Compound and organic light-emitting device containing the same

Abstract

The present invention provides a compound and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of the filing dates of Korean Patent Application No. 10-2018-0142001, filed on November 16, 2018, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2019-0145979, filed on November 14, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0003] The present disclosure relates to compounds and organic light-emitting devices including the same. Background Art

[0004] Generally, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using organic materials. Organic light emitting devices using the organic light emitting phenomenon have characteristics such as wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed, and therefore, many studies have been conducted on them.

[0005] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. The organic material layer often has a multilayer structure including different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of an organic light-emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0006] There is an ongoing need to develop materials for organic materials used in these organic light emitting devices.

[0007] [Prior art literature]

[0008] [Patent Document]

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the invention

[0010] Technical issues

[0011] An object of the present invention is to provide a compound and an organic light-emitting device comprising the same.

[0012] Technical Solution

[0013] In one aspect of the present disclosure, a compound represented by the following Chemical Formula 1 is provided:

[0014] [Chemical formula 1]

[0015]

[0016] Wherein, in Chemical Formula 1,

[0017] X 1 To X 3 are each independently N or CH, provided that X 1 To X 3 At least two of them are N, Y 1 and Y 2 are each independently O or S,

[0018] L is a single bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 heteroarylene, provided that L is bonded to position *1 or position *2,

[0019] Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, and

[0020] R 1 To R 4 are each independently hydrogen; deuterium; halogen; cyano; nitro; amino; silyl; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 1-60 Haloalkyl; substituted or unsubstituted C 1-60 Alkoxy; substituted or unsubstituted C 1-60 Haloalkoxy; substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl; substituted or unsubstituted C 6-60 Aryl; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 heteroaryl, or adjacent substituents are combined with each other to form a C 6-60 Aromatic ring; C 6-60 A non-aromatic ring; or a C 2-60 Heteroaromatic ring.

[0021] In another aspect of the present disclosure, an organic light-emitting device is provided, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layers contain a compound represented by Chemical Formula 1.

[0022] Beneficial Effects

[0023] The compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light-emitting device, and may improve efficiency, achieve low driving voltage, and / or improve lifespan characteristics in the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4 is shown.

[0025] Figure 2 An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4 is shown. DETAILED DESCRIPTION

[0026] Hereinafter, the present disclosure will be described in more detail to help understanding of the present disclosure.

[0027] In this manual, represents a bond to another substituent, and a single bond represents the case where a single atom does not exist in the part represented by L.

[0028] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthio group; arylthio group; alkylsulfonyl group; arylsulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphino group; and heterocyclic group containing at least one of N, O and S atoms, or unsubstituted or substituted with substituents connected by two or more substituents among the substituents exemplified above. For example, "substituents connected by two or more substituents" can be biphenyl. That is, the biphenyl group can also be an aryl group, and can be interpreted as a substituent connected by two phenyl groups.

[0029] As used herein, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40.

[0030] Specifically, the carbonyl group may be a group having the following structural formula, but is not limited thereto.

[0031]

[0032] As used herein, the ester group may have a structure in which the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a group having the following structural formula, but is not limited thereto.

[0033]

[0034] As used herein, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a group having the following structural formula, but is not limited thereto.

[0035]

[0036] As used herein, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0037] As used herein, the boryl group specifically includes a trimethylboryl group, a triethylboryl group, a tert-butyldimethylboryl group, a triphenylboryl group, and a phenylboryl group, but is not limited thereto.

[0038] As used herein, examples of halogen groups include fluorine, chlorine, bromine, and iodine.

[0039] As used herein, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 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-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0040] As used herein, the alkenyl group may be straight or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0041] As used herein, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specific examples thereof include 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., but are not limited thereto.

[0042] As used herein, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, fluorenyl, etc., but are not limited thereto.

[0043] As used herein, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spirocyclic structure. In the case where the fluorenyl group is substituted, etc. However, the structure is not limited thereto.

[0044] As used herein, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl and the like, but are not limited thereto.

