Materials for electron transport layers, light-emitting devices, electronic equipment, light-emitting devices and lighting devices

Abstract

To provide a material for an electron transport layer with a low refractive index. , , , , , , , 【Solution means】The ratio of carbon atoms bonded by sp3 hybrid orbitals constituting a saturated hydrocarbon group is within a certain range, and it is a material for a light-emitting device or a material for an electron transport layer containing an organic compound having a pyridine skeleton, a diazine skeleton or a triazine skeleton. It contains at least one six-membered heteroaromatic ring containing 1 to 3 nitrogen atoms, has a plurality of aromatic hydrocarbon rings having 6 to 14 carbon atoms forming the ring, and at least two of the plurality of aromatic hydrocarbon rings are benzene rings, and contains an organic compound having a plurality of hydrocarbon groups forming bonds by sp3 hybrid orbitals. The ordinary light refractive index of the organic compound layer for any wavelength in the range of 455 nm or more and 465 nm or less is 1.5 or more and 1.75 or less, and it is also a material for an electron transport layer.​​​​​​​​​​​​​​​​

Description

[Technical Field]

[0001] One aspect of the present invention relates to an organic compound, a light-emitting device, a display module, and a lighting module. This relates to displays, light-emitting devices, electronic equipment, lighting devices, and electronic devices. One aspect of the invention is not limited to the above-mentioned technical field. The field of expertise is related to products, methods, or methods of manufacture. Or, one aspect of the present invention is , process, machine, manufacture, or composition of matter -) is the subject matter. Therefore, one aspect of the present invention disclosed herein is more specifically Technical fields include semiconductor devices, display devices, liquid crystal display devices, light-emitting devices, lighting devices, and energy storage devices. Examples include a device, a memory device, an imaging device, a method for driving them, or a method for manufacturing them. It can be listed. [Background technology]

[0002] Electroluminescence (EL) using organic compounds The practical application of light-emitting devices (organic EL devices) that utilize these (ence) is progressing. The basic configuration of a light-emitting device is an organic compound layer (EL layer) containing light-emitting material between a pair of electrodes. It is a device with a voltage applied to it to inject a carrier, and the carrier is then re-injected. By utilizing the binding energy, it is possible to obtain light emission from a light-emitting material.

[0003] Since such light-emitting devices are self-emissive, when used as pixels in a display, they become liquid crystals. Compared to other displays, it has advantages such as higher visibility and the elimination of the need for a backlight, and flat panel displays. It is suitable as a spray element. Furthermore, a display using such a light-emitting device is Furthermore, the ability to manufacture it in a thin and lightweight form is a major advantage. In addition, its extremely fast response speed is also a significant feature. It is one of the signs.

[0004] Furthermore, these light-emitting devices allow for the continuous formation of a light-emitting layer in two dimensions. This allows for the emission of light in a planar manner. This is different from point light sources such as incandescent bulbs and LEDs, This is a characteristic that is difficult to obtain with linear light sources such as fluorescent lamps, and therefore it is a surface light source that can be applied to lighting and the like. It also has high utility value.

[0005] Displays and lighting devices using light-emitting devices in this manner are applicable to a wide range of electronic devices. While suitable, research and development are underway to find light-emitting devices with even better characteristics.

[0006] One of the issues often raised when discussing organic light-emitting diodes (OLEDs) is light extraction efficiency. It has low efficiency. In particular, attenuation due to reflection caused by the difference in refractive index of adjacent layers is a factor in the effectiveness of the element. This is a major factor in reducing the efficiency. To mitigate this effect, low refractive index is used inside the EL layer. A configuration has been proposed in which layers made of a specific material are formed (see, for example, Non-Patent Document 1).

[0007] Light-emitting devices with this configuration have higher light extraction efficiency than light-emitting devices with conventional configurations. This makes it possible to create a light-emitting device with high external quantum efficiency, but such low temperature The refractive index layer is placed inside the EL layer without adversely affecting other important properties in the light-emitting device. It is not easy to form, because it requires a low refractive index and high carrier transport properties. This is because reliability is a trade-off when used in light-emitting devices. In organic compounds, carrier transportability and reliability stem from the presence of unsaturated bonds. Large organic compounds with many unsaturated bonds tend to have a high refractive index, which is the reason for this. ru. [Prior art documents] [Non-patent literature]

[0008] [Non-Patent Document 1] Jaeho Lee, et al., "Synergetic electrode architecture for efficient graphene-based flexible organic light-emitting diodes," Nature Communications, June 2, 2016, DOI: 10.1038 / ncomms11791 [Overview of the project] [Problems that the invention aims to solve]

[0009] In one aspect of the present invention, a novel material for a light-emitting device or a novel material for an electron transport layer is provided. The objective is to provide a novel light-emitting device material or electric material with a low refractive index in one aspect of the present invention. The objective is to provide a material for a subtransport layer. Alternatively, in one aspect of the present invention, the refractive index is small To provide a novel material for light-emitting devices or an electron transport layer that is both cracked and has carrier transport properties. The objective is to achieve the following: Alternatively, in one aspect of the present invention, the refractive index is small and electron transport properties are The objective is to provide novel materials for light-emitting devices or electron transport layers.

[0010] One aspect of the present invention aims to provide a novel organic compound. In this embodiment, the objective is to provide a novel organic compound having carrier transport properties. In one aspect of the present invention, the objective is to provide a novel organic compound having electron transport properties. In one aspect of the present invention, the objective is to provide an organic compound with a low refractive index. In one aspect of the present invention, an organic compound having a low refractive index and carrier transport properties is provided. The objective is to achieve the following: Alternatively, in one aspect of the present invention, the refractive index is small and electron transport properties are The objective is to provide organic compounds that possess these properties.

[0011] Alternatively, in another aspect of the present invention, the objective is to provide a light-emitting device with high luminescence efficiency. Alternatively, in one aspect of the present invention, a light-emitting device, light-emitting apparatus, or electronic device with low power consumption is provided. The purpose is to provide instruments, display devices, and electronic devices, respectively.

[0012] Furthermore, the description of these problems does not preclude the existence of other problems. The approach does not necessarily have to solve all of these problems. This will become clear from the description in the specification, drawings, claims, etc., and the specification, drawings It is possible to extract other issues from the descriptions in the surfaces, claims, etc.

[0013] The present invention only needs to solve one of the above-mentioned problems. [Means for solving the problem]

[0014] One aspect of the present invention relates to the proportion of carbon atoms bonded in sp3 hybrid orbitals constituting a saturated hydrocarbon group. However, there are some that have a pyridine skeleton, diazine skeleton, or triazine skeleton within a certain range. This is a material for light-emitting devices containing a compound. This material for light-emitting devices has a low refractive index and Because it possesses both optical properties and electron transport properties, it is used in photoelectric devices such as light-emitting devices and photoelectric conversion elements. Because it is suitable for electron transport layers in electronic devices, it can be used as an electron transport layer material. It's also possible.

