Novel compound and organic light-emitting device comprising same

Abstract

The present disclosure relates to a novel compound and an organic light-emitting device comprising same, and more particularly, to a novel compound and an organic light-emitting device comprising same, the compound being capable of improving device performance characteristics such as low voltage, high efficiency, and long lifespan, when applied to an organic material layer of an electron transport region, particularly an N-type charge generation layer (N-CGL), an electron transport layer (ETL), or a hole blocking layer (HBL), in an organic light-emitting device.

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, long lifespan, as well as color purity, color stability with respect to changes in current and voltage, and ease of device fabrication are important, so research and development are underway according to each method. The structure of organic light-emitting diodes can be broadly classified into single-emissive structures with one light-emitting part and stacked-emissive structures with two or more light-emitting parts. Among these, the tandem structure, which stacks two or more light-emitting parts, is mainly adopted for organic light-emitting diodes with a long lifespan.

[0006] Meanwhile, organic light-emitting diodes with such a tandem structure are equipped with a charge generation layer (CGL) between the light-emitting layers to double the current efficiency generated in the light-emitting layer and facilitate charge distribution. This charge generation layer is a layer that generates charges, namely electrons and holes, and performs functions such as preventing the driving voltage from rising by doubling the current efficiency generated in the light-emitting layer and facilitating charge distribution. This charge generation layer is generally composed of a P-type charge generation layer and an N-type charge generation layer.

[0007] Currently, regarding compounds applied to charge generation layers, particularly N-type charge generation layers, there is a growing demand for the development of high-performance devices, necessitating the development of new materials capable of exhibiting high performance such as low voltage, high efficiency, and long lifespan. Furthermore, N-type charge generation layers typically have a form in which a dopant, such as lithium (Li), is doped into a host composed of organic compounds. Since lithium has relatively low resistance among metallic materials, N-type charge generation layers using it as a dopant exhibit low resistance, leading to lateral leakage current (LLC). This causes unnecessary light emission to adjacent subpixels, degrading the display quality of the device. Additionally, charge distribution to the P-type charge generation layer is not smooth, resulting in charge imbalance in the light-emitting layer, which in turn increases the progressive driving voltage and reduces lifespan; therefore, it is required to improve these aspects.

[0008] The present invention aims to provide a novel compound capable of improving device performance, such as low voltage, high efficiency, and long lifespan, when applied to organic layers in the electron transport region of an organic light-emitting device, such as an N-type charge generation layer (N-CGL), an electron transport layer (ETL), and a hole blocking layer (HBL). In particular, the invention aims to provide a novel compound capable of improving not only low voltage, high efficiency, and long lifespan but also the display quality and reliability of the device when applied as a host for an N-type charge generation layer, and an organic light-emitting device containing the same.

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

[0010] In order to solve the aforementioned problem,

[0011] In one embodiment, the present invention provides a novel compound represented by the following chemical formula 1.

[0012]

[0013] In the above chemical formula 1,

[0014] Ar1 is the above structural formula 1, and

[0015] R1 is each independently hydrogen, deuterium, halogen group, cyano group, nitro group, nitrile group, hydroxyl group, thiol 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 C3–C30 cycloalkenyl group, substituted or unsubstituted C2–C50 heterocycloalkenyl 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 Selected from the group consisting of an aryloxy group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C1-C30 thio group, a substituted or unsubstituted C1-C30 amine group, a substituted or unsubstituted C1-C30 silyl group, and a substituted or unsubstituted C1-C30 phosphine oxide group, and adjacent ones may bond with each other to form a substituted or unsubstituted ring.

[0016] L1 and L2 are each independently substituted or unsubstituted C6–C30 arylene groups or substituted or unsubstituted C2–C30 heteroarylene groups, and

[0017] m and n are each independently integers from 0 to 2, and

[0018] In the above structural formula 1,

[0019] R2 is independently hydrogen or deuterium, one of which is a position bonded to L2.

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

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

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

[0023] A tandem organic light-emitting diode comprising the novel compound described above is provided.

[0024] The novel compound of the present invention is an electron-rich SP 2 It is a compound formed by combining 1,10-phenanthroline containing two nitrogen (N) atoms in hybrid orbitals and chrysene, which has high electron mobility and excellent electron transport capability, and has excellent thermal stability and improved carrier mobility. As a result, when applied to organic layers in electron transport regions of organic light-emitting devices such as N-type charge generation layer (N-CGL), electron transport layer (ETL), and hole blocking layer (HBL), it is possible to improve device performance such as low voltage, high efficiency, long lifespan, and color purity.

[0025] In particular, when applied as a host for an N-type charge generation layer, it is possible to achieve low voltage, high efficiency, and long lifespan, as well as minimize the occurrence of LLC and facilitate charge distribution between the P-type charge generation layer and its adjacent layers, thereby improving the display quality and reliability of the device. Furthermore, by binding to dopants of the N-type charge generation layer, such as lithium (Li) and ytterbium (Yb), to form a smooth gap state, it is possible to prevent the phenomenon of dopants moving to adjacent layers, such as the P-type charge generation layer. Additionally, by facilitating electron transfer from the N-type charge generation layer to its adjacent layers through the formed gap state, the efficiency and lifespan of the device can be improved. Moreover, it is possible to mitigate the problem of increased driving voltage that occurs when electrons injected into the N-type charge generation layer move to the adjacent layer due to the LUMO energy level difference between the N-type charge generation layer and its adjacent layer.

