport material, it is desirable to have a material that can effectively receive electrons from the cathode and transfer them to the light-emitting layer, and has high electron mobility.

[0119] The electron injection layer (EIL) is a layer that injects electrons from an electrode and has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emitting layer or emitting material, prevents the movement of excitons generated in the emitting layer to the hole injection layer, and also has excellent thin film formation ability. A compound is preferred.

[0120] Additionally, the organic layer may further include a hole blocking layer (hole blocking layer, HBL). The hole blocking layer may be located between the emissive layer and the electron transport layer and reduces the problem of holes from the hole injection layer invading the electron transport layer. Furthermore, the organic layer may further include known organic layers, such as a layer that simultaneously performs electron injection and transport.

[0121] Among the organic layers of such organic light-emitting devices, the novel compound according to Formula 1 of the present invention has excellent electron transport ability and can be applied to an electron injection layer, an electron transport layer, a layer that simultaneously injects and transports electrons, or a hole blocking layer.

[0122] Meanwhile, the configuration of the organic light-emitting device can be varied or modified in various ways. According to one embodiment, the device may be a tandem-type organic light-emitting device in which two or more light-emitting parts (or light-emitting units) including a light-emitting layer between a first electrode and a second electrode are provided. In the case of such a tandem structure, a charge generation layer (CGL) may be further included as one of the organic layers in addition to the organic layers mentioned above. Generally, the charge generation layer is composed of multiple layers including an N-type charge generation layer and a P-type charge generation layer, but is not limited thereto and may be composed of a single layer.

[0123] The novel compound of the present invention can be applied to the charge generation layer of such a tandem organic light-emitting diode, specifically to the N-type charge generation layer. Generally, the N-type charge generation layer includes a host and a dopant, and the novel compound of the present invention can be applied as the host. Here, the dopant may be an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal, a rare earth metal compound, a lanthanum metal, or a lanthanum metal compound. More specifically, it may be one or more metals selected from lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), ytterbium (Yb), samarium (Sm), tin (Sn), copper (Cu), titanium (Ti), cadmium (Cd), mercury (Hg), lead (Pb), bismuth (Bi), zinc (Zn), iron (Fe), cobalt (Co), nickel (Ni), indium (In), gallium (Ga), thorium (Th), uranium (U), silver (Ag), aluminum (Al), gold (Au), molybdenum (Mo), niobium (Nb), palladium (Pd), platinum (Pt), and europium (Eu); and according to one embodiment, the metal may be selected from lithium or ytterbium. The ratio of these dopants can be doped to 0.1 to 20 wt% relative to the total host material, specifically to 0.5 to 15 wt%, and this is not limited and may vary depending on the type of metal.

[0124] The present invention will be explained in more detail below through examples of compound synthesis and organic light-emitting diodes according to one embodiment of the present invention. The following synthesis examples and examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following examples.

[0125] Synthesis of compounds

[0126] <Synthesis Example 1> Synthesis of Compound 1

[0127]

[0128] (4-bromonaphthalen-1-yl)triphenylsilane (20 g, 43.00 mmol) and Bis(pinacolato)diboron (14.18 g, 55.90 mmol) were added to a 500 ml round-bottom flask. Pd(dppf)Cl2 (0.94 g, 1.3 mmol) and KOAc (12.65 g, 128.9 mmol) were added, and the mixture was stirred under reflux for 6 hours in 200 ml of 1,4-Dioxane. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-1 (14.3 g, 65.00 %) was obtained by purification and recrystallization using column chromatography.

[0129]

[0130] 2-bromo-1,10-phenanthroline (10 g, 38.60 mmol) and Compound 1-1 (21.76 g, 42.50 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.34 g, 1.20 mmol) and calcium carbonate (16.00 g, 115.80 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1 (15.0 g, 68.8%) was obtained by purification and recrystallization using column chromatography.

[0131] <Synthesization Example 2> Synthesis of Compound 2

[0132]

[0133] 2-bromo-4-phenyl-1,10-phenanthroline (10 g, 29.80 mmol) and Compound 1-1 (16.82 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 2 (13.0 g, 77.2%) was obtained by purification and recrystallization using column chromatography.

[0134] <Synthesization Example 3> Synthesis of Compound 3

[0135]

[0136] 2-bromo-9-phenyl-1,10-phenanthroline (10 g, 29.80 mmol) and Compound 1-1 (16.82 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 3 (12.7 g, 75.4%) was obtained by purification and recrystallization using column chromatography.