[0015] One aspect of the present invention relates to a six-membered heteroaromatic ring containing one to three nitrogen atoms, having at least one such ring. A material for a light-emitting device or an electron transport layer containing an organic compound, wherein the organic compound The glass transition temperature of the compound is 90°C or higher, and the refractive index of the layer made of the organic compound is 1.5 or higher. It is a material for light-emitting devices or an electron transport layer material with a coefficient of 1.75 or less. One embodiment of the invention has at least one six-membered heteroaromatic ring containing one to three nitrogen atoms. A material for a light-emitting device or an electron transport layer containing an organic compound, wherein the organic compound The glass transition temperature is 90°C or higher, and the s of the organic compound is equal to the total number of carbon atoms in the molecule. The proportion of total carbon atoms forming bonds in p3 hybrid orbitals is between 10% and 60%. It is a material for light-emitting devices or an electron transport layer. Alternatively, one aspect of the present invention is 1 to Luminescent compounds containing an organic compound having at least one six-membered heteroaromatic ring containing three nitrogen atoms. A material for a device or an electron transport layer, wherein the glass transition temperature of the organic compound is 90 It is above ℃, 1 The results of measuring the aforementioned organic compound by H-NMR showed a concentration of less than 4 ppm. The integral value of the signal is 1 / 2 times or more the integral value of the signal of 4 ppm or more, It is a material for vise applications or for electron transport layers.

[0016] Furthermore, the heteroaromatic ring in the above organic compound must be a triazine ring or a diazine ring. Preferably, it is a triazine ring or a pyrimidine ring. Also, the above Gala The transition temperature is preferably 100°C or higher, more preferably 110°C or higher. More preferably, the temperature is 120°C or higher.

[0017] One aspect of the present invention relates to a six-membered heteroaromatic ring containing one to three nitrogen atoms, having at least one such ring. It has multiple aromatic hydrocarbon rings, each having 6 to 14 carbon atoms forming a ring, and multiple aromatic At least two of the hydrocarbon rings are benzene rings, and they form bonds via sp3 hybrid orbitals. It contains an organic compound having multiple hydrocarbon groups, and the layer made of the organic compound is 455 nm or longer. The ordinary refractive index for any wavelength of light in the range of 465 nm or less is 1.5 or greater. The material is a light-emitting device material or an electron transport layer material with a coefficient of 0.75 or less. The benzene ring is a monocyclic benzene ring, that is, a benzene ring that is not fused with any other aromatic hydrocarbon rings. A ring is preferred.

[0018] Another aspect of the present invention is a six-membered heteroaromatic ring containing one to three nitrogen atoms, at least one It has multiple aromatic hydrocarbon rings, each having 6 to 14 carbon atoms forming a ring, and multiple aromatic At least two of the aromatic hydrocarbon rings are benzene rings, forming bonds via sp3 hybrid orbitals. This includes organic compounds having multiple hydrocarbon groups, and the total number of carbon atoms in the molecule of the organic compound The proportion of total carbon atoms forming bonds with sp3 hybrid orbitals is between 10% and 60%. The following are materials for light-emitting devices or materials for electron transport layers.

[0019] In the above configuration, the bonds in the organic compound are formed by sp3 hybrid orbitals relative to the total number of carbon atoms in the molecule. A material for light-emitting devices in which the proportion of the total number of carbon atoms forming the material is between 10% and 50%. , or a material for electron transport layers.

[0020] Another aspect of the present invention is a six-membered heteroaromatic ring containing one to three nitrogen atoms, at least one It has multiple aromatic hydrocarbon rings, each having 6 to 14 carbon atoms forming a ring, and multiple aromatic At least two of the aromatic hydrocarbon rings are benzene rings, forming bonds via sp3 hybrid orbitals. It contains organic compounds having multiple hydrocarbon groups, and the measurement of organic compounds by 1H-NMR is performed. The integral value of signals less than 4 ppm in the results is the integral value of signals 4 ppm or greater. It is a material for light-emitting devices or an electron transport layer, with a value of more than half of the above.

[0021] In each of the above configurations, the organic compounds contained in the material for the light-emitting device or the material for the electron transport layer The molecular weight of the substance is preferably between 500 and 2000.

[0022] In each of the above configurations, the organic compounds contained in the material for the light-emitting device or the material for the electron transport layer Within the molecule of the substance, the hydrocarbon group is bonded to an aromatic hydrocarbon ring, and the hydrocarbon group The aromatic hydrocarbon ring to which it is bonded has the lowest unoccupied orbital (Lowest Unoccupied M The olecular orbital (LUMO) is not distributed, i.e., organic compounds Within the molecule of a substance, the LUMO is distributed in rings other than the aromatic hydrocarbon ring to which the hydrocarbon group is bonded. It is preferable that the hydrocarbon group to which the hydrocarbon group is bonded is... In this specification, "no LUMO is distributed in the ring" means that the hydrocarbon group is bonded to the ring. The distribution density of LUMOs in an aromatic hydrocarbon ring is 0.0 in terms of isovalue. 6 [electrons / au 3 It means less than 0.02, more preferably less than 0.02. It tastes good.

[0023] In each of the above configurations, the organic compounds contained in the material for the light-emitting device or the material for the electron transport layer At least one of the aromatic hydrocarbon rings to which the hydrocarbon group is bonded within the molecule of a substance is Preferably, it is a benzene ring.

[0024] In each of the above configurations, the organic compounds contained in the material for the light-emitting device or the material for the electron transport layer The substance has at least three benzene rings, and all three benzene rings are six-membered heteropolymer rings. It is preferable that it bond to the fragrance ring.

[0025] In each of the above configurations, the organic compounds contained in the material for the light-emitting device or the material for the electron transport layer The substance has at least three benzene rings, and all three benzene rings are six-membered heteropolymer rings. Bonded to the benzene ring, two of the three benzene rings are either substituted or unsubstituted phenyl It is preferable that the group is a hydrocarbon group and does not have the hydrocarbon group.

[0026] In each of the above configurations, the organic compounds contained in the material for the light-emitting device or the material for the electron transport layer The material is a material for light-emitting devices or an electron transport material having a substituted or unsubstituted pyridyl group. It is a layering material.

[0027] In the above configuration, the six-membered heteroaromatic ring is preferably a triazine ring.

[0028] Alternatively, in the above configuration, the six-membered heteroaromatic ring is preferably a pyrimidine ring. .

[0029] In each of the above configurations, the hydrocarbon group forming a bond with sp3 hybrid orbitals is an alkyl group. It is preferable that it be a cycloalkyl group.

[0030] In the above configuration, the alkyl group preferably has branching with 3 to 5 carbon atoms. stomach.

[0031] Furthermore, in the above-mentioned light-emitting device material or electron transport layer material, the organic compound The lath transition temperature is preferably 90°C or higher. More preferably, the glass transition temperature is The temperature is 100°C or higher, more preferably 110°C or higher, and particularly preferably 120°C. That's all.

[0032] Another aspect of the present invention is an organic compound represented by the general formula (G1).

