Organic compounds and organic light-emitting devices comprising the same

Abstract

The present application relates to a compound represented by the following chemical formula I and an organic light-emitting device comprising the same, which is used in a light efficiency improving layer provided in an organic light-emitting device, so that a high-efficiency long-life organic light-emitting device with improved low-voltage driving, light-emitting efficiency, color purity, and life characteristics can be achieved. Chemical formula I:

Description

Technical Field

[0001] This invention relates to an organic compound and a high-efficiency organic light-emitting device. The organic compound is used as a material for a light efficiency improvement layer (capping layer) in the organic light-emitting device. By using the organic compound in the light efficiency improvement layer, the organic light-emitting device significantly improves the light-emitting characteristics of the device, such as low-voltage driving, luminous efficiency, color purity, and lifetime. Background Technology

[0002] Organic light-emitting devices can not only be formed on transparent substrates, but also have advantages over plasma display panels or inorganic electroluminescent (EL) displays, such as being able to be driven at low voltages below 10V, having lower power consumption, and outstanding color reproduction. They can also display three colors: green, blue, and red, and have recently attracted much attention as a new generation of display devices.

[0003] However, in order for such organic light-emitting devices to exhibit the aforementioned characteristics, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, must first be supported by stable and efficient materials. However, stable and efficient organic layer materials for organic light-emitting devices have not yet been fully developed.

[0004] Therefore, in order to achieve more stable organic light-emitting devices and devices with high efficiency, long lifespan, and large size, further improvements are needed in efficiency and lifespan characteristics. In particular, there is an urgent need to develop a material for forming the organic layers of organic light-emitting devices.

[0005] In addition to research on improving the characteristics of organic light-emitting devices by changing the properties of each organic layer material, the technique of improving color purity and luminous efficiency by optimizing the optical thickness between the anode and the cathode is considered to be one of the important factors in improving device performance. One example of this method is to use a light efficiency improvement layer (capping layer) on the electrode to improve light efficiency and obtain excellent color purity.

[0006] The efficiency of organic light-emitting devices can be divided into internal luminous efficiency and external luminous efficiency. Internal luminous efficiency is related to the exciton generation and light conversion efficiency in various organic layers such as hole transport layer, light-emitting layer, and electron transport layer between the first electrode and the second electrode. External luminous efficiency refers to the efficiency of light generated in the organic layer being extracted to the outside of the organic light-emitting device. In order to improve the light extraction efficiency, a light efficiency improvement layer (capping layer) is used, which is adjusted to the optimal refractive index.

[0007] However, there is an urgent need to design and develop an optimized light efficiency improvement layer to achieve high-efficiency devices without compromising process efficiency such as deposition and other light-emitting properties, including device lifetime characteristics. Summary of the Invention

[0008] Technical issues

[0009] Therefore, the object of the present invention is to provide a material for a light efficiency improvement layer (capping layer) in an organic light-emitting device and a high-efficiency organic light-emitting device containing the same, so as to improve various light-emitting characteristics of the organic light-emitting device such as low voltage driving, luminous efficiency, lifetime and color purity.

[0010] Technical solution

[0011] To address the aforementioned problem, the present invention provides an organic compound represented by the following chemical formula I for use in a light efficiency improvement layer (capping layer).

[0012] Chemical Formula I:

[0013]

[0014] The characteristic structure of Formula I, the specific compounds derived therefrom, and the definitions of X1, L1 to L3, and Ar1 to Ar3 will be described below.

[0015] Furthermore, the present invention provides an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, and further comprising a light efficiency improvement layer (capping layer) formed on at least one side of the upper or lower portion of the first electrode and the second electrode opposite to the organic layer, wherein the light efficiency improvement layer comprises an organic compound represented by the chemical formula I.

[0016] The effects of the invention

[0017] The organic compounds of this invention can improve the external light extraction efficiency of organic light-emitting devices (OLEDs), and therefore can be usefully used as light efficiency improvement layer materials in OLEDs. Thus, by using the compounds of this invention in the light efficiency improvement layer, high-efficiency, long-life OLEDs with improved low-voltage driving characteristics, luminous efficiency, color purity, and lifetime characteristics can be achieved, and these OLEDs can be usefully used in various lighting and display devices. Attached Figure Description

[0018] Figure 1 A simplified cross-sectional view is provided to illustrate the concept and structure of the organic light-emitting device of the present invention.

[0019] Figure 2A simplified cross-sectional view is provided to illustrate the structure of an organic light-emitting device according to an embodiment of the present invention.

[0020] Figure 3 A simplified cross-sectional view is provided to illustrate the structure of an organic light-emitting device according to an embodiment of the present invention. Detailed Implementation

[0021] The present invention will now be described in more detail.

[0022] The compound of the present invention for the light efficiency improvement layer is characterized in that it is a compound incorporating three moiety having a characteristic structure into a framework represented by the following chemical formula I.

[0023] Due to these structural features, the organic compound represented by the chemical formula I of the present invention can be used as a capping layer material in organic light-emitting devices, thereby achieving high-efficiency organic light-emitting devices with improved low-voltage driving characteristics, luminous efficiency, color purity, lifetime characteristics, etc.

[0024] Chemical Formula I:

[0025]

[0026] In the chemical formula I,

[0027] X1 is selected from any one of O, S, SO (sulfur monoxide), SO2 (sulfur dioxide), NR1, CR2R3, SiR4R5, and GeR6R7.

[0028] R1 to R7 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 50 carbon atoms, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, cyano and halogen.

[0029] L1 to L3 are divalent linking groups, which are directly bonded or selected from arylene groups with 6 to 30 carbon atoms (substituted or unsubstituted) and heteroarylene groups with 2 to 50 carbon atoms (substituted or unsubstituted). o, p, and q are integers from 0 to 2. When o, p, and q are 2, the plurality of L1 to L3 are each the same or different from each other.

[0030] Ar1 to Ar3 may be the same as or different from each other, and each is independently a cyano (CN) or selected from any of the following: aryl groups with 6 to 30 substituted or unsubstituted carbon atoms and heteroaryl groups with 2 to 50 substituted or unsubstituted carbon atoms.

[0031] According to one embodiment of the present invention, L1 to L3 are divalent linking groups, which can be arylene groups with 6 to 30 carbon atoms that are directly bonded, substituted, or unsubstituted. According to a preferred embodiment, they can be phenylene groups that are directly bonded, substituted, or unsubstituted.

[0032] According to one embodiment of the present invention, Ar1 to Ar3 may be the same as or different from each other, and may each be an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted. According to a preferred embodiment, Ar1 to Ar3 may each be a naphthyl group, either substituted or unsubstituted.

[0033] According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be structural formula 1 or any one selected from structural formula 2.

[0034] Structure 1:

[0035]

[0036] Structure 2:

[0037]

[0038] In each of the structural formulas in structural formula 2,

[0039] X can be the same as or different from each other, and can be N or CR independently. 11 Y is selected from O, S, NR 12 CR 13 R 14 SiR 15 R 16 and GeR 17 R 18 middle.