[0045] As used herein, the aryl in aralkyl, aralkenyl, alkylaryl and arylamine is the same as the example of the aforementioned aryl. In the present specification, the alkyl in aralkyl, alkylaryl and alkylamine is the same as the example of the aforementioned alkyl. In the present specification, the heteroaryl in heteroarylamine can apply the description of the aforementioned heteroaryl. In the present specification, the alkenyl in the aralkenyl is the same as the example of the aforementioned alkenyl. In the present specification, the description of the aforementioned aryl can be applied, except that the arylene is a divalent group. In the present specification, the description of the aforementioned heteroaryl can be applied, except that the sub-heteroarylene is a divalent group. In the present specification, the description of the aforementioned aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present specification, the description of the aforementioned heteroaryl can be applied, except that the heterocycle is not a monovalent group but is formed by combining two substituents.

[0046] As used herein, an aromatic ring is a fused monocyclic or polycyclic ring in which the entire molecule has aromaticity while containing only carbon as a ring-forming atom. The aromatic ring is not particularly limited, but preferably has 6 to 60 carbon atoms, or 6 to 30 carbon atoms, or 6 to 20 carbon atoms. In addition, examples of aromatic rings include benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, pyrene rings, etc., but are not limited thereto.

[0047] As used herein, non-aromatic rings are fused monocyclic or polycyclic rings in which the entire molecule contains only carbon as ring atoms and has non-aromaticity. The non-aromatic ring is not particularly limited, but preferably has 6 to 60 carbon atoms, or 6 to 30 carbon atoms, or 6 to 20 carbon atoms. In addition, examples of non-aromatic rings include indene rings, fluorene rings, etc., but are not limited thereto. In this regard, indene rings, fluorene rings, etc. are unsubstituted or substituted with one or more substituents, and the types of substituents are mentioned above.

[0048] As used herein, a heteroaromatic ring is a condensed monocyclic or polycyclic ring in which the entire molecule has aromaticity while containing one or more heteroatoms selected from N, O and S as ring-forming atoms in addition to carbon. The heteroaromatic ring is not particularly limited, but preferably has 2 to 60 carbon atoms, or 2 to 30 carbon atoms, or 2 to 20 carbon atoms. In addition, examples of the heteroaromatic ring include a benzofuran ring, a benzothiophene ring, an indole ring, a carbazole ring, etc., but are not limited thereto.

[0049] Meanwhile, in the present disclosure, a compound represented by Chemical Formula 1 is provided. In particular, the compound has a 6-membered heterocyclic group containing two or three N atoms connected to dibenzofuran (when Y 2 When Y is O) / dibenzothiophene (when Y 2 When the compound is used as a host of an organic light-emitting device, the organic light-emitting device exhibits improved efficiency, low driving voltage and / or improved lifespan characteristics.

[0050] However, when a 6-membered heterocyclic group containing two or three N atoms in Chemical Formula 1 is used and connected to dibenzofuran through a linking group L (when Y 2 When Y is O) / dibenzothiophene (when Y 2 When a compound bonded at positions other than *1 and *2 (when L is S) is used as a host of an organic light-emitting device, there is a problem that both the efficiency and life characteristics of the organic light-emitting device are deteriorated. That is, when the oxygen atom of dibenzofuran (or the sulfur atom of dibenzothiophene) corresponding to HOMO and the 6-membered heterocyclic group containing a N atom bonded to L corresponding to LUMO are located in the same direction or in opposite directions, it seems that as the electron / hole transport characteristics are relatively reduced, the balance of holes and electrons in the light-emitting layer is reduced.

[0051] Furthermore, when a 6-membered heterocyclic group containing a nitrogen atom and a carbazolyl group are both used in combination with dibenzofuran (when Y 2 When Y is O) / dibenzothiophene (when Y 2 When a compound bonded to the same benzene ring of dibenzofuran (or dibenzothiophene) (when S is used as the main body of an organic light-emitting device, there is a problem that both the efficiency and life characteristics of the organic light-emitting device are deteriorated. It is believed that the stability of the compound is reduced due to the repulsive force between the non-bonding electrons of the oxygen atom of dibenzofuran (or the sulfur atom of dibenzothiophene), the non-bonding electrons of the N atom in the 6-membered heterocyclic ring, and the non-bonding electrons of the N atom in the carbazole group.