[0033] [ka]

[0034] In the general formula (G1) above, A represents a six-membered heteroaromatic ring containing one to three nitrogen atoms. Yes. Also, R 0 These are hydrogen, alkyl groups having 1 to 6 carbon atoms, and alicyclic groups having 3 to 10 carbon atoms. Represents either a formula group or a substituent represented by formula (G1-1). 1 ~R 15 few At least one of them is a substituted phenyl group, and the others are independently hydrogen and carbon. Alkyl groups with 1 to 6 atoms, alicyclic groups with 3 to 10 carbon atoms, substituted or unsubstituted rings Aromatic hydrocarbon groups having 6 to 14 carbon atoms, substituted or unsubstituted pyridyl groups that form the compound. It represents either of the following. A substituted phenyl group has one or two substituents, and Each substituent can independently be an alkyl group having 1 to 6 carbon atoms or an alicyclic group having 3 to 10 carbon atoms. Aromatic hydrocarbon groups with 6 to 14 carbon atoms forming a ring, substituted or unsubstituted, substituted Alternatively, it may be a heteroaromatic ring group with 3 to 9 carbon atoms forming an unsubstituted ring. Incidentally, the organic compound represented by the above general formula (G1) has a plurality of hydrocarbon groups selected from an alkyl group having 1 to 6 carbon atoms and an alicyclic group having 3 to 10 carbon atoms, and the ratio of the total number of carbon atoms forming bonds with sp3 hybrid orbitals to the total number of carbon atoms in the molecule is 10% or more and 60% or less.

[0035] Another aspect of the present invention is an organic compound represented by the general formula (G2).

[0036]

Chemical formula

[0037] In the above general formula (G2), A represents a 6-membered heteroaromatic ring containing 1 to 3 nitrogen atoms. Also, R 0 represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 3 to 10 carbon atoms, or a substituent represented by the formula (G2-1). Also, R , R 2 , R 4 , R 7 , R 9 , R 12 , R 14 at least one of is a phenyl group having a substituent, and the others are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 14 carbon atoms forming a substituted or unsubstituted ring, a substituted or unsubstituted pyridyl group. The phenyl group having a substituent has one or two substituents, and each of the substituents is independently an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 14 carbon atoms forming a substituted or unsubstituted ring, a substituted or unsubstituted pyridyl group. The phenyl group having a substituent has one or two substituents, and each of the substituents is independently an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 14 carbon atoms forming a substituted or unsubstituted ring, an aromatic hydrocarbon group having 6 to 14 carbon atoms forming a substituted or unsubstituted ring, a complex having 3 to 9 carbon atoms forming a substituted or unsubstituted ring to 14, It is one of the following: an aromatic ring group. Note that the organic compound represented by the above general formula (G2) is a carbon Carbonization selected from alkyl groups with 1 to 6 elementary atoms and alicyclic groups with 3 to 10 carbon atoms It has multiple hydrogen groups and forms bonds with sp3 hybrid orbitals relative to the total number of carbon atoms in the molecule. The proportion of total carbon atoms is between 10% and 60%.

[0038] In each of the above configurations, A in general formula (G2) is a pyridine ring, a pyrimidine ring, a pyrazine ring It is preferable that it be either a pyridazine ring or a triazine ring.

[0039] Another aspect of the present invention is an organic compound represented by the general formula (G3).

[0040] [ka]

[0041] In the above general formula (G3), Q 1 ~Q 3 Of these, 2 or 3 represent N, and Q 1 ~Q 3 If 2 of them are N, the remaining 1 represents CH. Also R 1 ~R 15 at least One of them is a phenyl group with substituents, and the other is independently a hydrogen atom and a 1-carbon atom. Alkyl groups up to 6 carbon atoms, alicyclic groups having 3 to 10 carbon atoms, forming substituted or unsubstituted rings. Either an aromatic hydrocarbon group with 6 to 14 carbon atoms, or a substituted or unsubstituted pyridyl group. This indicates that a substituted phenyl group has one or two substituents, and each substituent is Each independently includes an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 3 to 10 carbon atoms, and a substituted group. Alternatively, an aromatic hydrocarbon group having 6 to 14 carbon atoms forming an unsubstituted ring, substituted or unsubstituted. It is one of the heteroaromatic ring groups having 3 to 9 carbon atoms forming the exchange ring. Organic compounds represented by general formula (G3) are alkyl groups having 1 to 6 carbon atoms and carbon atoms. It has multiple hydrocarbon groups selected from alicyclic groups with 3 to 10 atoms, and the total number of carbon atoms in the molecule In contrast, the proportion of total carbon atoms forming bonds with sp3 hybrid orbitals is between 10% and 60%. It is below.

[0042] Another aspect of the present invention is an organic compound represented by the general formula (G4).

[0043] [ka]

[0044] In the above general formula (G4), Q 1 ~Q 3 Of these, 2 or 3 represent N, and Q 1 ~Q 3 If 2 of them are N, the remaining 1 represents CH. Also, R 2 , R 4 , R 7 , R 9 , R 12 , R 14 At least one of them is a substituted phenyl group, and the others are each a phenyl group. In addition, hydrogen, alkyl groups having 1 to 6 carbon atoms, alicyclic groups having 3 to 10 carbon atoms, substitution Alternatively, aromatic hydrocarbon groups with 6 to 14 carbon atoms forming an unsubstituted ring, substituted or unsubstituted. Represents one of the substituted pyridyl groups. A substituted phenyl group can have one or two substitutions. It has a substitution group, and each substituent is independently an alkyl group having 1 to 6 carbon atoms, and a alkyl group having 3 carbon atoms. Aromatic groups having 6 to 14 carbon atoms forming alicyclic groups of up to 10 alicyclic groups, or substituted or unsubstituted rings. Hydrocarbon groups, heteroaromatic ring groups with 3 to 9 carbon atoms forming a substituted or unsubstituted ring, It is one of the following. Note that the organic compound represented by the above general formula (G4) has 1 to 1 carbon atoms. It has multiple hydrocarbon groups selected from 6 alkyl groups and alicyclic groups having 3 to 10 carbon atoms. And the total number of carbon atoms in the molecule that form bonds with sp3 hybrid orbitals The percentage is between 10% and 60%.

[0045] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), the substituted phenyl group is represented by the following formula (G1- It is preferable to represent it as in 2).

[0046] [ka]

[0047] In the above general formula (G1-2), α represents a substituted or unsubstituted phenylene group. Also, R 20 This includes alkyl groups having 1 to 6 carbon atoms, alicyclic groups having 3 to 10 carbon atoms, or This represents an aromatic hydrocarbon group with 6 to 14 carbon atoms forming a substituted or unsubstituted ring. Furthermore, m and n represent 1 to 2. Note that when m is 2, multiple α are the same but different. It is also possible to do so if n is 2. 20 These can be the same or different.

[0048] In the above configuration, the group represented by the above general formula (G1-2) is R 2 and R 4 either It is preferable that one or both are present (wherein the group represented by general formula (G1-2) is R 2 and R 4If both conditions are met, the two groups represented by the above general formula (G1-2) are the same (It may be different, however.)

[0049] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In organic compounds represented by (G4), a substituted phenyl group is represented by the following general formula (G It is preferable that it be represented as 1-3).

[0050] [ka]

[0051] In the above general formula (G1-3), R 21 hydrogen, alkyl groups having 1 to 6 carbon atoms, carbon Alicyclic groups having 3 to 10 elementary atoms, or substituents represented by the general formula (G1-3-1), It represents a difference of 1. Also, R 22 This represents a substituent represented by the general formula (G1-3-1). In general formula (G1-3-1), R 23 and R 24 These are hydrogen and alkyl groups having 1 to 6 carbon atoms. R represents either a group or an alicyclic group having 3 to 10 carbon atoms. 23 and R 24 At least one of them is an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 3 to 10 carbon atoms. It is an alicyclic group. 23 and R 24 Both are alkyl groups having 1 to 6 carbon atoms. It is more preferable that n is an alicyclic group having 3 to 10 carbon atoms. Also, n is 0 to 2 This represents multiple R. 21 These may be the same or different. Note that if n is 0, R 23 and R 24 At least one of them has 1 to 6 carbon atoms It shall be either an alkyl group or an alicyclic group having 3 to 10 carbon atoms.