[0040] The R 11 To R 18They may be the same as or different from each other, and are each independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 50 carbon atoms, substituted or unsubstituted amino with 1 to 50 carbon atoms, substituted or unsubstituted silyl, and substituted or unsubstituted germanyl.

[0041] Multiple R 11 They can connect with each other to form alicyclic or aromatic monocyclic or polycyclic compounds.

[0042] The R 13 With R 14 R 15 With R 16 and R 17 With R 18 They can connect with each other to form alicyclic or aromatic monocyclic or polycyclic compounds.

[0043] The carbon atoms of the alicyclic or aromatic monocyclic or polycyclic alicyclic compounds formed can be substituted by heteroatoms selected from O, S, N, P, Si, and Ge.

[0044] R selected from each of the above structural formulas 11 To R 18 Any one of them is connected to L1 to L3 in the chemical formula I.

[0045] According to an embodiment of the present invention, more specifically, the structural formula 2 can be represented by the following structural formula 2-1, so A1 to A4 can be the same as or different from each other, and can each be independently selected from any of the following structural formulas 2-1.

[0046] Structural Formula 2-1:

[0047]

[0048] In each of the structural formulas in structural formula 2-1,

[0049] X can be the same as or different from each other, and can be N or CR independently. 11 Y is selected from O, S, NR 12 CR 13 R 14 SiR 15 R 16 and GeR 17 R 18 middle.

[0050] R a To R c and the R 11 To R 18 They may be the same as or different from each other, and are each independently selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 50 carbon atoms, substituted or unsubstituted amino with 1 to 50 carbon atoms, substituted or unsubstituted silyl, and substituted or unsubstituted germanyl.

[0051] Multiple R 11 They can connect with each other to form alicyclic or aromatic monocyclic or polycyclic compounds.

[0052] Furthermore, the R a With R b R 13 With R 14 R 15 With R 16 and R 17 With R 18 They can connect with each other to form alicyclic or aromatic monocyclic or polycyclic compounds.

[0053] Furthermore, the carbon atoms of the alicyclic or aromatic monocyclic or polycyclic compounds further formed can be replaced by heteroatoms selected from O, S, N, P, Si, and Ge.

[0054] R selected from each of the above structural formulas a To R c and R 11 To R 18 Any one of them is connected to L1 to L3 in the chemical formula I.

[0055] According to one embodiment of the present invention, at least one of Ar1 to Ar3 may be structural formula 1 or structural formula 2-2 as described below.

[0056] Structure 1:

[0057]

[0058] Structural Formula 2-2:

[0059]

[0060] In the aforementioned structural formula 2-2,

[0061] Y is selected from O, S, SO (sulfur monoxide), SO2 (sulfur dioxide), and NR. 21 In, the R 21 It is selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, substituted or unsubstituted germanyl groups, cyano groups, and halogen groups.

[0062] R 31 To R 35 They may be the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, substituted or unsubstituted germanyl groups, cyano groups, and halogens.

[0063] The R 31 To R 35 Any one of them is a part connected to L1 to L3.

[0064] Furthermore, the R 32 To R 35 Each of the substituents can connect to each other or to adjacent substituents to further form alicyclic or aromatic monocyclic or polycyclic compounds. Therefore, according to an embodiment of the present invention, the structural formula 2 can be any one selected from the following structural formula 3.

[0065] Structure 3:

[0066]

[0067] In the aforementioned structural formula 3.

[0068] Y is selected from S, SO (sulfur monoxide), SO2 (sulfur dioxide), and NR. 21 In, the R 21It is selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, substituted or unsubstituted germanyl groups, cyano groups, and halogen groups.

[0069] R 31 To R 43 They may be the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, substituted or unsubstituted germanyl groups, cyano groups, and halogens.

[0070] The R 31 To R 43 Any one of them is a part connected to L1 to L3.

[0071] According to one embodiment of the present invention, Ar1 to Ar3 may be the same as or different from each other, and may each be independently of the following structural formula 1 or structural formula 2.

[0072] Furthermore, "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, cyano, halogen, hydroxy, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aliphatic aromatic mixed cycloalkyl, amino, silyl and germanyl, or substituted by substituents linked by two or more of the substituents, or not having any substituents.

[0073] Regarding the definition of "substituted or unsubstituted", for specific examples, a substituted aryl group refers to phenyl, biphenyl, naphthyl, fluorenyl, pyrene, phenanthryl, perylene, tetrabenzoyl, anthracene, etc., which are substituted with other substituents such as deuterium. A substituted heteroaryl group refers to pyridyl, thiophene, triazine, quinolinyl, phenanthrolinyl, imidazolyl, thiazolyl, oxazolyl, carbazole, and their fused heterocyclic groups, such as benzoquinolinyl, benzimidazolyl, benzooxazolyl, benzothiazolyl, benzocarbazole, dibenzothiophene, dibenzofuranyl, etc., which are substituted with other substituents such as deuterium.

[0074] Furthermore, in this invention, interconnection or connection with adjacent groups to further form a ring means that adjacent substituents in the specified substituents can be interconnected, or that the specified substituents can be interconnected with other adjacent groups to form substituted or unsubstituted alicyclic or aromatic rings. "Adjacent groups" can refer to substituents that are substituted on an atom directly bonded to the atom substituted by the substituent, substituents that are stereoscopically closest to the substituent, or another substituent that is substituted on the atom substituted by the substituent. For example, two substituents ortho-substituted on a benzene ring and two substituents substituted on the same carbon atom in an alicyclic ring can be interpreted as "adjacent groups."

[0075] In this invention, the alkyl group can be straight-chain or branched, 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, 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-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0076] In this invention, the alkoxy group can be straight-chain or branched. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably within the range that does not cause steric hindrance, i.e., 1 to 20. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, i-propoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

[0077] In this invention, alkyl and alkoxy can be deuterated alkyl or alkoxy, haloalkyl or alkoxy, respectively, referring to alkyl or alkoxy groups substituted by deuterium or halogen groups.

[0078] In this invention, the aromatic hydrocarbon ring or aryl group can be monocyclic or polycyclic. Polycyclic refers to a group that is directly connected to or fused with other cyclic groups. The other cyclic groups can be aromatic hydrocarbon rings, but can also be other types of cyclic groups, such as aliphatic heterocycles, aliphatic hydrocarbon rings, aromatic heterocycles, etc. Examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, etc. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, tetrabenzoyl, trefyl, fluorenyl, acenaphthene, triphenylene, fluoranyl, etc., but the scope of this invention is not limited to these examples.

[0079] In this invention, the fluorene group is a structure formed by two cyclic organic compounds linked by a single atom, examples of which include... , , wait.

[0080] In this invention, the fluorene group includes an open fluorene group structure, wherein the open fluorene group is a structure in which the connection of one cyclic organic compound is broken in a structure in which two cyclic organic compounds are connected by one atom. Examples of such structures include... , wait.

