Organic compound, light-emitting device, optical device, electronic equipment, light-emitting apparatus, and lighting apparatus

Abstract

To provide a novel organic compound with favorable thermophysical properties.SOLUTION: An organic compound represented by General Formula (G1) below is provided. (At least one of X1 to X5 is a secondary or tertiary alkyl group having 3 to 6 carbon atoms in which a carbon atom bonded to a phenyl group branches. Each of R1 to R7 is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or the like. Ar1 represents a condensed heteroaromatic ring skeleton composed of two or more rings, and Ar2 represents an aryl group. n is any of 1 to 3.)SELECTED DRAWING: None

Description

[Technical Field]

[0001] One aspect of the present invention is an organic compound, a light-emitting element, a light-emitting device, a display module, a lighting device, a The present invention relates to a light module, a display device, a light-emitting device, an electronic device, and a lighting device. The present invention is not limited to the above-mentioned technical fields. The field relates to an article, a method, or a manufacturing method. Alternatively, one aspect of the present invention is Process, machine, manufacture, or composition of matter Therefore, the technology of one aspect of the present invention disclosed in the present specification more specifically relates to Fields of application include semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, and power storage devices. Examples of the present invention include a memory device, an imaging device, a driving method thereof, or a manufacturing method thereof. It can be done. [Background technology]

[0002] Electroluminescence (EL) using organic compounds Light-emitting devices (organic EL devices) that utilize these materials are being put to practical use. The basic structure of a light-emitting device is an organic compound layer (EL layer) containing a light-emitting material between a pair of electrodes. A voltage is applied to this element to inject carriers, and the regeneration of these carriers By utilizing the bond energy, light can be emitted from the light-emitting material.

[0003] Since such light-emitting devices are self-luminous, when they are used as pixels in a display, Compared to flat panel displays, they have the advantage of being highly visible and not requiring a backlight. The light-emitting device is suitable for use as a display element. Another major advantage is that it can be manufactured to be thin and lightweight. It is one of the signs.

[0004] In addition, these light-emitting devices can be fabricated with a continuous two-dimensional light-emitting layer. This is a point light source, such as an incandescent bulb or LED, and This is a feature that is difficult to obtain with linear light sources such as fluorescent lamps, so it is used as a surface light source that can be applied to lighting, etc. It is also highly useful as a tool.

[0005] Displays and lighting devices using such light-emitting devices are suitable for use in a variety of electronic devices. However, research and development is ongoing to find light-emitting devices with better characteristics ( For example, see Patent Document 1. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 2019-085387 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of one embodiment of the present invention is to provide a novel organic compound. In one embodiment, an object of the present invention is to provide an organic compound having good thermal properties. In one embodiment, an object is to provide an organic compound that has good color purity and can be vapor deposited at a low temperature.

[0008] Another object of one embodiment of the present invention is to provide a novel blue light-emitting material. An object of one embodiment of the present invention is to provide a blue light-emitting material having good thermal properties. An object of one embodiment of the present invention is to provide a blue light-emitting material with high solubility. In one aspect of the present invention, there is provided a blue light-emitting material having good color purity and a low deposition temperature. The purpose is to:

[0009] Alternatively, in one embodiment of the present invention, a light-emitting device having good characteristics can be provided, and the deposition temperature can be low. Another object of the present invention is to provide an organic compound having a long life. The present invention aims to provide an organic compound that can be used to provide a light-emitting device and that can be deposited at a low temperature.

[0010] Alternatively, in one embodiment of the present invention, a light-emitting device having good characteristics can be provided, and the deposition temperature can be low. Another object of the present invention is to provide a blue light-emitting material having a long life. The present invention aims to provide a blue light-emitting material that can be vapor-deposited at a low temperature and that can provide a light-emitting device with high efficiency. Alternatively, in one embodiment of the present invention, a blue LED having good initial characteristics and a good life span and having a low deposition temperature is provided. The object is to provide a color emitting material.

[0011] Alternatively, in one embodiment of the present invention, a light-emitting device, a light-emitting apparatus, an electronic device, or the like that has a long lifetime and is easy to manufacture is provided. The present invention aims to provide a device for detecting a temperature difference and a display device for detecting a temperature difference.

[0012] The description of these problems does not preclude the existence of other problems. The embodiment does not necessarily have to solve all of these problems. The above will be made clear from the description, drawings, claims, etc. It is possible to extract other issues from the descriptions in the patent, claims, etc.

[0013] The present invention is intended to solve any one of the above problems. [Means for solving the problem]

[0014] One embodiment of the present invention is an organic compound represented by the following general formula (G1).

[0015] [ka]

[0016] However, in the above general formula (G1), X 1 ~X 5 At least one of the carbon atoms is 3 or more. A secondary or tri-alkyl group having 6 carbon atoms and a branched carbon atom attached to the phenyl group. alkyl group, and the remainders are independently hydrogen or an alkyl group having 1 to 6 carbon atoms. cycloalkyl groups having 3 to 12 carbon atoms and unsubstituted or unsubstituted cycloalkyl groups having 6 to 13 carbon atoms. or an aryl group substituted with an alkyl group. 1 ~R 7 Each independently hydrogen, alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms, Alkyl groups and unsubstituted or alkyl-substituted aryl groups having 6 to 13 carbon atoms Ar 1 is a substituted or unsubstituted group having 8 to 60 carbon atoms, and represents a fused heteroaromatic ring skeleton having two or more rings, and Ar 2 is a substituted or unsubstituted carbon atom having 6 to 10 carbon atoms. It represents an aryl group having a prime number of 25. In addition, n is any one of 1 to 3, and n is 2 or 3. If there is, Ar 1 The two or three groups bonded to each other may be the same or different. stomach.

[0017] Alternatively, another aspect of the present invention is the above-mentioned structure, 1 is a substituted or unsubstituted carbon An organic compound having a fused heteroaromatic ring skeleton with 8 to 60 carbon atoms and 3 to 9 rings. be.

[0018] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 1 Substituted or unsubstituted carbon An organic compound having a prime number of 8 to 60 carbon atoms and a fused heteroaromatic ring skeleton with 3 to 7 rings. is.

[0019] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the X 1 ~X 5 At least one of is a secondary or tertiary compound having 3 or 4 carbon atoms and a branched carbon atom attached to the phenyl group alkyl group, and the remainders are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms; Cycloalkyl groups having 3 to 12 carbon atoms and unsubstituted or is an organic compound that is either an aryl group substituted with an alkyl group.

[0020] Another embodiment of the present invention is an organic compound having the above structure, wherein n is 2. .

[0021] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 1 is represented by the following general formula (B1) The heteroaromatic ring skeleton is an organic compound represented by any one of the following formulas (B1 to (B4):

[0022] [ka]

[0023] However, in the formula, Q 1 and Q 2 Each independently represents an oxygen atom or a sulfur atom. In the general formula (B1), R10 ~R 21 One or two of the groups represent a single bond, and the remaining each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 3 to 12 carbon atoms, and unsubstituted or alkyl-substituted cycloalkyl groups having 6 to 13 carbon atoms. In addition, in the above general formula (B2), R 30 ~R 41 One or two of the groups represented by the formula (I) represent a single bond, and the remaining groups each independently represent hydrogen, a group having 1 to 10 carbon atoms, or a group having 1 to 10 carbon atoms. alkyl groups having 3 to 6 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms, and alkyl groups having 6 to 12 carbon atoms. 13 represents either an unsubstituted or alkyl-substituted aryl group. In general formula (B3), R 50 ~R 61 One or two of the following represent a single bond, and the rest are Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a silyl group having 3 to 12 carbon atoms, cycloalkyl groups and unsubstituted or alkyl-substituted groups having 6 to 13 carbon atoms; In addition, in the above general formula (B4), R 70 ~R 81 Noi One or two of them represent a single bond, and the rest are each independently hydrogen, a C1 to C6 alkyl groups, cycloalkyl groups having 3 to 12 carbon atoms, and cycloalkyl groups having 6 to 13 carbon atoms represents either an unsubstituted or alkyl-substituted aryl group.

[0024] Alternatively, another aspect of the present invention is the above-mentioned structure, wherein the Ar 1 is represented by the following general formula (B1-1 ) or (B3-1).

[0025] [ka]

[0026] However, in the formula, Q 1 and Q 2 Each independently represents an oxygen atom or a sulfur atom. 12 , R 18 , R 52 and R 58 represents a single bond.

[0027] Alternatively, another embodiment of the present invention is a compound represented by the following general formula (G1-1) in the above structure: It is an organic compound.

[0028] [ka]

[0029] However, in the above general formula (G1-1), X 11 ~X 15 At least one has the number of carbon atoms A secondary or branched alkyl group having 3 to 6 carbon atoms and a branched carbon atom bonded to the phenyl group. or a tertiary alkyl group, and the remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or alkyl groups, cycloalkyl groups having 3 to 12 carbon atoms, and unsubstituted alkyl groups having 6 to 13 carbon atoms. It is either a substituted or alkyl-substituted aryl group. 21 ~X 2 5 At least one of the alkyl groups is an alkyl group having 3 to 6 carbon atoms and is bonded to a phenyl group. a secondary or tertiary alkyl group in which the carbon atom at the end of the alkyl group is branched, and the remaining carbon atoms are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms; Also, Ar 21and Ar 22 each independently represents a substituted or unsubstituted group having 6 to 10 carbon atoms; It represents an aryl group having 25 carbon atoms.

[0030] Another embodiment of the present invention is a light-emitting device including any of the above organic compounds.

[0031] Another embodiment of the present invention is a light-emitting device including the above light-emitting device and a sensor, an operation button, a speaker, or a Or, it is an electronic device having a microphone.

[0032] Another embodiment of the present invention is a semiconductor device including the above light-emitting device, a transistor, or a substrate, and The light emitting device has the following.

[0033] Another embodiment of the present invention is a lighting device including the light-emitting device and a housing. .

[0034] In this specification, the term "light-emitting device" includes an image display device using a light-emitting device. In addition, a connector such as anisotropic conductive film or TCP (Tape) is attached to the light-emitting device. Module with Carrier Package attached, printed on TCP Modules with wiring boards or light-emitting devices with COG (Chip On Glass) s) method, a module in which an IC (integrated circuit) is directly mounted may also be included in the category of light-emitting device. Furthermore, lighting fixtures and the like may include a light-emitting device. [Effects of the Invention]

[0035] According to one embodiment of the present invention, a novel organic compound can be provided. In one embodiment of the present invention, an organic compound having good thermal properties can be provided. It is possible to provide an organic compound having good color purity and requiring a low deposition temperature.

[0036] Alternatively, in one embodiment of the present invention, a novel blue light-emitting material can be provided. In one embodiment, a blue light-emitting material having good thermal properties can be provided. In one embodiment, a blue light-emitting material having good color purity and vapor deposition at a low temperature can be provided. .

[0037] Alternatively, in one embodiment of the present invention, a light-emitting device having good characteristics can be provided, and the deposition temperature can be low. Alternatively, in one embodiment of the present invention, an organic compound having a long lifetime can be provided. A device can be provided, and an organic compound can be provided that can be deposited at a low temperature. In one aspect of the present invention, an organic compound having good initial characteristics and life span and a low deposition temperature is provided. It can be provided.

[0038] Alternatively, in one embodiment of the present invention, a light-emitting device having good characteristics can be provided, and the deposition temperature can be low. Alternatively, in one embodiment of the present invention, a blue light-emitting material with excellent lifetime can be provided. It is possible to provide an optical device and a blue light-emitting material that can be vapor-deposited at a low temperature. In one aspect of the present invention, a blue light-emitting material having good initial characteristics and a good life span and having a low deposition temperature is provided. Fees can be provided.

[0039] Alternatively, in one embodiment of the present invention, a light-emitting device, a light-emitting apparatus, an electronic device, or the like that has a long lifetime and is easy to manufacture is provided. A device and a display device can each be provided.

[0040] The description of these effects does not preclude the existence of other effects. The embodiment does not necessarily have to have all of these effects. , the specification, drawings, claims, etc., and It is possible to extract other effects from the claims and other descriptions. [Brief explanation of the drawings]

[0041] [Figure 1] 1(A), 1(B) and 1(C) are schematic diagrams of light-emitting devices. [Figure 2] 2(A) and 2(B) are conceptual diagrams of an active matrix light emitting device. [Figure 3] 3(A) and 3(B) are conceptual diagrams of an active matrix light emitting device. [Figure 4] FIG. 4 is a conceptual diagram of an active matrix light emitting device. [Figure 5] 5(A) and 5(B) are conceptual diagrams of a passive matrix light emitting device. [Figure 6] 6(A) and 6(B) are diagrams showing the lighting device. [Figure 7] 7(A), 7(B1), 7(B2) and 7(C) are diagrams showing electronic devices. [Figure 8] 8(A), 8(B) and 8(C) are diagrams showing electronic devices. [Figure 9] FIG. 9 is a diagram showing a lighting device. [Figure 10] FIG. 10 is a diagram showing a lighting device. [Figure 11] FIG. 11 is a diagram showing an in-vehicle display device and a lighting device. [Figure 12] 12(A) and 12(B) are diagrams showing electronic devices. [Figure 13] 13(A), 13(B) and 13(C) are diagrams showing electronic devices. [Figure 14] Figures 14(A) and 14(B) are 1H NMR charts of 3,10tBuPCA2Nbf(IV)-02. [Figure 15]Figure 15 shows the absorption and emission spectra of 3,10tBuPCA2Nbf(IV)-02 in a toluene solution. [Figure 16] Figure 16 shows the absorption and emission spectra of 3,10tBuPCA2Nbf(IV)-02 in a thin film state. [Figure 17] Figures 17(A) and 17(B) are 1H NMR charts of 3,10mtBuPCA2Nbf(IV)-02. [Figure 18] Figure 18 shows the absorption and emission spectra of 3,10mtBuPCA2Nbf(IV)-02 in a toluene solution. [Figure 19] Figure 19 shows the absorption and emission spectra of 3,10mtBuPCA2Nbf(IV)-02 in a thin film state. [Figure 20] FIG. 20 shows the luminance-current density characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 21] FIG. 21 shows the current efficiency-luminance characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 22] FIG. 22 shows the luminance-voltage characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 23] FIG. 23 shows the current-voltage characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 24] FIG. 24 shows the external quantum efficiency-luminance characteristics of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 25] FIG. 25 shows the emission spectra of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. [Figure 26] Figure 26 shows the emission spectra of 3,10tBuPCA2Nbf(IV)-02, 3,10mtBuPCA2Nbf(IV)-02, 3,10mmEtPCA2Nbf(IV)-02, 3,10mmHexPCA2Nbf(IV)-02, and 3,10PCA2Nbf(IV)-02 in the solution state. [Figure 27]Figure 27 shows the relationship between weight and temperature in thermogravimetry-differential thermal analysis of 3,10tBuPCA2Nbf(IV)-02, 3,10mtBuPCA2Nbf(IV)-02, 3,10mmEtPCA2Nbf(IV)-02, 3,10mmHexPCA2Nbf(IV)-02, and 3,10PCA2Nbf(IV)-02. [Figure 28] FIG. 28 is a graph showing the change in luminance with respect to the driving time of the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device 1. In FIG. [Figure 29] Figure 29 shows the absorption and emission spectra of 3,10 mm EtPCA2Nbf(IV)-02 in toluene solution. [Figure 30] Figure 30 shows the absorption and emission spectra of 3,10 mm EtPCA2Nbf(IV)-02 in a thin film state. DETAILED DESCRIPTION OF THE INVENTION

[0042] Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The present invention is not limited to the above description, and the form and details thereof may be changed without departing from the spirit and scope of the present invention. It will be readily apparent to those skilled in the art that various modifications may be made to the present invention. It should not be construed as being limited to the description of the embodiments.

[0043] (Embodiment 1) In this embodiment, an organic compound of one embodiment of the present invention will be described.

[0044] An organic compound according to one embodiment of the present invention is represented by the following general formula (G1).

[0045] [ka]

[0046] In the organic compound represented by the general formula (G1), X1 ~X 5 At least one An alkyl group having 3 to 6 carbon atoms, and the carbon atom bonded to the phenyl group is branched. It is either a secondary or tertiary alkyl group. Hereinafter, this refers to the alkyl group. In the organic compound represented by the general formula (G1), X 1 ~X 5 At least one of the branched chain alkyl groups is sublimable or The solubility in the solvent is improved, and the organic compound represented by the general formula (G1) can be formed into a film and purified. As a result, the organic compound and the organic compound can be easily used. The device using the compound is an organic compound and device with good productivity and reliability. can be done.

[0047] That is, in the alkyl group bonded to the phenyl group at the 9-position of the carbazolyl group, The carbon directly bonded to the alkyl group is branched, which suppresses intermolecular interactions. The sublimation property or solubility in solvents is improved. Since the conjugation is difficult to extend in the phenyl group, even if an alkyl group is introduced into the phenyl group, the emission spectrum Furthermore, when an alkyl group is introduced into the phenyl group, the absorption spectrum is resistant to change. This is preferable because it also improves thermal resistance.

[0048] The alkyl group having 3 to 6 carbon atoms is an alkyl group having 3 or 4 carbon atoms. and the carbon atom attached to the phenyl group is a branched secondary or tertiary alkyl group. These are preferred because they can be synthesized inexpensively and have good sublimation properties.

[0049] Also, X 1 ~X5 At least one of X is the branched chain alkyl group. 1 ~X 5 Of Other than the branched-chain alkyl group, each independently is hydrogen, an alkyl group having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms and unsubstituted or unsubstituted cycloalkyl groups having 6 to 13 carbon atoms. It is to be noted that, from the viewpoint of synthesis cost, Preferably they are hydrogen.

[0050] In addition, the bonding position of the branched chain alkyl group is X 1 ~X 5 By being either The branched alkyl group has almost no effect on the HOMO level or LUMO level. One of the characteristics of the organic compound represented by the general formula (G1) is that The organic compound represented by the general formula (G1) is X 1 ~X 5 Any of the above branched alkyl groups By having the branched-chain alkyl group, the HO The MO level, LUMO level, emission spectrum, and band gap remain almost unchanged, and the heat resistance It is possible to improve the viscosity, sublimation property, and solubility.

[0051] Furthermore, X 1 ~X 5 is a carbazolyl group possessed by the arylamine contained in the above general formula (G1). It is a group that bonds to the phenyl group at the 9th position of the phenyl group. 1 ~X 5 At least one of them is The branched chain alkyl group is such a branched chain alkyl group, but among the carbon atoms of the branched chain alkyl group, The carbon bonded to the group is a branched secondary or tertiary alkyl group, It is also possible to improve the reliability of light-emitting devices using the material.

[0052] The above-mentioned alkyl group having 3 to 6 carbon atoms and bonded to a phenyl group Specific examples of branched secondary or tertiary alkyl groups include those represented by the following structural formula (X Examples of the groups include groups represented by (X-1) to (X-9).

[0053] [ka]

[0054] In addition, in the organic compound represented by the general formula (G1), R 1 ~R 7 are independent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and unsubstituted or alkyl-substituted aryl groups having 6 to 13 carbon atoms. Either one.

[0055] Furthermore, n is any one of 1 to 3, and when n is 2 or 3, Ar 1 To bind to The two or three groups may be the same or different. If it is 2 or 3, Ar 1 may have a plurality of the same substituents bonded to each other, or may have different structures. A plurality of such substituents may be bonded.

[0056] Also, Ar 1 is a substituted or unsubstituted fused heterocyclic ring having 8 to 60 carbon atoms and two or more rings; represents an aromatic ring skeleton, and Ar 2 represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms; represent.