[0052] In the above configuration, the group represented by the above general formula (G1-3) is the general formula (G1), the general formula ( In organic compounds represented by general formula (G2), general formula (G3), and general formula (G4), R 2 oh Call R 4 It is preferable that either one or both of the above (however, general formula (G1-3) The group represented by R 2 and R 4 If both conditions are met, the following is represented by the general formula (G1-3) above: The two bases may be the same or different.

[0053] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), aromatic compounds with 6 to 14 carbon atoms forming a ring. If the hydrocarbon group has substituents, the substituents may be alkyl groups having 1 to 6 carbon atoms, carbon Alicyclic groups with 3 to 10 elementary atoms, unsubstituted aromatic hydrocarbon groups with 6 to 14 carbon atoms, Substituted with an alkyl group having 1 to 6 carbon atoms or an alicyclic group having 3 to 10 carbon atoms It is preferable that the ring-forming aromatic hydrocarbon group has 6 to 14 carbon atoms. stomach.

[0054] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula Organic compounds represented by (G4), and the above general formulas (G1-2) and (G1- 3) A phenyl group having substituents represented by the above, the number of carbon atoms forming the ring is 6 to 1 The aromatic hydrocarbon groups of 4 are phenyl, naphthyl, phenantrenyl, and fluorenyl. It is preferable that it be one of the bases.

[0055] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula ( Organic compounds represented by the above general formula (G4), and the above general formula (G1-2) and general formula (G1-3 A phenyl group having substituents represented by ) and having 6 to 14 carbon atoms forming the ring. The aromatic hydrocarbon group can be represented by any one of the following formulas (ra-1) to (ra-15). This is preferable.

[0056] [ka]

[0057] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), the substituted or unsubstituted pyridyl group is an unsubstituted pyridyl group. A lysyl group, or a pyridyl group substituted with one or more methyl groups, is preferred. stomach.

[0058] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), the alicyclic group is a cycloal group having 3 to 6 carbon atoms. It is preferable that it be a kill group.

[0059] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), the alkyl group having 1 to 6 carbon atoms is a carbon atom. Preferably, it is an alkyl group having three to five branching positions.

[0060] Another aspect of the present invention is an organic compound represented by the general formula (G4').

[0061] [ka]

[0062] In the above general formula (G4'), Q 1 ~Q 3 Of these, 2 or 3 represent N, and Q 1 ~Q 3 If two of them are N, the remaining one represents CH. Also, R 2 This is expressed by the following formula (R 2 -1 ) is represented as R 4 , R 7 , R 9 , R 12 , R 14 Each of these is independent of the following equation (r-1)~(r It represents one of the following (R 2 -1) In this case, β is substituted or unsubstituted phenyl R represents a len group, or a substituted or unsubstituted biphenyldiyl group. 25 is, equation (r-1 ) represents one of the following: (r-17), where n is either 1 or 2. Note that the above general formula (G4 The organic compounds represented by ') are alkyl groups having 1 to 6 carbon atoms and alkyl groups having 3 to 6 carbon atoms. It has multiple hydrocarbon groups selected from 10 alicyclic groups, and the sp ratio is relative to the total number of carbon atoms in the molecule. The proportion of total carbon atoms forming bonds in three hybrid orbitals is between 10% and 60%.

[0063] [ka]

[0064] Furthermore, (R in the organic compound represented by the above general formula (G4') 2 The above formula (R 2 - 1) can be expressed as one of the following equations (r-1) to (r-20).

[0065] [ka]

[0066] As shown in formulas (r-1), (r-2), (r-5), and (r-6), an aluminum compound is attached to the phenyl group at the meta position. Substitutions such as kill groups or cycloalkyl groups result in lower film density and a lower refractive index. This is preferable. Also, as in formulas (r-5) and (r-6), alkyl groups can be added to the phenyl group. When there are two cycloalkyl groups, the total carbon is easily bonded in sp3 hybrid orbitals. The number of elementary atoms can be increased, reducing synthesis costs, which is preferable. Also, equation (r-3) As in (r-4), an alkyl group or cycloalkyl group is substituted at the para position relative to the phenyl group. This is preferable because it allows for a higher rate of carrier mobility. Equations (r-19) and (r-20) As shown above, when a pyridyl group is present, electrons can be easily injected from the cathode or electron injection layer. This allows for a reduction in the driving voltage, which is preferable.

[0067] In the above configuration, the above formula (R 2 The β expressed in (-1) is given by the following equation (β-1) ~ (β-1 It is preferable that it be represented by any one of 4).

[0068] [ka]

[0069] Another aspect of the present invention is the following structural formula (100), (120), (121), (20 It is an organic compound represented by any one of (0), (123), or (412).

[0070] [ka]

[0071] Furthermore, another aspect of the present invention is a light emission device using an organic compound which is an aspect of the present invention described above. This is a vice. Furthermore, the present invention also includes a light-emitting device having a guest material in addition to the above organic compound. Include it.

[0072] Furthermore, the EL layer between the pair of electrodes and the light-emitting layer contained in the EL layer are according to one aspect of the present invention. Light-emitting devices formed using organic compounds are also included in the present invention. In addition to the light-emitting device, it has a layer containing an organic compound (e.g., a cap layer) in contact with the electrode. In addition to the light-emitting device, Light-emitting devices having transistors, substrates, etc. are also included in the scope of the invention. It has an optical device and one of the following: a sensor, an operation button, a speaker, or a microphone. Electronic devices and lighting devices are also included in the scope of the invention.

[0073] Furthermore, one aspect of the present invention includes a light-emitting device having a light-emitting device, and further includes a light-emitting device This also includes lighting devices. Therefore, in this specification, light-emitting devices refer to image This refers to a display device or light source (including lighting devices). It also refers to a light-emitting device, for example, an FPC ( Flexible Printed Circuit) or TCP (Tape Ca Modules with connectors such as the rrier Package attached, TCP endpoint A module with a printed circuit board, or a light-emitting device with COG (Chip O All modules with directly mounted ICs (integrated circuits) using the nGlass method are also equipped with light-emitting lenses. It shall be included in the place. [Effects of the Invention]

[0074] In one aspect of the present invention, a novel material for a light-emitting device or a novel material for an electron transport layer is provided. This can be done. In one aspect of the present invention, a novel light-emitting device material or electron transport with a low refractive index is provided. A material for layer transfer can be provided. Alternatively, in one aspect of the present invention, a material with a low refractive index and To provide a novel material for light-emitting devices or an electron transport layer that has carrier transport properties. This is possible. Alternatively, in one aspect of the present invention, a novel electron transporter having a low refractive index and electron transport properties is available. We can provide materials for optical devices or electron transport layers.

[0075] In one aspect of the present invention, a novel organic compound can be provided. Or, in one aspect of the present invention Therefore, it is possible to provide novel organic compounds that have carrier transport properties. Or, this invention In one embodiment of the present invention, a novel organic compound having electron transport properties can be provided. In one embodiment, an organic compound with a low refractive index can be provided. Or, an embodiment of the present invention This method provides an organic compound that has a low refractive index and carrier transport properties. Alternatively, in one aspect of the present invention, an organic compound having a low refractive index and electron transport properties is provided. It can be provided.