[0081] Furthermore, the carbon atom of the ring can be replaced by one or more heteroatoms selected from N, S, and O, examples of which include... , , , wait.

[0082] In this invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing one or more heteroatoms, examples of which include thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, indolocarbazole, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, phenanthrolyl, thiazolyl, isoxazolyl, oxadiazolyl, thiazolyl, benzothiazolyl, phenthiazolyl, etc., but are not limited thereto.

[0083] In this invention, aliphatic hydrocarbon rings or cycloalkyl groups refer to non-aromatic rings composed only of carbon and hydrogen atoms. Examples include monocyclic or polycyclic rings, which can be further substituted by other substituents. Polycyclic rings refer to groups directly connected or fused with other cyclic groups. Other cyclic groups can be aliphatic hydrocarbon rings, but can also be other types of cyclic groups, such as aliphatic heterocycles, aromatic hydrocarbon rings, aromatic heterocycles, etc. Specifically, this includes cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and other cycloalkyl groups, cyclohexane, cyclopentane, and other cycloalkanes, as well as cyclohexene and cyclobutene, but are not limited thereto.

[0084] In this invention, aliphatic heterocycles or heterocyclic alkyl groups refer to aliphatic rings containing one or more heteroatoms, including heteroatoms such as O, S, Se, N, or Si. They also include monocyclic or polycyclic rings, which can be further substituted by other substituents. Polycyclic rings refer to groups such as heterocyclic alkyl groups and heterocyclic alkanes that are directly connected or fused with other cyclic groups. The other rings can be aliphatic heterocycles, but they can also be other types of cyclic groups, such as aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aromatic heterocycles, etc.

[0085] In this invention, an aliphatic-aromatic mixed ring (base) refers to a ring formed by the interconnection and fusion of two or more rings, wherein the aliphatic ring and aromatic ring are fused together to form a ring with overall non-aromaticity. More specifically, it can be an aliphatic hydrocarbon ring fused with an aromatic hydrocarbon ring base, an aliphatic heterocycle fused with an aromatic hydrocarbon ring base, an aliphatic heterocycle fused with an aromatic heterocycle base, an aromatic hydrocarbon ring fused with an aliphatic hydrocarbon ring base, an aromatic heterocycle fused with an aliphatic hydrocarbon ring base, an aromatic hydrocarbon ring fused with an aliphatic heterocycle base, an aromatic heterocycle fused with an aliphatic heterocycle base, an aromatic heterocycle fused with an aliphatic heterocycle base, etc. Furthermore, the polycyclic aliphatic-aromatic mixed ring may contain heteroatoms such as N, O, S, Si, Ge, and P in addition to carbon.

[0086] In embodiments of the present invention, silyl groups include -SiH3, alkylsilyl, arylsilyl, alkylarylsilyl, arylheteroarylsilyl, and heteroarylsilyl. Arylsilyl represents a silyl group in which one, two, or three hydrogen atoms in -SiH3 are substituted by an aryl group. Alkylsilyl represents a silyl group in which one, two, or three hydrogen atoms in -SiH3 are substituted by an alkyl group. Alkylarylsilyl represents a silyl group in which one hydrogen atom in -SiH3 is substituted by an alkyl group and the remaining two hydrogen atoms are substituted by an aryl group, or two hydrogen atoms are substituted by an alkyl group and the remaining one hydrogen atom is substituted by an aryl group. Arylheteroarylsilyl represents a silyl group in -SiH3 in which one hydrogen atom is substituted by an aryl group and the remaining two hydrogen atoms are substituted by a heteroaryl group, or two hydrogen atoms are substituted by an aryl group and the remaining one hydrogen atom is substituted by a heteroaryl group. Heteroarylsilyl represents a silyl group in -SiH3 in which one, two, or three hydrogen atoms are substituted by a heteroaryl group. Examples of the arylsilyl group include substituted or unsubstituted monoarylsilyl groups, substituted or unsubstituted diarylsilyl groups, and substituted or unsubstituted triarylsilyl groups, and the alkylsilyl groups and heteroarylsilyl groups also fall into the same category.

[0087] In this invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, aryl group, etc. Specific examples of such silyl groups may include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, stilbene silyl, methylcyclobutylsilyl, dimethylfuranylsilyl, etc., but are not limited thereto.

[0088] In this invention, germanium-based (or germanium-alkyl) may include -GeH3, alkylgermanium-based, arylgermanium-based, heteroarylgermanium-based, alkylarylgermanium-based, alkylheteroarylgermanium-based, arylheteroarylgermanium-based, etc., and their definitions follow those described in the silane group. As a substituent obtained by replacing the silicon atom (Si) in the silane group with a germanium atom (Ge), it can be applied to each substituent.

[0089] Furthermore, specific examples of the germanium group may include trimethylgermanane, triethylgermanane, triphenylgermanane, trimethoxygermanane, dimethoxyphenylgermanane, diphenylmethylgermanane, stilbene germanane, methylcyclobutylgermanane, dimethylfuranylgermanane, etc., and one or more hydrogen atoms in the germanium group may be replaced by substituents in the same manner as in the case of the aryl group.

[0090] In this invention, the amino group can be –NH2, alkylamino, arylamino, arylheteroarylamino, etc. Aromaticamino refers to an amine substituted with an aryl group, alkylamino refers to an amine substituted with an alkyl group, and arylheteroarylamino refers to an amine substituted with both aryl and heteroaryl groups. Examples of arylamino groups include substituted or unsubstituted monoarylamino, substituted or unsubstituted diarylamino, or substituted or unsubstituted triarylamino. The aryl and heteroaryl groups in the aromatic amino and arylheteroarylamino groups can be monocyclic aryl, monocyclic heteroaryl, polycyclic aryl, or polycyclic heteroaryl. Aromatic amino and arylheteroarylamino groups containing two or more of the aforementioned aryl or heteroaryl groups can include monocyclic aryl (heteroaryl), polycyclic aryl (heteroaryl), or simultaneously include both monocyclic aryl (heteroaryl) and polycyclic aryl (heteroaryl). Furthermore, the aryl and heteroaryl groups in the aromatic amino and arylheteroarylamino groups can be selected from the examples of the aforementioned aryl and heteroaryl groups.

[0091] Specific examples of halogen groups used in this invention may include fluorine (F), chlorine (Cl), bromine (Br), etc.

[0092] Furthermore, various specific examples of the substituents according to the invention can be clearly identified in the specific compounds described below.

[0093] As described above, due to their structural specificity, the organic compounds of the present invention represented by the chemical formula I can be used as a light efficiency enhancement layer (capping layer) in organic light-emitting devices. Preferred examples of the compounds of the present invention represented by chemical formula I include the following compounds, but are not limited thereto.