[0052] Specifically, according to the bonding position of L, the compound represented by Chemical Formula 1 can be represented by Chemical Formula 1A when the linking group L is bonded to position *1, and can be represented by Chemical Formula 1B when the linking group L is bonded to position *2:

[0053] [Chemical Formula 1A]

[0054]

[0055] [Chemical formula 1B]

[0056]

[0057] Wherein, in Chemical Formulas 1A and 1B,

[0058] X 1 To X 3 , Y 1 , Y 2 , L, Ar 1 ,Ar 2 and R 1 To R 4 As defined in Formula 1 above.

[0059] Preferably, X 1 To X 3 Can be N.

[0060] Preferably, L may be a single bond, phenylene, biphenylene, naphthylene, dibenzofuranylene, dibenzothiophenylene or carbazolylene. More preferably, L may be 1,4-phenylene, 2,2'-biphenylene, 4,4'-biphenylene, 1,2-naphthylene, 1,4-naphthylene, 2,7-naphthylene, 1,4-dibenzofuranylene, 4,6-dibenzofuranylene, 1,6-dibenzothiophenylene, 4,6-dibenzothiophenylene or 4,9-carbazolylene.

[0061] Preferably, Ar 1 and Ar 2 can be each independently phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl. More preferably, Ar 1 It can be phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl, and Ar 2 It may be phenyl.

[0062] Preferably, R 1 To R 4 can be independently hydrogen or phenyl, more preferably, R 1 , R 2 and R 4 is hydrogen and R 3 is phenyl, or R 1 To R 4 Two adjacent substituents in may be combined with each other to form a structure represented by the following Chemical Formula 2:

[0063] [Chemical formula 2]

[0064]

[0065] Wherein, in Chemical Formula 2,

[0066] Y 3 For CZ 1 Z 2 ,O,S or NZ 3 ,

[0067] Z 1 To Z 3 Each independently is C 1-10 Alkyl or C 6-20 Aryl, and

[0068] * means bonded to R 1 To R 4 The bonding positions of two adjacent carbon atoms in each carbon atom.

[0069] Specifically, when R 1 To R 4 When two adjacent substituents in Chemical Formula 1 are bonded to each other to form a structure represented by Chemical Formula 2, 1 To R 4 Two adjacent carbon atoms in each carbon atom of are combined with * in Chemical Formula 2 to form a condensed ring, wherein Chemical Formula 1 can be represented by any one of the following Chemical Formulas 3-1 to 3-6:

[0070] [Chemical formula 3-1]

[0071]

[0072] [Chemical formula 3-2]

[0073]

[0074] [Chemical formula 3-3]

[0075]

[0076] [Chemical formula 3-4]

[0077]

[0078] [Chemical formula 3-5]

[0079]

[0080] [Chemical formula 3-6]

[0081]

[0082] In the chemical formulas 3-1 to 3-6, Y 3 For CZ1 Z 2 ,O,S or NZ 3 ,

[0083] Z 1 To Z 3 Each independently is C 1-10 Alkyl or C 6-20 Aryl, and

[0084] X 1 To X 3 , Y 1 , Y 2 , L, Ar 1 and Ar 2 As defined in Formula 1 above.

[0085] More preferably, Z 1 To Z 3 may each independently be methyl or phenyl, and most preferably, Z 1 and Z 2 can be methyl and Z 3 It may be phenyl.

[0086] Preferably, the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-6:

[0087] [Chemical formula 1-1]

[0088]

[0089] [Chemical formula 1-2]

[0090]

[0091] [Chemical formula 1-3]

[0092]

[0093] [Chemical formula 1-4]

[0094]

[0095] [Chemical formula 1-5]

[0096]

[0097] [Chemical formula 1-6]

[0098]

[0099] Among them, in Chemical Formulas 1-1 to 1-6,

[0100] L is substituted or unsubstituted C6-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroarylene,

[0101] R 3 is hydrogen or phenyl,

[0102] Y 4 is O, S, or N (phenyl), and

[0103] X 1 To X 3 , Y 1 , Y 2 ,Ar 1 and Ar 2 As defined in Formula 1 above.