[0026] In addition, the compound of the present invention has a low RE value (reorganization energy) below a certain level and satisfies a ratio of hole-to-electron mobility constants close to 1, thereby having effects such as increasing the efficiency of the device.

[0027] The above effects and additional effects are described in detail below.

[0028] 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.

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

[0032] 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.

[0033] 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 in which two phenyl groups are connected. That is, the biphenyl group corresponds to an aryl group and simultaneously corresponds to a substituent with two phenyl groups connected, and simultaneously corresponds to an aryl group substituted with one phenyl group.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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, more specifically 6 to 30, and even more specifically 6 to 20.

[0046] In the present specification, a 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, etc., and if two or more heteroatoms are included, the heteroatoms may be the same or different from each other. Such a heteroaryl group may be a monocyclic or 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, more specifically 2 to 30, and even more specifically 2 to 20.

[0047] 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, but is not limited thereto.

[0048] 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.

[0049] In this specification, * or in the chemical formula or structural formula indicates the joint location.

[0050] In this specification, the same symbols within a single chemical formula or structural formula may be the same or different from each other.

[0051] In the present specification, when ranges such as "C2 to C50" or "integers from 0 to 7" are described, they may be reduced to various ranges within the described range even without special description, and this is 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.

[0052] In this specification, interaction with a dopant may mean that an organic compound in an N-type charge generation layer binds to a dopant comprising a metal element such as an alkali metal, alkaline earth metal, rare earth metal, or lanthanum metal, and according to one embodiment, may include the meaning of the organic compound and the dopant binding or coordinating to form a gap state. Smooth interaction with a dopant in an organic compound applied to an N-type charge generation layer acts as an important factor in improving the performance of a tandem device.

[0053] In this specification, 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).

[0054] In this specification, k et (e) The value is the electron mobility constant, and k et(h) is the hole mobility constant, and k is the ratio of the hole and electron mobility constants. et (e) / k et (h) can be calculated according to Equation 1 below.

[0055]

[0056] In Equation 1 above, 8.6173324*10⁻⁵ (eV / (degree·K)) is the Boltzmann constant.

[0057] In this specification, D means Deuterium, which is deuterium.

[0058] The present invention will be described in detail below.

[0059] The present invention relates to a novel compound and an organic light-emitting device containing the same.

[0060] Specifically, the novel compound of the present invention is represented by the following chemical formula 1.

[0061]

[0062] In the above chemical formula 1,

[0063] Ar1 is the above structural formula 1, and

[0064] R1 is each independently hydrogen, deuterium, halogen group, cyano group, nitro group, nitrile group, hydroxyl group, thiol 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 C3–C30 cycloalkenyl group, substituted or unsubstituted C2–C50 heterocycloalkenyl 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 Selected from the group consisting of an aryloxy group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C1-C30 thio group, a substituted or unsubstituted C1-C30 amine group, a substituted or unsubstituted C1-C30 silyl group, and a substituted or unsubstituted C1-C30 phosphine oxide group, and adjacent ones may bond with each other to form a substituted or unsubstituted ring.

[0065] L1 and L2 are each independently substituted or unsubstituted C6–C30 arylene groups or substituted or unsubstituted C2–C30 heteroarylene groups, and

[0066] m and n are each independently integers from 0 to 2, and

[0067] In the above structural formula 1,

[0068] R2 is independently hydrogen or deuterium, one of which is a position bonded to L2.

[0069] According to one embodiment of the present invention, the substituent in the case of being substituted in the definition of 'substituted or unsubstituted' may be composed of one or more selected from deuterium, halogen group, cyano group, nitro group, nitrile group, hydroxyl group, thiol group, -CF3, -CD3, C1-C30 alkyl group, C3-C30 cycloalkyl group, C1-C30 heterocycloalkyl group, C1-C30 silyl group, C6-C30 aryl group, and C2-C30 heteroaryl group, and according to one embodiment, deuterium, halogen group, cyano group, nitro group, nitrile group, hydroxyl group, thiol group, -CF3, -CD3, methyl group, ethyl group, t-butyl group, adamantyl group, norbornene group, cyclohexyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, It may consist of one or more selected from phenanthrene group, pyrene group, fluoranthene group, clacene group, anthracene group, benzoanthracene group, benzophenanthrene group, dimethylfluorene group, diphenylfluorene group, spirobifluorene group, trimethylsilyl group, triphenylsilyl group, silol group, pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinazolin group, naphthiridine group, benzofuran group, dibenzofuran group, benzothiophen group, dibenzothiophen group, benzoxazole group, benzothiazole group, carbazole group, and phenanthroline group, but is not particularly limited thereto.

[0070] The novel compound of the present invention has a structure in which 1,10-phenanthroline and a clacene group are combined, and specifically, the clacene group is attached to a position right next to the nitrogen (N) of 1,10-phenanthroline, and the clacene group is located at the terminal end because no substituent other than hydrogen or deuterium is attached to the clacene group.

[0071] According to one embodiment of the present invention, the formula 1 may be represented by any one of the following formulas 1-1 to 1-5. The following formulas 1-2 to 1-5 represent cases in which adjacent R1s in formula 1 are bonded to each other to form a substituted or unsubstituted benzene ring.