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[0176] As described above, the organic compounds of the present invention can be synthesized and realized through the structural features of their skeletons and the portions introduced therein, resulting in the use of the organic compounds of the present invention in the light efficiency improvement layer of organic light-emitting devices to further improve the low-voltage driving characteristics, luminous efficiency, color purity, lifetime characteristics, etc. of the devices.

[0177] Furthermore, the compounds of the present invention can be applied to devices according to conventional organic light-emitting device preparation methods. An organic light-emitting device according to an embodiment of the present invention can be composed of a structure including a first electrode, a second electrode and an organic layer disposed therebetween. In addition to using the organic compounds of the present invention in the organic layer of the device, conventional device preparation methods and materials can be used to prepare the device.

[0178] The organic layer of the organic light-emitting device of the present invention can be a single-layer structure or a multilayer structure composed of two or more organic layers stacked together. For example, it can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and a light efficiency improvement layer (capping layer). However, it is not limited to this and may also include fewer or more organic layers.

[0179] An embodiment of the present invention is an organic light-emitting device having a light efficiency improvement layer (CPL), comprising a substrate, a first electrode (anode), an organic layer, a second electrode (cathode) and a light efficiency improvement layer, wherein the light efficiency improvement layer may be formed on the lower part of the first electrode (bottom emission) or the upper part of the second electrode (top emission).

[0180] According to one embodiment of the present invention, the method of forming a light efficiency improvement layer on the upper part of the second electrode (top emission) specifically involves the emission of light formed in the light-emitting layer toward the cathode. When the light emitted toward the cathode passes through the light efficiency improvement layer (CPL) formed by the compound of the present invention with a relatively low refractive index, the wavelength of the light is amplified, thereby improving the light efficiency.

[0181] Refer to the following Figures 1 to 3 Specific examples of the organic light-emitting device of the present invention are as follows.

[0182] An organic light-emitting device may be configured to include a substrate 100, a first electrode 210, a second electrode 220, one or more organic layers 310-360 sandwiched inside the first and second electrodes, and a light efficiency improvement layer 400, wherein the light efficiency improvement layer may be disposed outside at least one of the first and second electrodes.

[0183] In the two sides of the first electrode or the second electrode, the side adjacent to the organic layer sandwiched between the first electrode and the second electrode is the inner side, and the side not adjacent to the organic layer is the outer side. That is, in the organic light-emitting device of the present invention, when the light efficiency improvement layer 400 is provided on the outer side of the first electrode 210, the first electrode 210 is sandwiched between the light efficiency improvement layer 400 and the organic layers 310 to 360; when the light efficiency improvement layer 400 is provided on the outer side of the second electrode 220, the second electrode 220 is sandwiched between the light efficiency improvement layer 400 and the organic layers 310 to 360.

[0184] In this case, as follows: Figure 3 As shown, the method of forming a light efficiency improvement layer on the upper part of the second electrode (top emission) can also include a reflection layer (not shown) to reflect the light emitted between the first electrode 210 and the substrate 100 and to emit additional light to the upper part of the second electrode.

[0185] As described above, the organic light-emitting device of the present invention can insert one or more organic layers inside the first electrode and the second electrode, and can form a light efficiency improvement layer on the outside of at least one of the first electrode and the second electrode. That is, the light efficiency improvement layer can be formed simultaneously on the outside of the first electrode and the outside of the second electrode, or it can be formed only on the outside of the first electrode or the outside of the second electrode.

[0186] In this case, the light efficiency improvement layer may contain the compound of the present invention for light efficiency improvement layer, may contain one or more compounds of the present invention for light efficiency improvement layer, or may also contain known compounds, and the thickness of the light efficiency improvement layer may be from 100 Å to 4000 Å.

[0187] Furthermore, the first light efficiency improvement layer and the second light efficiency improvement layer can be multi-layer structures with multiple layers stacked on top of each other. Therefore, it can be a multi-layer structure with multiple first light efficiency improvement layers and multiple second light efficiency improvement layers stacked on top of each other. In this case, the first light efficiency improvement layer and the second light efficiency improvement layer can be stacked alternately, and there is no restriction on their stacking order.

[0188] On the other hand, in the organic light-emitting device of the present invention, the light efficiency improvement layer can be a structure with a refractive index gradient, which can gradually decrease or gradually increase from the inside to the outside. Therefore, a refractive index gradient can be achieved in the light efficiency improvement layer by gradually changing the concentration of the compound used in the light efficiency improvement layer of the present invention and depositing the light efficiency improvement layer.

[0189] The organic layer structure of the specific organic light-emitting device according to the present invention will be described in more detail in the following embodiments.

[0190] Furthermore, the organic light-emitting device of the present invention can be prepared as follows: a metal or a conductive metal oxide or alloy thereof is deposited on a substrate to form an anode using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation; an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon; and then a material that can be used as a cathode is deposited thereon.

[0191] In addition to the methods described above, organic light-emitting devices can be fabricated by sequentially depositing an anode 210 material, organic layers 310-360, and a cathode 220 material on a substrate 100. The organic layers can be a multilayer structure including a hole injection layer 310, a hole transport layer 320, an electron blocking layer 330, a light-emitting layer 360, an electron transport layer 350, and an electron injection layer 340, but are not limited to this; they can also be a single-layer structure. Furthermore, besides deposition methods, the organic layers can also be fabricated using various polymer materials through solvent processes, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer, to create fewer layers.

[0192] The substrate 100 can be a substrate commonly used in organic light-emitting devices, especially a transparent glass substrate or a flexible plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and water resistance.

[0193] The anode 210 is typically preferably a material with a low work function so that holes can be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention include metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; 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 SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto.

[0194] The cathode 220 is typically preferably made of a material with a low work function, so that electrons can be easily injected into the organic layer. Specific examples of cathode materials include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or multilayer materials such as LiF / Al or LiO2 / Al.

[0195] The hole injection layer 310 is a material that can effectively receive holes injected from the anode at low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material should be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, aromatic amines, hexanitrile hexaazabenzobenzene, quinacridones, perylenes, anthraquinones, and conductive polymers such as polyaniline and polythiophene.

[0196] Hole transport layer 320 is a material capable of receiving holes transported from the anode or hole injection layer and transferring them to the light-emitting layer. Suitable materials should have high hole mobility. Specific examples include, but are not limited to, aryl amine organic compounds, conductive polymers, and block copolymers that have both conjugated and non-conjugated parts.

[0197] An electron blocking layer (not shown) is a layer that blocks the movement of electrons. It can be formed on top of the hole transport layer. A material that blocks the movement of electrons without affecting the transport of holes can be used as the electron blocking layer. Furthermore, a light-emitting layer can be formed on the electron blocking layer, and a hole blocking layer, an electron transport layer, and an electron injection layer can also be formed thereon.