[0076] Alternatively, in another aspect of the present invention, a light-emitting device with high luminescence efficiency can be provided. Alternatively, in one aspect of the present invention, a light-emitting device, light-emitting apparatus, electronic device with low power consumption, Display devices and electronic devices can be provided separately.

[0077] Furthermore, 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. Furthermore, other effects are... This will become clear from the description in the specification, drawings, claims, etc., and the specification, drawings Furthermore, it is possible to extract other effects from the descriptions in the claims and other documents. [Brief explanation of the drawing]

[0078] [Figure 1] Figures 1(A), 1(B), and 1(C) are schematic diagrams of the light-emitting device. [Figure 2] Figures 2(A) and 2(B) are conceptual diagrams of an active matrix type light-emitting device. [Figure 3] Figures 3(A) and 3(B) are conceptual diagrams of an active matrix type light-emitting device. [Figure 4] Figure 4 is a conceptual diagram of an active matrix type light-emitting device. [Figure 5] Figures 5(A) and 5(B) are conceptual diagrams of a passive matrix type light-emitting device. [Figure 6] Figures 6(A) and 6(B) are diagrams representing lighting devices. [Figure 7] Figures 7(A), 7(B1), 7(B2), and 7(C) are diagrams representing electronic devices. [Figure 8] Figures 8(A), 8(B), and 8(C) are diagrams representing electronic devices. [Figure 9] Figure 9 is a diagram representing a lighting device. [Figure 10] Figure 10 is a diagram representing a lighting device. [Figure 11] Figure 11 is a diagram representing an in-vehicle display device and lighting system. [Figure 12] Figures 12(A) and 12(B) are diagrams representing electronic devices. [Figure 13] Figures 13(A), 13(B), and 13(C) are diagrams representing electronic devices. [Figure 14] Figure 14 shows the MS spectrum of mmtBumBP-dmmtBuPTzn. [Figure 15] Figure 15 shows the measured refractive index data for mmtBumBP-dmmtBuPTzn. [Figure 16] Figure 16 shows the MS spectrum of mmtBumBPTzn. [Figure 17] Figure 17 shows the measured refractive index data for mmtBumPTzn. [Figure 18] Figure 18 shows the MS spectrum of mmtBumTPTzn. [Figure 19] Figure 19 shows the measured refractive index data for mmtBumTPTzn. [Figure 20] Figure 20 shows the MS spectrum of mmtBumBP-dmmtBuPPm. [Figure 21] Figure 21 shows the measured refractive index data for mmtBumBP-dmmtBuPPm. [Figure 22] Figure 22 shows the measured refractive index data for mmtBumBP-dmmtBuPTzn, mPn-mDMePyPTzn, Li-6mq, and Liq. [Figure 23] Figure 23 shows the luminance-current density characteristics of light-emitting device 1 and comparative light-emitting device 1. [Figure 24] Figure 24 shows the current efficiency-luminance characteristics of light-emitting device 1 and comparative light-emitting device 1. [Figure 25] Figure 25 shows the luminance-voltage characteristics of light-emitting device 1 and comparison light-emitting device 1. [Figure 26] Figure 26 shows the current-voltage characteristics of light-emitting device 1 and comparison light-emitting device 1. [Figure 27] Figure 27 shows the blue index-luminance characteristics of light-emitting device 1 and comparison light-emitting device 1. [Figure 28] Figure 28 shows the emission spectra of light-emitting device 1 and comparison light-emitting device 1. [Figure 29] Figure 29 shows the measured refractive index data for mmtBumBPTzn and mPn-mDMePyPTzn. [Figure 30] Figure 30 shows the luminance-current density characteristics of light-emitting device 2 and comparison light-emitting device 2. [Figure 31]Figure 31 shows the current efficiency - luminance characteristics of the light - emitting device 2 and the comparative light - emitting device 2. [Figure 32] Figure 32 shows the luminance - voltage characteristics of the light - emitting device 2 and the comparative light - emitting device 2. [Figure 33] Figure 33 shows the current - voltage characteristics of the light - emitting device 2 and the comparative light - emitting device 2. [Figure 34] Figure 34 shows the blue index - luminance characteristics of the light - emitting device 2 and the comparative light - emitting device 2. [Figure 35] Figure 35 shows the emission spectra of the light - emitting device 2 and the comparative light - emitting device 2. [Figure 36] Figure 36 shows the luminance - current density characteristics of the light - emitting device 3, the light - emitting device 4, and the light - emitting device 5. [Figure 37] Figure 37 shows the current efficiency - luminance characteristics of the light - emitting device 3, the light - emitting device 4, and the light - emitting device 5. [Figure 38] Figure 38 shows the luminance - voltage characteristics of the light - emitting device 3, the light - emitting device 4, and the light - emitting device 5. [Figure 39] Figure 39 shows the current density - voltage characteristics of the light - emitting device 3, the light - emitting device 4, and the light - emitting device 5. [Figure 40] Figure 40 shows the power efficiency - luminance characteristics of the light - emitting device 3, the light - emitting device 4, and the light - emitting device 5. [Figure 41] Figure 41 shows the emission spectra of the light - emitting device 3, the light - emitting device 4, and the light - emitting device 5. [Figure 42] Figure 42 shows the external quantum efficiency - luminance characteristics of the light - emitting device 3, the light - emitting device 4, and the light - emitting device 5. [Figure 43] Figure 43 is a diagram showing the reliability of the light - emitting device 3, the light - emitting device 4, and the light - emitting device 5. [Figure 44] Figure 44 shows the absorption spectrum and the emission spectrum of the dehydrated acetone solution of Li - 6mq. [Figure 45] Figure 45 is a diagram showing the luminance - current density characteristics of the light - emitting device 6, the light - emitting device 7, and the comparative light - emitting device 3. [Figure 46] Figure 46 shows the current efficiency-luminance characteristics of light-emitting device 6, light-emitting device 7, and comparative light-emitting device 3. [Figure 47] Figure 47 shows the luminance-voltage characteristics of light-emitting device 6, light-emitting device 7, and comparison light-emitting device 3. [Figure 48] Figure 48 shows the current density-voltage characteristics of light-emitting device 6, light-emitting device 7, and comparison light-emitting device 3. [Figure 49] Figure 49 shows the external quantum efficiency-luminance characteristics of light-emitting device 6, light-emitting device 7, and comparative light-emitting device 3. [Figure 50] Figure 50 shows the emission spectra of light-emitting device 6, light-emitting device 7, and reference light-emitting device 3. [Figure 51] Figure 51 shows the normalized luminance-time variation characteristics of light-emitting device 6, light-emitting device 7, and comparative light-emitting device 3. [Figure 52] Figure 52 shows the MS spectrum of mmtBumTPTzn-02. [Figure 53] Figure 53 shows the measured refractive index data for mmtBumTPTzn-02. [Figure 54] Figure 54 shows the MS spectrum of mmtBumTPTzn-04. [Figure 55] Figure 55 shows the measured refractive index data for mmtBumTPTzn-04. [Figure 56] Figure 56 shows the MS spectrum of mmtBuPh-mDMePyPTzn. [Figure 57] Figure 57 shows the measured refractive index data for mmtBuPh-mDMePyPTzn. [Figure 58] Figure 58 shows the MS spectrum of mmchmBPTzn. [Figure 59] Figure 59 shows the measured refractive index data for mmchmBPTzn. [Figure 60] Figure 60 shows the MS spectrum of mmtBuTPTzn-03. [Figure 61]Figure 61 shows the data of the refractive index measurement of mmtBuTPTzn-03. [Figure 62] Figure 62 shows the MS spectrum of mmtBumBP2Tzn. [Figure 63] Figure 63 shows the data of the refractive index measurement of mmtBumBP2Tzn. [Figure 64] Figure 64 shows the MS spectrum of oBP-mmtBumBPTzn. [Figure 65] Figure 65 shows the data of the refractive index measurement of oBP-mmtBumBPTzn. [Figure 66] Figure 66 shows the MS spectrum of oBP-mmtBuBPTzn. [Figure 67] Figure 67 shows the data of the refractive index measurement of oBP-mmtBuBPTzn. [Figure 68] Figure 68 shows the MS spectrum of mmtBuPh-mPyPTzn. [Figure 69] Figure 69 shows the data of the refractive index measurement of mmtBuPh-mPyPTzn. [Figure 70] Figure 70 shows the MS spectrum of mmtBuBP-mDMePyPTzn. [Figure 71] Figure 71 shows the data of the refractive index measurement of mmtBuBP-mDMePyPTzn. [Figure 72] Figure 72 shows the graph representing the luminance-current density characteristics of light-emitting device 8, light-emitting device 9, and comparative light-emitting device 4. [Figure 73] Figure 73 shows the graph representing the luminance-voltage characteristics of light-emitting device 8, light-emitting device 9, and comparative light-emitting device 4. [Figure 74] Figure 74 shows the graph representing the current efficiency-luminance characteristics of light-emitting device 8, light-emitting device 9, and comparative light-emitting device 4. [Figure 75] Figure 75 shows the graph representing the current density-voltage characteristics of light-emitting device 8, light-emitting device 9, and comparative light-emitting device 4. [Figure 76] Figure 76 shows the graph representing the external quantum efficiency-luminance characteristics of light-emitting device 8, light-emitting device 9, and comparative light-emitting device 4. [Figure 77] Figure 77 shows the emission spectra of light-emitting device 8, light-emitting device 9, and comparison light-emitting device 4. [Figure 78] Figure 78 shows the luminance-current density characteristics of light-emitting device 10 and comparative light-emitting device 5. [Figure 79] Figure 79 shows the luminance-voltage characteristics of light-emitting device 10 and comparison light-emitting device 5. [Figure 80] Figure 80 shows the current efficiency-luminance characteristics of light-emitting device 10 and comparative light-emitting device 5. [Figure 81] Figure 81 shows the current density-voltage characteristics of the light-emitting device 10 and the comparative light-emitting device 5. [Figure 82] Figure 82 shows the external quantum efficiency-luminance characteristics of light-emitting device 10 and comparative light-emitting device 5. [Figure 83] Figure 83 shows the emission spectra of light-emitting device 10 and comparison light-emitting device 5. [Figure 84] Figure 84 shows the MS spectrum of mmtBuBP-mDMePyPTzn-02. [Figure 85] Figure 85 shows the measured refractive index data for mmtBuBP-mDMePyPTzn-02. [Figure 86] Figure 86 shows the MS spectrum of oBP2-mmtBuPh-mDMePyPTzn. [Figure 87] Figure 87 shows the measured refractive index data for oBP2-mmtBuPh-mDMePyPTzn. [Figure 88] Figure 88 shows the MS spectrum of oBP-mmtBuPh-mDMePyPTzn. [Figure 89] Figure 89 shows the measured refractive index data for oBP-mmtBuPh-mDMePyPTzn. [Figure 90] Figure 90 shows the MS spectrum of tBu-TmPPPyTz. [Figure 91] Figure 91 shows the MS spectrum of tBu-TmPPPyTz-02. [Modes for carrying out the invention]