[0104] For example, the compound may be any one selected from the following compounds:

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] Meanwhile, the compound represented by Chemical Formula 1 can be prepared, for example, according to a preparation method as shown in the following Reaction Scheme 1.

[0126] [Reaction Scheme 1]

[0127]

[0128] In Reaction Scheme 1, X and X' are each independently halogen, preferably bromine or chlorine, and the definition of each substituent is as defined above.

[0129] Step 1-1 is a step of preparing compound S-3 by Suzuki coupling reaction of compound S-1 and S-2, and step 1-2 is a step of preparing the compound represented by Chemical Formula 1 by Suzuki coupling reaction of compound S-3 and S-4. At this time, the Suzuki coupling reaction is preferably carried out under a palladium catalyst and a base, and the reactive group used for the reaction can be modified to a reactive group known in the art. Such a preparation method can be further illustrated in the preparation examples described below.

[0130] In another embodiment of the present invention, an organic light-emitting device comprising the compound represented by Chemical Formula 1 is provided. As an example, an organic light-emitting device is provided, which includes: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layers comprise the compound represented by Chemical Formula 1.

[0131] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic material layers.

[0132] In addition, the organic material layer may include a light emitting layer, wherein the light emitting layer includes the compound represented by Chemical Formula 1. In particular, the compound according to the present invention may be used as a host in the light emitting layer. Specifically, the compound according to the present invention may be used as a green phosphorescent host in the light emitting layer.

[0133] In addition, the organic material layer may include an electron transport layer or an electron injection layer, wherein the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1.

[0134] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure in which, in addition to the light-emitting layer, it also includes a hole injection layer and a hole transport layer disposed between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer disposed between the light-emitting layer and the second electrode. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic material layers or a larger number of organic material layers.

[0135] In addition, the organic light-emitting device according to the present invention may be a normal type organic light-emitting device in which an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers and an anode are sequentially stacked on a substrate. For example, Figure 1 and Figure 2 Schematic diagram of a structure of an organic light emitting device according to an embodiment of the present disclosure.

[0136] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in the light emitting layer.

[0137] Figure 2 An example of an organic light-emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in one or more layers of the hole injection layer, the hole transport layer, the light-emitting layer, and the electron transport layer. For example, the compound represented by Chemical Formula 1 may be contained in the light-emitting layer.

[0138] The organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic material layers contain the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0139] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured as follows: a metal, a conductive metal oxide, or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a material that can be used as a cathode is deposited on the organic material layer. In addition to such a method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0140] In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic material layer by a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0141] In addition to such a method, an organic light emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0142] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0143] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but not limited thereto.

[0144] As the cathode material, it is generally preferred to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO 2 / Al; and so on, but not limited to.

[0145] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably such a compound: it has the ability to transport holes, so it has the effect of injecting holes in the anode and the excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and the ability to form a thin film is excellent. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, polyaniline, conductive polymers based on polythiophene, etc., but are not limited thereto.

[0146] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is suitably a material having a large hole mobility, which can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. As the hole transport material, a compound represented by Chemical Formula 1 is used, or an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated part and a non-conjugated part, etc. are used as the hole transport material, but it is not limited thereto.

[0147] The electron blocking layer refers to a layer formed on the hole transport layer and preferably arranged in contact with the light emitting layer to adjust the hole mobility, prevent the electrons from excessively moving, and increase the possibility of hole-electron combination, thereby improving the efficiency of the organic light emitting device. The electron blocking layer includes an electron blocking material, and examples of such an electron blocking material include a compound represented by Chemical Formula 1 or an arylamine-based organic material, etc., but are not limited thereto.

[0148] The luminescent material is preferably a material that can receive holes and electrons transmitted from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; diphenylethylene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoquinoline-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene, and the like, but are not limited thereto.