[0057] The above Ar 1The substituted or unsubstituted groups having 8 to 60 carbon atoms and Specific examples of the fused heteroaromatic ring skeleton having two or more rings include those represented by the following structural formula (Ar 1 -1)~ (Ar 1 -39) and the like.

[0058] [ka]

[0059] In addition, the above Ar 2 The substituted or unsubstituted groups having 6 to 2 carbon atoms are listed as the groups represented by The aryl group of 5 includes a phenyl group, a tolyl group, a dimethylphenyl group, a trimethylphenyl group, and phenyl group, propylphenyl group, dipropylphenyl group, butylphenyl group, dibutylphenyl group phenyl group, cyclohexylphenyl group, naphthyl group, naphthylphenyl group, phenylnaphthyl phenyl group, biphenyl group, terphenyl group, fluorenyl group, 9,9-dimethylfluorenyl group group, phenanthryl group, 9,9-diphenylfluorenyl group, spirofluorenyl group, Examples include phenylenyl, pyrenyl, anthryl, and 9-phenylanthryl groups. Specifically, the following structural formula (Ar 2 -1)~(Ar 2 -49) etc. It can be done.

[0060] [ka]

[0061] [ka]

[0062] In addition, Ar1 is a substituted or unsubstituted ring having 8 to 60 carbon atoms and 3 to 9 rings. A condensed heteroaromatic ring skeleton is preferred because it has high sublimability, and the number of substituted or unsubstituted carbon atoms is The compound has a fused heteroaromatic ring skeleton with 8 to 60 carbon atoms and 3 to 7 rings, and is heat-resistant. It is more preferable because it is high.

[0063] Among them, the Ar 1 is any one of the heteroaromatic ring skeletons represented by the following general formulas (B1) to (B4): Any of these organic compounds is more preferred because it exhibits good blue light emission.

[0064] [ka]

[0065] In the above general formulas (B1) to (B4), Q 1 and Q 2 are each independently an oxygen atom or a sulfur atom. 10 ~R 21 Either or 1 or 2 represents a single bond, and the remaining groups are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or alkyl groups, cycloalkyl groups having 3 to 12 carbon atoms, and unsubstituted or alkyl groups. In addition, the aryl group represented by the general formula (B) has 6 to 13 carbon atoms and is substituted with aryl groups having 6 to 13 carbon atoms. 2) In R 30 ~R 41 One or two of the following represent a single bond, and the remaining are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, alkyl groups and unsubstituted or alkyl-substituted aryl groups having 6 to 13 carbon atoms In addition, in the general formula (B3), R 50 ~R 61 One of Or, 2 represents a single bond, and the remaining groups are each independently hydrogen or alkyl having 1 to 6 carbon atoms. groups, cycloalkyl groups having 3 to 12 carbon atoms, and unsubstituted or alkyl-substituted groups In addition, the aryl group represented by the general formula (B4) has 6 to 13 carbon atoms. In R 70 ~R 81 One or two of the following represent a single bond, and the remaining are each independently and hydrogen, alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms. and unsubstituted or alkyl-substituted aryl groups having 6 to 13 carbon atoms. Represents either one.

[0066] Among the general formulae (B1) to (B4), the general formula (B1) or (B3) The heteroaromatic ring skeleton represented by the following general formula (B1-1) or (B1-2) is more preferred because it emits blue light. or (B3-1), the heteroaromatic ring structure increases the luminescence quantum yield. However, in the formula, Q 1 and Q 2 each independently represents an oxygen atom or a sulfur atom Also, R 12 , R 18 , R 52 and R 58 represents a single bond.

[0067] [ka]

[0068] In addition, in the organic compound represented by the general formula (G1), Ar 1 is represented by the above general formula (B3- The heteroaromatic ring structure represented by 1) is an organic compound that exhibits high color purity and excellent blue light emission. It is preferable that R 1 ~R7 is hydrogen, which makes synthesis easy. That is, the organic compound according to one embodiment of the present invention is represented by the following general formula (G1-1): It is preferable that the organic compound is an organic compound that can be easily dissolved.

[0069] [ka]

[0070] However, in the above general formula (G1-1), X 11 ~X 15 At least one has the number of carbon atoms A secondary or branched alkyl group having 3 to 6 carbon atoms and a branched carbon atom bonded to the phenyl group. or a tertiary alkyl group, and the remainders are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or alkyl groups, cycloalkyl groups having 3 to 12 carbon atoms, and unsubstituted alkyl groups having 6 to 13 carbon atoms. It is either a substituted or alkyl-substituted aryl group. 21 ~X 2 5 At least one of the alkyl groups is an alkyl group having 3 to 6 carbon atoms and is bonded to a phenyl group. a secondary or tertiary alkyl group in which the carbon atom at the end of the alkyl group is branched, and the remaining carbon atoms are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms; Also, Ar 21 and Ar 22 each independently represents a substituted or unsubstituted group having 6 to 10 carbon atoms; It represents an aryl group having 25 carbon atoms.

[0071] The organic compound represented by the general formula (G1-1) is an organic compound that exhibits good blue light emission. Also, X 11 ~X 15At least 1 of and X 21 ~X 25 At least one of An alkyl group having 3 to 6 carbon atoms, and the carbon atom bonded to the phenyl group is branched. By having a secondary or tertiary alkyl group, sublimation properties are improved.

[0072] In the organic compound represented by the general formula (G1-1), X 11 ~X 15 and X 21 No To X 25 The organic compounds in which all of the amines are hydrogen have a relatively large molecular weight and Due to the presence of multiple skeletons and furan rings, the temperature for sublimation purification is close to 400°C. When the heating temperature reaches about 400°C, the organic compound may burn before it sublimes. On the other hand, the organic compound according to one embodiment of the present invention is X 11 ~X 15 At least one of and X 21 ~X 25 At least one of the alkyl groups has 3 to 6 carbon atoms and phenyl The carbon attached to the alkyl group has a branched secondary or tertiary alkyl group, which allows the molecule to Although the amount increases, the interaction between molecules can be reduced, and the sublimation temperature decreases. This prevents scorching during sublimation purification. Also, the evaporation temperature is reduced. Furthermore, the reliability of light-emitting devices using this organic compound is also improved. To rise.

[0073] In the above explanation, when a group or ring described as "substituted or unsubstituted" has a substituent, In this case, the substituent is preferably an alkyl group having 1 to 6 carbon atoms, an alkyl group having 3 to 12 carbon atoms, or and unsubstituted or alkyl-substituted cycloalkyl groups having 6 to 13 carbon atoms. It is more preferable to select an aryl group having 1 to 6 carbon atoms. Alkyl groups and cycloalkyl groups having 3 to 12 carbon atoms, more preferably cycloalkyl groups having 3 to 12 carbon atoms The alkyl group has 1 to 6 carbon atoms. In addition, from the viewpoint of ease of synthesis and availability of raw materials, From this perspective, groups or rings described as "substituted or unsubstituted" are preferably unsubstituted. I wish.

[0074] The alkyl group having 1 to 6 carbon atoms mentioned above includes a methyl group. , ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, pentyl group and hexyl groups. In addition, cycloalkyl groups having 3 to 12 carbon atoms and As the alkyl group, a cyclopropyl group, a cyclohexyl group, a norbornyl group, a decyl group, and the like are preferable. Further, examples of the alkyl group having 6 to 13 carbon atoms include a hydroxyl group, ... The aryl group is preferably a phenyl group, a biphenyl group, a naphthyl group, or a fluorenyl group. groups, etc.

[0075] Specific examples of organic compounds having the above structure are shown below.

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka]

[0080]

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[0081]

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[0082]

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[0084]

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[0086]

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[0089]

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[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] Next, an example of a method for synthesizing the organic compound of the present invention as described above will be described. The organic compounds represented by the general formula (G1) are shown below. 1 ~ X 5 , R 1 ~R 7 , Ar 1 , Ar 2 and n are the same as above, so they are repeated. The explanation will be omitted.

[0094] [ka]

[0095] The organic compound represented by the general formula (G1) can be prepared by the synthesis of the compound (a1) as shown in the following synthesis scheme. ) and an arylamine compound (a2) by cross-coupling reaction to obtain B 1 Examples include halogens such as chlorine, bromine, and iodine, and triflate groups. B 2 Examples of the group include hydrogen and organotin groups.

[0096] [ka]

[0097] This reaction can proceed under various conditions, for example, in the presence of a base. Metal-catalyzed synthesis methods can be applied. For example, Ullmann coupling and The Wigg-Buchwald reaction can be used.

[0098] In this example, n equivalents of compound (a2) are reacted with compound (a1), and n is 2 or more, that is, two or more of the substituents in parentheses are bonded to compound (G1), and If the substituents are not the same, compound (a2) is added to compound (a1) one by one. It may be allowed to react.

[0099] When n is 1, the organic compound represented by general formula (g1) can be synthesized as shown in the following synthesis scheme: In this way, the compound (a3) ​​and the arylamine compound (a4) or the compound (a5) are ) and an arylamine compound (a6) by cross-coupling reaction to obtain B 1 Examples include halogens such as chlorine, bromine, and iodine, and triflate groups. B 2 Examples of the group include hydrogen and organotin groups.

[0100] [ka]

[0101] [ka]

[0102] In the above manner, the organic compound of one embodiment of the present invention can be synthesized.

[0103] (Embodiment 2) In this embodiment, a light-emitting device according to one embodiment of the present invention will be described.

[0104] FIG. 1A shows a light-emitting device according to one embodiment of the present invention. The device has a first electrode 101, a second electrode 102, and an EL layer 103. The layer 103 includes the organic compound described in Embodiment 1.

[0105] The EL layer 103 has a light-emitting layer 113, which contains a light-emitting material. Between the light-emitting layer 113 and the first electrode 101, a hole injection layer 111 and a hole transport layer 112 are provided. The organic compound represented by the general formula (G1-1) in the first embodiment is a blue compound. Since it efficiently emits fluorescence, it is preferably used as a light-emitting material.

[0106] The light-emitting layer 113 may also contain a host material together with the light-emitting material. The host material is an organic compound having carrier transport properties. In this case, multiple organic compounds may be included in the electronic import. The organic compound having a hole transport property and the organic compound having a hole transport property are contained in the light-emitting layer 113. This is preferable because it is possible to adjust the carrier balance in the organic compound. Although both of them may be organic compounds having electron transport properties, their electron transport properties are different. It is also possible to adjust the electron transport property in the light-emitting layer 113 by using the carrier balancer. By appropriately adjusting the wavelength, it is possible to provide a light-emitting device with a long life. In addition, the organic compound host material and the light-emitting material are intertwined. The structure may be such that an exciplex having an appropriate emission wavelength is formed. This allows for efficient energy transfer to the light-emitting material, resulting in high efficiency and a long lifespan. It is possible to provide a light-emitting device having the above structure.

[0107] In FIG. 1A, the EL layer 103 includes a light-emitting layer 113, a hole-injection layer 111, and a hole-transport layer. In addition to the electron transport layer 112, an electron transport layer 114 and an electron injection layer 115 are also shown. The structure of the substrate is not limited to these. It is also possible to omit any of these layers. It may also have layers having other functions.

[0108] Next, examples of the detailed structure and materials of the light-emitting device will be described. As described above, the light-emitting device has a pair of electrodes, a first electrode 101 and a second electrode 102, between which a light-emitting element is formed. The EL layer 103 is made up of a plurality of layers, and the EL layer 103 has a plurality of layers. The organic compound disclosed in the first embodiment is included.

[0109] The first electrode 101 is made of a metal, alloy, or conductive material having a large work function (specifically, 4.0 eV or more). It is preferable to form the film using a compound such as a carboxylic acid or a mixture thereof. For example, indium tin oxide (ITO), silicon Indium oxide-tin oxide and indium oxide-zinc oxide containing silicon or silicon oxide , indium oxide containing tungsten oxide and zinc oxide (IWZO), etc. These conductive metal oxide films are usually formed by sputtering, but they can also be formed by sol-gel deposition. It is also possible to fabricate it by applying a method such as a quartz crystal process. Zinc was produced using a target containing 1 to 20 wt% zinc oxide added to indium oxide. Also, tungsten oxide and zinc oxide are used. The indium oxide (IWZO) contains 0.5% tungsten oxide relative to the indium oxide. Sputtering was performed using a target containing 5-5 wt% of zinc oxide and 0.1-1 wt% of zinc oxide. It can also be formed by the method. In addition, gold (Au), platinum (Pt), nickel (Ni) , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Nitrides of metallic materials (e.g., titanium nitride), copper (Cu), palladium (Pd), or Graphene can also be used. By using it in the layer 103 that is in contact with the first electrode 101, the electric field can be controlled regardless of the work function. You will be able to select the pole material.

[0110] The EL layer 103 preferably has a laminated structure, but there is no particular limitation on the laminated structure. hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer, carrier block layer Various layer structures can be applied, such as an exciton blocking layer, a charge generating layer, etc. In this embodiment, as shown in FIG. 1(A), a hole injection layer 111, a hole transport layer 112, a light emitting layer 11 1(B) and the structure having an electron transport layer 114 and an electron injection layer 115 in addition to the structure shown in FIG. As shown in the figure, in addition to the hole injection layer 111, the hole transport layer 112, and the light emitting layer 113, an electron transport layer 114 is formed. Two types of structures will be described, one having a charge generating layer 14 and the other having a charge generating layer 116. The materials used are specifically shown below.

[0111] The hole injection layer 111 is a layer containing a substance having acceptor properties. The substance can be either an organic compound or an inorganic compound.

[0112] Acceptor substances include compounds with electron-withdrawing groups (halogen groups and cyano groups). The compound can be used, for example, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroethylene. Quinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,10,11- Hexacyano-1,4,5,8,9,12-hexaazatriphenylene (abbreviation: HAT- CN), 1,3,4,5,7,8-hexafluorotetracyano-naphthoquinodimethane ( Abbreviation: F6-TCNNQ), 2-(7-dicyanomethylene-1,3,4,5,6,8,9 , 10-octafluoro-7H-pyren-2-ylidene)malononitrile, etc. In particular, when an electron-withdrawing group is attached to a condensed aromatic ring with multiple heteroatoms, such as HAT-CN, The bonded compound is thermally stable and is therefore preferred. Radialene derivatives containing halogen or cyano groups such as Specifically, α,α',α''-1,2,3-cyclopropanetriyl Lidentris[4-cyano-2,3,5,6-tetrafluorobenzeneacetonitrile] , α,α',α''-1,2,3-cyclopropanetriylidenetris[2,6-dichloro b-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α, α',α''-1,2,3-Cyclopropanetriylidenetris[2,3,4,5,6- Pentafluorobenzeneacetonitrile, etc. Acceptor substances In addition to the organic compounds mentioned above, molybdenum oxide, vanadium oxide, ruthenium oxide, tungsten oxide, manganese oxide, etc. can be used. Phthalocyanines such as phthalocyanine (abbreviated as HPc) and copper phthalocyanine (CuPc) The complex compound, 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl 4,4'-bis(N-[4-[N'-(3- Methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl Aromatic amine compounds such as dichloromethane (abbreviation: DNTPD) or poly(3,4-ethylenedioxycarbonyl) Polymers such as poly(dithiophene) / poly(styrene sulfonate) (PEDOT / PSS) The hole injection layer 111 can be formed even if the material has an acceptor property. By applying an electric field, electrons can be extracted from the hole transport layer (or hole transport material) that Cut.

[0113] The hole injection layer 111 may be formed by adding the above-mentioned acceptor substance to a material having a hole transporting property. It is also possible to use a composite material in which a material having hole transport properties is combined with an acceptor material. By using a composite material containing a metal, it is possible to select a material to form an electrode regardless of its work function. That is, the first electrode 101 can be made of not only a material with a large work function but also a material with a specific work function. It becomes possible to use materials with small coefficients of thermal conductivity.

[0114] Examples of materials having hole transport properties that can be used in the composite material include aromatic amine compounds and carbazole. Derivatives, aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.), etc. Various organic compounds having hole transport properties can be used for the composite material. The material is 1 x 10 -6 cm 2 It is preferable that the material has a hole mobility of 1 / Vs or more. The following describes materials that can be used as the material having hole transport properties in the composite material. Specific examples of organic compounds are listed below.

[0115] Aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl) )-N,N'-diphenyl-p-phenylenediamine (DTDPPA), 4,4' -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation Name: DPAB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl }-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: D NTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenyl Carbazole derivatives Specific examples of the compound include 3-[N-(9-phenylcarbazol-3-yl)-N-phenyl]carbazol-3-yl ... Nylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N -(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazol PCzPCA2 (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenyl Carbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1 ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tri bis[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(N -carbazolyl)]phenyl-10-phenylanthracene (abbreviation: CzPA), 1,4 -Bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraphenylbenzene Examples of aromatic hydrocarbons that can be used include 2-tert-butyl- 9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2-tert- Butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3,5-diphenyl)anthracene 2-tert-butyl-9,10-biphenylanthracene (abbreviation: DPPA), bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9,10-di(2 -naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: :DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9 ,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA), 2-te rt-Butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene, 9,1 0-Bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7-tetramethyl 1-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetramethyl-9, 10-Di(2-naphthyl)anthracene, 9,9'-bianthryl, 10,10'-diphenyl phenyl-9,9'-bianthryl, 10,10'-bis(2-phenylphenyl)-9, 9'-bianthryl, 10,10'-bis[(2,3,4,5,6-pentaphenyl)phenyl]phenyl] phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra(tert-butyl)perylene, etc. , pentacene, coronene, etc. may also be used. They may have a vinyl skeleton. Examples of aromatic hydrocarbons having a phenyl skeleton include 4,4'-bis(2,2-diphenyl) vinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2,2-diphenyl vinyl)phenyl]anthracene (abbreviation: DPVPA), and the like.

[0116] In addition, poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenyl) PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine] N'-phenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( Polymer compounds such as [(phenyl)benzidine] (abbreviation: Poly-TPD) can also be used. Cut.