[0072]

[0073]

[0074] In the above chemical formulas 1-1 to 1-5, Ar1, L1, L2, m, and n are the same as their definitions in chemical formula 1, and

[0075] R1 is each independently hydrogen, deuterium, halogen group, cyano group, nitro group, nitrile group, hydroxyl group, thiol 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 C3–C30 cycloalkenyl group, substituted or unsubstituted C2–C50 heterocycloalkenyl 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 It may be selected from the group consisting of an aryloxy group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C1-C30 thio group, a substituted or unsubstituted C1-C30 amine group, a substituted or unsubstituted C1-C30 silyl group, and a substituted or unsubstituted C1-C30 phosphine oxide group.

[0076] Meanwhile, according to one embodiment of the present invention, any one or more of R1 may not be hydrogen. Specifically, when R1 is not hydrogen, each may independently be deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heterocycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heteroaryl group, and when substituted, the substituent may be deuterium.

[0077] According to one embodiment, the non-hydrogen R1 may each independently be deuterium, -CD3, methyl group, ethyl group, t-butyl group, adamantyl group, norbornene group, cyclohexyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, phenanthrene group, pyrene group, fluoranthene group, clacene group, anthracene group, benzoanthracene group, benzophenanthrene group, dimethylfluorene group, diphenylfluorene group, spirobifluorene group, trimethylsilyl group, triphenylsilyl group, silol group, pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinazolin group, naphthiridine group, benzofuran group, benzothiophen group, dibenzofuran group, dibenzothiophen group, benzoxazole group, or benzothiazole group. There are, and one or more deuterium atoms may be additionally substituted. However, it is not specifically limited to this. In this way, when one or more of R1 are not hydrogen, the structural and thermal stability may be relatively superior compared to the case where all of R1 are hydrogen, and it may be desirable to lower the driving voltage and improve the lifespan.

[0078] More specifically, the above chemical formula 1 can be represented by the following chemical formula 2. As such, R1 at the position immediately adjacent to the nitrogen (N) of 1,10-phenanthroline may not be hydrogen.

[0079]

[0080] In the above Chemical Formula 2, Ar1, L1, L2, m, and n are the same as their definitions in the above Chemical Formula 1, and

[0081] R1 is each independently a deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heterocycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heteroaryl group, and adjacent ones may bond with each other to form a substituted or unsubstituted ring, and specific examples of such R1 are the same as those described above.

[0082] o can be an integer from 0 to 6, specifically an integer from 0 to 4, further an integer from 0 to 3, further an integer from 0, 1, or 2.

[0083] According to one embodiment, the above chemical formula 1 can be represented by the following chemical formula 3.

[0084]

[0085] In the above chemical formula 3, Ar1, L1, L2, m, and n are the same as the definitions in the above chemical formula 1.

[0086] Meanwhile, according to one embodiment of the present invention, the structural formula 1 may be represented as one of the following structural formulas 1-1 to 1-6.

[0087]

[0088]

[0089] In the above structural formulas 1-1 to 1-6, R2 is independently hydrogen or deuterium, and * is a position bonded to L2.

[0090] According to one embodiment of the present invention, all of R2 may be hydrogen, or at least one may be deuterium. Specifically, all of R2 may be hydrogen, 1 to 10 of R2 may be deuterium, or all of R2 may be deuterium. When deuterium is substituted, low voltage and long lifespan of the device can be expected.

[0091] According to the foregoing, the above structural formula 1 may be any one of the following structural formulas.

[0092]

[0093] Meanwhile, according to one embodiment of the present invention, L1 and L2 may each be independently substituted or unsubstituted C6-C25 arylene groups or substituted or unsubstituted C2-C25 heteroarylene groups, more specifically may be substituted or unsubstituted C6-C20 arylene groups or substituted or unsubstituted C2-C20 heteroarylene groups, and even more specifically may be substituted or unsubstituted C6-C15 arylene groups or substituted or unsubstituted C2-C15 heteroarylene groups, and in the case of substitution, the substituents are omitted as they are as described above.

[0094] According to one embodiment, L1 and L2 may each independently be a phenylene group, a naphthylene group, a biphenylene group, a terphenylene group, a phenanthrenylene group, a pyrenylene group, a fluoranthenylene group, a chrysenylene group, anthracenylene group, a benzoanthracenylene group, a benzophenanthrenylene group, a dimethylfluorenylene group, a diphenylfluorenylene group, a spirobifluorenylene group, a pyridinylene group, a pyrimidinylene group, a pyridazinylene group, a pyrazinylene group, a triazinylene group, a quinolilene group, an isoquinolilene group, a quinazolilene group, a naphthiridinylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzoxazolilene group, or a benzothiazolylene group, wherein one or more Deuterium may be additionally substituted, but is not specifically limited thereto. These L1s, L2s, or L1 and L2s may be the same or different from each other.

[0095] According to a more specific embodiment, L1 and L2 may each independently be one of the following structural formulas. In the following structural formulas, * indicates a bonding position.

[0096]

[0097] According to a more specific embodiment, L1 and L2 may each independently be one of the following structural formulas. When a deuterium-substituted linker is applied, an improvement in the lifespan of the device can be expected.

[0098]

[0099] Meanwhile, according to one embodiment of the present invention, m and n may each be independently 0, 1, or 2. Specifically, m+n may be 1 or greater, and a structure in which 1,10-phenanthroline and clacene groups are combined by at least one linker may be preferable in that it can lower the driving voltage and improve the lifespan. More specifically, m+n may be an integer from 1 to 3, and even more specifically, may be 1 or 2.