[0137] <Synthesization Example 4> Synthesis of Compound 5

[0138]

[0139] A 250 ml round-bottom 3-neck flask was floated with nitrogen gas for 15 minutes, and 60 ml of THF was added to 1,4-dibromonaphthalene (10.00 g, 35 mmol). The mixture was stirred for 10 minutes until the reaction mixture dissolved, then the temperature was lowered to -85°C to -90°C, 13.17 ml of 2.5 M n-butyllithium solution was added dropwise, and the mixture was maintained for 1 hour. At -78°C, 4-(chlorodiphenylsilyl)benzonitrile (11.74 g, 36.7 mmol) dissolved in THF (20 ml) was added dropwise. After adding the solution, the mixture was heated to room temperature for 2 hours. After the reaction was complete, the mixture was washed with water until neutral, filtered, dried, and recrystallized with toluene to obtain compound 5-1 (12.0 g, 69.9%).

[0140]

[0141] Compound 5-1 (20 g, 40.80 mmol) and Bis(pinacolato)diboron (13.46 g, 53.00 mmol) were added to a 500 ml round-bottom flask. Pd(dppf)Cl2 (0.90 g, 1.2 mmol) and KOAc (12.00 g, 122.3 mmol) were added, and the mixture was stirred under reflux for 6 hours in 200 ml of 1,4-Dioxane. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 5-2 (12.71 g, 58.00%) was obtained by purification and recrystallization using column chromatography.

[0142]

[0143] 2-bromo-1,10-phenanthroline (10 g, 38.60 mmol) and compound 5-2 (22.82 g, 42.50 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.34 g, 1.20 mmol) and calcium carbonate (16.00 g, 115.80 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 5 (13.7 g, 60.2%) was obtained by purification and recrystallization using column chromatography.

[0144] <Synthesis Example 5> Synthesis of Compound 6

[0145]

[0146] 2-bromo-9-phenyl-1,10-phenanthroline (10 g, 29.80 mmol) and compound 5-2 (17.64 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 6 (13.7 g, 68.9%) was obtained by purification and recrystallization using column chromatography.

[0147] <Synthesis Example 6> Synthesis of Compound 8

[0148]

[0149] 2-bromo-4-phenyl-1,10-phenanthroline (10 g, 29.80 mmol) and compound 5-2 (17.64 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 8 (14.2 g, 71.5%) was obtained by purification and recrystallization using column chromatography.

[0150] <Synthesis Example 7> Synthesis of Compound 9

[0151]

[0152] 2-(4-bromophenyl)-1,10-phenanthroline (10 g, 29.80 mmol) and Compound 1-1 (16.82 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 9 (13.4 g, 79.5%) was obtained by purification and recrystallization using column chromatography.

[0153] <Synthesis Example 8> Synthesis of Compound 10

[0154]

[0155] 2-(4-bromophenyl)-9-phenyl-1,10-phenanthroline (10 g, 24.30 mmol) and Compound 1-1 (13.70 g, 26.70 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.84 g, 0.70 mmol) and calcium carbonate (10.08 g, 72.90 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 10 (13.0 g, 74.6%) was obtained by purification and recrystallization using column chromatography.

[0156] <Synthesis Example 9> Synthesis of Compound 11

[0157]

[0158] 2-(4-bromophenyl)-4-phenyl-1,10-phenanthroline (10 g, 24.30 mmol) and Compound 1-1 (13.70 g, 26.70 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.84 g, 0.70 mmol) and calcium carbonate (10.08 g, 72.90 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 11 (12.5 g, 71.7%) was obtained by purification and recrystallization using column chromatography.

[0159] <Synthesis Example 10> Synthesis of Compound 13

[0160]

[0161] 2-(4-bromophenyl)-1,10-phenanthroline (10 g, 29.80 mmol) and compound 5-2 (17.64 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 13 (13.8 g, 69.5%) was obtained by purification and recrystallization using column chromatography.

[0162] <Synthesization Example 11> Synthesis of Compound 14

[0163]

[0164] 2-(4-bromophenyl)-9-phenyl-1,10-phenanthroline (10 g, 24.30 mmol) and compound 5-2 (14.38 g, 26.70 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.84 g, 0.70 mmol) and calcium carbonate (10.08 g, 72.90 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 14 (12.2 g, 67.6%) was obtained by purification and recrystallization using column chromatography.