[0117] Materials having hole transport properties that can be used in composite materials include carbazole skeletons, dibenzofuran skeletons, and It is preferable that the compound has any one of an orchid skeleton, a dibenzothiophene skeleton, and an anthracene skeleton. In particular, a dibenzofuran ring or a dibenzothiophene ring-containing substituent is preferred. Aromatic amines, aromatic monoamines with a naphthalene ring, or 9-fluorenyl groups It may also be an aromatic monoamine bonded to the nitrogen of the amine via an arylene group. When these organic compounds are substances having an N,N-bis(4-biphenyl)amino group, This is preferable because it allows the production of a light-emitting device with a long life. Specifically, the substance is N-(4-biphenyl)-6,N-diphenylbenzo[b]na. N,N-bis(4-bis[1,2-d]furan-8-amine (abbreviation: BnfABP) phenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviation :BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d]f BnfBB1BP), N,N-Bis(4-biphenyl)benzo[b]naphtho[1,2-d]furan-6-amine (Abbreviation: BBABnf(6)), N,N-bis(4-biphenyl)benzo[b]naphtho[ 1,2-d]furan-8-amine (abbreviation: BBABnf(8)), N,N-bis(4-biphenyl)- Phenyl)benzo[b]naphtho[2,3-d]furan-4-amine (abbreviation: BBABnf (II)(4)), N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4- Amino-p-terphenyl (abbreviation: DBfBB1TP), N-[4-(dibenzothiophene [N-4-yl)phenyl]-N-phenyl-4-biphenylamine (abbreviation: ThBA1B P), 4-(2-naphthyl)-4',4''-diphenyltriphenylamine (abbreviation: B BAβNB), 4-[4-(2-naphthyl)phenyl]-4',4''-diphenyltrimethylsilyl Phenylamine (abbreviation: BBAβNBi), 4,4'-diphenyl-4''-(6;1' -binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB), 4,4'- Diphenyl-4''-(7;1'-binaphthyl-2-yl)triphenylamine (abbreviation: BBAαNβNB-03), 4,4'-diphenyl-4''-(7-phenyl)naphthyl -2-yltriphenylamine (abbreviation: BBAPβNB-03), 4,4'-diphenyl -4''-(6;2'-binaphthyl-2-yl)triphenylamine (abbreviation: BBA(β N2)B) 4,4'-diphenyl-4''-(7;2'-binaphthyl-2-yl)triphenyl Phenylamine (abbreviation: BBA(βN2)B-03), 4,4'-diphenyl-4''- (4;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB), 4,4'-diphenyl-4''-(5;2'-binaphthyl-1-yl)triphenylamine (abbreviation: BBAβNαNB-02), 4-(4-biphenylyl)-4'-(2-naphthyl) 4-(3-biphenyl)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), (phenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenyl mTPBiAβNBi, 4-(4-biphenylyl)-4'-[4-( 2-naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβ NBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviated as αNBA) 1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP ), 4,4'-diphenyl-4''-[4'-(carbazol-9-yl)biphenyl- 4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl [1,1'-biphenyl-4-yl-9H-carbazol-9-yl]phenyl 4-[4'-(carbazol-9-yl)amine (abbreviation: YGTBi1BP-02) )biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenyla amine (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3 -yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobi[9 H-fluorene]-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1'- Biphenyl]-4-yl)-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation Name: BBASF), N,N-bis([1,1'-biphenyl]-4-yl)-9,9'- Spirobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1 '-biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl) -9,9'-spiro-bi[9H-fluorene]-4-amine (abbreviation: oFBiSF), N -(4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibene Zofuran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]- N-[3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviation: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluorene-9- 4-phenyl-3'-(9-phenylyl)triphenylamine (abbreviation: BPAFLP), mBPAFLP, 4-phenyl -4'-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine( Abbreviation: BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole- 3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4' '-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PC BBi1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole- 3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl) -4''-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation : PCBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3 -yl)phenyl]-9,9'-spirobi[9H-fluorene]-2-amine (abbreviation: P CBASF), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4 -(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2 -amine (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluorene) -2-yl)-9,9'-spirobi[9H-fluorene]-4-amine, N,N-bis( 9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluoren 9,9-dimethyl-9H-fluoren-2-ylamine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl) -9,9'-Spirobi[9H-fluorene]-2-amine, N,N-bis(9,9-dimethyl) (9,9'-spirobi[9H-fluorene]-1-(ethyl-9H-fluoren-2-yl)-9,9'-spirobi[9H-fluorene]-1- amines and the like.

[0118] The hole transport material used in the composite material has a HOMO level of -5.7 eV. It is more preferable that the HOMO level is a relatively deep one of -5.4 eV or more. The hole-transporting material used in the composite material has a relatively deep HOMO level. This facilitates the injection of holes into the hole transport layer 112, and also makes it possible to produce a light-emitting device with a long life. This makes it easier to obtain the vise.

[0119] The composite material may further contain a fluoride of an alkali metal or an alkaline earth metal (preferably or the atomic ratio of fluorine atoms in the layer is 20% or more), the refractive index of the layer is This also allows a layer with a low refractive index to be formed inside the EL layer 103. This can improve the external quantum efficiency of the light-emitting device.

[0120] By forming the hole injection layer 111, the hole injection property is improved, and the driving voltage is small. In addition, organic compounds with acceptor properties can be easily vapor-deposited. It is an easy-to-use material because it is easy to form a film.

[0121] The hole transport layer 112 is formed by including a material having a hole transport property. The material is 1 x 10 -6 cm 2 It is preferable that the hole mobility is / Vs or more. The material having the hole transport property is 4,4'-bis[N-(1-naphthyl)-N-phenylene]. N,N'-bis(3-methylphenyl)-N ,N'-Diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD) , 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenyl amino]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene) 4-phenyl-3'-(9-yl)triphenylamine (abbreviation: BPAFLP), -phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4- Phenyl-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carboxylate) PCBBi1BP, 4-(1-naphthyl)triphenylamine (9H-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9 H-carbazol-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-di Methyl-N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl] N-phenyl-N-[4-(9 -phenyl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[9H- Compounds with an aromatic amine skeleton, such as fluorene-2-amine (abbreviation: PCBASF) and 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N -carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl) 3,3'-bis(9-phenyl)-9-phenylcarbazole (abbreviation: CzTP), -9H-carbazole (abbreviated as PCCP), and compounds with a carbazole skeleton. 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene)( Abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-phenyl)- (Dibenzothiophene-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldi Compounds with a thiophene skeleton, such as benzothiophene (abbreviated as DBTFLP-IV), , 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation Name: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl) (phenyl)phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) Among the above, compounds having an aromatic amine skeleton are preferred. Compounds with a carbazole skeleton and other compounds have good reliability and high hole transport properties. This is preferable because it also contributes to reducing the driving voltage. The materials having hole transport properties that are mentioned above can also be used as materials for forming the hole transport layer 112. The organic compound described in Embodiment 1 can be suitably used. Therefore, it can be used as a material for forming the hole transport layer 112.

[0122] The organic compound described in the first embodiment has a low refractive index and a bulky alkyl group bonded thereto. Therefore, when used in a light-emitting device, it is possible to obtain a film with a low refractive index. The efficiency is increased, and a device with high luminous efficiency can be obtained.

[0123] The light-emitting layer 113 contains a light-emitting material and a host material. They may contain both at the same time, or may be a laminate of two layers with different compositions.

[0124] The emitting material may be a fluorescent material, a phosphorescent material, or a thermally activated delayed fluorescence (T The light emitting substance may be a substance exhibiting ADF or other luminescent substances.

[0125] In the light-emitting layer 113, materials that can be used as fluorescent materials include, for example: 5,6-bis[4-(10-phenyl-9-anthryl)phenyl]-2,2'-bipyridine PAP2BPy, 5,6-bis[4'-(10-phenyl-9-anthracene] N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-biphenyl bis(3-methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluorene 9-yl)phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn ), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-di Phenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazo (4'-(10-phenyl-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation Name: YGAPA), 4-(9H-carbazol-9-yl)-4'-(9,10-diphenyl N,9-diphenyl-2-anthryltriphenylamine (abbreviation: 2YGAPPA) N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole -3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra(tert- Butyl)perylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'- (9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBA PA), N,N''-(2-tert-butylanthracene-9,10-diyldi-4, 1-phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine] (abbreviation: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2 -anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: 2PCAPPA) , N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'- Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N', N',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chryse N-(9,10,15-tetraamine (abbreviation: DBC1), Coumarin 30, 10-Diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3- Amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)] [N,9-diphenyl-9H-carbazol-3-amine (abbreviated as 2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine] :2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N '-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,1 0-Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-t Triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis (1,1'-biphenyl-2-yl)-N-[4-(9H-carbazol-9-yl)phenyl] N,N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), ,9-triphenylanthracene-9-amine (abbreviation: DPhAPhA), Coumarin 54 5T, N,N'-diphenylquinacridone (abbreviation: DPQd), rubrene, 5,12-biphenyl Bis(1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BP T), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl- 4H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl 6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizidine] 4H-pyran-4-ylidene}propanedinitrile (abbreviation: DCM2), N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5, 11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N' -Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,1 0-diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1, 1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij ]quinolizin-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitri (abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7,7- Tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine -9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CJTB), 2-(2,6-bis{2-[4-(dimethylamino)phenyl]ethenyl} -4H-pyran-4-ylidene)propanedinitrile (abbreviation: BisDCM), 2-{2 ,6-bis[2-(8-methoxy-1,1,7,7-tetramethyl-2,3,6,7-tetramethyl- tetrahydro-1H,5H-benzo[ij]quinolizin-9-yl)ethenyl]-4H-pi N,N'-(pyridin-4-yl)propanedinitrile (abbreviation: BisDCJ™), Benzene-1,6-diyl)bis[(6,N-diphenylbenzo[b]naphtho[1,2-d] furan)-8-amine] (abbreviation: 1,6BnfAPrn-03), 3,10-bis[N- (9-phenyl-9H-carbazol-2-yl)-N-phenylamino]naphtho[2, 3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf(IV)-0 2), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenylamino]naphtho 3,10FrA2Nbf(I V)-02) are particularly notable. Prn, condensed aromatic compounds such as pyrenediamine compounds like 1,6BnfAPrn-03 Aromatic diamine compounds are preferred because they have high hole trapping properties, excellent luminous efficiency, and reliability. It is preferable to use other fluorescent materials. The organic compound represented by the general formula (G1-1) can also be used as a fluorescent material.

[0126] The light-emitting device of one embodiment of the present invention uses the organic compound described in Embodiment 1. The organic compound described in the first embodiment is an organic compound that is easy to purify and vapor-deposit. Since it is a compound, it is possible to provide a highly reliable light-emitting device. It is possible to improve the thermal properties while maintaining color purity, resulting in excellent color purity and reliability. Therefore, a light-emitting device with good performance can be provided.

[0127] In the light-emitting layer 113, when a phosphorescent material is used as the light-emitting material, Examples of suitable materials include tris{2-[5-(2-methylphenyl)-4-(2,6- Dimethylphenyl)-4H-1,2,4-triazol-3-yl-κN2]phenyl- {κC}iridium(III) (abbreviation: [Ir(mpptz-dmp)3]), tris(5 -methyl-3,4-diphenyl-4H-1,2,4-triazolato)iridium(III ) (abbreviation: [Ir(Mptz)3]), tris[4-(3-biphenyl)-5-isopropyl pyr-3-phenyl-4H-1,2,4-triazolato]iridium(III) (abbreviation: Organometallics with a 4H-triazole skeleton, such as [Ir(iPrptz-3b)3] Iridium complexes and tris[3-methyl-1-(2-methylphenyl)-5-phenyl- 1H-1,2,4-triazolato]iridium(III) (abbreviation: [Ir(Mptz1- mp)3]), tris(1-methyl-5-phenyl-3-propyl-1H-1,2,4- Triazolato)iridium(III) (abbreviation: [Ir(PrPrptz1-Me)3]) Organometallic iridium complexes with 1H-triazole skeletons, such as fac-tris[1- (2,6-diisopropylphenyl)-2-phenyl-1H-imidazole]iridium (III) (abbreviation: [Ir(iPrpmi)3]), tris[3-(2,6-dimethylphenyl) (phenyl)-7-methylimidazo[1,2-f]phenanthridinato]iridium(III ) (abbreviation: [Ir(dmpimpt-Me)3]) Organic metal iridium complexes and bis[2-(4',6'-difluorophenyl)pyridinato- N,C 2’ ]iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FI r6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C 2’ ]Ili Dium(III) picolinate (abbreviation: FIrpic), bis{2-[3',5'-bis (Trifluoromethyl)phenyl]pyridinato-N,C 2’}Iridium(III) pico Linate (abbreviation: [Ir(CF3ppy)2(pic)]), bis[2-(4',6'- Difluorophenyl)pyridinato-N,C 2’ ]Iridium(III) acetylacetonate Phenylpyridine derivatives with electron-withdrawing groups such as thiol (abbreviation: FIracac) are used. These include organometallic iridium complexes that use iridium as a ligand. These exhibit blue phosphorescence. It is a compound having an emission spectrum peak between 440 nm and 520 nm. do.

[0128] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), tris(4-t-butyl-6-phenylpyrimidinato)yl Ir(tBuppm)3), (acetylacetonato)bis(Ir(tBuppm)3) (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidinato)iridium(III) (abbreviation: [Ir(tBuppm)2(ac ac)]), (acetylacetonato)bis[6-(2-norbornyl)-4-phenylpiperidinyl] [Ir(nbppm)2(acac)]), (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Pyrimidinato]iridium(III) (abbreviation: [Ir(mpmppm)2(acac)] ), (acetylacetonato)bis(4,6-diphenylpyrimidinato)iridium(II I) (abbreviation: [Ir(dppm)2(acac)]) Organic metal iridium complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl) Rupirazinato)iridium(III) (abbreviation: [Ir(mppr-Me)2(acac) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyridine) Dinato)iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) Organometallic iridium complexes with pyrazine skeletons such as tris(2-phenylpyridinium) Nat-N,C 2’ ) Iridium(III) (abbreviation: [Ir(ppy)3]), bis(2- Phenylpyridinato-N,C 2’ ) Iridium(III) acetylacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinolinato)iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), tris(benzyl) Tribenzo[h]quinolinato)iridium(III) (abbreviation: [Ir(bzq)3]), tris (2-phenylquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir(pq) 3]), bis(2-phenylquinolinato-N,C 2’ ) Iridium(III) acetylacetone Setonate (abbreviation: [Ir(pq)2(acac)]), [2-d3-methyl-8-(2 -pyridinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(5-d3 [Ir -methyl-2-pyridyl-κN2)phenyl-κ]iridium(III) (5mppy-d3)2(mbfpypy-d3)]), [2-d3-methyl-(2-py lysinyl-κN)benzofuro[2,3-b]pyridine-κC]bis[2-(2-pyrid ... [Ir(ppy)2(mbf)(phenyl-κC)]iridium(III) In addition to organometallic iridium complexes with pyridine skeletons such as tripypy-d3), (acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: [T b(acac)3(Phen)]) and other rare earth metal complexes. It is a compound that mainly exhibits green phosphorescence, with an emission spectrum from 500 nm to 600 nm. The organometallic iridium complexes with pyrimidine skeletons have high reliability and It is particularly preferable because it has outstanding luminous efficiency.

[0129] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimidinyl] Nato]iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis [4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridine Ir(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalen-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organogold compounds with pyrimidine skeletons, such as [Ir(d1npm)2(dpm)] iridium complexes of the genus acetylacetonatobis(2,3,5-triphenylpyrazine) Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-triphenylpyrazinate)(dipivaloylmethanato)iridium(III)(abbreviation Name: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis (4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: [Ir(Fd pq)2(acac)]), and organometallic iridium complexes with pyrazine skeletons such as Tris(1-phenylisoquinolinato-N,C 2’ ) Iridium(III) (abbreviation: [Ir (piq)3]), bis(1-phenylisoquinolinato-N,C 2’ ) Iridium (II I) Pyridyl acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with iridium skeletons, 2,3,7,8,12,13,17,18 -octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complexes such as tris(1,3-diphenyl-1,3-propanedionato) (monophenyl Anthroline) europium(III) (abbreviation: [Eu(DBM)3(Phen)]), Tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthate) (Troline) europium(III) (abbreviation: [Eu(TTA)3(Phen)]) These are compounds that exhibit red phosphorescence, Its emission spectrum peaks at 600 nm to 700 nm. The organometallic iridium complex emits red light with good chromaticity.

[0130] In addition to the phosphorescent compounds described above, known phosphorescent light-emitting substances may be selected and used. stomach.

[0131] TADF materials include fullerene and its derivatives, acridine and its derivatives, and eosin. Derivatives of magnesium (Mg), zinc (Zn), cadmium, etc. can also be used. (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P d) and the like. Examples of the metal-containing porphyrin include: For example, the protoporphyrin-tin fluoride complex (SnF2(Pro to IX), mesoporphyrin-tin fluoride complex (SnF2(Meso IX)), Hematoporphyrin-tin fluoride complex (SnF2(Hemato IX)), Copropor Phyllin tetramethyl ester-tin fluoride complex (SnF2(Copro III-4M e)), octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethiop Porphyrin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin -platinum chloride complex (PtCl2OEP) and the like.

[0132] [ka]

[0133] In addition, 2-(biphenyl-4-yl)-4,6-bis(12-phenyl)-4-phenyl-4-methyl-4-phenyl ... (phenylindolo[2,3-a]carbazol-11-yl)-1,3,5-triazine ( Abbreviation: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT zn), 2-{4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-3-yl] 4,6-diphenyl-1,3,5-triazine (abbreviated as '4,6-diphenyl-1,3,5-triazine- ...') Name: PCCzPTzn), 2-[4-(10H-phenoxazin-10-yl)phenyl ]-4,6-diphenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4 -(5-phenyl-5,10-dihydrophenazin-10-yl)phenyl]-4,5- Diphenyl-1,2,4-triazole (abbreviation: PPZ-3TPT), 3-(9,9-diphenyl Methyl-9H-acridin-10-yl)-9H-xanthen-9-one (Acr XTN), bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl] Sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[a π electrons of clidin-9,9'-anthracen]-10'-one (abbreviation: ACRSA), etc. Heterocyclic compounds having either or both of a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring are also used. The heterocyclic compound may be a π-electron rich heteroaromatic ring or a π-electron deficient heteroaromatic ring. Since it has an aromatic ring, it has high electron transporting properties and hole transporting properties, which is preferable. Among the skeletons with a toe-shaped heteroaromatic ring, pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyridine skeleton) The arazine skeleton, pyridazine skeleton, and triazine skeleton are preferred because they are stable and reliable. In particular, benzofuropyrimidine skeleton, benzothienopyrimidine skeleton, benzofuropyrimidine skeleton, The benzothienopyrazine and benzothienopyrazine skeletons are preferred because they have high acceptor properties and good reliability. Among the skeletons having a π-electron-rich heteroaromatic ring, acridine skeletons, pheno The xanthazine skeleton, phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are It is preferable that the compound has at least one of the above skeletons because it is stable and reliable. The furan skeleton is a dibenzofuran skeleton, and the thiophene skeleton is a dibenzothiophene skeleton. The pyrrole skeleton is preferably an indole skeleton, a carbazole skeleton, or a methylpyrrole skeleton. carbazole skeleton, indolocarbazole skeleton, bicarbazole skeleton, 3-(9-phenyl-9H- A carbazole-3-yl)-9H-carbazole skeleton is particularly preferred. A substance in which a π-type heteroaromatic ring and a π-electron-deficient heteroaromatic ring are directly bonded is called a π-electron-rich heteroaromatic ring. The electron-donating property of the ring and the electron-accepting property of the π-electron-deficient heteroaromatic ring are both strong, and the S1 and T1 levels The energy difference between the levels is small, so thermally activated delayed fluorescence can be obtained efficiently. It is preferable that an electron-withdrawing group such as a cyano group is used instead of the π-electron-deficient heteroaromatic ring. In addition, the π-electron-rich skeleton may be an aromatic amine skeleton, a fluorine-containing skeleton, or the like. A phenazine skeleton or the like can be used. In addition, a xanthene skeleton can be used as a π-electron deficient skeleton. , thioxanthene dioxide skeleton, oxadiazole skeleton, triazole skeleton, imidazoline azole skeleton, anthraquinone skeleton, boron-containing skeletons such as phenylborane and boranthrene, Aromatic rings or heterocyclic rings containing nitrile or cyano groups such as benzonitrile or cyanobenzene Aromatic rings, carbonyl skeletons such as benzophenone, phosphine oxide skeletons, sulfone skeletons, etc. In this way, a π-electron deficient heteroaromatic ring and a π-electron rich heteroaromatic ring can be used. Using a π-electron deficient skeleton and a π-electron rich skeleton in place of at least one of the aromatic rings can be done.

[0134] [ka]

[0135] TADF materials have a small difference between the S1 and T1 levels, and triple intersystem crossing occurs due to reverse intersystem crossing. The function of converting energy from first excitation energy to singlet excitation energy Therefore, the triplet excitation energy can be converted to a single state by a small amount of thermal energy. It is possible to upconvert to doublet excited energy (reverse intersystem crossing), and efficiently convert the singlet excited state It is possible to generate triplet excitation energy and convert it into luminescence. .

[0136] In addition, exciplexes (exciplexes) that form excited states with two types of substances The difference between the S1 and T1 levels is extremely small, As a TADF material capable of converting triplet excitation energy into singlet excitation energy, It has all the functions.