[0100] Meanwhile, according to one embodiment of the present invention, the novel compound of the present invention may include one or more deuterium atoms. When deuterium is substituted, low voltage and a long lifespan of the device can be expected. Specifically, the novel compound of the present invention may satisfy one or more of the conditions 1) to 3) below in the above chemical formula 1, and more specifically, may satisfy one or both of conditions 2) and 3).

[0101] 1) At least one of R1 is deuterium or contains deuterium.

[0102] 2) At least one of the R2 is deuterium.

[0103] 3) m+n is 1 or greater, and at least one of L1 and L2 contains deuterium.

[0104] The novel compound of the present invention may have a deuterium substitution rate of 10% or more, specifically 15% or more, more specifically 20% or more, even more specifically 40% or more, and even more specifically 50% or more. Meanwhile, the deuterium substitution rate (%) can be calculated as (number of protons substituted with deuterium (D) / number of protons before substitution) x 100.

[0105] According to one embodiment of the present invention, the compound of the present invention according to Formula 1 may be selected from the group consisting of the following compounds 1-1 to 1-240, 2-1 to 2-240 and 3-1 to 3-240. The following compounds are merely examples for explaining the present invention and are not limited thereto.

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123] The novel compound of the present invention described so far is preferably applied to an organic layer within an organic light-emitting diode (OLED) in which an electron-transporting material is applied. In particular, when applied to a charge generation layer (CGL) in a tandem-type organic light-emitting diode, especially to an N-type charge generation layer (N-CGL), it can exhibit effects such as increased efficiency, reduced driving voltage, and extended lifespan. 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 hole blocking layer (HBL), and a layer that simultaneously performs electron injection and transport, where a compound with excellent electron mobility must be applied.

[0124] 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.

[0125] 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.

[0126] The organic light-emitting diode and tandem organic light-emitting diode according to the present invention will be described in more detail below.

[0127] 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 known organic layers constituting a light-emitting part, such as a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL).

[0128] The hole injection layer (HIL) is a layer that injects holes from the electrode, and as the hole injection material, a compound that has the ability to transport holes, has an excellent hole injection effect at the anode and an excellent hole injection effect on the emitting layer or emitting material, prevents the movement of excitons generated in the emitting layer to the electron injection layer or electron injection material, and also has excellent thin film formation ability is preferred.

[0129] 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.

[0130] The emissive layer (EML) is a layer that emits light through the recombination of electrons and holes. As the emissive material, it 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 the electron transport layer, respectively, and a material with good quantum efficiency for fluorescence or phosphorescence is preferred. Specifically, the emissive layer may include a host and a dopant.

[0131] 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.

[0132] 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.

[0133] Meanwhile, the organic layer may further include a hole blocking layer (hole defense layer, hole blocking layer, hole blocking layer, or 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 intruding into the electron transport layer. As the hole blocking layer is also one of the layers in the electron transport region, a material capable of transporting electrons is suitable.

[0134] Meanwhile, the organic layer may further include a layer that simultaneously performs electron injection and transport.

[0135] Among the organic layers of such organic light-emitting devices, the novel compound according to Formula 1 of the present invention is a material with excellent electron transport capability and is preferably applied to one or more of the electron injection layer, electron transport layer, hole blocking layer, and layers that simultaneously inject and transport electrons in the electron transport region.

[0136] Meanwhile, the configuration of the organic light-emitting device may 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 stacked. In the case of such a tandem structure, in addition to the organic layers mentioned above, a charge generation layer (CGL) that controls the balance of charges may be further included as one of the organic layers, and such charge generation layers may be located at one or more locations between two adjacent light-emitting parts. Generally, the charge generation layer is composed of multiple layers including an N-type charge generation layer (N-CGL) that acts to inject electrons and a P-type charge generation layer (P-CGL) that acts to inject holes, but is not limited thereto and may be composed of a single layer.

[0137] 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. The N-type charge generation layer may be composed of an organic layer doped with a dopant such as a metal, and specifically may be composed of a host and a dopant. In this case, the novel compound of the present invention may be applied as the host.

[0138] Meanwhile, the dopant may be a material containing a metal element, and specifically, may be one or more of a metal, a metal compound, and an organic complex of a metal. Here, the metallic elements may be, in detail, one or more 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). According to one embodiment, it may be an alkali metal, an alkaline earth metal, a rare earth metal, a lanthanum metal, etc., and as a specific embodiment, it may be lithium or ytterbium. The ratio of such dopant may 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 element.

[0139] The present invention will be explained in more detail below with reference to synthetic examples, embodiments, experimental examples, etc. However, the following contents do not limit the scope of the present invention.

[0140] Synthesis Examples 1 to 15: Synthesis of Compounds

[0141] [Synthesis Example 1] Synthesis of Compound 1-1

[0142]

[0143] 6-bromochrysene (79 g, 257 mmol) and (4-chlorophenyl)boronic acid (48.26 g, 309 mmol) were added to a round-bottom flask. Pd(PPh3)4 (8.92 g, 8 mmol) and calcium carbonate (106.63 g, 772 mmol) were added, and the mixture was stirred under reflux in a mixture of 800 ml of 1,4-Dioxane and 240 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-1(1) (82 g, 94%) was obtained by purification and recrystallization by column chromatography.