[0149] The light-emitting layer may include a host material and a dopant material as described above. The light-emitting layer may include a fused aromatic ring derivative, a heterocyclic compound, etc. as a host material. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0150] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene, Diindenopyrene, etc. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, the metal complex includes iridium complex, platinum complex, etc., but are not limited thereto.

[0151] The hole blocking layer is formed on the light emitting layer, preferably disposed in contact with the light emitting layer. The hole blocking layer serves as a layer that improves the efficiency of the organic light emitting device by controlling electron mobility and preventing holes from excessively moving to increase the possibility of hole-electron combination. The hole blocking layer contains a hole blocking material, and examples of such a hole blocking material include azine derivatives (including triazine); triazole derivatives; Oxadiazole derivatives; phenanthroline derivatives; compounds having electron-withdrawing groups, such as phosphine oxide derivatives, etc., but not limited thereto.

[0152] The electron injection and transport layer is a layer that simultaneously functions as an electron injection layer and an electron transport layer for injecting electrons from the electrode and for transporting the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. Such an electron injection and transport material is a material that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer, and a material having a high electron mobility is suitable. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; Alq complexes containing 3 complexes; organic free radical compounds; hydroxyflavone-metal complexes; etc., but not limited thereto. In addition, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, but not limited thereto.

[0153] In addition, the electron injection and transport layer may be formed of separate layers such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light emitting layer or the hole blocking layer, and the above electron injection and transport materials may be used as the electron transport material contained in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and the electron injection material contained in the electron injection layer includes LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone and thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and the like.

[0154] Examples of metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0155] The organic light emitting device according to the present invention may be a front-side emission type, a rear-side emission type, or a double-side emission type according to the materials used.

[0156] Furthermore, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0157] The preparation of the compound represented by Chemical Formula 1 and an organic light-emitting device including the same will be described in detail in the following examples. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of the present invention.

[0158] Preparation Example 1: Preparation of Compound 1

[0159]

[0160] Step 1) Synthesis of intermediate A-1

[0161] Under nitrogen atmosphere, 3-bromo-7-chlorodibenzo[b,d]furan (20 g, 71 mmol) and bis(pinacolato)diboron (28.1 g, 71 mmol) were added to 400 ml of 1,4-dichlorobenzene. In alkane (Diox), it is stirred and refluxed. Afterwards, potassium triphosphate (45.2g, 213.1mmol) is added and stirred sufficiently, followed by addition of bis(dibenzylideneacetone) palladium (1.2g, 2.1mmol) and tricyclohexylphosphine (1.2g, 4.3mmol). After reacting for 3 hours, and after being cooled to room temperature, the organic layer is filtered to remove salt, and the filtered organic layer is then distilled. The distillate is dissolved again in 233mL of 10 times chloroform, washed twice with water, and the organic layer is separated. After adding anhydrous magnesium sulfate and stirring, the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized by chloroform and ethanol to prepare white solid compound A-1 (12.4g, 53%).

[0162] MS:[M+H] + =329.6

[0163] Step 2) Synthesis of intermediate B-1

[0164] Under nitrogen atmosphere, A-1 (20g, 60.9mmol) and 2-chloro-4-(dibenzo [b, d] furan-3-yl) -6-phenyl -1,3,5- triazine (21.8g, 60.9mmol) were added to 400ml tetrahydrofuran, which was stirred and refluxed. Subsequently, potassium carbonate (25.2g, 182.6mmol) was dissolved in 25ml water, stirred thoroughly, and then tetrakis (triphenylphosphine) palladium (2.1g, 1.8mmol) was added thereto. After reacting for 3 hours, and after cooling to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was then distilled. The distillate was dissolved again in 638mL of 20 times chloroform, washed twice with water, and the organic layer was separated. After adding anhydrous magnesium sulfate and stirring, the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized by chloroform and ethyl acetate to prepare white solid compound B-1 (21g, 66%).