[0137] As an index of the T1 level, the phosphorescence observed at low temperatures (for example, from 77 K to 10 K) As for TADF materials, the fluorescent spectrum is at the short wavelength end. Draw a tangent line at the wavelength of the extrapolated line and define the energy of the wavelength as the S1 level. When a tangent line is drawn at the base of the short wavelength side and the energy of the wavelength of the extrapolated line is taken as the T1 level, The difference between S1 and T1 is preferably 0.3 eV or less, and more preferably 0.2 eV or less. It is more preferable that:

[0138] In addition, when a TADF material is used as a light-emitting material, the S1 level of the host material is It is preferable that the T1 level of the host material is higher than the T1 level of the TADF material. It is preferable that the temperature is higher than the above level.

[0139] The host material of the light-emitting layer may be a material having an electron transporting property or a material having a hole transporting property, Various carrier transport materials can be used, such as TADF materials.

[0140] Materials with hole transport properties include organic compounds with an amine skeleton or a π-electron-rich heteroaromatic ring skeleton. Organic compounds are preferred. For example, 4,4'-bis[N-(1-naphthyl)-N-phenylalanine] N,N'-bis(3-methylphenyl)-N,N'-biphenyl (abbreviation: NPB), -Diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4, 4'-Bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino] ]biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene-9 -yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenyl mBPAFLP, 4-phenyl 4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation : PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazo PCBBi1BP), 4-(1-naphthyl-3-yl)triphenylamine )-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation : PCBAN), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-carboxylate) PCBNBB, 9,9-dimethyl -N-phenyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]phenyl ]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl 9,9'-spirobi[(9H-fluoro-3-yl-9H-carbazol-3-yl)phenyl]-9,9'-spirobi[(9H-fluoro ... compounds with aromatic amine skeletons such as PCBASF, 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)benzene 3,6-bis(3,5-diphenylphenyl)bis(3,6-diphenylbenzoyl)biphenyl (abbreviation: CBP) -9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H -carbazole (abbreviated as PCCP), and ',4''-(Benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluorene phenyl-9-yl)dibenzothiophene (abbreviation: DBTFLP-III), 4-[ 4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Compounds with a thiophene skeleton, such as thiophene (abbreviated as DBTFLP-IV), and 4, 4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: D BF3P-II), 4-{3-[3-(9-phenyl-9H-fluoren-9-yl)fluorene phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) and other furan skeletons Among the above, compounds having an aromatic amine skeleton and Compounds having a rubazole skeleton have good reliability, high hole transport properties, and are easy to drive. This is preferable because it also contributes to voltage reduction.

[0141] Examples of materials having electron transport properties include bis(10-hydroxybenzo[h]quinolinol). Nat)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato) )(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8- Quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) phenolato]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) Metal complexes such as phenolatozinc(II) (abbreviation: ZnBTZ) and π-electron-deficient heteroaromatic complexes An organic compound having an aromatic ring skeleton is preferred. An organic compound having a π-electron-deficient heteroaromatic ring skeleton is preferred. Examples of compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)- )-1,3,4-oxadiazole (abbreviation: PBD), 3-(4-biphenylyl)-4- Phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxa diazol-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1 ,3,4-oxadiazol-2-yl)phenyl]-9H-carbazole (abbreviation: CO 11), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl- 1H-benzimidazole) (abbreviation: TPBI), 2-[3-(dibenzothiophene-4 -yl)phenyl]-1-phenyl-1H-benzimidazole (abbreviation: mDBTBIm Heterocyclic compounds with polyazole skeletons such as 2-[3-(dibenzothiophene)-II] and (4-phenyl)dibenzo[f,h]quinoxaline (abbreviation: 2mDBTPDB q-II), 2-[3'-(dibenzothiophen-4-yl)biphenyl-3-yl]di Benzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II), 2-[3'-( 9H-carbazol-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxalate 4,6-bis[3-(phenanthrene-9-yl)phenyl]phenanthren-9-yl]phenanthren-9-yl ... phenyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-diphenyl)pyrimidine 4,8-zothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), Bis[3-(dibenzothiophen-4-yl)phenyl]benzo[h]quinazoline (abbreviation Heterocyclic compounds with diazine skeletons such as 4,8mDBtP2Bqn and 3,5-biphenyls bis[3-(9H-carbazol-9-yl)phenyl]pyridine (abbreviation: 35DCzPP y), 1,3,5-tri[3-(3-pyridyl)phenyl]benzene (abbreviation: TmPyP B) and other heterocyclic compounds having a pyridine skeleton. Heterocyclic compounds having a pyridine skeleton and heterocyclic compounds having a pyridine skeleton have good reliability. In particular, heterocyclic compounds having a diazine (pyrimidine or pyrazine) skeleton are preferred. It has high transportability and also contributes to reducing the driving voltage.

[0142] The TADF materials that can be used as host materials are listed above as TADF materials. When a TADF material is used as a host material, the TA The triplet excitation energy generated in the DF material is converted to singlet excitation energy by reverse intersystem crossing. The energy is then transferred to the light-emitting material, thereby increasing the luminous efficiency of the light-emitting device. In this case, the TADF material acts as an energy donor, and the light-emitting material acts as an energy acceptor.

[0143] This is very effective when the luminescent material is a fluorescent material. To obtain high luminous efficiency, the S1 level of the TADF material should be higher than the S1 level of the fluorescent material. It is preferable that the T1 level of the TADF material is higher than the S1 level of the fluorescent material. Therefore, the T1 level of the TADF material is preferably higher than the T1 level of the fluorescent material. Higher is preferable.

[0144] In addition, T that exhibits emission that overlaps with the wavelength of the lowest energy absorption band of the fluorescent substance It is preferable to use an ADF material, which allows the TADF material to be converted into a fluorescent material. This is preferable because the transfer of excitation energy becomes smooth and light emission can be obtained efficiently.

[0145] In addition, singlet excitation energy is efficiently generated from triplet excitation energy by reverse intersystem crossing. For this to occur, it is preferable that carrier recombination occurs in the TADF material. The triplet excitation energy generated in the DF material is transferred to the triplet excitation energy of the fluorescent material. For this purpose, it is preferable that the fluorescent substance has a luminophore ( It is preferable that the compound has a protecting group around the π bond (the skeleton that causes light emission). A saturated hydrocarbon is preferred, specifically a hydrocarbon having 3 to 10 carbon atoms. The alkyl groups listed below, substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, A trialkylsilyl group having 3 to 10 protecting groups is preferred, and a group having a plurality of protecting groups is more preferred. Substituents without π bonds have poor carrier transport function, and therefore, The distance between the TADF material and the luminophores of the fluorescent material can be reduced without significantly affecting carrier recombination. Here, the luminophore is the molecule that causes light emission in a fluorescent substance. The luminophore preferably has a skeleton with a π bond and contains an aromatic ring. Preferably, the aromatic ring has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of the heteroaromatic ring include a phenanthrene skeleton, a stilbene skeleton, an acridone skeleton, and a phenanthren skeleton. Examples of the hydroxyazine skeleton include naphthalene skeleton and anthracene skeleton. skeleton, fluorene skeleton, chrysene skeleton, triphenylene skeleton, tetracene skeleton, pyrene skeleton perylene skeleton, coumarin skeleton, quinacridone skeleton, naphthobisbenzofuran skeleton Fluorescent materials that emit light with high fluorescence quantum yields are preferred.

[0146] When a fluorescent substance is used as the light-emitting substance, the host material is a material having an anthracene skeleton. A material having an anthracene skeleton is preferably used as a host material for a fluorescent material. When used as a host material, it is possible to realize a light-emitting layer having good luminous efficiency and durability. The materials having an anthracene skeleton used as the material include a diphenylanthracene skeleton, In particular, a substance having a 9,10-diphenylanthracene skeleton is preferred because it is chemically stable. In addition, when the host material has a carbazole skeleton, the hole injection and transport properties are improved. However, a benzocarbazole skeleton in which a benzene ring is further condensed to a carbazole is preferred. When it contains carbazole, the HOMO becomes shallower by about 0.1 eV than that of carbazole, making it easier for holes to enter. In particular, when the host material contains a dibenzocarbazole skeleton, The HOMO is shallower than that of sol by about 0.1 eV, making it easier for holes to enter, and the hole transport Therefore, it is also preferable as a host material. Preferred are those having a 9,10-diphenylanthracene skeleton and a carbazole skeleton (or It is a substance that simultaneously has a benzocarbazole skeleton and a dibenzocarbazole skeleton. From the viewpoint of the hole injection and transport properties, a benzofluorene skeleton was used instead of a carbazole skeleton. A dibenzofluorene skeleton may also be used. Examples of such materials include 9-phenyl 3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole ( Abbreviation: PCzPA), 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H- Carbazole (abbreviation: PCPN), 9-[4-(10-phenyl-9-anthracenyl) phenyl]-9H-carbazole (abbreviation: CzPA), 7-[4-(10-phenyl-9 -anthryl)phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBC zPA), 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[ b]naphtho[1,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{ 4-(9-phenyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene sen (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)phenyl] In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA are preferred because they show very good properties. It is a good choice.

[0147] The host material may be a mixture of a plurality of substances. When used, a material having an electron transporting property and a material having a hole transporting property may be mixed. It is preferable to mix a material having an electron transport property with a material having a hole transport property. Therefore, the transport property of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. The weight ratio of the content of the material having hole transport properties to the content of the material having electron transport properties is The ratio of the material having hole transport properties to the material having electron transport properties may be 1:19 to 19:1. In addition, as the material having a hole transporting property in the mixed host material, Organic compounds can be used.

[0148] A phosphorescent material can be used as part of the mixed material. When a fluorescent substance is used as a luminescent substance, the luminescent substance transfers excitation energy to the fluorescent substance. It can be used as an energy donor.

[0149] Furthermore, these mixed materials may form an exciplex. The exciplex is formed to emit light that overlaps with the wavelength of the lowest energy absorption band of By selecting such a combination, energy transfer becomes smooth and light emission can be obtained efficiently. In addition, the use of this configuration is also preferable because the driving voltage is reduced.

[0150] At least one of the materials forming the exciplex may be a phosphorescent material. By doing so, triplet excitation energy is efficiently converted to singlet excitation energy by reverse intersystem crossing. can be converted to

[0151] As a combination of materials that efficiently form exciplexes, HO It is preferable that the MO level is equal to or higher than the HOMO level of the material having electron transport properties. When the LUMO level of the material having electron transport properties is higher than the LUMO level of the material having electron transport properties, It is preferable that the LUMO level and the HOMO level of the material are determined by cyclic voltammetry. From the electrochemical properties (reduction potential and oxidation potential) of the material measured by CV measurement It can be derived.

[0152] The formation of an exciplex is determined by, for example, the emission spectrum of a material having hole transport properties, the emission spectrum of a material having electron transport properties, The emission spectrum of the material having the above structure and the emission spectrum of the mixed film of these materials are shown in Fig. In comparison, the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each material ( This can be confirmed by observing the phenomenon of a new peak on the long wavelength side. Alternatively, transient photoluminescence (PL) of materials with hole transport properties and electron transport properties can be observed. The transient PL of the materials with the same properties and the transient PL of the mixed film of these materials were compared. The transient PL lifetime of the film has a longer-lived component than the transient PL lifetime of each material, or a delayed component. This can be confirmed by observing the difference in transient response, such as the percentage of In addition, the above-mentioned transient PL may be read as transient electroluminescence (EL). That is, the transient EL of a material with hole transport properties and the transient E of a material with electron transport properties are By comparing the transient EL of the L and the mixed films and observing the difference in the transient response, The formation of exciplexes can be confirmed.

[0153] The electron transport layer 114 is a layer containing a substance having an electron transport property. Examples of the electron-transporting material include those listed as the materials having electron-transporting properties that can be used as the host material. can be used.

[0154] The electron transport layer 114 has an electron mobility of 600 when the square root of the electric field strength [V / cm] is 1×10 -7 cm 2 / Vs or more 5×10 -5 cm 2 / Vs or less. The amount of electrons injected into the light-emitting layer is controlled by reducing the electron transport property in the electron transport layer 114. This can prevent the light-emitting layer from becoming an electron-excess state. The transport layer 114 is made of a material having electron transport properties and an elemental alkali metal or alkaline earth metal. It is preferable that the hole injection layer contains a compound or a complex. and the HOMO level of the material having hole transport properties in the composite material is −5.7 In the case of a substance with a relatively deep HOMO level of more than -5.4 eV, the lifetime is In this case, the material having electron transport properties is particularly preferable because it has a HOMO The electron transporting material preferably has an electron level of -6.0 eV or higher. The organic compound is preferably an organic compound having an anthracene skeleton, and more preferably an organic compound having an anthracene skeleton and a heterocyclic skeleton. It is more preferable that the heterocyclic skeleton is an organic compound containing both a nitrogen-containing heterocyclic skeleton and a nitrogen-containing heterocyclic skeleton. A five-membered ring skeleton or a nitrogen-containing six-membered ring skeleton is preferred, and examples of these heterocyclic skeletons include pyrazole. ring, imidazole ring, oxazole ring, thiazole ring, pyrazine ring, pyrimidine ring, pyri Nitrogen-containing five-membered ring skeleton or nitrogen-containing six-membered ring skeleton containing two heteroatoms in the ring, such as the Dadzin ring The case is particularly preferred. In addition, the alkali metal or alkaline earth metal may be used as a simple substance, a compound or The complex preferably contains an 8-hydroxyquinolinato structure. For example, 8-hydroxyquinolinato-lithium (abbreviation: Liq), 8-hydroxyquinolinato- In particular, monovalent metal ion complexes include sodium (Naq). Among them, lithium complexes are preferred, and Liq is more preferred. If the methyl group contains a methyl group, the methyl group may be substituted (e.g., 2-methyl or 5-methyl). In addition, an alkali metal or alkali metal compound may be used in the electron transport layer. The elemental, compound or complex of earth metals has a concentration difference (even if it is 0) in the thickness direction. It is preferred that the hydroxyl group is present.

[0155] Between the electron transport layer 114 and the second electrode 102, a lithium fluoride layer was formed as an electron injection layer 115. Lithium fluoride (LiF), Cesium fluoride (CsF), Calcium fluoride (CaF2), 8-hydrogen Alkali metal or alkaline earth metals such as lithium quinolinate (abbreviation: Liq) The electron injection layer 115 may be a layer containing a metal or a compound thereof. The layer is made of a material containing an alkali metal or alkaline earth metal or a compound thereof. As the electride, for example, calcium carbonate may be used. Examples include a material in which electrons are highly added to a mixed oxide of silicon and aluminum.

[0156] Note that the electron-injecting layer 115 is formed using a substance having an electron-transporting property (preferably a substance having a bipyridine skeleton). The fluoride of the alkali metal or alkaline earth metal is in a microcrystalline state in the organic compound having the above-mentioned structure. It is also possible to use a layer containing a concentration of 50 wt% or more of the refractive index of the layer. Since the layer has a low external quantum efficiency, it is possible to provide a light-emitting device with a better external quantum efficiency. It becomes Noh.

[0157] In addition, a charge generation layer 116 may be provided instead of the electron injection layer 115 (FIG. 1(B)). When a potential is applied to the charge generating layer 116, holes are generated in the layer in contact with the cathode side of the layer, and electrons are generated in the layer in contact with the anode side. The charge generation layer 116 is a layer that can inject electrons into the layer adjacent to it. At least a P-type layer 117 is included. The P-type layer 117 constitutes the hole injection layer 111 described above. It is preferable to form the P-type layer 1 using the composite material mentioned above as a material that can be used. 17 is a film containing the above-mentioned acceptor material and a hole transport material as materials constituting a composite material. By applying a potential to the P-type layer 117, electrons Electrons are injected into the transport layer 114 and holes are injected into the second electrode 102, which is the cathode, forming a light-emitting device. In addition, since the organic compound according to one embodiment of the present invention has a low refractive index, By using this for the P-type layer 117, a light emitting device with good external quantum efficiency can be obtained. can.

[0158] The charge generation layer 116 includes an electron relay layer 118 and an electron injection buffer layer 119 in addition to the P-type layer 117. Preferably, one or both of layers 119 are provided.

[0159] The electron relay layer 118 contains at least a substance having electron transport properties, and the electron injection buffer layer 1 The electrons are transferred smoothly by preventing the interaction between the P-type layer 117 and the P-type layer 119. The LUMO level of the substance having electron transport properties contained in the relay layer 118 is The LUMO level of the acceptor material in the electron transport layer 114 and the charge generation layer 116 It is preferable that the LUMO level of the electron relay layer 11 is between the LUMO level of the material contained in the adjacent layer. Specific energy levels of the LUMO level in the electron transporting materials used in 8 is set to -5.0 eV or more, preferably -5.0 eV or more and -3.0 eV or less. The electron-transporting material used in the electron relay layer 118 is a phthalocyanine-based material. It is preferred to use materials or metal complexes having metal-oxygen bonds and aromatic ligands.

[0160] The electron injection buffer layer 119 contains an alkali metal, an alkaline earth metal, a rare earth metal, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, lithium carbonate) Alkaline earth metal compounds (including carbonates such as titanium and cesium carbonate), alkaline earth metal compounds (oxides, halogens compounds of rare earth metals (including oxides, halides, carbonates) or compounds of rare earth metals (including oxides, halides, carbonates) It is possible to use a material with high electron injection properties, such as SiO 2 .

[0161] The electron injection buffer layer 119 is formed by containing a substance having an electron transporting property and a donor substance. When the donor material is an alkali metal, an alkaline earth metal, or a rare earth metal, and their compounds (alkali metal compounds (oxides such as lithium oxide, halides , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, compounds of rare earth metals (including oxides, halides, carbonates) In addition to tetrathianaphthacene (abbreviated as TTN), nickelocene, decamethicone, An organic compound such as nickelocene can also be used. The electron transport layer 114 may be formed using the same material as that used for forming the electron transport layer 114 described above. This can be done.

[0162] The material forming the second electrode 102 is preferably one having a small work function (specifically, 3.8 eV or less). Bottom) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs). Lithium metals, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or 2 of the Periodic Table of Elements, and alloys containing these elements (MgAg, Rare earth metals such as AlLi), europium (Eu), ytterbium (Yb) and the like, However, when the second electrode 102 and the electron transport layer are connected to each other, By providing an electron injection layer, it is possible to use Al, Ag, ITO, silicon, etc., regardless of the magnitude of the work function. Various conductive materials such as indium oxide-tin oxide containing silicon oxide or silicon oxide are used as the second These conductive materials can be used as the electrode 102. It is possible to form the film using dry methods such as inkjet printing, spin coating, etc. It may also be formed by a wet method using a sol-gel method, or by using a paste of a metal material. Alternatively, the layer may be formed by a wet method.

[0163] The EL layer 103 can be formed by various methods, including dry and wet methods. For example, vacuum deposition, gravure printing, offset printing, screen printing, etc. A printing method, an ink jet method, a spin coating method, or the like may also be used.

[0164] Furthermore, the above-mentioned electrodes or layers may be formed using different film formation methods.

[0165] The structure of the layer provided between the first electrode 101 and the second electrode 102 is the same as that described above. However, it is not limited to the above. The first electrode 101 and the second electrode 102 are arranged so as to suppress quenching caused by the A preferred configuration is one in which a light-emitting region where holes and electrons recombine is provided at a location away from O2.

[0166] Furthermore, recombination in the hole transport layer or electron transport layer in contact with the light-emitting layer 113, particularly in the light-emitting layer 113 The carrier transport layer close to the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is determined by the luminescent material that constitutes the luminescent layer or the luminescent material contained in the luminescent layer. It is preferable that the material be made of a substance having a band gap larger than the band gap of the material. I wish.