[0165] <Synthesis Example 12> Synthesis of Compound 15

[0166]

[0167] 2-(4-bromophenyl)-4-phenyl-1,10-phenanthroline (10 g, 24.30 mmol) and compound 5-2 (14.38 g, 26.70 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.84 g, 0.70 mmol) and calcium carbonate (10.08 g, 72.90 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 15 (12 g, 66.5%) was obtained by purification and recrystallization using column chromatography.

[0168] <Synthesization Example 13> Synthesis of Compound 17

[0169]

[0170] 2-(3-bromophenyl)-1,10-phenanthroline (10 g, 29.80 mmol) and Compound 1-1 (16.82 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 17 (13.6 g, 80.7%) was obtained by purification and recrystallization using column chromatography.

[0171] <Synthesization Example 14> Synthesis of Compound 49

[0172]

[0173] (6-bromonaphthalen-2-yl)triphenylsilane (20 g, 43.00 mmol) and Bis(pinacolato)diboron (14.18 g, 55.90 mmol) were added to a 500 ml round-bottom flask. Pd(dppf)Cl2 (0.94 g, 1.3 mmol) and KOAc (12.65 g, 128.9 mmol) were added, and the mixture was stirred under reflux for 6 hours in 200 ml of 1,4-Dioxane. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 49-1 (13.2 g, 60.00 %) was obtained by purification and recrystallization using column chromatography.

[0174]

[0175] 2-bromo-1,10-phenanthroline (10 g, 38.60 mmol) and compound 49-1 (21.76 g, 42.50 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.34 g, 1.20 mmol) and calcium carbonate (16.00 g, 115.80 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 49 (15.7 g, 72.0%) was obtained by purification and recrystallization using column chromatography.

[0176] <Synthesization Example 15> Synthesis of Compound 57

[0177]

[0178] 2-(4-bromophenyl)-1,10-phenanthroline (10 g, 29.80 mmol) and compound 49-1 (16.82 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 57 (12.8 g, 75.9%) was obtained by purification and recrystallization using column chromatography.

[0179] <Synthesization Example 16> Synthesis of Compound 65

[0180]

[0181] 2-(3-bromophenyl)-1,10-phenanthroline (10 g, 29.80 mmol) and compound 49-1 (16.82 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 65 (13.0 g, 77.2%) was obtained by purification and recrystallization using column chromatography.

[0182] <Synthesization Example 17> Synthesis of Compound 97

[0183]

[0184] 60 mL of THF was added to 1,4-dibromonaphthalene (10.00 g, 35 mmol) in a 250 mL round-bottom 3-neck flask, which was evacuated with nitrogen gas for 15 minutes. The mixture was stirred for 10 minutes until the reaction product dissolved, then the temperature was lowered to -85°C to -90°C, 13.17 mL of 2.5 M n-butyllithium solution was added dropwise, and the mixture was maintained for 1 hour after addition. Then, 5-chloro-5-phenyl-5H-dibenzo[b,d]silole (10.75 g, 36.7 mmol) dissolved in THF (20 mL) was added dropwise at -78°C. After addition, the mixture was heated to room temperature for 2 hours. After the reaction was complete, the mixture was washed with water until neutral, filtered, dried, and recrystallized with toluene to obtain compound 5-1 (11.5 g, 70.9%).

[0185]

[0186] 5-(4-bromonaphthalen-1-yl)-5-phenyl-5H-dibenzo[b,d]silole (20 g, 43.20 mmol) and Bis(pinacolato)diboron (14.25 g, 56.10 mmol) were added to a 500 ml round-bottom flask. Pd(dppf)Cl2 (0.94 g, 1.3 mmol) and KOAc (12.70 g, 129.5 mmol) were added, and the mixture was stirred under reflux for 6 hours in 200 ml of 1,4-Dioxane. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 97-2 (14.76 g, 67.00 %) was obtained by purification and recrystallization using column chromatography.

[0187]

[0188] 2-bromo-1,10-phenanthroline (10 g, 38.60 mmol) and compound 97-2 (21.67 g, 42.50 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.34 g, 1.20 mmol) and calcium carbonate (16.00 g, 115.80 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 49 (15.5 g, 71.4%) was obtained by purification and recrystallization using column chromatography.

[0189] <Synthesization Example 18> Synthesis of Compound 105

[0190]

[0191] 2-(4-bromophenyl)-1,10-phenanthroline (10 g, 29.80 mmol) and compound 97-2 (16.75 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 105 (13.3 g, 69.8%) was obtained by purification and recrystallization using column chromatography.