[0198] Hole-blocking layers (not shown) can be made of materials capable of blocking the movement of holes without affecting electron transport. Examples of such hole-blocking layers include 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,4-bis(N-carbazolyl)-1,1'-biphenyl (CBP), and 2-(4-biphenyl)-5-(4-tert-butyl) Examples of oxadiazoles include, but are not limited to, 2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD), bisbenzimidazo[2,1-a:1',2-b']anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-10,21-dione (PTCBI), or 4,7-diphenyl-1,10-phenanthroline (BPhen).

[0199] The luminescent layer 360 is a material that emits light in the visible light region by receiving and combining holes and electrons transmitted from the hole transport layer and the electron transport layer, respectively. Preferably, it is a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complex (Alq3), carbazole compounds, diluted styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzothiazole and benzimidazole compounds, poly(p-phenylene) (PPV) polymers, spiro compounds, polyfluorene, and fluorene.

[0200] The electron transport layer 350 is a material that can effectively receive electrons injected from the cathode and transfer them to the light-emitting layer. Suitable materials should have high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but are not limited to these.

[0201] The electron injection layer 340 can be formed by depositing an electron injection layer material on top of the electron transport layer. Known materials such as LiF, NaCl, CsF, Li2O, and BaO can be used as the electron injection layer material.

[0202] And, despite Figures 1 to 3 Although not shown in the figure, according to an embodiment of the present invention, an organic layer with various functions may be additionally formed between the light efficiency improvement layer 400 and the first electrode 210 or between the light efficiency improvement layer 400 and the second electrode 220, and an organic layer with various functions may be additionally formed on the upper and lower (outer surface) parts of the cover layer 400.

[0203] Depending on the materials used, the organic light-emitting device of the present invention can be a front-emitting type, a back-emitting type, or a double-sided-emitting type.

[0204] Furthermore, the organic compounds of the present invention can act on organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors, based on similar principles to those used in organic light-emitting devices.

[0205] The present invention will now be described in more detail through preferred embodiments. However, these embodiments are only used to illustrate the present invention more specifically, and the scope of the present invention is not limited thereto. It will be apparent to those skilled in the art that various changes and modifications can be made to the present invention within the scope and technical concept of the present invention.

[0206] Synthesis Example 1: Synthesis of compound 70

[0207] (1) Preparation Example 1: Synthetic Intermediate 70-1

[0208]

[0209] 100 g of phenanthrene-9,10-dione, 2.9 g of dibenzoyl peroxide, and 10 g of Br2 were added to 100 mL of nitrobenzene. The mixture was then stirred and heated to 120 °C. When HBr began to form, 176 g of Br2 was added dropwise, and the mixture was stirred for 2 hours. The reaction was confirmed to be complete by TLC and HPLC. The mixture was then cooled to room temperature and EtOH was added for solidification. The mixture was then filtered and thoroughly washed with EtOH to obtain 25 g of a yellow intermediate 70-1.

[0210] (2) Preparation Example 2: Synthetic Intermediate 70-2

[0211]

[0212] 10 g of intermediate 70-1 and 5.1 g of (4-bromophenyl)methanamine were added to 300 mL of DMSO, and the mixture was heated to 200 °C and stirred for 24 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled to room temperature and then cured with MeOH. The mixture was then filtered and thoroughly washed with MeOH to obtain 7 g of yellow intermediate 70-2.

[0213] (3) Preparation Example 3: Synthesis of compound 70

[0214]

[0215] 7 g of intermediate 70-2, 7 g of (4-cyanophenyl)boronic acid, and 1.36 g of palladium catalyst were added to toluene, followed by 17 g of potassium carbonate (aqueous solution) and ethanol. The mixture was heated to 80 °C and stirred for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled to room temperature and filtered. It was then recrystallized from monochlorobenzene to give 3 g of compound 70 (a pale yellow solid).

[0216] LC / MS: m / z=599[(M)+]

[0217] Synthesis Example 2: Synthesis of compound 132

[0218] (1) Preparation Example 1: Synthetic Intermediate 132-1

[0219]

[0220] 10 g of 1-(4-(benzo[d]oxazol-5-yl)phenyl)ethan-1-one, 6.07 g of 4-bromobenzothioamide, 21.12 g of KBrO3, and 10 mol% of lipase were added to H2O at 35 °C and stirred for 10 minutes. After confirming the reaction was complete by TLC and HPLC, the organic layer was extracted with MC and H2O and concentrated. The solid was then cured with EtOH to give 11.8 g (yield 64.6%) of intermediate 132-1.

[0221] (2) Preparation Example 2: Synthesis Intermediate 132-2

[0222]

[0223] 10 g of intermediate 132-1, 7.26 g of 1,2,4-tribromobenznen, 12.76 g of K₂CO₃, 0.26 g of palladium catalyst (Pd cat.), and Pcy₃H·BF₄ were added to dimethylacetamide and stirred. The mixture was heated to 140 °C for 14 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified by silica gel column chromatography and recrystallized to give 2.8 g (yield 20.7%) of intermediate 132-2.

[0224] (3) Preparation Example 3: Synthesis of compound 132

[0225]

[0226] 10 g of intermediate 132-2, 8.87 g of benzo[d]oxazole, 10.3 g of K2CO3, 0.08 g of palladium catalyst (Pd cat.), 1.35 g of Cu(OAc)2, and 19.54 g of PPh3 were added to xylene and stirred. The mixture was heated to 160 °C for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified by silica gel column chromatography and recrystallized to give 5.56 g (45% yield) of compound 132.

[0227] LC / MS: m / z = 663[(M)+]

[0228] Synthesis Example 3: Synthesis of compound 145

[0229] (1) Preparation Example 1: Synthetic Intermediate 145-1

[0230]

[0231] 20 g of 1-(4-bromophenyl)ethan-1-one, 17.7 g of (4-cyanophenyl)boronic acid, 42 g of potassium carbonate (aqueous solution (aq)), and 3.5 g of palladium catalyst (Pd cat.) were added to toluene and EtOH and stirred. The mixture was then heated to 80 °C and refluxed for 12 hours. The reaction was confirmed to be complete by TLC and HPLC, followed by extraction with MC and H2O. The organic layer was then separated and concentrated, and the resulting solid was purified by column chromatography to give 17 g (77% yield) of intermediate 145-1.

[0232] (2) Preparation Example 2: Synthetic Intermediate 145-2

[0233]

[0234] 17 g of intermediate 145-1, 11.1 g of 4-bromobenzothioamide, 38.5 g of KBrO3, and 10 mol% of lipase were added to H2O at 35 °C and stirred for 10 minutes. The reaction was confirmed to be complete by TLC and HPLC. The organic layer was extracted with MC and H2O and concentrated. The solid was then cured with EtOH to obtain 20.5 g (64% yield) of intermediate 145-2.

[0235] (3) Preparation Example 3: Synthetic Intermediate 145-3

[0236]

[0237] 20.5 g of intermediate 145-2, 10.3 g of 1,2,4-tribromobenzene, 18.4 g of K₂CO₃, 0.4 g of palladium catalyst (Pd cat.), and Pcy₃H·BF₄ were added to dimethylacetamide and stirred. The mixture was heated to 140 °C for 14 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified by silica gel column chromatography and recrystallized to give 5 g (18% yield) of intermediate 145-3.