[0144] LC / MS: [(M+H)+]= 339.83

[0145]

[0146] 6-(4-chlorophenyl)chrysene (80 g, 236 mmol) and Bis(pinacolato)diboron (71.95 g, 283 mmol) were added to a round-bottom flask. Tris(dibenzylideneacetone)dipalladium(0) (6.49 g, 7 mmol) and Sphos (6.79 g, 17 mmol) were added, and the mixture was stirred under reflux in 800 ml of 1,4-Dioxane mixed solution. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-1(2) (98 g, 96%) was obtained by purification and recrystallization by column chromatography.

[0147] LC / MS: [(M+H)+]= 431.35

[0148]

[0149] 2-bromo-1,10-phenanthroline (40 g, 154 mmol) and 2-(4-(chrysen-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (79.72 g, 185 mmol) were added to a round-bottom flask. Pd(PPh3)4 (5.35 g, 5 mmol) and calcium carbonate (64.01 g, 463 mmol) were added, and the mixture was stirred under reflux in a mixed solution of 400 ml of 1,4-dioxane and 120 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-1 (56 g, 75%) was obtained by purification and recrystallization using column chromatography.

[0150] LC / MS: [(M+H)+]= 483.18

[0151] [Synthesis Example 2] Synthesis of Compound 1-2

[0152]

[0153] 2-bromo-1,10-phenanthroline (35 g, 135 mmol) and 2-(3-(chrysen-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69.76 g, 162 mmol) were added to a round-bottom flask. Pd(PPh3)4 (4.68 g, 4 mmol) and calcium carbonate (56.01 g, 405 mmol) were added, and the mixture was stirred under reflux in a mixture of 350 ml of 1,4-dioxane and 105 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-2 (42 g, 64%) was obtained by purification and recrystallization using column chromatography.

[0154] LC / MS: [(M+H)+]= 483.18

[0155] [Synthesis Example 3] Synthesis of Compounds 1-3

[0156]

[0157] 2-bromo-1,10-phenanthroline (35 g, 135 mmol) and 2-(2-(chrysen-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69.76 g, 162 mmol) were added to a round-bottom flask. Pd(PPh3)4 (4.68 g, 4 mmol) and calcium carbonate (56.01 g, 405 mmol) were added, and the mixture was stirred under reflux in a mixture of 350 ml of 1,4-dioxane and 105 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-3 (36 g, 55%) was obtained by purification and recrystallization using column chromatography.

[0158] LC / MS: [(M+H)+]= 483.18

[0159] [Synthesis Example 4] Synthesis of Compound 1-12

[0160]

[0161] 2-bromo-9-phenyl-1,10-phenanthroline (35 g, 104 mmol) and 42-(4-(chrysen-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (53.92 g, 125 mmol) were added to a round-bottom flask. Pd(PPh3)4 (3.62 g, 3 mmol) and calcium carbonate (43.29 g, 313 mmol) were added, and the mixture was stirred under reflux in a mixture of 350 ml of 1,4-dioxane and 105 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-12 (42 g, 72%) was obtained by purification and recrystallization using column chromatography.

[0162] LC / MS: [(M+H)+]= 559.68

[0163] [Synthesis Example 5] Synthesis of Compound 1-13

[0164]

[0165] 2-bromo-9-phenyl-1,10-phenanthroline (35 g, 104 mmol) and 2-(3-(chrysen-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (49.43 g, 115 mmol) were added to a round-bottom flask. Pd(PPh3)4 (3.62 g, 3 mmol) and calcium carbonate (43.29 g, 313 mmol) were added, and the mixture was stirred under reflux in a mixture of 305 ml of 1,4-dioxane and 105 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-13 (48 g, 82%) was obtained by purification and recrystallization using column chromatography.

[0166] LC / MS: [(M+H)+]= 559.68

[0167] [Synthesis Example 6] Synthesis of Compound 1-15

[0168]

[0169] 2-bromo-9-phenyl-1,10-phenanthroline (30 g, 89 mmol) and 2-(4-(chrysen-6-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (47.30 g, 98 mmol) were added to a round-bottom flask. Pd(PPh3)4 (3.10 g, 3 mmol) and calcium carbonate (37.11 g, 268 mmol) were added, and the mixture was stirred under reflux in a mixture of 300 ml of 1,4-dioxane and 90 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-15 (30 g, 65%) was obtained by purification and recrystallization using column chromatography.

[0170] LC / MS: [(M+H)+]= 609.23

[0171] [Synthesis Example 7] Synthesis of Compound 1-16

[0172]

[0173] 2-bromo-9-phenyl-1,10-phenanthroline (30 g, 89 mmol) and 2-(4-(chrysen-6-yl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (47.30 g, 98 mmol) were added to a round-bottom flask. Pd(PPh3)4 (3.10 g, 3 mmol) and calcium carbonate (37.11 g, 268 mmol) were added, and the mixture was stirred under reflux in a mixture of 300 ml of 1,4-dioxane and 90 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-16 (30 g, 65%) was obtained by purification and recrystallization using column chromatography.

[0174] LC / MS: [(M+H)+]= 609.23

[0175] [Synthesization Example 8] Synthesis of Compound 1-132

[0176]

[0177] 2-bromo-9-phenyl-1,10-phenanthroline (10 g, 30 mmol) and 2-(3'-(chrysen-6-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (18.13 g, 36 mmol) were added to a round-bottom flask. Pd(PPh3)4 (1.03 g, 1 mmol) and calcium carbonate (12.37 g, 89 mmol) were added, and the mixture was stirred under reflux in a mixture 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 1-132 (13 g, 68.63%) was obtained by purification and recrystallization using column chromatography.