[0079] The embodiments of the present invention will be described in detail below with reference to the drawings. However, the present invention is as follows Not limited to the description, the form and details thereof may be described without departing from the spirit and scope of the present invention. Those skilled in the art will readily understand that the invention can be modified in various ways. Therefore, the present invention is as follows: This should not be interpreted as being limited to the contents described in the embodiments.

[0080] (Embodiment 1) Among organic compounds with carrier transport properties that can be used in organic EL elements, One of the materials with low efficacy is 1,1-bis-(4-bis(4-methylphenyl)-amino- Phenyl-cyclohexane (abbreviated as TAPC) is known. Materials with a low refractive index are E When used in the L layer, it is possible to increase the external quantum efficiency of the light-emitting device, therefore TAPC It is expected that by using this, a light-emitting device with good external quantum efficiency can be obtained. However, However, TAPC has a low glass transition temperature, which gives it problems with heat resistance. It can pass holes, but it is practically impossible to pass electrons.

[0081] Furthermore, in order to obtain a material with a low refractive index, atoms with low atomic refraction are introduced into the molecule, Alternatively, it is preferable to introduce substituents with low molecular refraction. Substituents with low molecular refraction include saturates. Examples include nitrate hydrocarbon groups and cyclic saturated hydrocarbon groups.

[0082] Typically, there is a trade-off relationship between carrier transportability and refractive index, and improving carrier transportability is important. It is commonly believed that the refractive index increases. This is because the carrier transport properties in organic compounds are This is largely due to the presence of unsaturated bonds, and organic compounds with many unsaturated bonds are prone to refractory behavior. This is because the conversion rate tends to be high.

[0083] Furthermore, due to the low LUMO level required, electron-transporting organic compounds originally have hole transport properties. Rather than being a highly mobile organic compound, it possesses mobility and stability, which are essential for use in organic EL devices. It is known to be difficult to bring out its characteristics. Therefore, satiety, which negatively affects these characteristics, The introduction of natto hydrocarbon groups was considered undesirable.

[0084] However, contrary to these conventional theories, the inventors have developed a material that combines carrier transportability with a low refractive index. As a compound, carbon atoms that form bonds in sp3 hybrid orbitals that constitute saturated hydrocarbon groups The proportion of offspring having a pyridine skeleton, diazine skeleton, or triazine skeleton within a certain range We have discovered a material for light-emitting devices containing a compound. Because it possesses both optical properties such as refractive index and electron transport properties, it is used in light-emitting devices and photoelectric conversion devices, etc. It is suitable for the electron transport layer of photoelectronic devices, and as an electron transport layer material It can also be used. Organic compounds, among the substituents that the organic compound has, form bonds with sp3 hybrid orbitals. By optimizing the number of substituents on the carbon atom, or their substitution positions, high electron transport can be achieved. It is possible to achieve a low refractive index while maintaining ferrous properties. Furthermore, in the organic compound, By keeping the proportion of carbon atoms forming bonds with sp3 hybrid orbitals within a certain range, low refractometers can be achieved. In addition to high refractive index and high electron transport properties, this light-emitting diode also possesses heat resistance due to its high glass transition temperature. Materials for vises and materials for electron transport layers can be obtained.

[0085] Furthermore, by using a material for light-emitting devices, which is one aspect of the present invention, in the EL layer of a light-emitting device... By taking advantage of its low refractive index, the efficiency of light extraction in the EL layer is improved. This allows for an improvement in the luminous efficiency of light-emitting devices.