[0192] <Synthesization Example 19> Synthesis of Compound 113

[0193]

[0194] 2-(3-bromophenyl)-1,10-phenanthroline (10 g, 29.80 mmol) and compound 97-2 (16.75 g, 32.80 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.04 g, 0.90 mmol) and calcium carbonate (12.37 g, 89.50 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 113 (12.7 g, 66.6%) was obtained by purification and recrystallization using column chromatography.

[0195] <Synthesization Example 20> Synthesis of Compound 193

[0196]

[0197] 2-(4-bromonaphthalen-1-yl)-1,10-phenanthroline (10 g, 26.00 mmol) and Compound 1-1 (14.63 g, 28.60 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.90 g, 0.80 mmol) and calcium carbonate (10.76 g, 77.90 mmol) were added, and the mixture was stirred under reflux for 12 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 193 (11.8 g, 65.8%) was obtained by purification and recrystallization using column chromatography.

[0198] Fabrication of Tandem Organic Light Emitting Diodes: Application of N-Type Charge Generation Layer

[0199] Comparison Example 1

[0200] After patterning an ITO substrate to serve as the anode so that the light-emitting area was 2 mm × 2 mm, it was cleaned with isopropyl alcohol and UV ozone, respectively. Subsequently, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus, and a vacuum level of 1 × 10⁻⁶-7 The pressure was applied to torr. Subsequently, plasma treatment was performed for 3 minutes under an N2 atmosphere. First, a HAT-CN compound was vacuum-deposited to form a first hole injection layer with a thickness of 5 nm. On top of this, an NPB material was vacuum-deposited to form a first hole transport layer with a thickness of 20 nm. Next, a green first emissive layer with a thickness of 20 nm was formed by co-depositing a GH-1 material as the host and a GD-1 material as the dopant at a mass ratio of approximately 10%. A first electron transport layer with a thickness of 20 nm was formed by vacuum-depositing a TmPyPb compound on this first emissive layer. Subsequently, an N-type charge generation layer with a thickness of 10 nm was formed by co-depositing a Li material as the dopant onto the BPhen material as the host at a mass ratio of 2%. Afterward, a P-type charge generation layer with a thickness of 5 nm was formed by vacuum-depositing a HAT-CN compound. This layer is also utilized as a second hole injection layer. A second hole transport layer with a thickness of 50 nm was formed by vacuum depositing NPB material on top of this. Subsequently, a second green emissive layer with a thickness of 20 nm was formed by co-depositing GH-1 material as the host and GD-1 material as the dopant at a mass ratio of approximately 10%. On top of this emissive layer, a second electron transport layer with a thickness of 20 nm was formed by co-depositing TmPyPb compound as the host and Liq compound as the dopant at a mass ratio of approximately 33%. Subsequently, an electron injection layer with a thickness of 1 nm was formed by vacuum depositing LiF material. Finally, the final tandem organic light-emitting diode was fabricated by forming a cathode by depositing aluminum (Al) to a thickness of 50 nm. The structures of the previously used HAT-CN, NPB, GH-1, GD-1, TmPyPb, BPhen, and Liq materials are shown in Table 1 below.

[0201]

[0202] Comparative Examples 2 to 13

[0203] An organic light-emitting diode was fabricated in the same manner as Comparative Example 1, except that Comparative Compounds 1 to 12 of Table 2 below were used instead of BPhen as the N-type charge generation layer host.

[0204]

[0205] Examples 1 to 20

[0206] An organic light-emitting diode was fabricated in the same manner as Comparative Example 1, except that the compounds of the present invention synthesized in Synthesis Examples 1 to 20 above were used instead of BPhen as the N-type charge-generating layer host.

[0207] Experimental example

[0208] The driving voltage, efficiency, and lifetime of the organic light-emitting diodes of Comparative Examples 1 to 13 and Examples 1 to 20 prepared above were evaluated, respectively. The evaluation results are as shown in Table 3 below.