[0178] LC / MS: [(M+H)+]= 574.78

[0179] [Synthesization Example 9] Synthesis of Compound 1-212

[0180]

[0181] 2-bromo-9-phenyl-1,10-phenanthroline (14 g, 42 mmol) and 22-(4-(chrysen-6-yl-d11)phenyl-2,3,5,6-d4)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (22.33 g, 50 mmol) were added to a round-bottom flask. Pd(PPh3)4 (1.45 g, 1 mmol) and calcium carbonate (17.32 g, 125 mmol) were added, and the mixture was stirred under reflux in a mixed solution of 140 ml of 1,4-Dioxane and 52 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-212 (13 g, 58.21%) was obtained by purification and recrystallization using column chromatography.

[0182] LC / MS: [(M+H)+]= 635.78, Deuterium Substitution Rate = 57.6%

[0183] [Synthesization Example 10] Synthesis of Compound 1-214

[0184]

[0185] 2-bromo-9-phenyl-1,10-phenanthroline (11 g, 33 mmol) and 2-(4-(chrysen-6-yl)phenyl-2,3,5,6-d4)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (17.11 g, 39 mmol) were added to a round-bottom flask. Pd(PPh3)4 (1.14 g, 1 mmol) and calcium carbonate (13.61 g, 98 mmol) were added, and the mixture was stirred under reflux in a mixed solution of 110 ml of 1,4-dioxane and 33 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-214 (14 g, 75.79%) was obtained by purification and recrystallization using column chromatography.

[0186] LC / MS: [(M+H)+]= 563.71, deuterium substitution rate = 15.3%

[0187] [Synthesization Example 11] Synthesis of Compound 1-216

[0188]

[0189] 2-bromo-9-phenyl-1,10-phenanthroline (15 g, 45 mmol) and 2-(4-(chrysen-6-yl-d11)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (23.70 g, 54 mmol) were added to a round-bottom flask. Pd(PPh3)4 (1.55 g, 1 mmol) and calcium carbonate (18.55 g, 134 mmol) were added, and the mixture was stirred under reflux in a mixture of 150 ml of 1,4-dioxane and 45 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-216 (20 g, 79.42%) was obtained by purification and recrystallization using column chromatography.

[0190] LC / MS: [(M+H)+]= 570.75, Deuterium Substitution Rate = 42.3%

[0191] [Synthesization Example 12] Synthesis of Compound 1-220

[0192]

[0193] 2-bromo-9-phenyl-1,10-phenanthroline (20 g, 60 mmol) and 2-(3-(chrysen-6-yl-d11)phenyl-2,4,5,6-d4)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (31.89 g, 72 mmol) were added to a round-bottom flask. Pd(PPh3)4 (2.07 g, 2 mmol) and calcium carbonate (24.74 g, 179 mmol) were added, and the mixture was stirred under reflux in a mixture of 200 ml of 1,4-dioxane and 60 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-220 (30 g, 87.61%) was obtained by purification and recrystallization using column chromatography.

[0194] LC / MS: [(M+H)+]= 574.78, Deuterium Substitution Rate = 57.6%

[0195] [Synthesization Example 13] Synthesis of Compound 1-224

[0196]

[0197] 2-bromo-9-phenyl-1,10-phenanthroline (20 g, 60 mmol) and 2-(3-(chrysen-6-yl)phenyl-2,4,5,6-d4)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (31.10 g, 72 mmol) were added to a round-bottom flask. Pd(PPh3)4 (2.07 g, 2 mmol) and calcium carbonate (24.74 g, 179 mmol) were added, and the mixture was stirred under reflux in a mixture of 200 ml of 1,4-dioxane and 60 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-224 (28 g, 83.40%) was obtained by purification and recrystallization using column chromatography.

[0198] LC / MS: [(M+H)+]= 563.71, deuterium substitution rate = 15.3%

[0199] [Synthesization Example 14] Synthesis of Compound 1-226

[0200]

[0201] 2-bromo-9-phenyl-1,10-phenanthroline (20 g, 60 mmol) and 2-(3-(chrysen-6-yl-d11)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (31.61 g, 72 mmol) were added to a round-bottom flask. Pd(PPh3)4 (2.07 g, 2 mmol) and calcium carbonate (24.74 g, 179 mmol) were added, and the mixture was stirred under reflux in a mixture of 200 ml of 1,4-dioxane and 60 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-226 (28 g, 82.37%) was obtained by purification and recrystallization using column chromatography.

[0202] LC / MS: [(M+H)+]= 570.75, Deuterium Substitution Rate = 42.3%

[0203] [Synthesization Example 15] Synthesis of Compound 1-239

[0204]

[0205] 2-bromo-1,10-phenanthroline (20 g, 77 mmol) and 2-(chrysen-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30.08 g, 85 mmol) were added to a round-bottom flask. Pd(PPh3)4 (2.68 g, 2 mmol) and calcium carbonate (32.00 g, 232 mmol) were added, and the mixture was stirred under reflux in a mixture of 200 ml of 1,4-dioxane and 60 ml of H2O. Once the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-239 (20 g, 63.7%) was obtained by purification and recrystallization using column chromatography.