[0238] (4) Preparation Example 4: Synthesis of compound 145

[0239]

[0240] 5 g of intermediate 145-3, 4.2 g of benzo[d]oxazole, 19.4 g of K2CO3, 0.04 g of palladium catalyst (Pd cat.), 0.6 g of Cu(OAc)2, and 2.3 g of PPh3 were added to xylene and stirred. The mixture was heated to 160 °C for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified by silica gel column chromatography and recrystallized to give 2.8 g (49% yield) of compound 145.

[0241] LC / MS: m / z = 647[(M)+]

[0242] Synthesis Example 4: Synthesis of compound 147

[0243] (1) Preparation Example 1: Synthetic Intermediate 147-1

[0244]

[0245] 20 g of 1-(4-bromophenyl)ethan-1-one, 17.7 g of (4-cyanophenyl)boronic acid, 42 g of potassium carbonate (aqueous solution (aq)), and 3.5 g of palladium catalyst (Pd cat.) were added to toluene and EtOH and stirred. The mixture was then heated to 80 °C and refluxed for 12 hours. The reaction was confirmed to be complete by TLC and HPLC, and extracted with MC and H2O. The organic layer was then separated and concentrated, and the resulting solid was purified by column chromatography to give 17 g (77% yield) of intermediate 147-1.

[0246] (2) Preparation Example 2: Synthetic Intermediate 147-2

[0247]

[0248] 10 g of intermediate 147-1, 11.3 g of 3-bromobenzothioamide, 38.5 g of KBrO3, and 10 mol% of lipase were added to H2O at 35 °C and stirred for 10 minutes. The reaction was confirmed to be complete by TLC and HPLC. The organic layer was extracted with MC and H2O and concentrated. The solid was then cured with EtOH to obtain 19 g (59% yield) of intermediate 147-2.

[0249] (3) Preparation Example 3: Synthetic Intermediate 147-3

[0250]

[0251] 19 g of intermediate 147-2, 10.3 g of 1,2,4-tribromobenzene, 18.4 g of K₂CO₃, 0.4 g of palladium catalyst (Pd cat.), and Pcy₃H·BF₄ were added to dimethylacetamide and stirred. The mixture was heated to 140 °C for 14 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified by silica gel column chromatography and recrystallized to give 5.3 g (20% yield) of intermediate 147-3.

[0252] (4) Preparation Example 4: Synthesis of compound 147

[0253]

[0254] 5 g of intermediate 147-3, 4.4 g of benzo[d]oxazole, 20.6 g of K2CO3, 0.04 g of palladium catalyst (Pd cat.), 0.6 g of Cu(OAc)2, and 2.3 g of PPh3 were added to xylene and stirred. The mixture was heated to 160 °C for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified by silica gel column chromatography and recrystallized to give 3 g (50% yield) of compound 147.

[0255] LC / MS: m / z = 647[(M)+]

[0256] Synthesis Example 5: Synthesis of compound 251

[0257] (1) Preparation Example 1: Synthetic Intermediate 251-1

[0258]

[0259] At 0°C, 100 g of N-bromosuccinimide was slowly added to 1200 mL of 98% sulfuric acid and stirred for 10 minutes. Then, 50 g of phenanthrene-9,10-dione was added and the mixture was stirred at room temperature for 24 hours. After confirming the reaction was complete by TLC and HPLC, the reaction solution was added to ice water and stirred. The mixture was then filtered to obtain 75 g of the orange intermediate 251-1.

[0260] (2) Preparation Example 2: Synthetic Intermediate 251-2

[0261]

[0262] 10 g of intermediate 251-1 and 5.1 g of (4-bromophenyl)methanamine were added to 300 mL of DMSO, and the mixture was heated to 200 °C and stirred for 24 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled to room temperature and then solidified with MeOH. The mixture was then filtered and thoroughly washed with MeOH to obtain 7 g of intermediate 251-2 (a yellow solid).

[0263] (3) Preparation Example 3: Synthesis of compound 251

[0264]

[0265] 7 g of intermediate 251-2, 7 g of (4-cyanophenyl)boronic acid, and 1.36 g of palladium catalyst were added to toluene, followed by 17 g of potassium carbonate (aqueous solution) and ethanol. The mixture was heated to 80 °C and stirred for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled to room temperature and filtered. It was then recrystallized from monochlorobenzene to give 3 g of compound 251 (a pale yellow solid).

[0266] LC / MS: m / z=599[(M)+]

[0267] Synthesis Example 6: Synthesis of compound 286

[0268] (1) Preparation Example 1: Synthesis of compound 286

[0269]

[0270] 1 g of compound 147 was added to H2O2 and stirred for 10 hours. The reaction was then confirmed to be complete by TLC and HPLC. After filtration and recrystallization with MCB, 0.9 g (yield 86%) of compound 286 was obtained.

[0271] LC / MS: m / z=679[(M)+]

[0272] Synthesis Example 7: Synthesis of compound 287

[0273] (1) Preparation Example 1: Synthesis of compound 287

[0274]

[0275] 1 g of compound 145 was added to H2O2 and stirred for 10 hours. The reaction was confirmed to be complete by TLC and HPLC. After filtration and recrystallization with MCB, 0.85 g (yield 81%) of compound 287 was obtained.

[0276] LC / MS: m / z=679[(M)+]

[0277] Synthesis Example 8: Synthesis of compound 288

[0278] (1) Preparation Example 1: Synthetic Intermediate 288-1

[0279]

[0280] 50 g of intermediate 70-1, 64 g of aniline, 17.9 g of 4-formylbenzonitrile, and 70.2 g of 60% ammonium acetate were added to AcOH and stirred. The mixture was then heated to 110 °C and stirred for 4 hours. The reaction was confirmed to be complete by TLC and HPLC. After cooling, the reaction solution was added to H₂O, the solid was filtered, and then purified by silica gel column chromatography to obtain 51 g (67% yield) of intermediate 288-1.

[0281] (2) Preparation Example 2: Synthesis of compound 288

[0282]

[0283] 10 g of intermediate 288-1, 8.6 g of benzo[d]oxazole, 40 g of K2CO3, 0.32 g of palladium catalyst (Pd cat.), 5.3 g of Cu(OAc)2, and 4.7 g of PPh3 were added to xylene and stirred. The mixture was heated to 160 °C for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified by silica gel column chromatography and recrystallized to give 6 g (53% yield) of compound 288.

[0284] LC / MS: m / z = 630[(M)+]

[0285] Synthesis Example 9: Synthesis of compound 289

[0286] (1) Preparation Example 1: Synthetic Intermediate 289-1

[0287]

[0288] 50 g of intermediate 251-1, 64 g of aniline, 25.3 g of 4-bromoaldehyde, and 70.2 g of 60% ammonium acetate were added to AcOH and stirred. The mixture was then heated to 110 °C and stirred for 4 hours. The reaction was confirmed to be complete by TLC and HPLC. After cooling, the reaction solution was added to H₂O, the solid was filtered, and then purified using a silica gel column to obtain 63 g (76% yield) of intermediate 289-1.