[0209] Classification N-type Charge Generation Layer Current Density (mA / cm2) Driving Voltage (V) Current Efficiency (cd / A) Lifetime (T95) Host Dopant Comparative Example 1 BP hen Li 106.74 18.26 18 3.10 Comparative Example 2 Comparative Compound 1 Li 106.64 120.60 18 0.75 Comparative Example 3 Comparative Compound 2 Li 106.62 120.94 18 2.40 Comparative Example 4 Comparative Compound 3 Li 106.64 119.88 18 8.20 Comparative Example 5 Comparative Compound 4 Li 106.71 119.42 18 9.10 Comparative Example 6 Comparative Compound 5 Li 106.70 119.32 19 1.25 Comparative Example 7 Comparative Compound 6Li106.66119.45183.60 Comparative Example 8 Comparative Compound 7Li106.62120.56191.30 Comparative Example 9 Comparative Compound 8Li106.71120.82187.95 Comparative Example 10 Comparative Compound 9Li106.78119.80187.75 Comparative Example 11 Comparative Compound 10Li106.70118.40184.90 Comparative Example 12 Comparative Compound 11Li106.62119.49187.50 Comparative Example 13 Comparative Compound 12Li106.76118.96185.30 Example 1 Compound 1Li106.57121.19198.20 Example Compound 2 2Li106.46122.81207.25 Example 3 Compound 3Li106.60121.10205.65 Example 4 Compound 5Li106.51124.57198.85 Example 5 Compound 6Li106.55123.50205.30 Example 6 Compound 8Li106.43123.57214.05 Example 7 Compound 9Li106.57123.35205.55 Example 8 Compound 10Li106.53123.44214.50 Example 9 Compound 11Li106.55122.97208.80 Example 10 Compound 13Li106.49124.55203.60 Example 11 Compound 14Li106.51124.91209.15 Example 12 Compound 15Li106.46125.97217.55 Example 13 Compound 17Li106.61121.11194.20 Example 14 Compound 49Li106.59121.58203.60 Example 15 Compound 57Li106.58122.80198.45 Example 16 Compound 65Li106.61122.72193.25 Example 17 Compound 97Li106.59121.44201.85 Example 18 Compound 105Li106.53122.59200.00 Example 19 Compound 113Li106.61122.98193.28 Example 20 Compound 193Li106.61120.97191.42.

[0210] As can be seen in Table 3 above, it was confirmed that the organic light-emitting devices of the embodiments according to the present invention exhibit lower voltage, higher efficiency, and longer lifespan than the organic light-emitting devices of the comparative examples. Specifically, comparative compounds 1 and 2 have a structure in which a methyl group (-CH3) is bonded to silicon (Si) as a trimethylsilane group, and their thermal stability is poor, making them undesirable in terms of lifespan.

[0211] Compared to comparative compounds 3 to 5, the compound of the present invention has a silicon-containing substituent bonded right next to the nitrogen (N) of 1,10-phenanthroline, thereby forming an intramolecular hydrogen bond between the nitrogen of 1,10-phenanthroline and the hydrogen of the adjacent linker. This reduces the dihedral angle between 1,10-phenanthroline and the linker, resulting in a reduced RE value (reorganization energy) and an increase in conjugation length. On the other hand, comparative compounds 3 to 5 form a large dihedral angle between 1,10-phenanthroline and the linker, and the aforementioned intramolecular hydrogen bond is absent. Consequently, when the molecule accepts electrons, the linker rotates, thereby increasing the RE value. In conclusion, the compound of the present invention, having a low RE value above a certain level, is effective in increasing device efficiency. For reference, the RE value is calculated as (Electron Extraction Potential, EEP) - (Electron Affinity, EA), where EEP is the energy when the structure becomes a cation in the anion state, and EA is the anion energy in the ground structure (neutral).

[0212] Meanwhile, compared to comparative compounds 6 to 8, the compound of the present invention has naphthylene directly bonded to silicon (Si) as a linker, which reduces the energy level difference between the N-type charge generation layer and the adjacent electron transport layer, thereby maximizing the tunneling effect that allows electrons to move. The electron injection capability is improved by the tunneling effect, which can improve low voltage and lifespan.

[0213] Meanwhile, 1,10-phenanthroline is desirable to be applied as an N-type charge generation layer host compared to cores such as triazine, pyrimidine, and benzimidazole, as in comparative compounds 9 to 12, in that it can easily combine with lithium, a dopant included in the N-type charge generation layer, to form a smooth gap state and effectively improve the electronic properties of the N-type charge generation layer, and exhibits actual low voltage, high efficiency, and long lifespan characteristics.