[0206] LC / MS: [(M+H)+]= 407.15

[0207] Meanwhile, although synthetic examples of exemplary compounds according to the present invention have been described above, they are all based on the Miyaura boration reaction, Suzuki cross-coupling, Buchwald-Hartwig cross-coupling reaction, and Friedlander synthesis reaction, and it will be easily understood by those skilled in the art that even if other substituents defined in Formula 1 are bonded in addition to the substituents specified in the specific synthetic examples, the above reaction proceeds.

[0208] Fabrication of Tandem Organic Light Emitting Diodes: Use of Li Dopants

[0209] [Comparison Example 1]

[0210] After forming an anode by patterning an ITO substrate to have a light-emitting area of ​​2mm x 2mm, the substrate was cleaned with isopropyl alcohol and UV ozone, respectively. Subsequently, the ITO substrate was mounted in the holder of a vacuum deposition equipment, and the vacuum level was set to 1x10 -7Pressure was applied to reach torr. Plasma treatment was carried out for 3 minutes under an N2 atmosphere.

[0211] A first hole injection layer (HIL) was formed by vacuum depositing a HAT-CN compound to a thickness of 5 nm on a substrate, and a first hole transport layer (HTL) was formed by vacuum depositing an NPB material to a thickness of 20 nm on top of it. Subsequently, a green first emissive layer (EML) with a thickness of 20 nm was formed by co-depositing a GH-1 material as a host and a GD-1 material as a dopant at a mass ratio of approximately 10%. A first electron transport layer (ETL) was formed on top of this by vacuum depositing a TmPyPB material to a thickness of 20 nm. On top of this, an N-type charge generation layer (N-CGL) with a thickness of 10 nm was formed by co-depositing a BPhen material as a host and a lithium (Li) dopant at a mass ratio of approximately 2%. A P-type charge generation layer (P-CGL) was formed on top of this by vacuum depositing a HAT-CN material to a thickness of 5 nm. This layer is also utilized as a second hole injection layer (HIL). Subsequently, a second hole transport layer (HTL) was formed by vacuum depositing NPB material to a thickness of 50 nm. On top of this, a green second emissive layer (EML) 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%. Subsequently, a second electron transport layer (ETL) with a thickness of 20 nm was formed by co-depositing TmPyPB material as the host and Liq material as the dopant at a mass ratio of approximately 33%. An electron injection layer (EIL) was formed on top of this by vacuum depositing LiF material to a thickness of 1 nm. The fabrication of the tandem organic light-emitting diode was completed by vacuum depositing Al to a thickness of 50 nm as the cathode. The structures of the HAT-CN, NPB, GH-1, GD-1, TmPyPB, BPhen, and Liq materials used here are shown in Table 1 below.

[0212]

[0213] [Comparison Examples 2 to 10]

[0214] A tandem organic light-emitting diode was fabricated in the same manner as Comparative Example 1, except that Comparative Compounds 1 to 9 of Table 2 below were used instead of BPhen as the host material for the N-type charge generation layer.

[0215]

[0216] [Examples 1 to 15]

[0217] A tandem 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 15 were used instead of BPhen as the host material for the N-type charge generation layer.

[0218] Experimental Example 1. Evaluation of Tandem Organic Light Emitting Diodes

[0219] The performance of the previously fabricated tandem organic light-emitting diode was evaluated. Specifically, the driving voltage, luminous efficiency, and lifetime (T95), which is the time to reach 95% of the initial brightness, were measured at a current density of 10 mA / cm2. The measurement results are shown in Table 3 below.

[0220]

[0221] As shown in Table 3 above, it was confirmed that the driving voltage of the embodiments using the compounds of the present invention was lower and the efficiency and lifespan were further improved compared to the comparative examples using BPhen and comparative compounds as the host material of the N-type charge generation layer.

[0222] Specifically, it was confirmed that device performance was improved when comparative compounds were used in which condensed aryl groups, such as clacene groups, pyrene groups, and triphenylene groups, were bonded to 1,10-phenanthroline compared to BPhen, a conventionally known 1,10-phenanthroline-based material. However, there are structural differences compared to the compounds of the present invention, in that comparative compounds 1 and 2 contain clacene groups but their bonding position is not located right next to the nitrogen (N) of 1,10-phenanthroline; comparative compounds 3 and 4 have non-clacene condensed aryl groups, such as pyrene groups and triphenylene groups, bonded; and comparative compounds 5 to 9 have clacene groups bonded right next to the nitrogen (N) of 1,10-phenanthroline but the clacene groups are not located at the terminal end but are positioned as linkers substituted with bulky substituents. Consequently, there were limitations in performance improvement in driving voltage, efficiency, and lifespan compared to the compounds of the present invention. In the case of Comparative Compound 1, the LUMO value is -1.57 eV, which is a shallow energy level and is undesirable in terms of energy barrier, so electron transfer to the adjacent electron transport layer may not be smooth. In the case where the clacene group is located as a linker rather than at the terminal end, as in Comparative Compounds 5 to 9, problems with structural planarity and conjugation may occur, which may cause problems with crystallization and hinder electron movement, which may also cause problems during the deposition process.

[0223] Experimental Example 2. Measurement of RE Value and Ratio of Hole and Electron Mobility Constants

[0224] RE values ​​(reorganization energy) of the previously synthesized compounds of the present invention and comparative compounds, and k, the ratio of hole and electron mobility constants. et (e) / k et (h) was calculated at the DFT b3lyp / 6-31g(d) level using the Gaussian 09 program. The results are shown in Table 4 below.