[0165] MS:[M+H] + =525

[0166] Step 3) Synthesis of Compound 1

[0167] Under nitrogen atmosphere, B-1 (20 g, 38.2 mmol) and (9-phenyl-9H-carbazole-3-yl)boronic acid (11 g, 38.2 mmol) were added to 400 ml of 1,4-dihydro-1,4-diol. alkane (Diox), stirred and refluxed. Afterwards, potassium triphosphate (24.3g, 114.5mmol) was dissolved in 24ml water, fully stirred, and then dibenzylideneacetone palladium (0.7g, 1.1mmol) and tricyclohexylphosphine (0.6g, 2.3mmol) were added thereto. After 8 hours of reaction, and after cooling to room temperature, the obtained solid was filtered. The solid was dissolved in 763mL of 30 times 1,2-dichlorobenzene (DCB), washed twice with water, and the organic layer was separated. After adding anhydrous magnesium sulfate and stirring, the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized by DCB and ethyl acetate to prepare fluorescent solid compound 1 (10.9g, 52%).

[0168] MS:[M+H] + =731.8

[0169] Preparation Example 2: Preparation of Compound 2

[0170]

[0171] Fluorescent solid compound 2 (15.3 g, 73%) was prepared in the same manner as in Preparation Example 1, except that in step 2 of Preparation Example 1, 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine to prepare intermediate B-2.

[0172] MS:[M+H] + =731.8

[0173] Preparation Example 3: Preparation of Compound 3

[0174]

[0175] Fluorescent solid compound 3 (13.8 g, 66%) was prepared in the same manner as in Preparation Example 1, except that 3-bromo-6-chlorodibenzo[b,d]furan was used instead of 3-bromo-7-chlorodibenzo[b,d]furan to prepare intermediate A-2 in step 1 of Preparation Example 1, and the prepared intermediate A-2 was used instead of intermediate A-1 in step 2 of Preparation Example 1.

[0176] MS:[M+H] + =731.8

[0177] Preparation Example 4: Preparation of Compound 4

[0178]

[0179] Fluorescent solid compound 4 (11.7 g, 56%) was prepared in the same manner as in Preparation Example 1, except that 3-bromo-6-chlorodibenzo[b,d]furan was used instead of 3-bromo-7-chlorodibenzo[b,d]furan to prepare intermediate A-2 in step 1 of Preparation Example 1, and the prepared intermediate A-2 was used instead of intermediate A-1 in step 2 of Preparation Example 1, and (9-phenyl-9H-carbazole-1-yl)boric acid was used instead of (9-phenyl-9H-carbazole-3-yl)boric acid.

[0180] MS:[M+H] + =731.8

[0181] Preparation Example 5: Preparation of Compound 5

[0182]

[0183] Fluorescent solid compound 5 (12.1 g, 58%) was prepared in the same manner as in Preparation Example 1, except that 7-bromo-2-chlorodibenzo[b,d]furan was used instead of 3-bromo-7-chlorodibenzo[b,d]furan to prepare intermediate A-3 in step 1 of Preparation Example 1, and the prepared intermediate A-3 was used instead of intermediate A-1 in step 2 of Preparation Example 1 and 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine to prepare intermediate B-4.

[0184] MS:[M+H] + =731.8

[0185] Example 1

[0186] It is coated with a thickness of The ITO (indium tin oxide) of the glass substrate as the film is put into the distilled water dissolved with the detergent therein, and carry out ultrasonic cleaning. In this case, the product manufactured by Fischer Co. is used as a detergent, and the distilled water filtered twice by the filter manufactured by Millipore Co. is used as distilled water. After ITO was cleaned for 30 minutes, distilled water was used to repeat ultrasonic cleaning twice for 10 minutes. After cleaning with distilled water, the substrate was ultrasonically cleaned with isopropyl alcohol, acetone and methanol solvent, then dried, and then transferred to a plasma cleaner. In addition, oxygen plasma was used to clean the substrate for 5 minutes, and then transferred to a vacuum depositor.

[0187] On the thus prepared ITO transparent electrode, the following HT-A compound and the following PD compound were thermally vacuum deposited at a weight ratio of 95:5. to form a hole injection layer, and then only the following HT-A compound is deposited to To form a hole transport layer, the following HT-B compound was thermally vacuum deposited onto the hole transport layer. to form an electron blocking layer.