[0167] Next, we developed a light-emitting device (a stacked element, a tandem element) that has a structure in which multiple light-emitting units are stacked. The embodiment of the light-emitting device (also referred to as a "light-emitting device") will be described with reference to FIG. A light-emitting device has multiple light-emitting units between the electrode and the cathode. The EL layer 103 has a structure similar to that of the EL layer 103 shown in FIG. The light emitting device shown in FIG. 1(A) or The light-emitting device shown in FIG. 1(B) is a light-emitting device having one light-emitting unit. It can be said that.

[0168] In FIG. 1C, a first light-emitting unit 511 and a second light-emitting unit 512 are disposed between the anode 501 and the cathode 502. The second light-emitting unit 512 is stacked, and the first light-emitting unit 511 and the second light-emitting unit A charge generating layer 513 is provided between the anode 501 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in FIG. 1(A), respectively. The same as that described in the first light-emitting unit 51 can be applied. The first and second light-emitting units 512 may have the same or different configurations.

[0169] When a voltage is applied between the anode 501 and the cathode 502, the charge generating layer 513 generates a light emitting The electron-injecting unit has the function of injecting electrons into one light-emitting unit and holes into the other light-emitting unit. In 1(C), when a voltage is applied so that the anode potential is higher than the cathode potential, In this case, the charge generating layer 513 injects electrons into the first light-emitting unit 511 and Any material capable of injecting holes into the gate 512 may be used.

[0170] The charge generation layer 513 is formed to have the same structure as the charge generation layer 116 described in FIG. 1B. The composite material of an organic compound and a metal oxide has the properties of carrier injection, carrier transport, and the like. It has excellent electrical properties, making it possible to achieve low voltage and low current driving. When the anode side of the unit is in contact with the charge generating layer 513, the charge generating layer 513 is the light emitting unit. Since it can also function as a hole injection layer for the light-emitting unit, the light-emitting unit does not need to have a hole injection layer. Both are good.

[0171] In addition, when the electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer Since the electron injection layer 119 plays the role of an electron injection layer in the light-emitting unit on the anode side, the light-emitting layer The unit does not necessarily need to have an electron injection layer.

[0172] Although the light-emitting device having two light-emitting units has been described in FIG. 1C, the light-emitting device having three or more light-emitting units may be used. The same can be applied to a light-emitting device in which the above light-emitting units are stacked. As in the light-emitting device according to the present embodiment, a plurality of light-emitting units are electrically connected between a pair of electrodes. By separating the layers with the generation layer 513, high brightness light emission is possible while keeping the current density low. This allows for the realization of devices with even longer life. In addition, low voltage operation is possible, resulting in low power consumption. A light emitting device can be realized.

[0173] In addition, by making the light color of each light-emitting unit different, the light-emitting device as a whole can be For example, a light-emitting device having two light-emitting units can be used to obtain light of a desired color. In this device, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. By obtaining a color, it is possible to obtain a light-emitting device that emits white light as a whole. be.

[0174] In addition, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512, and Each layer such as the charge generating layer 513 and the electrodes can be formed by, for example, a deposition method (including a vacuum deposition method), a droplet discharge method, or the like. It can be formed by a method such as inkjet printing, coating, or gravure printing. They can also be used in low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers). ), or may include a polymeric material.

[0175] (Embodiment 3) In this embodiment, a light-emitting device using the light-emitting device described in Embodiment 2 will be described. do.

[0176] In this embodiment, a light-emitting device manufactured using the light-emitting device described in Embodiment 2 will be described. 2A is a top view of a light-emitting device, and FIG. This light emitting device is a cross-sectional view taken along the lines AB and CD in FIG. The light emission of the source is controlled by a driving circuit section (source line driving circuit) 601 shown by the dotted line. 604 includes a pixel portion 602 and a driver circuit portion (gate line driver circuit) 603. The sealing substrate 605 is a sealing material, and the inside surrounded by the sealing material 605 is a space 607. It is.

[0177] The lead wiring 608 is connected to the source line driver circuit 601 and the gate line driver circuit 603. The wiring is for transmitting signals, and the FPC (flexible printed circuit board) is the external input terminal. Video signal, clock signal, start signal, reset signal, etc. from the input circuit 609 Although only the FPC is shown here, this FPC has a printed wiring board. The light emitting device in this specification may be a light emitting device. This includes not only the device itself but also the state in which an FPC or PWB is attached to it. do.

[0178] Next, the cross-sectional structure will be described with reference to FIG. A source line driver circuit 601 and a pixel portion are formed. , one pixel in the pixel section 602 is shown.

[0179] The element substrate 610 may be a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, or the like. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl It is made using a plastic substrate made of a material such as fluoride, polyester, or acrylic resin. It is enough to manufacture it.

[0180] The structure of the transistors used in the pixels and driver circuits is not particularly limited. The transistor may be a top-type transistor or a staggered type transistor. The transistor may be a gate type transistor or a bottom gate type transistor. The semiconductor material is not particularly limited, and examples thereof include silicon, germanium, silicon carbide, and nitride. Gallium or the like can be used. Alternatively, in-type metal oxides such as In-Ga-Zn-based metal oxides can be used. An oxide semiconductor containing at least one of tungsten, gallium, and zinc may be used.

[0181] The crystallinity of the semiconductor material used in the transistor is not particularly limited. A semiconductor having crystallinity (microcrystalline semiconductor, polycrystalline semiconductor, single crystal semiconductor, or a semiconductor having a partially crystalline region) When a semiconductor having crystallinity is used, the transistor This is preferable because it can suppress deterioration of the star characteristics.

[0182] Here, in addition to the transistors provided in the pixels and the driver circuits, It is preferable to use an oxide semiconductor for a semiconductor device such as a transistor. In particular, it is preferable to use an oxide semiconductor having a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than silicon, the off-state of the transistor can be This can reduce the current in the

[0183] The oxide semiconductor preferably contains at least indium (In) or zinc (Zn). In addition, In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is preferable that the oxide semiconductor contains an oxide represented by the formula (metal such as La, Ce or Hf). More preferable.

[0184] In particular, the semiconductor layer has a plurality of crystal portions, and the c-axes of the crystal portions are aligned with the surface on which the semiconductor layer is formed, Or, an oxide film oriented perpendicular to the upper surface of the semiconductor layer and having no grain boundary between adjacent crystal portions. It is preferable to use a nitride semiconductor film.

[0185] By using such materials for the semiconductor layer, fluctuations in electrical characteristics are suppressed, resulting in high reliability. This makes it possible to realize a low-power transistor.

[0186] Furthermore, the transistor having the above-described semiconductor layer can be used as a transistor due to its low off-state current. It is possible to retain the charge stored in the capacitor for a long period of time through such a transistor. By applying a transistor to each pixel, the gradation of the image displayed in each display area can be maintained while driving It is also possible to shut down the circuit. As a result, electronic devices with extremely low power consumption can be realized. It can be realized.

[0187] For stabilizing the characteristics of the transistor, it is preferable to provide an underlayer film. Inorganic films such as silicon oxide film, silicon nitride film, silicon oxynitride film, and silicon nitride oxide film The insulating film can be formed as a single layer or a laminated layer. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, etc.), ALD ( Formed using Atomic Layer Deposition (ALD), coating, printing, etc. It should be noted that the undercoat film need not be provided if it is not necessary.

[0188] The FET 623 indicates one of the transistors formed in the driving circuit section 601. The drive circuit is made up of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment, a driver integrated type in which a driving circuit is formed on a substrate is shown. However, this is not necessarily required, and the drive circuit can be formed externally rather than on the substrate. .

[0189] The pixel section 602 includes a switching FET 611, a current control FET 612 and its driver. The pixel is formed by a plurality of pixels including a first electrode 613 electrically connected to the drain. However, the present invention is not limited to this, and a pixel unit that combines three or more FETs and a capacitance element may also be used. good.

[0190] An insulator 614 is formed to cover the end of the first electrode 613. It can be formed by using a photosensitive acrylic resin film of a mold.

[0191] In order to improve the coverage of the EL layer and the like to be formed later, the insulating material 614 is For example, the material of the insulator 614 is When a positive photosensitive acrylic resin is used, the radius of curvature ( It is preferable that the insulating material 614 has a curved surface having a thickness of 0.2 μm to 3 μm. Either a negative photosensitive resin or a positive photosensitive resin can be used.

[0192] An EL layer 616 and a second electrode 617 are formed on the first electrode 613. Here, the material used for the first electrode 613 functioning as an anode is a material having a work function of It is desirable to use a large material, for example, an ITO film or an indium-silicon-containing film. Indium tin oxide film, indium oxide film containing 2 to 20 wt% zinc oxide, titanium nitride film, In addition to single layer films such as ROM film, tungsten film, Zn film, and Pt film, titanium nitride film and aluminum film are also available. a titanium nitride film and an aluminum-based film; A three-layer structure with a silicon film can be used. The resistance is low, good ohmic contact can be achieved, and the electrode can also function as an anode. .

[0193] The EL layer 616 can be formed by a deposition method using a deposition mask, an inkjet method, or a spin coating method. The EL layer 616 is formed by various methods such as the above. Other materials that make up the EL layer 616 include low molecular weight compounds, may be a polymer compound (including an oligomer or a dendrimer).

[0194] Furthermore, a material used for the second electrode 617 formed on the EL layer 616 and functioning as a cathode As the material, materials with a small work function (Al, Mg, Li, Ca, or their alloys or compounds) It is preferable to use a material such as MgAg, MgIn, or AlLi. When the light generated in 6 is transmitted through the second electrode 617, the second electrode 617 is Thin metal films and transparent conductive films (ITO, indium tin oxide containing 2-20 wt% zinc oxide) It uses lamination of indium tin oxide containing indium and silicon, zinc oxide (ZnO, etc.) It's good to do that.

[0195] The first electrode 613, the EL layer 616, and the second electrode 617 form a light-emitting device. The light-emitting device is the light-emitting device described in embodiment 2. The element part is formed with a plurality of light emitting devices. The light-emitting device according to the second embodiment and the light-emitting device having other configurations are It's okay if there is a mixture of these.

[0196] Furthermore, the sealing substrate 604 is bonded to the element substrate 610 with a sealing material 605. A light-emitting device is placed in a space 607 surrounded by a sub-substrate 610, a sealing substrate 604, and a sealing material 605. The space 607 is filled with a filler material. In some cases, the gas is filled with an inert gas (nitrogen, argon, etc.), and in other cases, it is filled with a sealing material. By forming a recess in the sealing substrate and providing a desiccant there, deterioration due to the influence of moisture can be prevented. This is a preferable configuration because it can suppress the degradation.

[0197] It is preferable to use epoxy resin or glass frit for the sealing material 605. It is desirable that these materials be as impermeable to moisture and oxygen as possible. Materials used for the sealing substrate 604 include glass substrates, quartz substrates, and FRP (Fiber Reinforced Plastics). reinforced plastics), PVF (polyvinyl fluoride), polyester A plastic substrate made of polyester, acrylic resin, or the like can be used.

[0198] Although not shown in Figure 2, a protective film may be provided on the second electrode. The protective film is an organic resin film. The exposed portion of the sealant 605 may be covered with a protective film. A protective film may be formed on the surfaces and sides of the pair of substrates, the sealing layer, the insulating layer, and the like. A rim layer, etc. may be provided over the exposed side surface.

[0199] The protective film can be made of a material that is difficult for impurities such as water to permeate. It is possible to effectively prevent impurities such as these from diffusing from the outside to the inside.

[0200] The materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers and the like can be used, for example, aluminum oxide, hafnium oxide, hafnium Lanthanum silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide , titanium oxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide , cerium oxide, scandium oxide, erbium oxide, vanadium oxide or indium oxide Materials containing hafnium, aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, titanium nitride, niobium nitride, molybdenum nitride, zirconium nitride, or gallium nitride, etc. Materials, nitrides containing titanium and aluminum, oxides containing titanium and aluminum , oxides containing aluminum and zinc, sulfides containing manganese and zinc, cerium and sulfides containing erbium and strontium, oxides containing erbium and aluminum, yttrium Materials containing oxides containing lithium and zirconium can be used.

[0201] The protective film can be formed using a film formation method that provides good step coverage. One such method is atomic layer deposition (ALD). The ALD method can be used to form protective materials. It is preferable to use it for films. By using the ALD method, it is possible to eliminate cracks, pinholes, etc. It is possible to form a protective film with reduced defects or with a uniform thickness. Damage to the processed member when forming the protective film can be reduced.

[0202] For example, by forming a protective film using the ALD method, it is possible to fabricate a surface with complex irregularities or a surface with a touch panel. A uniform protective film with few defects can be formed on the top, sides and back of the panel. .

[0203] In this manner, a light-emitting device manufactured using the light-emitting device described in Embodiment 2 is obtained. It is possible.

[0204] The light emitting device in this embodiment uses the light emitting device described in Embodiment 2. In this way, a light emitting device having excellent characteristics can be obtained. Since the light-emitting device has good light-emitting efficiency, it is possible to make it a light-emitting device with low power consumption. do.

[0205] In FIG. 3, a light-emitting device that emits white light is formed, and a colored layer (color filter) is provided. FIG. 3(A) shows an example of a full-color light-emitting device. an insulating film 1002, a gate insulating film 1003, gate electrodes 1006, 1007, 1008, The first interlayer insulating film 1020, the second interlayer insulating film 1021, the peripheral portion 1042, and the pixel portion 1040 , the driving circuit unit 1041, the first electrodes 1024W, 1024R, and 1024G of the light-emitting device , 1024B, a partition wall 1025, an EL layer 1028, a second electrode 1029 of the light-emitting device, and an encapsulant. A stop substrate 1031, a seal material 1032, etc. are shown in the figure.

[0206] In addition, in FIG. 3(A), the colored layers (red colored layer 1034R, green colored layer 1034G, blue The colored layer 1034B is provided on a transparent substrate 1033. A transparent substrate 1 on which a colored layer and a black matrix are provided may be further provided. The colored layer and the black matrix are aligned and fixed to the substrate 1001. The dust 1035 is covered with an overcoat layer 1036. The light-emitting layer is where light does not pass through the colored layers and goes out, and the light passes through the colored layers of each color and goes out. The light that does not pass through the colored layer is white, and the light that passes through the colored layer is red, green, or blue. This allows images to be expressed using four color pixels.

[0207] In FIG. 3(B), the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer An example in which a layer 1034B) is formed between the gate insulating film 1003 and the first interlayer insulating film 1020 As shown in the figure, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. is also good.

[0208] In the light emitting device described above, light is taken in toward the substrate 1001 on which the FET is formed. The light emitting device has a bottom emission structure, but the light is taken in from the sealing substrate 1031 side. The light emitting device may have a top emission structure. A cross-sectional view of the light-emitting device is shown in FIG. 4. In this case, a substrate that does not transmit light is used as the substrate 1001. Until the connection electrode that connects the FET and the anode of the light-emitting device is fabricated, The third interlayer insulating film 1037 is then formed in the same manner as in the case of the multi-emission light emitting device. The insulating film is formed to cover the electrode 1022. This insulating film may also play a role in planarization. The interlayer insulating film 1037 is formed using the same material as the second interlayer insulating film, as well as other known materials. It is possible.

[0209] The first electrodes 1024W, 1024R, 1024G, 1024B of the light emitting device are The anode is used as the anode, but it can also be the cathode. In the case of an optical device, the first electrode is preferably a reflective electrode. The EL layer 103 has the same structure as that described in the second embodiment and emits white light. The device structure is such that light can be obtained.

[0210] In the top emission structure shown in Figure 4, the colored layers (red colored layer 1034R, green colored layer The sealing is performed by a sealing substrate 1031 provided with a blue color layer 1034G and a blue color layer 1034B. The sealing substrate 1031 has a black matrix disposed between the pixels. A coloring layer (red coloring layer 1034R, green coloring layer 1034G, The blue colored layer 1034B and the black matrix 1035 are overcoat layers 1036 The sealing substrate 1031 may be covered with a light-transmitting substrate. In addition, although an example of full color display using four colors, red, green, blue, and white, has been shown here, There is no limitation, and full color display may be performed using four colors of red, yellow, green, and blue, or three colors of red, green, and blue. .

[0211] In a top-emission type light-emitting device, the microcavity structure can be suitably applied. The light-emitting device having a microcavity structure has a first electrode as a reflective electrode and a second electrode as a This is achieved by using a semi-transparent and semi-reflective electrode. The device has at least an EL layer, and at least a light-emitting layer that serves as a light-emitting region.

[0212] The reflectance of the reflective electrode for visible light is 40% to 100%, preferably 70% to 100%. %, and its resistivity is 1×10 -2 The film is assumed to be less than Ωcm. The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1×10 -2 It is assumed that the film has a resistance of Ωcm or less.

[0213] The light emitted from the light-emitting layer included in the EL layer is reflected by the reflective electrode and the semi-transparent and semi-reflective electrode. The sound is reflected and resonates.

[0214] The light-emitting device is made by changing the thickness of the transparent conductive film, the composite material, the carrier transport material, etc. By doing so, the optical distance between the reflective electrode and the semi-transmissive / semi-reflective electrode can be changed. This strengthens the light of the resonating wavelength between the reflective electrode and the semi-transparent and semi-reflective electrode, and It can attenuate light of wavelengths that are not

[0215] The light reflected by the reflective electrode and returned (first reflected light) is semi-transmitted from the light emitting layer. The light that directly enters the semi-reflective electrode (first incident light) interferes greatly with the reflective electrode. The optical distance of the light-emitting layer is (2n-1)λ / 4 (where n is a natural number greater than or equal to 1, and λ is the amplified It is preferable to adjust the optical distance to a wavelength of the first light. By matching the phase of the reflected light with the phase of the first incident light, the light emitted from the light-emitting layer can be further amplified. do.

[0216] In the above configuration, even if the EL layer has a structure having a plurality of light-emitting layers, it may be a single light-emitting layer. For example, it may be combined with the configuration of the tandem light emitting device described above. In addition, a plurality of EL layers are provided in one light-emitting device with a charge generating layer sandwiched therebetween, and each EL layer The present invention may be applied to a configuration in which a single or multiple light-emitting layers are formed on the substrate.

[0217] The microcavity structure makes it possible to enhance the front-direction emission intensity of specific wavelengths. This allows for lower power consumption. In the case of a light-emitting device that displays images using a single pixel, the yellow light emission not only improves brightness, but also Since a microcavity structure tailored to the wavelength of each color can be applied, it is possible to achieve light-emitting devices with excellent characteristics. It can be placed.

[0218] The light emitting device in this embodiment uses the light emitting device described in Embodiment 2. In this way, a light emitting device having excellent characteristics can be obtained. Since the light-emitting device has good light-emitting efficiency, it is possible to make it a light-emitting device with low power consumption. do.

[0219] Up to this point, we have explained about active matrix light emitting devices, but from now on we will be talking about passive light emitting devices. A passive matrix light-emitting device will be described. 5A is a perspective view showing the light emitting device, and FIG. 5B) is a cross-sectional view of FIG. 5A cut along XY. In FIG. 5, on a substrate 951, An EL layer 955 is provided between the electrode 952 and the electrode 956. The ends of the electrode 952 are It is covered with an insulating layer 953. A partition wall layer 954 is provided on the insulating layer 953. The sidewalls of the partition layer 954 become thicker between one sidewall and the other sidewall as they approach the substrate surface. That is, the cross section of the partition wall layer 954 in the short side direction has a slope such that the gap between the partition walls becomes narrower. The bottom side (the side that faces the same direction as the surface direction of the insulating layer 953 and is in contact with the insulating layer 953) ) is the upper side (the side that faces in the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953). In this way, by providing the partition layer 954, it is possible to prevent the light emitting device from being damaged by static electricity or the like. In addition, the present invention can also be applied to passive matrix light emitting devices. A light-emitting device having high reliability or low power consumption, which uses the light-emitting device according to the second aspect. A small light emitting device can be produced.