[0225]

[0226] As shown in Table 4, the compounds of the present invention have relatively lower RE values ​​than the comparative compounds, and at the same time k et (e) / k et It was confirmed that the (h) value was close to 1. As such, since the RE value of the compounds of the present invention is relatively low, charge loss is minimal during the charge recombination process, allowing for smooth electron movement. Furthermore, electrons are effectively transferred between molecules, which is consequently effective in terms of improving device efficiency. At the same time, k close to 1 et (e) / k et It is desirable in that the electron and hole mobility values ​​(h) approximate each other, allowing for even distribution within the organic layer, and consequently improving device characteristics such as current efficiency by increasing charge recombination efficiency.

[0227] The novel compound of the present invention has a structure in which 1,10-phenanthroline and a clacene group are combined. Specifically, the structural features include the fact that the clacene group is bonded to a position right next to the nitrogen (N) of 1,10-phenanthroline, and that the clacene group is located at the outermost end because no substituent other than hydrogen or deuterium is bonded to the clacene group. This results in high electron mobility, excellent electron transport capability, superior thermal stability, and improved carrier mobility, thereby enabling the improvement of device performance such as low voltage, high efficiency, long lifespan, and color purity. In particular, when applied as a host for an N-type charge generation layer, it is possible to achieve low voltage, high efficiency, and long lifespan, as well as minimize the occurrence of LLC and facilitate charge distribution between the P-type charge generation layer and its adjacent layers, thereby consequently improving the display quality and reliability of the device. Furthermore, by binding to dopants in the N-type charge generation layer, such as lithium (Li) and ytterbium (Yb), to form a smooth gap state, the phenomenon of dopants moving to adjacent layers, such as the P-type charge generation layer, can be prevented. Additionally, by facilitating electron transfer from the N-type charge generation layer to the adjacent layer through the formed gap state, the efficiency and lifespan of the device can be improved. Moreover, the problem of increased driving voltage caused by the LUMO energy level difference between the N-type charge generation layer and the adjacent layer, which occurs when electrons injected into the N-type charge generation layer move to the adjacent layer, can be mitigated. Furthermore, the compound of the present invention has a low RE value (reorganization energy) below a certain level and satisfies a ratio of hole-to-electron mobility constants close to 1, thereby facilitating electron movement and consequently increasing the efficiency of the device.

Claims

1. A novel compound represented by the following chemical formula 1: In the above chemical formula 1, Ar1 is the above structural formula 1, and R1 is each independently hydrogen, deuterium, halogen group, cyano group, nitro group, nitrile group, hydroxyl group, thiol 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 C3–C30 cycloalkenyl group, substituted or unsubstituted C2–C50 heterocycloalkenyl 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 Selected from the group consisting of an aryloxy group, a substituted or unsubstituted C2-C30 heteroaryloxy group, a substituted or unsubstituted C1-C30 thio group, a substituted or unsubstituted C1-C30 amine group, a substituted or unsubstituted C1-C30 silyl group, and a substituted or unsubstituted C1-C30 phosphine oxide group, and adjacent ones may bond with each other to form a substituted or unsubstituted ring. L1 and L2 are each independently substituted or unsubstituted C6–C30 arylene groups or substituted or unsubstituted C2–C30 heteroarylene groups, and m and n are each independently integers from 0 to 2, and In the above structural formula 1, R2 is independently hydrogen or deuterium, one of which is a position bonded to L2.

2. In Paragraph 1, A novel compound characterized in that the above chemical formula 1 is represented by the following chemical formula 2: In the above Chemical Formula 2, Ar1, L1, L2, m, and n are the same as their definitions in the above Chemical Formula 1, and R1 is each independently a deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 heterocycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heteroaryl group, and adjacent ones may bond with each other to form a substituted or unsubstituted ring. o is an integer from 0 to 6.

3. In Paragraph 1, A novel compound characterized in that the above structural formula 1 is represented by one of the following structural formulas 1-1 to 1-6: In the above structural formulas 1-1 to 1-6, R2 is independently hydrogen or deuterium, and * is the position connected to the above L2.

4. In Paragraph 3, A novel compound characterized in that the above structural formula 1 is one of the following structural formulas:

5. In Paragraph 1, A novel compound characterized in that the above m+n is 1 or greater.

6. In Paragraph 1, A novel compound characterized in that the above chemical formula 1 satisfies one or more of the following conditions 1) to 3): 1) At least one of R1 is deuterium or contains deuterium. 2) At least one of the R2 is deuterium. 3) m+n is 1 or greater, and at least one of L1 and L2 contains deuterium.

7. In Paragraph 1, A novel compound characterized by a deuterium substitution rate of 10% or more.

8. In Paragraph 1, A novel compound characterized by being selected from the group consisting of the following compounds 1-1 to 1-240, 2-1 to 2-240 and 3-1 to 3-240:

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 characterized in that one or more of the above organic layers comprise a compound according to 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 one or more of an electron injection layer, an electron transport layer, a hole blocking layer, a layer that simultaneously injects and transports electrons, and 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 A tandem organic light-emitting device comprising: a charge generation layer each located at one or more of the locations between two adjacent light-emitting parts; One or more of the charge generation layers include an N-type charge generation layer and a P-type charge generation layer, and A tandem organic light-emitting diode characterized in that the N-type charge generating layer comprises a compound according to any one of claims 1 to 8.

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