[0086] Furthermore, the electron transport layer material according to one aspect of the present invention has high electron transport properties and therefore emits light. It is suitable for the electron transport layer of the EL layer of a device, and its low refractive index is utilized to make it suitable for EL It is also possible to improve the efficiency of extracting light in the layer, thus improving the luminous efficiency of the light-emitting device. This can improve the electron transport layer material according to one aspect of the present invention, which has high electron Because it possesses transportability and light (especially visible light) transmittance, it is suitable for the electron transport layer of photoelectric conversion devices. It is suitable.

[0087] In other words, one aspect of the present invention is a light-emitting device that can be used in the EL layer of a light-emitting device Materials for chairs, or electron transport layers in EL layers of light-emitting devices, or electrons in photoelectric conversion devices. This is an electron transport layer material that can be used in the sub-transport layer. It is a material for the light-emitting device or The electron transport layer material comprises at least one six-membered heteroaromatic ring containing one to three nitrogen atoms. It contains an organic compound having a glass transition temperature of 90°C or higher, and the organic A material for light-emitting devices or It is a material for electron transport layers. Alternatively, one aspect of the present invention is a 6-membered material containing 1 to 3 nitrogen atoms. Materials for light-emitting devices or electronics comprising an organic compound having at least one heteroaromatic ring in the ring. A transport layer material wherein the glass transition temperature of the organic compound is 90°C or higher, and the organic compound The total number of carbon atoms forming bonds with sp3 hybrid orbitals relative to the total number of carbon atoms in the molecule of the compound. The proportion of is between 10% and 60% for materials used in light-emitting devices or electron transport layers. Alternatively, one aspect of the present invention involves a heteroaromatic ring with a six-membered ring containing one to three nitrogen atoms. A material for a light-emitting device or an electron transport layer containing at least one organic compound, The glass transition temperature of the organic compound is 90°C or higher. 1 H-NMR The integral value of signals less than 4 ppm in the measurement results is the same as the integral value of signals 4 ppm or greater. It is a material for light-emitting devices or an electron transport layer that is more than half the integral value of [the specified value].

[0088] Furthermore, the heteroaromatic ring in the above organic compound must be a triazine ring or a diazine ring. Preferably, it is a triazine ring or a pyrimidine ring. Also, the above Gala The transition temperature is preferably 100°C or higher, more preferably 110°C or higher. More preferably, the temperature is 120°C or higher.

[0089] Furthermore, if anisotropy occurs in the material, the refractive index relative to ordinary light (ordina) The refractive index for ry) and the refractive index for extraordinary light (extra-ordinary refractive index) are different. This can happen. If the thin film being measured is in such a state, anisotropy analysis can be performed. The refractive index can be separated into the ordinary refractive index and the extraordinary refractive index, and the refractive index of each can be calculated. In the details, if the measured material has both an ordinary refractive index and an extraordinary refractive index, The refractive index is used as the indicator.

[0090] Furthermore, one aspect of the present invention relates to a light-emitting device that can be used in the EL layer of a light-emitting device. Materials for use in light-emitting devices, or electron transport layers in EL layers of light-emitting devices, or electrons in photoelectric conversion devices. This is an electron transport layer material that can be used in transport layers. The material for the transport layer has at least one six-membered heteroaromatic ring containing one to three nitrogen atoms. It has multiple aromatic hydrocarbon rings, each having 6 to 14 carbon atoms forming a ring, and multiple aromatic At least two of the hydrocarbon rings are benzene rings, and they form bonds via sp3 hybrid orbitals. It contains an organic compound having multiple hydrocarbon groups, and the layer made of the organic compound is 455 nm or longer. The ordinary refractive index for any wavelength of light in the range of 465 nm or less is 1.5 or greater. The material is a light-emitting device material or an electron transport layer material with a coefficient of 0.75 or less. The benzene ring should ideally be a monocyclic benzene ring, that is, a benzene ring that is not fused with any other aromatic rings. It seems so.

[0091] Furthermore, the percentage of the total number of carbon atoms forming bonds with sp3 hybrid orbitals as shown in the above configuration. This affects the refractive index of organic compounds. That is, when bonds are formed in sp3 hybrid orbitals As the total number of carbon atoms increases, the refractive index decreases, so the light-gathering properties of light-emitting devices using this increase in refractive index. This can improve the efficiency of the vehicle's departure.

[0092] Another aspect of the present invention relates to a light-emitting device that can be used in the EL layer of the light-emitting device. Device materials, or electron transport layers and photoelectric conversion devices in the EL layer of light-emitting devices. These are electron transport layer materials that can be used in electron transport layers, and these materials are 1 to 3 It has at least one six-membered heteroaromatic ring containing nitrogen atoms, and the number of carbon atoms forming the ring It has 6 to 14 aromatic hydrocarbon rings, and of the multiple aromatic hydrocarbon rings, at least The two are benzene rings and have multiple hydrocarbon groups that form bonds with sp3 hybrid orbitals. It contains organic compounds, and the bonds in the organic compounds are formed by sp3 hybrid orbitals relative to the total number of carbon atoms in the molecule. It is preferable that the proportion of the total number of carbon atoms formed is between 10% and 60%.

[0093] Furthermore, the percentage of the total number of carbon atoms forming bonds with sp3 hybrid orbitals as shown in the above configuration. This affects the refractive index of organic compounds. That is, when bonds are formed in sp3 hybrid orbitals As the total number of carbon atoms increases, the refractive index decreases, so the light-gathering properties of light-emitting devices using this increase in refractive index. This can improve the ejection efficiency. However, the total amount of sp3 hybrid orbitals forming bonds When the number of carbon atoms becomes too large, the LUMO (Luminous Molecular Weight) between adjacent molecules in an organic compound increases. The overlap of orbits is hindered, resulting in reduced carrier transport capabilities (such as electron transport and injection capabilities). Therefore, the total number of carbon atoms in the molecule that form bonds with sp3 hybrid orbitals The proportion of atoms is preferably 10% to 60%, and more preferably 20% to 50%. Furthermore, the total number of carbon atoms in the molecule that form bonds with sp3 hybrid orbitals It is preferable that the proportion of atoms be between 20% and 40%.

[0094] Another aspect of the present invention relates to a light-emitting device that can be used in the EL layer of the light-emitting device. Device materials, or electron transport layers in EL layers of light-emitting devices and photoelectric conversion devices These are electron transport layer materials that can be used in electron transport layers, and these materials consist of 1 to 3 It has at least one six-membered heteroaromatic ring containing a nitrogen atom, and the number of carbon atoms forming the ring is It has a plurality of aromatic hydrocarbon rings, of which at least 2 One is a benzene ring, and it has multiple hydrocarbon groups that form bonds with sp3 hybrid orbitals. The results of measuring organic compounds by 1H-NMR, including organic compounds, showed concentrations of less than 4 ppm. It is preferable that the integrated value of the signal is at least half the integrated value of the signal with a signal strength of 4 ppm or higher. It's nice.