[0188] On the electron blocking layer, the compound 1 prepared in the previous preparation example 1 and the following GD compound were vacuum deposited at a weight ratio of 85:15. to form a light-emitting layer.

[0189] On the light-emitting layer, the following ET-A compound was vacuum deposited onto On the hole blocking layer, the following ET-B compound and the following Liq compound were thermally vacuum deposited at a weight ratio of 2:1. Then LiF and magnesium were mixed in a weight ratio of 1:1. The electron injection and transport layer is formed by vacuum deposition of Mg and Ag in a weight ratio of 1:4. to form a cathode, thereby manufacturing an organic light-emitting device.

[0190]

[0191] During the above process, the vapor deposition rate of the organic material is maintained at to The vapor deposition rate of lithium fluoride was maintained at The deposition rates of silver and magnesium were kept at The vacuum during deposition was maintained at 2 × 10 -7 Up to 5×10 -6 Support, thereby manufacturing an organic light-emitting device.

[0192] Example 2 to Example 5

[0193] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in the following Table 1 were used instead of Compound 1. The structures of the compounds used in Examples 1 to 5 are as follows:

[0194]

[0195] Comparative Examples 1 and 2

[0196] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1. The structures of Compounds GH-A and GH-B in Table 1 below are as follows:

[0197]

[0198] The driving voltage, efficiency and lifespan (T95) were measured by applying current to the organic light emitting devices manufactured in the above Examples and Comparative Examples, and the results are shown in Table 1 below. 2 The voltage and efficiency are measured at a current density of 20 mA / cm 2 The time required for the brightness to decrease to 95% of the initial brightness at a current density of .

[0199] [Table 1]

[0200]

[0201] As shown in Table 1, the organic light-emitting devices of the Examples using the compounds of the present disclosure as the host material of the light-emitting layer exhibited excellent device characteristics in terms of driving voltage, efficiency and lifespan, compared to the organic light-emitting devices of Comparative Examples 1 and 2 using comparative compounds GH-A and GH-B (each of which was used as a host material) in which the triazine group was substituted at a position different from that of the compounds of the present disclosure. In general, considering that the luminous efficiency and lifespan characteristics of the organic light-emitting device have a trade-off relationship with each other, it can be seen that the organic light-emitting device using the compounds of the present disclosure exhibits significantly improved device characteristics compared to the devices of the comparative examples.

[0202] [Explanation of Reference Numerals]

[0203] 1: Substrate 2: Anode

[0204] 3: Light-emitting layer 4: Cathode

[0205] 5: Hole injection layer 6: Hole transport layer

[0206] 7: Electron blocking layer 8: Hole blocking layer

[0207] 9: Electron injection and transport layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, X1 to X3 are each independently N or CH, provided that at least two of X1 to X3 are N, Y1 and Y2 are each independently O or S, L is a single bond; or deuterium-substituted or unsubstituted C 6-20 Arylene; provided that L is bonded to position *2, Ar1 and Ar2 are each independently deuterated or unsubstituted C 6-20 Aryl; and R1 to R4 are each independently hydrogen; deuterium; halogen; or C 6-20 Aryl.

2. The compound according to claim 1, Wherein X1 to X3 are N.

3. The compound according to claim 1, Wherein L is a single bond, a phenylene group, a biphenylene group or a naphthylene group.

4. The compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl or biphenyl.

5. The compound according to claim 1, wherein R1 to R4 are each independently hydrogen or phenyl.

6. The compound according to claim 1, The compound is represented by any one of the following chemical formulas 1-5 to 1-6: [Chemical formula 1-5] [Chemical formula 1-6] in, In Chemical Formulas 1-5 to 1-6, L is phenylene or biphenylene, R3 is hydrogen or phenyl, and X1 to X3, Y1, Y2, Ar1 and Ar2 are as defined in claim 1.

7. The compound according to claim 1, The compound is any one selected from the following compounds:

8. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 7.

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