[0220] The light emitting device described above is composed of a large number of minute light emitting devices arranged in a matrix. Since it is possible to control each of these, it can be suitably used as a display device for displaying images. It is a light-emitting device.

[0221] This embodiment mode can be freely combined with other embodiment modes.

[0222] (Fourth embodiment) In this embodiment, an example in which the light-emitting device described in Embodiment 2 is used as a lighting device is shown in FIG. 6(B) is a top view of the lighting device, and FIG. 6(A) is a diagram showing the lighting device in FIG. 6(B). FIG. 5 is a cross-sectional view of the ef section.

[0223] The lighting device of this embodiment is a light-transmitting substrate 400 serving as a support, on which a first The first electrode 401 is formed on the substrate 10. The first electrode 401 is the same as the first electrode 10 in the second embodiment. When light is extracted from the first electrode 401 side, the first electrode 401 is made of a transparent material. The material is formed from a material having the following properties.

[0224] A pad 412 for supplying a voltage to the second electrode 404 is formed on the substrate 400 .

[0225] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is the same as that in Embodiment 2. The configuration of the EL layer 103 in the light-emitting device 100, or the combination of the light-emitting units 511, 512 and the charge-generating layer 513 For details about these configurations, please refer to the relevant descriptions.

[0226] The second electrode 404 is formed to cover the EL layer 403. When light is extracted from the first electrode 401 side, the second electrode 102 corresponds to the second electrode 102. The first electrode 404 is formed of a highly reflective material. The voltage is supplied by connecting

[0227] As described above, a light-emitting device having the first electrode 401, the EL layer 403, and the second electrode 404 is provided. The lighting device shown in this embodiment is a light-emitting device with high luminous efficiency. Therefore, the lighting device in this embodiment is a lighting device with low power consumption. can be done.

[0228] The substrate 400 on which the light emitting device having the above structure is formed is sealed with a sealing substrate 407. The lighting device is completed by fixing and sealing using sealing materials 405 and 406. Either 405 or 406 may be used. In addition, the inner sealing material 406 (FIG. 6(B) ) (not shown) can also be mixed with a desiccant, which can absorb moisture. This leads to improved reliability.

[0229] In addition, a part of the pad 412 and the first electrode 401 is extended outside the sealing materials 405 and 406. By providing this, it can be used as an external input terminal. An IC chip 420 equipped with the above may be provided.

[0230] As described above, the lighting device according to the present embodiment includes the light-emitting device according to the second embodiment as the EL element. This allows the lighting device to consume less power.

[0231] (Embodiment 5) In this embodiment, an example of an electronic device including the light-emitting device described in embodiment 2 as a part thereof is as follows. The light-emitting device described in embodiment 2 has good luminous efficiency and low power consumption. As a result, the electronic device described in this embodiment has low power consumption. It is possible to make an electronic device with a small light emitting part.

[0232] Examples of electronic devices to which the light-emitting device is applied include television sets (televisions, (also called television receivers), computer monitors, digital cameras, digital digital video cameras, digital photo frames, mobile phones (also known as mobile phones or mobile phone devices) (hereinafter referred to as "games"), portable game machines, personal digital assistants, sound reproduction devices, large game machines such as pachinko machines Specific examples of these electronic devices are listed below.

[0233] 7A shows an example of a television device. The television device includes a housing 710 A display unit 7103 is built into the housing 1. In this case, a stand 7105 is used to hold the housing The display unit 7103 can display images. The display portion 7103 has the light-emitting devices described in Embodiment 2 arranged in matrix. It is composed of the following.

[0234] The television device can be operated using the operation switches on the housing 7101 or a separate remote control. This can be done by the remote control device 7110. This allows you to control the channel and volume, and the image displayed on the display unit 7103 In addition, the remote control operation device 7110 can be operated. A display portion 7107 for displaying information output from the

[0235] The television device is assumed to be equipped with a receiver, modem, etc. It can receive television broadcasts and can also communicate by wire or wireless via a modem. By connecting to a network, you can send and receive data in one direction (sender to receiver) or two directions (sender to receiver). It is also possible to communicate information between the recipient and the receiver, or between receivers themselves.

[0236] FIG. 7(B1) shows a computer, which includes a main body 7201, a housing 7202, a display portion 7203, and a keyboard. keyboard 7204, external connection port 7205, pointing device 7206, etc. This computer is configured to display the light-emitting devices according to the second embodiment in a matrix. The display portion 7203 is fabricated by using the LCD panel 7201 as a display portion. The computer shown in FIG. 7(B2) may have a keyboard 7 204, a second display unit 7210 is provided instead of the pointing device 7206. The second display portion 7210 is a touch panel type. Input can be made by operating the input display with a finger or a special pen. The second display unit 7210 can display not only input images but also other images. The display unit 7203 may also be a touch panel. The screen may be scratched or broken when stored or transported due to the connection. It is also possible to prevent problems from occurring.

[0237] FIG. 7C shows an example of a mobile terminal. The mobile phone is built in a housing 7401. In addition to the display unit 7402, operation buttons 7403, an external connection port 7404, a speaker 740 5, a microphone 7406, etc. The mobile phone is equipped with the light-emitting device described in the second embodiment. The display unit 7402 is made up of devices arranged in a matrix.

[0238] The mobile terminal shown in FIG. 7C allows users to input information by touching the display portion 7402 with a finger or the like. In this case, it is possible to make a call or create an email. Operations such as turning on / off the camera can be performed by touching the display portion 7402 with a finger or the like.

[0239] The screen of the display unit 7402 has three main modes. The first is a display mode that mainly displays images. The first mode is a display mode, and the second mode is an input mode that mainly inputs information such as characters. This is a display + input mode that combines two modes: display mode and input mode.

[0240] For example, when making a call or creating an email, the display unit 7402 is used to input characters. This is the main character input mode, and you can input characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display portion 7402. I wish.

[0241] In addition, the mobile terminal may include a sensor for detecting tilt, such as a gyro or acceleration sensor. By providing a device, the orientation of the mobile terminal (portrait or landscape) can be determined and the screen display of the display portion 7402 can be displayed. The display can be switched automatically.

[0242] The screen mode can be switched by touching the display portion 7402 or by operating the housing 7401. This is done by operating the button 7403. Also, depending on the type of image displayed on the display unit 7402, For example, if the image signal to be displayed on the display unit is a video signal, If it is data, the display mode is switched to, and if it is text data, the input mode is switched to.

[0243] In the input mode, the optical sensor of the display unit 7402 detects a signal and displays it. If there is no input by touch operation on the part 7402 for a certain period of time, the screen mode is changed to the input mode. Alternatively, the display mode may be switched from the normal mode to the display mode.

[0244] The display portion 7402 can also function as an image sensor. By touching the device with your palm or fingers and capturing an image of your palm print or fingerprint, you can authenticate your identity. In addition, a backlight that emits near-infrared light to the display unit or a sensing light that emits near-infrared light By using a source, it is also possible to image finger veins, palm veins, etc.

[0245] FIG. 8(A) is a schematic diagram showing an example of a cleaning robot.

[0246] The cleaning robot 5100 has a display 5101 on the top surface and multiple The camera 5102, the brush 5103, and the operation button 5104 are also shown. However, the underside of the cleaning robot 5100 is provided with tires, a suction port, etc. The robot 5100 also has an infrared sensor, an ultrasonic sensor, an acceleration sensor, a piezo sensor, It is equipped with various sensors such as a sensor, a light sensor, and a gyro sensor. 100 is equipped with wireless communication means.

[0247] The cleaning robot 5100 moves by itself, detects the dust 5120, and sucks it out from the suction port on the bottom. It can suck up dirt.

[0248] In addition, the cleaning robot 5100 analyzes the image captured by the camera 5102 and detects the wall, furniture, or It can detect obstacles such as steps. Image analysis can also detect obstacles such as wiring. If an object that may get tangled in the brush 5103 is detected, the rotation of the brush 5103 can be stopped. can.

[0249] The display 5101 can display the remaining battery level and the amount of dust sucked. The route traveled by the cleaning robot 5100 can be displayed on the display 5101. In addition, the display 5101 is a touch panel, and the operation button 5104 is It may be provided in the ray 5101.

[0250] The cleaning robot 5100 can communicate with a portable electronic device 5140 such as a smartphone. The images captured by the camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the Cleaning Robot 5100 can check the status of the room even when he is away from home. In addition, the display on the display 5101 can be displayed on a mobile electronic device such as a smartphone. You can also check it at 5140.

[0251] The light-emitting device according to one embodiment of the present invention can be used for the display 5101 .

[0252] The robot 2100 shown in FIG. 8(B) includes a computing device 2110, an illuminance sensor 2101, a microphone 2102, upper camera 2103, speaker 2104, display 2105, It is equipped with an internal camera 2106, an obstacle sensor 2107, and a movement mechanism 2108.

[0253] The microphone 2102 has a function of detecting the user's voice and environmental sounds. The speaker 2104 has a function of emitting sound. The device 2102 and the speaker 2104 can be used to communicate with the user. It is possible.

[0254] The display 2105 has the function of displaying various information. Any information desired by the user can be displayed on the display 2105. The display 2105 may be equipped with a touch panel. It may be an information terminal that can be charged by placing it in a fixed position on the robot 2100. and enables data transfer.

[0255] The upper camera 2103 and the lower camera 2106 are used to capture images of the surroundings of the robot 2100. The obstacle sensor 2107 detects the obstacles in the robot 210 by using the moving mechanism 2108. When moving forward, the robot can sense whether there are any obstacles in its path. 00 uses an upper camera 2103, a lower camera 2106, and an obstacle sensor 2107. The light-emitting device according to one embodiment of the present invention can recognize the surrounding environment and move safely. It can be used for the display 2105.

[0256] FIG. 8(C) is a diagram showing an example of a goggle-type display. For example, a housing 5000, a display unit 5001, a speaker 5003, an LED lamp 5004, Connection terminal 5006, sensor 5007 (force, displacement, position, velocity, acceleration, angular velocity, rotation speed, Distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage, power, radiation (including those that measure radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), The device includes a microphone 5008, a display unit 5002, a support unit 5012, earphones 5013, and the like.

[0257] The light-emitting device of one embodiment of the present invention can be used for the display portion 5001 and the display portion 5002. .

[0258] FIG. 9 shows an example in which the light-emitting device according to the second embodiment is used in a desk lamp, which is a lighting device. The desk lamp shown in FIG. 9 has a housing 2001 and a light source 2002. As the light source 2, the lighting device described in the third embodiment may be used.

[0259] FIG. 10 shows an example in which the light-emitting device according to the second embodiment is used as an indoor lighting device 3001. The light-emitting device described in the second embodiment is a light-emitting device with high luminous efficiency. In this way, a lighting device with low power consumption can be obtained. The chair can be made large, so it can be used as a large-area lighting device. The light-emitting device described in the second embodiment is thin and can be used as a thin lighting device. This makes it possible to

[0260] The light-emitting device described in the second embodiment can also be mounted on the windshield or dashboard of an automobile. FIG. 11 shows the light emitting device according to the second embodiment mounted on the front windshield of an automobile. The display area 5200 to the display area 5203 are used for a class or a dashboard. 10 shows a display area provided using the light-emitting device described in Embodiment 2.

[0261] In this embodiment, the display area 5200 and the display area 5201 are provided on the windshield of a car. 1 is a display device incorporating the light-emitting device according to embodiment 2. By making the first electrode and the second electrode from light-transmitting electrodes, the opposite side is transparent. It is possible to provide a so-called see-through display device in which the image is seen through the screen. If it is displayed on the windshield of a car, it will not obstruct the view. In addition, when a transistor for driving is provided, an organic semiconductor Translucent organic transistors using conductive materials and transistors using oxide semiconductors are being developed. It is preferable to use a transistor having such a configuration.

[0262] The display region 5202 is provided with the light-emitting device described in Embodiment 2. The display area 5202 displays an image captured by an imaging means provided on the vehicle body. By doing so, it is possible to compensate for the visibility obstructed by the pillars. The display area 5203 provided on the board allows the view blocked by the car body to be displayed on the By projecting images from an external imaging device, blind spots are compensated for and safety is improved. By projecting images that complement the invisible parts, it becomes more natural. Safety checks can be carried out without any discomfort.

[0263] The display area 5203 also provides navigation information, speed, RPM, and various other information. The display items and layout can be changed as needed to suit the user's preferences. This information can also be set in the display areas 5200 to 5202. In addition, the display areas 5200 to 5203 can be used as lighting devices. It is also possible to

[0264] 12(A) and (B) show a foldable mobile information terminal 5150. The foldable mobile information terminal 5150 includes a housing 5151, a display area 5152, and a bending portion 515 12(A) shows the mobile information terminal 5150 in an unfolded state. Figure 5B) shows the mobile information terminal in a folded state. The mobile information terminal 5150 has a large display area. Despite having a range of 5152, it is compact and highly portable when folded.

[0265] The display area 5152 can be folded in half by the bend 5153. 3 is composed of an expandable member and multiple support members, and when folding, The bent portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more. It can be folded.

[0266] The display area 5152 is a touch panel (input / output) equipped with a touch sensor (input device). The light-emitting device of one embodiment of the present invention can be used in the display region 5152. Cut.

[0267] 13(A) to 13(C) show a foldable mobile information terminal 9310. 13(A) shows the mobile information terminal 9310 in an unfolded state. The mobile information terminal 9310 is shown in a state in which it is changing from one folded state to the other. FIG. 13C shows the portable information terminal 9310 in a folded state. The foldable design offers excellent portability and a seamless, large viewing area when unfolded. This provides excellent visibility of the display.

[0268] The display panel 9311 is supported by three housings 9315 connected by hinges 9313. The display panel 9311 is a touch panel equipped with a touch sensor (input device). The display panel 9311 may be a display panel (input / output device). The two housings 9315 are bent to open the mobile information terminal 9310. The light-emitting device of one embodiment of the present invention can be reversibly transformed from a folded state to a folded state. It can be used for the display panel 9311.

[0269] Note that the structure described in this embodiment mode may be obtained by appropriately combining the structures described in any of Embodiment Modes 1 to 4. They can be used in combination.

[0270] As described above, the light emitting device according to the second embodiment has a very wide range of application. This light emitting device can be applied to electronic devices in a wide range of fields. By using the light-emitting device described above, electronic devices with low power consumption can be obtained. [Example]

[0271] <Synthesis Example 1> In this example, N,N'-bis[9-( 4-tert-butylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl Nyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation This article describes the synthesis method of 3,10tBuPCA2Nbf(IV)-02. The structural formula of 10tBuPCA2Nbf(IV)-02 is shown below.

[0272] [ka]

[0273] Step 1: 2-chloro-9-(4-tert-butylphenyl)-9H-carbazole Synthesis of ru> Add 5.3 g (27 mmol) of 2-chloro-9H-carbazole to a 300 mL three-neck flask. 1-Bromo-4-tert-butylbenzene 10g (48mmol), sodium 7.7 g (80 mmol) of tert-butoxide was added to this mixture. Add 0.0 mL of the solution and 0.4 mL of a 10% hexane solution of tri(tert-butyl)phosphine. The mixture was degassed by stirring under reduced pressure. Add 0.15 g (0.27 mmol) of palladium (0) in acetone and heat for 1 hour under a nitrogen stream. The mixture was heated and stirred at 50°C for 13 hours. After stirring, toluene was added to the mixture, and Florisil, The mixture was filtered through celite and alumina under suction to obtain a filtrate, which was then concentrated to obtain a solid. This solid was purified by silica gel column chromatography (developing solvent: hexane) Ethanol was added to the obtained solid, and after ultrasonic irradiation, the solid was filtered to obtain a white solid. The synthesis scheme for Step 1 is shown below.

[0274] [ka]

[0275] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 1 above ( 1 H-NMR) This is shown below. In step 1, 2-chloro-9-(4-tert-butyl It was found that phenyl)-9H-carbazole was obtained. 1 H NMR(CD2Cl2,300MHz):δ=1.43(s,9H),7.22- 7.31(m,2H),7.36-7.48(m,5H),7.62-7.67(m,2 H),8.06(d,J1=8.4Hz,1H),8.11(dt,J1=7.8Hz, J2=1.2Hz,1H).

[0276] Step 2: N-phenyl-9-(4-tert-butylphenyl)-9H-carbazo Synthesis of 2-amino-2-amine In a 200 mL three-neck flask, add 5.0 g (15 mmol) of 2-chloro-9-(4-tert-butyl) -butylphenyl)-9H-carbazole, 2.1 g (23 mmol) aniline, 4. 3 g (45 mmol) of sodium tert-butoxide, 0.27 g (0.75 mmol) ol) di(1-adamantyl)-n-butylphosphine. 100 mL of ethanol was added, and the mixture was degassed by stirring under reduced pressure. Add 86 mg (0.15 mmol) of (dibenzylideneacetone)palladium(0) and The mixture was heated and stirred at 150°C for 6.5 hours under a stream of air. After stirring, toluene was added to the mixture. The mixture was suction filtered through Florisil, Celite, and alumina, and the filtrate was concentrated to give a solid. This solid was purified by silica gel column chromatography (developing solvent: toluene:hexane=1: The solid that could not be purified was purified by silica gel column chromatography (development The mixture was purified using a solvent mixture of toluene:hexane (1:3), then toluene:hexane (3:7). 4.0 g of a white solid was obtained in a yield of 68%. The synthetic scheme for Step 2 is shown below.

[0277] [ka]

[0278] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 H-NMR) This is shown below. In step 2, N-phenyl-9-(4-tert-butyl) It was found that 9H-phenyl-9H-carbazol-2-amine was obtained. 1 H NMR(DMSO-d6,300MHz):δ=1.38(s,9H),6.81 (t,J1=7.2Hz,1H),7.01-7.11(m,4H),7.18-7.3 0(m,5H),7.54(d,J1=8.4Hz,2H),7.68(d,J1=8. 7Hz, 2H), 8.03-8.08 (m, 2H), 8.36 (s, 1H).

[0279] <Step 3: Synthesis of 3,10tBuPCA2Nbf(IV)-02> In a 200 mL three-neck flask, add 0.86 g (2.3 mmol) of 3,10-dichloronaphtho[ 2,3-b;6,7-b']bisbenzofuran and 2.2 g (5.5 mmol) of N-furan Phenyl-9-(4-tert-butylphenyl)-9H-carbazol-2-amine, 8 2 mg (0.23 mmol) of di(1-adamantyl)-n-butylphosphine, 1.3 g (14 mmol) of sodium tert-butoxide was added to the mixture. 1 mL of xylene was added. The mixture was degassed by stirring under reduced pressure. 26 mg (46 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture. The mixture was heated and stirred at 150°C for 8 hours under a nitrogen stream. After stirring, the mixture was filtered to recover the solid. The obtained solid was washed with ethanol and water. The washed solid was purified by silica gel column chromatography. The solid was purified by chromatography (developing solvent: toluene) to obtain a solid. The resulting solid was recrystallized twice with 1.5 g of a yellow solid in a yield of 59%. By insublimation method, pressure 2.7 × 10 -2 Pa, argon flow rate 0 mL / min After sublimation purification, 0.40 g of a yellow solid was obtained, with a recovery rate of 38%. The synthesis scheme for Step 3 is shown below.