Claims

1. A novel compound represented by the following chemical formula 1: <Chemical Formula 1> In the above chemical formula 1, Ar1 to Ar3 are each independently substituted or unsubstituted C6 to C50 aryl groups, or substituted or unsubstituted C2 to C50 heteroaryl groups, wherein adjacent ones may or may not combine to form a substituted or unsubstituted ring. L1 is each independently a directly bonded, substituted, or unsubstituted C6–C50 arylene group, or a substituted or unsubstituted C2–C50 heteroarylene group, and R1 is each independently hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted C1–C30 alkyl group, substituted or unsubstituted C1–C30 alkenyl group, substituted or unsubstituted C1–C30 alkynyl group, substituted or unsubstituted C3–C30 cycloalkyl group, substituted or unsubstituted C1–C30 heterocycloalkyl group, substituted or unsubstituted C1–C30 alkoxy group, substituted or unsubstituted C1–C30 sulfide group, substituted or unsubstituted C6–C30 aryl group, substituted or unsubstituted C2–C30 heteroaryl group, substituted or unsubstituted C6–C30 aryloxy group, substituted or unsubstituted C2–C30 heteroaryloxy group, substituted or unsubstituted C1–C30 thio group, substituted or unsubstituted Selected from the group consisting of C1-C30 amine groups, substituted or unsubstituted C1-C30 silyl groups, and substituted or unsubstituted C1-C30 phosphine oxide groups, wherein adjacent groups may or may not combine to form a substituted or unsubstituted ring. a is an integer from 0 to 7, and b is an integer from 0 to 3.

2. In Paragraph 1, The above Chemical Formula 1 is a novel compound represented by the following Chemical Formula 2 or Chemical Formula 3: <Chemical Formula 2> <Chemical Formula 3> In the above chemical formulas 2 and 3, L1, R1, a, and b are identical to the definitions of Chemical Formula 1 above, and R2 is each independently selected from the group consisting of hydrogen, deuterium, halogen group, cyano group, fluorine group (-F), -CF3, C1-C10 alkyl group, C6-C20 aryl group, and C2-C20 heteroaryl group, and c is an integer from 0 to 5, each independently, and d is an integer from 0 to 4, each independently.

3. In Paragraph 2, A novel compound characterized in that the above chemical formula 1 is the following chemical formula 2-1 or 3-1: <Chemical Formula 2-1> <Chemical Formula 3-1> In the above chemical formulas 2-1 and 3-1, L1 and b are identical to the definitions in Chemical Formula 1 above, and R1 is independently a hydrogen or a phenyl group, and R2 is independently a hydrogen or cyano group.

4. In Paragraph 3, A novel compound characterized in that one or more of the above R1s are phenyl groups.

5. In Paragraph 3, A novel compound characterized in that one or more of the above R2s are cyano groups.

6. In Paragraph 1, A novel compound characterized in that the above b is 0 or 1, and when it is 1, L1 is a phenylene group or a naphthylene group.

7. In Paragraph 1, The above naphthylene linker is a novel compound having one of the following structural formulas N-1 to N-10: In the above structural formulas N-1 to N-10, Of the two bonding positions "*", one is a bonding position to L1, and the other is a bonding position to Si.

8. In Paragraph 1, The compound represented by the above chemical formula 1 is a novel compound selected from the group consisting of the following compounds 1 to 196: .

9. First electrode and second electrode; It includes one or more organic layers disposed between the first electrode and the second electrode, and An organic light-emitting device comprising one or more of the above organic layers, wherein the compound of any one of claims 1 to 8.

10. In Paragraph 9, An organic light-emitting device characterized in that the organic layer containing the above compound is an electron injection layer, an electron transport layer, a layer that simultaneously injects and transports electrons, a hole blocking layer, or a charge generation layer.

11. First electrode and second electrode; A plurality of light-emitting parts located between the first electrode and the second electrode; and It includes a charge generation layer located at at least one of two adjacent light-emitting parts; and A tandem organic light-emitting device comprising, wherein one or more of the charge-generating layers comprises an N-type charge-generating layer comprising a compound of any one of claims 1 to 8.

12. In Paragraph 11, A tandem organic light-emitting diode characterized in that the N-type charge generating layer further comprises one or more metals selected from lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), ytterbium (Yb), samarium (Sm), tin (Sn), copper (Cu), titanium (Ti), cadmium (Cd), mercury (Hg), lead (Pb), bismuth (Bi), zinc (Zn), iron (Fe), cobalt (Co), nickel (Ni), indium (In), gallium (Ga), thorium (Th), uranium (U), silver (Ag), aluminum (Al), gold (Au), molybdenum (Mo), niobium (Nb), palladium (Pd), platinum (Pt), and europium (Eu), metal compounds, and organic complexes of metals.

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