[0289] (2) Preparation Example 2: Synthesis of Compound 289

[0290]

[0291] 10 g of intermediate 289-1, 9.7 g of (4-cyanophenyl)boronic acid, and 1.52 g of palladium catalyst were added to toluene, followed by 36.4 g of potassium carbonate (aqueous solution) and ethanol. The mixture was heated to 80 °C and stirred for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled to room temperature and filtered. It was then recrystallized from monochlorobenzene to give 6.3 g (57% yield) of compound 289.

[0292] LC / MS: m / z = 674[(M)+]

[0293] Synthesis Example 10: Synthesis of compound 320

[0294] (1) Preparation Example 1: Synthetic intermediate 320-1

[0295]

[0296] 10 g of intermediate 251-2, 9 g of benzo[d]oxazole, 9 g of K2CO3, 0.1 g of palladium catalyst (Pd cat.), 1.4 g of Cu(OAc)2, and 5 g of PPh3 were added to xylene and stirred. The mixture was heated to 160 °C for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified using a silica gel column to obtain 4.8 g (42% yield) of intermediate 320-1.

[0297] (2) Preparation Example 2: Synthesis of compound 320

[0298]

[0299] 10 g of intermediate 19-2, 6.8 g of 9H-fluorene-2-carbonitrile, and 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-(ACI) were added to toluene, followed by the addition of 6.8 g of K₂CO₃(aq), 1 g of Pd(PPh₃)₄, and EtOH, and the mixture was stirred. The temperature was then raised to 80 °C and maintained for 4 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and the organic layer was concentrated by extraction with MC. The solution was then purified by silica gel column chromatography and crystallized to give 7.1 g (58% yield) of compound 320.

[0300] Synthesis Example 11: Synthesis of compound 513

[0301] (1) Preparation Example 1: Synthetic Intermediate 513-1

[0302]

[0303] 10 g of 2,7-dibromo-9,10-phenanthrenedione and 3.6 g of 4-(aminomethyl)benzonitrile were added to 300 mL of DMSO, and the mixture was heated to 200 °C and stirred for 24 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled to room temperature and solidified by adding MeOH. The mixture was then filtered and thoroughly washed with MeOH to obtain 6.6 g (51% yield) of intermediate 513-1.

[0304] (2) Preparation Example 2: Synthesis of compound 513

[0305]

[0306] 10 g of intermediate 513-1, 11.5 g of (5-Cyano-2-furyl)boronic acid, 11.6 g of K₂CO₃, 0.1 g of palladium catalyst (Pd cat.), 1.5 g of Cu(OAc)₂, and 5.5 g of PPh₃ were added to xylene and stirred. The mixture was heated to 160 °C for 12 hours. After confirming the completion of the reaction by TLC and HPLC, the mixture was cooled and filtered. The resulting product was then purified by silica gel column chromatography and recrystallized to give 5.1 g (49% yield) of compound 513.

[0307] Experimental Example 1: Optical Properties of the Compounds of the Present Invention

[0308] In an experimental example of this invention, a 25mm × 25mm quartz glass was cleaned. It was then installed in a vacuum chamber, and the base pressure was increased to 1 × 10⁻⁶. -6 When the temperature reaches a certain level (torr), the compound of the present invention and the comparative compound are deposited on a glass substrate respectively, and their optical properties are measured.

[0309] Examples 1 to 10

[0310] The compounds of the present invention shown in Table 1 below, which are used as light efficiency improvement layers in organic light-emitting devices, were deposited on glass substrates for 100 nm and their refractive indices were measured.

[0311] Quartz glass / Organic material (100nm)

[0312] Comparative Example 1

[0313] Except that CP1 was used instead of the compounds in Examples 1 to 10, the substrate of Comparative Example 1 was prepared in the same manner and its optical properties were measured.

[0314] Experimental Example 1: Optical properties of compounds from Examples 1 to 10

[0315] The refractive index of the substrates prepared according to the examples and comparative examples described above was determined using an ellipsometry (Elli-SE). The refractive index was measured in the blue wavelength range (450 nm), and the results are shown in Table 1.

[0316] Table 1

[0317] distinguish Refractive index (450nm) Example 1 (Compound 70) 2.42 Example 2 (Compound 145) 2.25 Example 3 (Compound 147) 2.38 Example 4 (Compound 251) 2.31 Example 5 (Compound 286) 2.27 Example 6 (Compound 287) 2.40 Example 7 (Compound 288) 2.33 Example 8 (Compound 289) 2.36 Example 9 (Compound 320) 2.39 Example 10 (Compound 513) 2.37 Comparative Example 1 (CP1) 1.70

[0318] As can be seen from Table 1, the refractive index of the compound of the present invention at a wavelength of 450 nm is significantly higher than that of the compound of Comparative Example 1. When the compound of the present invention with such a high refractive index is used in the light efficiency improvement layer of an organic light-emitting device, the efficiency during the process can be optimized.

[0319]

[0320] CP1

[0321] Device Example (CPL)

[0322] In an embodiment of the invention, the anode is patterned using an ITO glass substrate containing 25mm × 25mm × 0.7mm Ag, resulting in a light-emitting area of ​​2mm × 2mm before cleaning. After mounting the patterned ITO substrate in a vacuum chamber, it is subjected to a 1×10⁻⁶... -6 Under process pressures above Torr, organic layers and metals are deposited into the following structure.

[0323] Examples 11 to 44

[0324] A blue organic light-emitting device with the following device structure was prepared by using the compound according to the present invention in a light efficiency improvement layer (monolayer CPL) in the device, and then the luminescence and driving characteristics were measured.

[0325] Ag / ITO / hole injection layer (HAT-CN, 5nm) / hole transport layer (HT1, 100nm) / electron blocking layer (EB1, 10nm) / light emitting layer (20nm) / electron transport layer (ET1:Liq, 30nm) / LiF (1nm) / Mg:Ag (15nm) / light efficiency improvement layer (65nm)

[0326] A hole injection layer was formed on top of an Ag-containing ITO transparent electrode on a glass substrate by depositing a 5 nm thick HAT-CN film, followed by a 100 nm thick HT1 film to form a hole transport layer, and then a 10 nm thick EB1 film to form an electron blocking layer. Then, a 20 nm thick light-emitting layer was formed by co-depositing BH1 as the host compound and BD1 as the dopant compound. Next, a 30 nm thick electron transport layer (ET1 compound doped with 50% Liq) was deposited, followed by a 1 nm thick LiF film to form the electron injection layer. Finally, a 15 nm thick Mg:Ag film was formed at a 1:9 ratio to form the cathode.