[0280] [ka]

[0281] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 above ( 1 H-NMR) The numerical data is shown in Figure 14(A)(B) and below. It was found that 10tBuPCA2Nbf(IV)-02 was obtained. 1 H NMR(CD2Cl2,300MHz):δ=1.33(s,18H),7.03 -7.12(m,6H),7.18-7.21(m,6H),7.25-7.32(m, 8H),7.37-7.57(m,12H),7.87(d,J1=8.4Hz,2H) ,7.96(s,2H),8.09(d,J1=8.1Hz,4H),8.34(s,2 H).

[0282] Next, the absorption spectrum of 3,10tBuPCA2Nbf(IV)-02 in toluene solution The results of measuring the absorption and emission spectra are shown in Figure 15. The spectra and emission spectra are shown in Figure 16. The solid thin film was prepared by vacuum deposition on a quartz substrate. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (JASCO V 550) and subtracted the spectrum measured by placing only toluene in a quartz cell. The absorption spectrum of the thin film was measured using a spectrophotometer (Hitachi High-Technologies Corporation). A spectrophotometer (U4100, manufactured by ZEISS) was used. The quantum yield was measured using an absolute PL quantum yield measurement device (JASCO Corporation, FP-8600). A detector (Quantaurus-QY manufactured by Hamamatsu Photonics Co., Ltd.) was used.

[0283] From Figure 15, the toluene solution of 3,10tBuPCA2Nbf(IV)-02 is 430 nm The absorption peaks are observed at 408 nm, 348 nm, and the emission spectrum peak is at 448 nm. , 474 nm (excitation wavelength 408 nm). Thin films of A2Nbf(IV)-02 exhibited IR spectra at 434 nm, 416 nm, 349 nm and 265 nm. The absorption peak is observed at 482 nm (excitation wavelength 400 nm) ) was observed. From this result, it was found that 3,10tBuPCA2Nbf(IV)-02 exhibited a blue color. It has been confirmed that the compound can emit light, and can be used as a host for luminescent materials and fluorescent materials in the visible region. I found out that...

[0284] In addition, the quantum yield in toluene solution was measured and was found to be very high at 89%, with a yield of 3.10 tB uPCA2Nbf(IV)-02 was found to be suitable as a luminescent material. [Example]

[0285] In this example, N,N'-bis[9-( 3-tert-butylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl Nyl-naphtho[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviation This article describes the synthesis method of 3,10mtBuPCA2Nbf(IV)-02. The structural formula of 10mtBuPCA2Nbf(IV)-02 is shown below.

[0286] [ka]

[0287] Step 1: 2-chloro-9-(3-tert-butylphenyl)-9H-carbazole Synthesis of ru> Add 5.0 g (25 mmol) of 2-chloro-9H-carbazole to a 300 mL three-neck flask. 9.5g (45mmol) of 1-bromo-3-tert-butylbenzene, sodium 7.2 g (74 mmol) of tert-butoxide was added to this mixture. Add 25 mL of the solution and 0.4 mL of a 10% hexane solution of tri(tert-butyl)phosphine. The mixture was degassed by stirring under reduced pressure. Add 0.14 g (0.25 mmol) of palladium(0) in dichloromethane and The mixture was heated and stirred at 150°C for 11.5 hours. After stirring, toluene was added to the mixture, and the mixture was stirred at 150°C for 11.5 hours. The filtrate was filtered through suction through celite and alumina to obtain an oil. This oily substance was purified by silica gel column chromatography (developing solvent: hexane). The synthesis scheme for Step 1 was as follows: As shown below.

[0288] [ka]

[0289] Nuclear magnetic resonance spectroscopy ( 1 H-NMR) As shown below, this allows 2-chloro-9-(3-tert-butylphenyl) It was found that (phenyl)-9H-carbazole was obtained. 1H NMR(CDCl3,300MHz):δ=1.39(s,9H),7.23-7 .45(m,6H),7.45-7.57(m,3H),8.04(d,J1=8.4H z,1H),8.11(d,J1=7.8Hz,1H).

[0290] Step 2: N-phenyl-9-(3-tert-butylphenyl)-9H-carbazo Synthesis of 2-amino-2-amine In a 200 mL three-neck flask, add 7.9 g (24 mmol) of 2-chloro-9-(3-tert-butyl) -butylphenyl)-9H-carbazole, 3.3 g (35 mmol) of aniline, 6. 8 g (71 mmol) of sodium tert-butoxide, 0.42 g (1.2 mmol) l) Di(1-adamantyl)-n-butylphosphine was added to the mixture. 115 mL of bis( Add 0.14 g (0.24 mmol) of dibenzylideneacetone palladium (0) and The mixture was heated and stirred at 150°C for 6 hours under a stream of air. After stirring, toluene was added to the mixture, and the mixture was The mixture was filtered through Lorisil, Celite, and alumina, and the filtrate was concentrated to give a brown oil. This oil was purified by silica gel column chromatography (developing solvent: toluene:hexane = The oily residue that could not be purified was then purified with toluene:hexane (1:3, then toluene:hexane (1:2)). Silica gel column chromatography (eluent: hexane:ethyl acetate = 20:1) The resulting product was purified to give a pale yellow solid (7.2 g, 78% yield). The synthesis scheme for Step 2 is shown below. Shown below.

[0291] [ka]

[0292] Nuclear magnetic resonance spectroscopy of the pale yellow solid obtained in step 2 above ( 1 H-NMR measurement results The results are shown below. This resulted in N-phenyl-9-(3-tert-butyl)- It was found that 9H-(ethylphenyl)-9H-carbazol-2-amine was obtained. 1 H NMR(DMSO-d6,300MHz):δ=1.35(s,9H),6.82 (t,J1=6.9Hz,1H),7.00(dd,J1=8.4Hz,J2=1.8H z,1H),7.05(d,J1=1.8Hz,1H),7.11-7.33(m,7H ),7.40(dt,J1=7.8Hz,J2=1.8Hz,1H),7.50-7.6 1(m,3H),8.03-8.08(m,2H),8.36(s,1H).

[0293] <Step 3: Synthesis of 3,10mtBuPCA2Nbf(IV)-02> In a 200 mL three-neck flask, add 0.86 g (2.3 mmol) of 3,10-dichloronaphtho[ 2,3-b;6,7-b']bisbenzofuran and 2.2 g (5.5 mmol) of N-furan Phenyl-9-(3-tert-butylphenyl)-9H-carbazol-2-amine, 8 2 mg (0.23 mmol) of di(1-adamantyl)-n-butylphosphine, 1.3 g (14 mmol) of sodium tert-butoxide was added to the mixture. 1 mL of xylene was added. The mixture was degassed by stirring under reduced pressure. 26 mg (46 μmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture. The mixture was heated and stirred at 150°C for 21 hours under a nitrogen stream. After stirring, toluene was added to the mixture. The mixture was filtered through Florisil, Celite, and alumina, and the filtrate was concentrated to give a solid. The obtained solid was purified by silica gel column chromatography (developing solvent: toluene / hexane The solid was recrystallized from toluene / ethyl acetate to give a yellow solid. A white solid was obtained in 1.9 g, 75% yield.

[0294] The obtained solid (1.2 g) was purified by train sublimation under a pressure of 2.2× 10 -2The sublimation was carried out at 385°C under the conditions of 0 Pa and 0 mL / min argon flow rate. After purification, 1.0 g of a yellow solid was obtained with a recovery rate of 85%. The synthesis scheme for Step 3 is shown below. show.

[0295] [ka]

[0296] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 above ( 1 H-NMR) The numerical data is shown in Figure 17(A)(B) below. It was found that 10mtBuPCA2Nbf(IV)-02 was obtained. 1 H NMR(CD2Cl2,300MHz):δ=1.18(s,18H),7.05 -7.47(m,32H),7.89(d,J1=2.4Hz,2H),7.97(s, 2H), 8.06-8.11 (m, 4H), 8.36 (s, 2H).

[0297] Next, the absorption spectrum of toluene solution of 3,10mtBuPCA2Nbf(IV)-02 The results of measuring the absorption and emission spectra of the thin film are shown in Figure 18. The solid thin film was prepared on a quartz substrate by vacuum deposition. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (JASCO Corporation, Model V550). The spectrum measured using toluene alone in a quartz cell was subtracted from the spectrum shown. The absorption spectrum of the thin film was measured using a spectrophotometer (Hitachi High-Technologies Corporation). A spectrophotometer (U4100) was used. A fluorophotometer (K.K.) was used to measure the emission spectrum. The quantum yield was measured using an absolute PL quantum yield measurement device (JASCO Corporation). A Hamamatsu Photonics Quantaurus-QY was used.

[0298] From Figure 18, the toluene solution of 3,10mtBuPCA2Nbf(IV)-02 is 430n Absorption peaks are observed at 408 nm, 348 nm, and the emission spectrum peak is at 448 nm. m, 474 nm (excitation wavelength 408 nm). Thin films of PCA2Nbf(IV)-02 exhibited wavelengths of 434 nm, 416 nm, 349 nm, and The absorption peak is observed at 265 nm, and the emission spectrum peak is at 482 nm (excitation wavelength 40 From this result, it was found that 3,10mtBuPCA2Nbf(IV)-02 It was confirmed that the compound emits blue light, and can be used as a host for luminescent materials and fluorescent materials in the visible region. It turned out to be no.

[0299] In addition, the quantum yield in toluene solution was measured and was found to be very high at 89%, with a yield of 3.10 mt BuPCA2Nbf(IV)-02 was found to be suitable as a luminescent material. [Example]

[0300] Example 1 In this example, a light-emitting device and a comparative light-emitting device according to one embodiment of the present invention will be described. The structural formulae of the organic compounds used in this example are shown below.

[0301] [ka]

[0302] (Method for fabricating light-emitting device 1) First, indium tin oxide containing silicon oxide (ITSO) was sputtered onto a glass substrate. The first electrode 101 was formed by a film deposition method. The area was set to 2mm x 2mm.

[0303] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface was washed with water. After baking at 00°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0304] Then, 10 -4 The substrate is placed in a vacuum deposition apparatus whose inside pressure has been reduced to about 100 Pa. After vacuum baking at 170°C for 30 minutes in the heating chamber of the device, the substrate is left for about 30 minutes. Allow to cool.

[0305] Next, the first electrode 101 is formed so that the surface on which the first electrode 101 is formed faces downward. The substrate was fixed to a substrate holder provided in a vacuum deposition apparatus, and the following was formed on the first electrode 101: N,N-bis(4-biphenyl) represented by the above structural formula (i) was obtained by a vapor deposition method using resistance heating. BB(II)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine ABnf) and an electron acceptor material (OCHD-001) were mixed at a weight ratio of 1:0.1 (=B A hole injection layer 111 is formed by co-evaporation to a thickness of 10 nm (BABnf:OCHD-001). Successful.

[0306] Next, BBABnf is deposited on the hole injection layer 111 to a thickness of 20 nm. 3,3'-(naphthalene-1,4-diyl)bis(9-phenyl)- PCzN2) was evaporated to a thickness of 10 nm. A transport layer 112 was formed.

[0307] Next, 9-(1-naphthyl)-10-[4-(2-naphthyl)-2-methyl-1-propanol] represented by the above structural formula (iii) αN-βNPAnth) and the above structural formula (iv N,N'-bis[9-(4-tert-butylphenyl)-9H-carbazo] [2,3-b;6,7-b']bis[2-yl-2-yl]-N,N'-diphenyl-naphtho[2,3-b;6,7-b']bisbenzyl 3,10-BuPCA2Nbf(IV)-02 ) in a weight ratio of 1:0.015 (=αN-βNPAnth:3,10tBuPCA2N bf(IV)-02) to form a 25 nm thick light-emitting layer 113.

[0308] Then, on the light-emitting layer 113, 2-[3'-(dibenzothiophene)-2-(3-methyl-2-benzophenone]-1-yl]-2-(3-methyl-2-benzophenone)-1-yl]-2-(dibenzothiophene ... [phenyl-4-yl]biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2m DBTBPDBq-II) was evaporated to a thickness of 15 nm, and then 2, 9-Di(2-naphthyl)-4,7-diphenyl-1,10-phenanthroline (abbreviation: N BPhen) was evaporated to a thickness of 10 nm to form the electron transport layer 114.

[0309] After forming the electron transport layer 114, lithium fluoride (LiF) is deposited to a thickness of 1 nm to inject electrons. Then, aluminum is evaporated to a thickness of 200 nm. A second electrode 102 was formed to fabricate the light-emitting device 1 of this example.

[0310] (Method for fabricating light-emitting device 2) Light-emitting device 2 is a light-emitting device having a structure similar to that of light-emitting device 1. 2 is N,N'-bis[9-(3-tert-butylphenyl)-2-methylpropional]-2-one represented by the above structural formula (vii). (phenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3- b;6,7-b']bisbenzofuran-3,10-diamine (abbreviated as 3,10mtBuP The light-emitting device was fabricated in the same manner as in device 1, except that the ZnO was changed to Nbf(IV)-02.

[0311] (Method for producing comparative light-emitting device 1) Comparative light-emitting device 1 is 3,10tBuPCA2Nbf(IV) in light-emitting device 1. -02 is N,N'-bis[9-(3,5-diethyl phenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3 -b;6,7-b']bisbenzofuran-3,10-diamine (abbreviated as 3,10mmEt The light-emitting device was fabricated in the same manner as in device 1, except that PCA2 was changed to Nbf(IV)-02).

[0312] The device structures of the above light-emitting devices and the comparative light-emitting devices are summarized in the table below.

[0313] [Table 1]

[0314] The light-emitting device and the comparative light-emitting device were placed in a nitrogen atmosphere glove box. The process of sealing the light-emitting device with a glass substrate to prevent it from being exposed to the atmosphere (sealing material is used as a substrate) After applying the coating around the chip and performing UV treatment during sealing and heat treatment at 80°C for 1 hour, the initial characteristics Measurements were carried out on the following.

[0315] The luminance-current density characteristics of Light-emitting Device 1, Light-emitting Device 2, and Comparative Light-emitting Device 1 are shown in Fig. 20, the current efficiency-luminance characteristics are shown in Fig. 21, the luminance-voltage characteristics are shown in Fig. 22, and the current-voltage characteristics are shown in Fig. 23. The external quantum efficiency-luminance characteristics are shown in FIG. 23, the emission spectrum in FIG. 24, and the emission spectrum in FIG. 1000 cd / m for each light-emitting device and comparative light-emitting device 2 Key features in the vicinity As shown below.

[0316] [Table 2]

[0317] 20 to 25 show the light-emitting device 1, the light-emitting device 2, and the comparative light-emitting device according to one embodiment of the present invention. It was found that all of the optical devices 1 were EL devices with good luminous efficiency.

[0318] Here, 3,10tBuPCA2Nbf(IV) used as the luminescent material of light-emitting device 1 -02 and 3,10mtBuPCA2Nbf(I) used as the luminescent material for light-emitting device 2. V)-02 and 3,10 mm EtPCA2N used as the light-emitting material for comparative light-emitting device 1 bf(IV)-02 and N,N'-bis[9-(3,5- Dihexylphenyl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphthalene To[2,3-b;6,7-b']bisbenzofuran-3,10-diamine (abbreviated as 3,1 0mmHexPCA2Nbf(IV)-02) and 3,10 represented by the following structural formula (x) -bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino] Naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nbf The results of an investigation into the physical properties of (IV)-02) are shown below.

[0319] [ka]

[0320] 3,10tBuPCA2Nbf(IV)-02 is 3,10PCA2Nbf(IV)-0 The phenyl group substituted at the 9-position of the carbazolyl group in 2 has a tert-butyl group at the para-position. The substituted substance is 3,10mtBuPCA2Nbf(IV)-02, which is The meta-position of the phenyl group substituted at the 9-position of the carbazolyl group in A2Nbf(IV)-02 tert-butyl group is substituted on 3,10mmEtPCA2Nbf(IV) -02 is a substituted 3,10PCA2Nbf(IV)-02 carbazolyl group at the 9-position. It is a substance in which two ethyl groups are substituted at the meta position on the phenyl group, and 3,10mmHexP CA2Nbf(IV)-02 is a substance in which two n-hexyl groups are substituted at the meta position.

[0321] First, the emission spectra of the above five substances in toluene solution are shown in Figure 26. As can be seen, the peaks in the emission spectra of these five substances are all at similar positions. The spectral shapes are also almost identical. Even if the above-mentioned substituents are introduced into the phenyl group substituted at the 9-position of the benzoyl group, the substance itself This means that there is little effect on conjugation and little effect on the emission color.

[0322] That is, 3,10PCA2Nbf(IV)-02 exhibits blue luminescence with good color purity, , 3,10tBuPCA2Nbf(IV)-02, 3,10mtBuPCA2Nbf(I V)-02, 3,10mmEtPCA2Nbf(IV)-02, 3,10mmHexPC A2Nbf(IV)-02 has a wide range of emission and absorption spectra due to the introduction of substituents. Both of these organic compounds emit blue light with good color purity, and have almost no effect on the color temperature. On the other hand, 3,10PCA2Nbf(IV)-02 has a luminophore There is an arylamine bonded to a certain main skeleton, but the phenyl group of the arylamine When a similar substituent is introduced into the alkyl group, the emission spectrum shifts to the long wavelength side, and the color purity decreases. It is known that...

[0323] Next, we performed thermogravimetry-differential thermal analysis (TG-DTA) on these five substances. Differential Thermal Analysis (DTA) was performed. The measurement was performed using a high-vacuum differential thermobalance (manufactured by Bruker AXS, TG-D The weight was measured under the conditions of 10 Pa and a temperature rise rate of 10 °C / min. The relationship between the amount and temperature is shown in Figure 27. In addition, when the weight of the organic compound is reduced by 5%, The temperatures (weight loss temperatures) at which the weight loss reached 10% and -50% are shown in Table 3.

[0324] [Table 3]

[0325] From Figure 27 and Table 3, 9 of the carbazolyl groups in 3,10PCA2Nbf(IV)-02 are 3,10mmHexPCA is a substance in which an alkyl group is substituted on the phenyl group at the substituted position. The three substances except for 2Nbf(IV)-02 have a phenyl group substituted at the 9-position of the carbazolyl group. The weight loss temperature is lower than that of 3,10PCA2Nbf(IV)-02, which does not have a substituent. It was found that the sublimation property was improved.

[0326] In addition, the current density of the above light-emitting device 1, light-emitting device 2, and comparative light-emitting device 1 was 50 mA. / cm 2Figure 28 shows a graph showing the change in brightness over time. As shown, the light-emitting device 1 and the light-emitting device 2 are light-emitting devices according to an embodiment of the present invention. The light-emitting device 2 exhibited better characteristics than the comparative light-emitting device 1. Ethyl-substituted compounds such as 3,10mmEtPCA2Nbf(IV)-02 are It was found that although the quality improved, the reliability decreased.

[0327] In addition, 3,10mmHexPCA2Nbf(IV)-02 decomposes during sublimation purification. Therefore, a luminescent device using 3.10mmHexPCA2Nbf(IV)-02 was used. Since the device could not be fabricated, there is no device data. The sublimation of the metabolite is poor.

[0328] As described above, the organic compound according to one embodiment of the present invention has a phenyl bonded to the 9-position of the carbazolyl group. A secondary or tertiary alkyl group is bonded to the phenyl group, the carbon atom of which is branched. This improves sublimation properties and enables the production of a highly reliable light-emitting device. This becomes possible.

[0329] (Reference example 1) ≪Reference synthesis example 1≫ In this Reference Synthesis Example, the N,N'-bis[9-(3,5-diethylphenyl) yl)-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b; 6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmEtPCA This article describes the synthesis method of 3,10mmEtPCA2Nb The structural formula of f(IV)-02 is shown below.

[0330] [ka]

[0331] Step 1: 2-chloro-9-(3,5-diethylphenyl)-9H-carbazole Synthesis> Add 3.2 g (16 mmol) of 2-chloro-9H-carbazole to a 300 mL three-neck flask. , 1-bromo-3,5-diethylbenzene 5.0g (23mmol), sodium t 4.5g (47mmol) of ethyl erythritol-butoxide was added to the mixture. 80ml of xylene was added. Add 0.2 mL of a 10% hexane solution of L and tri(tert-butyl)phosphine, and The mixture was degassed by stirring under reduced pressure. t) palladium (0) 90 mg (0.16 mmol) was added and heated at 150 °C under a nitrogen stream. After stirring, toluene was added to the mixture, and the mixture was filtered through Florisil and Celite. The resulting mixture was filtered through alumina under suction to obtain a filtrate, which was then concentrated to obtain an oily substance. The oily substance was purified by silica gel column chromatography (developing solvent: hexane) to obtain a colorless A clear oil was obtained in 4.8 g, 93% yield. The synthesis scheme for Step 1 is shown below.

[0332] [ka]

[0333] The colorless, transparent oil obtained in step 1 was analyzed by nuclear magnetic resonance spectroscopy ( 1 H-NMR The results are shown below. It was found that (9H-phenyl)-9H-carbazole was obtained. 1H NMR(CDCl3,300MHz):δ=1.31(t,J1=7.5Hz,6 H),2.75(q,J1=7.5Hz,4H),7.12-7.31(m,2H),7 .36-7.44(m,3H),8.03(dd,J1=8.1Hz,J2=0.3Hz ,1H),8.25(ddd,J1=7.8Hz,J2=1.2Hz,J3=0.9Hz ,1H).

[0334] Step 2: N-[9-(3,5-diethylphenyl)-9H-carbazole-2-yl] Synthesis of [N-phenylamine] In a 300 mL three-neck flask, add 4.8 g (14 mmol) of 2-chloro-9-(3,5-diphenyl ether). (ethylphenyl)-9H-carbazole, 2.0 g (22 mmol) aniline, 4.2 g (43 mmol) of sodium tert-butoxide, 0.26 g (0.72 mmol) ) di(1-adamantyl)-n-butylphosphine. To this mixture was added 7 xylenes. 5 mL of bis(dibenzyl)propanol was added, and the mixture was degassed by stirring under reduced pressure. Add 83 mg (0.14 mmol) of diphenyldiphenylacetone palladium(0) and evaporate under a nitrogen atmosphere. The mixture was heated and stirred at 150°C for 7 hours under reduced pressure. After stirring, toluene was added to the mixture, and the mixture was stirred at 150°C for 7 hours under reduced pressure. The mixture was filtered through suction through celite and alumina, and the filtrate was concentrated to give a solid. Silica gel column chromatography (developing solvent: toluene:hexane = 3:7, then The oil was purified with toluene:hexane (2:3). Ethanol and hexane were added to the oil. After the mixture was irradiated with ultrasonic waves, the precipitated solid was collected to give 3.9 g of a white solid in a yield of 69%. The synthesis scheme for step 2 is shown below.

[0335] [ka]

[0336] Nuclear magnetic resonance spectroscopy of the white solid obtained in step 2 above ( 1 H-NMR) This allows N-[9-(3,5-diethylphenyl) It was found that [-9H-carbazol-2-yl]-N-phenylamine was obtained. 1 H NMR(DMSO-d6,300MHz):1.25(t,J1=7.8Hz,6 H),2.70(q,J1=7.8Hz,4H),6.82(t,J1=7.2Hz,1 H),7.00(dd,J1=8.4Hz,J2=1.8Hz,1H),7.07(d, J1=1.8Hz,1H),δ=7.12-7.31(m,10H),8.02-8.0 7(m,2H),8.37(s,1H).

[0337] <Step 3: Synthesis of 3,10mM EtPCA2Nbf(IV)-02> In a 200 mL three-neck flask, add 0.87 g (2.3 mmol) of 3,10-dichloronaphtho[ 2,3-b;6,7-b']bisbenzofuran and 2.2 g (5.5 mmol) of N-[ 9-(3,5-diethylphenyl)-9H-carbazol-2-yl]-N-phenyla amine, 82 mg (0.23 mmol) di(1-adamantyl)-n-butylphosphine Then, 1.3 g (14 mmol) of sodium tert-butoxide was added to the mixture. 25 mL of xylene was added to the mixture, and the mixture was degassed by stirring under reduced pressure. To this mixture, 26 mg (46 μmol) of bis(dibenzylideneacetone)palladium ( 0) was added, and the mixture was heated and stirred at 150°C for 14 hours under a nitrogen stream. Add ethylene, suction filter through Florisil, Celite, and alumina, and concentrate the filtrate to a solid. The resulting solid was purified by silica gel column chromatography (developing solvent: toluene, The solid was purified with hexane (1:2) to obtain a solid. The obtained solid was recrystallized with toluene / ethyl acetate. The resulting solid was crystallized to give 1.9 g of a yellow solid in a yield of 75%. The product was purified by sublimation at a pressure of 2.2 × 10 -2 Pa, argon flow rate 0 mL / m After sublimation purification, 0.93 g of yellow solid was obtained, with a recovery rate of The synthesis scheme for step 3 is shown below.

[0338] [ka]

[0339] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 above ( 1 H-NMR) This is shown below. In step 3, 3,10 mm EtPCA2Nbf(IV) It was found that -02 was obtained. 1 H NMR(CD2Cl2,300MHz):δ=1.12(t,J1=7.8Hz, 12H),2.60(q,J1=7.8Hz,8H),7.01(s,2H),7.06 -7.13(m,10H),7.20-7.44(m,18H),7.89(d,J1= 8.4Hz,2H),7.97(s,2H),8.04-8.10(m,4H),8.3 6(s,2H).

[0340] Next, the absorption spectrum of toluene solution of 3,10mmEtPCA2Nbf(IV)-02 The results of measuring the absorption and emission spectra of the thin film are shown in Figure 29. The solid thin film was prepared on a quartz substrate by vacuum deposition. The absorption spectrum of the toluene solution was measured using a UV-visible spectrophotometer (JASCO Corporation, Model V550). The spectrum measured using toluene alone in a quartz cell was subtracted from the spectrum shown. The absorption spectrum of the thin film was measured using a spectrophotometer (Hitachi High-Technologies Corporation). A spectrophotometer (U4100) was used. A fluorophotometer (K.K.) was used to measure the emission spectrum. The quantum yield was measured using an absolute PL quantum yield measurement device (JASCO Corporation). A Hamamatsu Photonics Quantaurus-QY was used.

[0341] From Figure 29, the toluene solution of 3,10mmEtPCA2Nbf(IV)-02 is 433n Absorption peaks were observed at 411 nm, 348 nm, 322 nm, and 280 nm, and the emission spectrum The spectral peaks were 451 nm and 478 nm (excitation wavelength 408 nm). From 0, the thin film of 3,10mmEtPCA2Nbf(IV)-02 is 436nm, 418 Absorption peaks are observed at 348 nm, 322 nm, and 280 nm, and the emission spectrum The peak was observed at 480 nm (excitation wavelength 400 nm). EtPCA2Nbf(IV)-02 was confirmed to emit blue light, and the luminescent material and the visible region It was found that these compounds can be used as hosts for fluorescent emitting materials.

[0342] In addition, the quantum yield of 3,10mmEtPCA2Nbf(IV)-02 in toluene solution was measured. The efficiency was measured at 88%, which was very high, and it was found to be suitable as a light-emitting material.

[0343] (Reference example 2) ≪Reference synthesis example 2≫ In this Reference Synthesis Example, N,N'-bis[9-(3,5-dihexylphenyl)-2-methyl-2-propanol] used in Example 3 was used. N,N'-diphenyl-9H-carbazol-2-yl]-N,N'-diphenyl-naphtho[2,3-b ;6,7-b']bisbenzofuran-3,10-diamine (abbreviation: 3,10mmHexP The synthesis method of CA2Nbf(IV)-02 is described. The structural formula of 2Nbf(IV)-02 is shown below.

[0344] [ka]

[0345] Step 1: 2-chloro-9-(3,5-dihexylphenyl)-9H-carbazole Synthesis of> Add 2.9 g (14 mmol) of 2-chloro-9H-carbazole to a 300 mL three-neck flask. 8.4g (26mmol) of 1-bromo-3,5-dihexylbenzene, sodium 4.2 g (43 mmol) of tert-butoxide was added to this mixture. Add 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine and The mixture was degassed by stirring under reduced pressure. Add 82 mg (10.14 mmol) of palladium(0) to the solution and heat for 15 minutes under a nitrogen stream. The mixture was heated and stirred at 0°C for 1.5 hours. After stirring, toluene was added to the mixture, and Florisil, The mixture was filtered through celite and alumina with suction to obtain a filtrate. The obtained filtrate was concentrated to give an oily product. This oily substance was purified by silica gel column chromatography (developing solvent: hexane). A colorless, transparent oil was obtained in 1.4 g with a yield of 22%. The synthesis scheme for Step 1 is shown below. show.

[0346] [ka]

[0347] Nuclear magnetic resonance spectroscopy ( 1 H-NMR) As shown below, in step 1, 2-chloro-9-(3,5-dihexylphenyl) It was found that (9H-nyl)-9H-carbazole was obtained. 1 H NMR(CDCl3,300MHz):δ=0.89(t,J1=6.9Hz,6 H),1.29-1.43(m,12H),1.68(quin,J1=7.8Hz,4 H),2.69(t,J1=7.8Hz,4H),7.11-7.31(m,5H),7 .36-7.44(m,3H),8.03(d,J1=8.4Hz,1H),8.09( dt, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H).

[0348] Step 2: N-[9-(3,5-dihexylphenyl)-9H-carbazole-2- Synthesis of [[(2-phenyl-1-yl)-N-phenylamine]> In a 200 mL three-neck flask, add 1.4 g (3.1 mmol) of 2-chloro-9-(3,5-dichloro- hexylphenyl)-9H-carbazole, 0.55 g (5.9 mmol) of aniline, 0.90 g (9.4 mmol) sodium tert-butoxide, 56 mg (0.1 6 mmol) di(1-adamantyl)-n-butylphosphine was added to the mixture. 20 mL of xylene was added, and the mixture was degassed by stirring under reduced pressure. Add 18 mg (31 μmol) of bis(dibenzylideneacetone)palladium(0) and The mixture was heated and stirred at 150°C for 7 hours under a stream of air. After stirring, toluene was added to the mixture, and the mixture was The mixture was filtered through Lorisil, Celite, and alumina, and the filtrate was concentrated to give a brown oil. .

[0349] In a 200 mL three-neck flask, add 2.7 g (6.1 mmol) of 2-chloro-9-(3,5-dichloro- hexylphenyl)-9H-carbazole, 0.85 g (9.1 mmol) of aniline, 1.8 g (18 mmol) sodium tert-butoxide, 0.11 g (0.30 1 mmol of di(1-adamantyl)-n-butylphosphine was added to the mixture. 30 mL of silane was added, and the mixture was degassed by stirring under reduced pressure. Add 35 mg (61 μmol) of bis(dibenzylideneacetone)palladium(0) and add nitrogen. The mixture was heated and stirred at 150°C for 7 hours under an air stream. After stirring, toluene was added to the mixture, and the resulting mixture was The mixture was suction filtered through Lysile, Celite, and alumina, and the filtrate was concentrated to give a brown oil. The two batches of oil were combined and subjected to silica gel column chromatography (eluent: toluene). The resulting mixture was purified with hexane (1:4) to give a yellow solid (1.7 g, 31% yield). The synthesis scheme is shown below.

[0350] [ka]

[0351] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 2 above ( 1 H-NMR) This allows N-[9-(3,5-dihexylphenyl) It was found that 9H-carbazol-2-yl-N-phenylamine was obtained. 1 H NMR(DMSO-d6,300MHz):δ=0.84(t,J1=7.2Hz ,6H),1.23-1.35(m,12H),1.62(quin,J1=7.8Hz ,4H),2.66(t,J1=7.8Hz,4H),6.81(tt,J1=6.9H z,J2=1.2Hz,1H),6.99(dd,J1=8.7Hz,J2=1.8Hz ,1H),7.07(d,J1=1.8Hz,1H),7.11-7.15(m,3H) ,7.18-7.32(m,7H),8.02-8.07(m,2H),8.35(s, 1H).

[0352] <Step 3: Synthesis of 3,10mmHexPCA2Nbf(IV)-02> In a 200 mL three-neck flask, add 0.54 g (1.4 mmol) of 3,10-dichloronaphtho[ 2,3-b;6,7-b']bisbenzofuran and 1.7 g (3.4 mmol) of N-[ 9-(3,5-dihexylphenyl)-9H-carbazol-2-yl]-N-phenyl Amine, 51 mg (0.14 mmol) di(1-adamantyl)-n-butylphosphine 0.83 g (8.6 mmol) of sodium tert-butoxide was added. 15 mL of xylene was added to the mixture, and the mixture was degassed by stirring under reduced pressure. To this mixture, 16 mg (29 μmol) of bis(dibenzylideneacetone)paradiazine was added. The mixture was heated and stirred at 150°C for 14.5 hours under a nitrogen stream. Toluene was added to the mixture, and the mixture was suction filtered through Florisil, Celite, and alumina. The solid was concentrated to give a solid. The solid was purified by silica gel column chromatography (developing solvent: The resulting solid was purified with toluene:hexane (1:2). The resulting precipitate was a yellow solid (1.7 g, 93% yield). The synthesis scheme for Step 3 is shown below. vinegar.

[0353] [ka]

[0354] Nuclear magnetic resonance spectroscopy of the yellow solid obtained in step 3 above ( 1 H-NMR) As a result, in step 3, 3,10mmHexPCA2Nbf(IV )-02 was obtained. 1 H NMR(CD2Cl2,300MHz):δ=0.83(t,J1=6.6Hz, 12H),1.17-1.31(m,24H),1.47-1.57(m,8H),2. 55(t,J1=7.8Hz,8H),6.98(s,2H),7.06-7.13(m ,10H),7.20-7.43(m,18H),7.88(d,J1=8.4Hz,2 H),7.96(s,2H),8.04-8.09(m,4H),8.35(s,2H) . [Explanation of symbols]

[0355] 101 first electrode 102 second electrode 103 EL layer 111 Hole injection layer 112 Hole transport layer 113 Light-emitting layer 114 Electron transport layer 115 Electron injection layer 116 Charge generation layer 117 P type layer 118 Electronic Relay Layer 119 Electron injection buffer layer 400 boards 401 First electrode 403 EL layer 404 Second electrode 405 Sealing material 406 Sealing material 407 Sealing substrate 412 Pad 420 IC chip 501 Anode 502 Cathode 511 First Light Emitting Unit 512 Second Light Emitting Unit 513 Charge generation layer 601 Driver circuit section (source line driver circuit) 602 Pixel section 603 Drive circuit section (gate line drive circuit) 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (Flexible Printed Circuit) 610 Element substrate 611 Switching FET 612 Current control FET 613 First electrode 614 Insulators 616 EL layer 617 Second electrode 618 Light-emitting devices 951 PCB 952 Electrode 953 Insulation Layer 954 Partition layer 955 EL layer 956 Electrode 1001 board 1002 Undercoat insulating film 1003 Gate insulating film 1006 Gate electrode 1007 Gate electrode 1008 gate electrode 1020 First interlayer insulating film 1021 Second interlayer insulating film 1022 Electrode 1024W First electrode 1024R First electrode 1024G First electrode 1024B First electrode 1025 Bulkhead 1028 EL layer 1029 Second electrode 1031 Sealing substrate 1032 Sealing material 1033 Transparent substrate 1034R Red color layer 1034G Green color layer 1034B Blue color layer 1035 Black Matrix 1036 Overcoat layer 1037 Third interlayer insulating film 1040 pixel section 1041 Drive circuit section 1042 Periphery 2001 Case 2002 light source 2100 Robot 2110 Arithmetic equipment 2101 Illuminance sensor 2102 Microphone 2103 Upper Camera 2104 Speaker 2105 Display 2106 Lower Camera 2107 Obstacle Sensor 2108 Moving mechanism 3001 Lighting equipment 5000 cabinets 5001 Display section 5002 Display section 5003 Speaker 5004 LED lamp 5006 Connection terminal 5007 Sensor 5008 Microphone 5012 Support part 5013 Earphones 5100 Cleaning Robot 5101 Display 5102 Camera 5103 Brush 5104 Operation button 5150 Personal Digital Assistant 5151 Case 5152 Display area 5153 Bend 5120 Garbage 5200 display area 5201 Display area 5202 Display area 5203 Display area 7101 Housing 7103 Display section 7105 Stand 7107 Display section 7109 Operation key 7110 Remote control device 7201 Main unit 7202 Case 7203 Display section 7204 keyboard 7205 External connection port 7206 Pointing Device 7210 Second display unit 7401 Housing 7402 Display section 7403 Operation button 7404 External connection port 7405 Speaker 7406 Microphone 9310 Mobile Information Terminal 9311 Display Panel 9313 Hinge 9315 chassis

Claims

1. An organic compound represented by the following general formula (G1): 【Chemical 1】 (However, in the above general formula (G1), X １ ~X ５ One of the R groups is a tertiary alkyl group having 4 to 6 carbon atoms and a branched carbon atom attached to the phenyl group, and the remaining R groups are hydrogen atoms. １ ~R ７ are each independently any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. １ represents any one of the fused heteroaromatic ring skeletons represented by the following general formulas (B1) to (B4): １ The two or three groups bonded to may be the same or different. 【Chemistry 2】 (However, in the formula, Q １ and Q ２ Each independently represents an oxygen atom or a sulfur atom. １０ ~R ２１ In the general formula (B2), one or two of R represents a single bond, and the remaining R each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. ３０ ~R ４１ One or two of the groups represented by R represent a single bond, and the remaining groups each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. ５０ ~R ６１ One or two of the following groups represent a single bond, and the remaining groups each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms. ７０ ~R ８１ one or two of the above represent a single bond, and the remaining groups each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an unsubstituted or alkyl-substituted aryl group having 6 to 13 carbon atoms.

2. In claim 1, The X １ ~X ５ An organic compound in which one of the carbon atoms is a tertiary alkyl group having four carbon atoms and the carbon atom attached to the phenyl group is branched, and the rest is hydrogen.

3. In claim 1 or claim 2, An organic compound in which n is 2.

4. In any one of claims 1 to 3, The Ar １ is a condensed heteroaromatic ring skeleton represented by the following general formula (B1-1) or (B3-1): 【Chemistry 3】 (However, in the formula, Q １ and Q ２ each independently represents an oxygen atom or a sulfur atom. １２ , R １８ , R ５２ and R ５８ represents a single bond.)

5. An organic compound represented by the following general formula (G1-1): 【Chemistry 4】 (However, in the above general formula (G1-1), X １１ ~X １５ One of the X's is a tertiary alkyl group having 4 to 6 carbon atoms and a branched carbon atom attached to the phenyl group, and the rest are hydrogen atoms. ２１ ~X ２５ One of the alkyl groups is a tertiary alkyl group having 4 to 6 carbon atoms and a branched carbon atom attached to the phenyl group, and the rest are hydrogen atoms. ２１ and Ar ２２ each independently represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

6. A light-emitting device comprising the organic compound according to any one of claims 1 to 5.

7. An optical device comprising the organic compound according to any one of claims 1 to 5.

8. A light-emitting device according to claim 6; An electronic device having a sensor, an operation button, a speaker, or a microphone.

9. A light-emitting device according to claim 6; A light-emitting device having a transistor or a substrate.

10. A lighting device comprising the light-emitting device according to claim 6 and a housing.

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