[0327] Furthermore, organic light-emitting devices are fabricated by depositing a light efficiency enhancement layer (capping layer) to a thickness of 65 nm using the compounds of chemical formula I of the present invention shown in Table 2 below.

[0328] Device Comparison Example 2

[0329] Except that the device structures of Examples 11 to 44 do not have a light efficiency improvement layer, the organic light-emitting device of Comparative Example 2 was prepared in the same way.

[0330] Device Comparison Example 3

[0331] Except that, in the device structures of Examples 11 to 44, the organic light-emitting device of Comparative Example 3 was prepared in the same manner as the device structure of Comparative Example 3, except that CP1 was used instead of the compound of the present invention as the light efficiency improvement layer compound.

[0332] Experimental Example 2: Luminescent Characteristics of Devices in Examples 11 to 44

[0333] The driving voltage, current efficiency, and color coordinates of the organic light-emitting devices prepared according to the examples and comparative examples were measured using a source meter (Model 237, Keithley) and a photometer (PR-650, PhotoResearch). The results, with 1000 nits as a reference, are shown in Table 2 below.

[0334] Table 2

[0335]

[0336]

[0337] As shown in Table 2, it can be confirmed that when the compound of Chemical Formula I of the present invention is used as a light efficiency improvement layer in a device, the driving voltage is reduced and the current efficiency is improved compared with existing devices without a light efficiency improvement layer and devices prepared using compounds used as existing light efficiency improvement layer materials (Comparative Examples 2 to 3).

[0338] HATCN HT1 BH1 BD1 ET1

[0339]

[0340] EB1 CP1

[0341]

Claims

1. An organic compound, characterized in that, Represented by the following chemical formula I: Chemical Formula I: ， In the chemical formula I, X1 is selected from any one of O, S, SO, SO2, NR1, CR2R3, SiR4R5, and GeR6R7. R1 to R7 may be the same as or different from each other, and each independently is selected from hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 50 carbon atoms, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, cyano, and halogen. L1 to L3 are divalent linking groups, which are directly bonded or selected from any one of substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms. o, p, and q are integers from 0 to 2. When o, p, and q are 2, the multiple L1 to L3 are either the same as or different from each other. Ar1 to Ar3 may be the same as or different from each other, and each is independently a cyano group or selected from any of the following: aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, and heteroaryl groups with 2 to 50 substituted or unsubstituted carbon atoms. The term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, cyano, halogen, hydroxy, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aliphatic-aromatic mixed cycloalkyl, amino, silyl, and germanyl, or substituted by a substituent linked by two or more of the substituents, or not having any substituents.

2. The organic compound according to claim 1, characterized in that, The L1 to L3 are divalent linking groups, which are directly bonded, substituted, or unsubstituted aryl groups with 6 to 30 carbon atoms. The Ar1 to Ar3 may be the same as or different from each other, and each is independently an aryl group with 6 to 30 substituted or unsubstituted carbon atoms.

3. The organic compound according to claim 1, characterized in that, The L1 to L3 are divalent linked groups, which are directly bonded, substituted or unsubstituted phenylene groups, and the Ar1 to Ar3 are each substituted or unsubstituted naphthyl groups.

4. The organic compound according to claim 1, characterized in that, At least one of Ar1 to Ar3 is either structural formula 1 or selected from structural formula 2: Structure 1: ， Structure 2: ， In each of the structural formulas in structural formula 2, X can be the same as or different from each other, and can be N or CR independently. 11 Y is selected from O, S, NR 12 CR 13 R 14 SiR 15 R 16 and GeR 17 R 18 any of them, The R 11 To R 18 They may be the same as or different from each other, and each independently comprises any one selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 50 carbon atoms, substituted or unsubstituted amino with 1 to 50 carbon atoms, substituted or unsubstituted silyl, and substituted or unsubstituted germanyl. Multiple R 11 They can connect with each other to form alicyclic or aromatic monocyclic or polycyclic rings. The R 13 With R 14 R 15 With R 16 and R 17 With R 18 They can connect with each other to form alicyclic or aromatic monocyclic or polycyclic rings. The carbon atoms of the alicyclic or aromatic monocyclic or polycyclic compounds formed can be substituted by heteroatoms selected from O, S, N, P, Si, and Ge. R selected from each of the above structural formulas 11 To R 18 Any one of them is connected to L1 to L3 in the chemical formula I. The term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aliphatic-aromatic mixed cycloalkyl, amino, silyl and germanyl, or substituted by substituents linked by two or more of the substituents, or not having any substituents.

5. The organic compound according to claim 4, characterized in that, At least one of Ar1 to Ar3 is the following structural formula 1 or structural formula 2-2: Structure 1: ， Structural Formula 2-2: ， In the aforementioned structural formula 2-2, Y is selected from O, S, SO, SO2 and NR. 21 any of them, The R 21 It is selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, substituted or unsubstituted germanyl groups, cyano groups, and halogen groups. R 31 To R 35 They may be the same as or different from each other, and each independently comprises any one selected from hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 50 carbon atoms, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, cyano, and halogen. The R 32 To R 35 They can connect with each other or with adjacent substituents to further form alicyclic or aromatic monocyclic or polycyclic compounds. The R 31 To R 35 Any one of them is a part connected to L1 to L3. The term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, cyano, halogen, hydroxy, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aliphatic-aromatic mixed cycloalkyl, amino, silyl, and germanyl, or substituted by a substituent linked by two or more of the substituents, or not having any substituents.

6. The organic compound according to claim 5, characterized in that, The structural formula 2-2 is selected from any one of the following structural formulas 3: Structure 3: ， In the aforementioned structural formula 3. Y is selected from O, S, SO, SO2 and NR. 21 any of them, The R 21 It is selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms, substituted or unsubstituted silyl groups, substituted or unsubstituted germanyl groups, cyano groups, and halogen groups. R 31 To R 43 They may be the same as or different from each other, and each independently comprises any one selected from hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl with 3 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 2 to 50 carbon atoms, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, cyano, and halogen. The R 31 To R 43 Any one of them is a part connected to L1 to L3. The term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, cyano, halogen, hydroxy, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aliphatic-aromatic mixed cycloalkyl, amino, silyl, and germanyl, or substituted by a substituent linked by two or more of the substituents, or not having any substituents.

7. The organic compound according to claim 4, characterized in that, Ar1 to Ar3 may be the same as or different from each other, and each independently conforms to either structural formula 1 or structural formula 2.

8. The organic compound according to claim 1, characterized in that, The chemical formula I is selected from any one of compounds 1 to 758: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， 。 9. An organic light-emitting device, comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, characterized in that, It also includes a light efficiency improvement layer, formed on at least one side of the upper or lower portion of the first and second electrodes opposite to the organic layer. The light efficiency improvement layer contains a compound represented by the chemical formula I.

10. The organic light-emitting device according to claim 9, characterized in that, The light efficiency improvement layer is formed at least at one of the lower portion of the first electrode and the upper portion of the second electrode.

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