[0095] Furthermore, the percentage of the total number of carbon atoms forming bonds with sp3 hybrid orbitals as shown in the above configuration. This affects the refractive index of organic compounds. That is, when bonds are formed in sp3 hybrid orbitals As the total number of carbon atoms increases, the refractive index decreases, so the light-gathering properties of light-emitting devices using this increase in refractive index. This can improve the extraction efficiency. Also, the total carbon that forms bonds in sp3 hybrid orbitals As the number of atoms increases, the heat resistance, such as the glass transition temperature, improves, which is desirable. However, sp3 hybridization When the total number of carbon atoms forming bonds in orbitals becomes too large, the intermolecular odor of organic compounds increases. The overlap of LUMO orbitals with adjacent molecules is inhibited, thereby hindering carrier transport (electricity). Because of the decrease in properties such as particle transport and injection, the results of measuring organic compounds by 1H-NMR were obtained. In this case, the integral of signals less than 4 ppm originating from protons of alkyl groups and alicyclic groups. The value is 1 in the integral value of signals of 4 ppm or more that originate from an aryl group or a heteroaromatic group. It is preferable that the ratio is 2 times or more, 2 times or less, and more preferably 1 time or more and 1.5 times or less.

[0096] Furthermore, the molecules of organic compounds contained in the above-mentioned light-emitting device material or electron transport layer material. The quantity is preferably 500 to 2000. More preferably 700 to 150. If the value is 0 or less, the thermal properties (glass transition temperature) are also high, and it becomes less likely to decompose during sublimation (deposition), so it is preferable. It seems so.

[0097] Furthermore, the molecules of organic compounds contained in the above-mentioned light-emitting device material or electron transport layer material. Within this, all hydrocarbon groups that form bonds with sp3 hybrid orbitals are aromatic carbonized water The hydrocarbon group is bonded to the elementary ring, and the aromatic hydrocarbon ring to which the hydrocarbon group is bonded does not have a LUMO (Low-Organization Molecular Weight). In other words, within the molecule of an organic compound, other than the aromatic hydrocarbon ring to which the hydrocarbon group is bonded. It is preferable that the LUMO is distributed in the ring. However, in the above, the hydrocarbon group is In this specification, the statement that no LUMO is distributed in the combining aromatic hydrocarbon ring means that The distribution density of LUMOs in an aromatic hydrocarbon ring to which hydrocarbon groups are bonded is the isosurface value (iso value) is 0.06 [electrons / au 3 Less than 0.0 It means less than 2.

[0098] Furthermore, the LUMO is mainly distributed on the heteroaromatic ring and the substituents directly bonded to it. This is more preferable. By using such molecules, adjacent organic compound molecules in the solid (membrane) state The LUMO orbitals become more likely to overlap, making it easier to transport electrons, thus increasing the drive voltage. It is expected that this will reduce the risk.

[0099] Note that the isosurface values ​​(isovalues) of LUMO are calculated using molecular orbital calculations such as Gaussian. It can be calculated using this method.

[0100] Furthermore, the molecules of organic compounds contained in the above-mentioned light-emitting device material or electron transport layer material. Within this, aromatic hydrocarbons bonded to hydrocarbon groups that form bonds in sp3 hybrid orbitals. Preferably, at least one of the rings is a benzene ring.

[0101] Furthermore, the odor of organic compounds contained in the above-mentioned materials for light-emitting devices or electron transport layers It has at least three benzene rings, and all three benzene rings are six-membered heteroatoms. Preferably bonded to the ring, and two of the three benzene rings are substituted or It is preferable that the phenyl group is unsubstituted and does not have a hydrocarbon group. Also, a 6-membered ring A triazine ring or a pyrimidine ring is preferred as the heteroaromatic ring.

[0102] Furthermore, the organic compounds contained in the above-mentioned materials for light-emitting devices or electron transport layers are It is preferable to have a substituted or unsubstituted pyridyl group. Having this group enhances the electron injection from the cathode or electron injection layer. Therefore, it is preferable.

[0103] Furthermore, the organic compounds contained in the above-mentioned materials for light-emitting devices or electron transport layers have Furthermore, hydrocarbon groups that form bonds with sp3 hybrid orbitals are alkyl groups or cycloalkyl groups. A 3L group is preferred, and the alkyl group has branching with 3 to 5 carbon atoms. preferable.

[0104] Furthermore, in the above-mentioned light-emitting device material or electron transport layer material, the organic compound The glass transition temperature is preferably 90°C or higher. The temperature is 100°C or higher, more preferably 110°C or higher, and particularly preferably 120°C. It is above ℃.

[0105] Next, a state of organic compounds contained in the above-mentioned light-emitting device material or electron transport layer material. The present invention can also be applied in various ways, and an organic compound that is one embodiment of the present invention will be described below. .

[0106] In other words, one aspect of the present invention is an organic compound represented by general formula (G1).

[0107] [ka]

[0108] In general formula (G1), A represents a six-membered heteroaromatic ring containing one to three nitrogen atoms. Also R 0 These are hydrogen, alkyl groups having 1 to 6 carbon atoms, and alicyclic groups having 3 to 10 carbon atoms. R represents either a substituent represented by formula (G1-1) or a substituent represented by formula (G1-1). 1 ~R 15 fewer In each case, one is a substituted phenyl group, and the others are, independently, hydrogen and carbon atoms. Alkyl groups with 1 to 6 carbon atoms, alicyclic groups with 3 to 10 carbon atoms, and substituted or unsubstituted rings. Aromatic hydrocarbon groups having 6 to 14 carbon atoms, substituted or unsubstituted pyridyl groups, It represents either. A substituted phenyl group has one or two substituents, and the substitution Each group independently consists of an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 3 to 10 carbon atoms, Aromatic hydrocarbon groups with 6 to 14 carbon atoms forming a substituted or unsubstituted ring, substituted or This is one of the heteroaromatic ring groups with 3 to 9 carbon atoms that form an unsubstituted ring. The organic compound represented by the above general formula (G1) is an alkyl group having 1 to 6 carbon atoms and It has multiple hydrocarbon groups selected from alicyclic groups having 3 to 10 carbon atoms, and the total carbon content within the molecule The ratio of the total number of carbon atoms forming bonds with sp3 hybrid orbitals to the number of atoms is 10% or more. It is less than 0%.

[0109] Furthermore, in the structure of the organic compound represented by the above general formula (G1), the bonds are formed by sp3 hybrid orbitals. The proportion of the total number of carbon atoms forming a compound affects the refractive index of the organic compound. That is, As the total number of carbon atoms forming bonds in sp3 hybrid orbitals increases, the refractive index decreases. This can improve the light extraction efficiency of light-emitting devices using this technology. As the total number of carbon atoms forming bonds in the orbitals increases, heat resistance, such as the glass transition temperature, improves. And it is preferable. However, the total number of carbon atoms forming bonds in sp3 hybrid orbitals becomes large. If this is excessive, the overlap of LUMO orbitals between adjacent molecules in organic compounds is inhibited. As a result, carrier transportability (such as electron transportability and injectionability) decreases, and the total amount within the molecule The ratio of the total number of carbon atoms to the total number of carbon atoms that form bonds with sp3 hybrid orbitals is 10%. Preferably, the above is 60% or less, and more preferably 20% to 50%. Furthermore, the total within the molecule The ratio of the total number of carbon atoms to the total number of carbon atoms that form bonds with sp3 hybrid orbitals should be 20% or less. It is preferable to keep it below 40%.

[0110] Furthermore, the organic compound represented by the above general formula (G1) is a six-membered ring containing one to three nitrogen atoms. A heteroaromatic ring and a six-membered aromatic ring (i.e., a substituted or unsubstituted phenyl group), and sp3 It is formed only from hydrocarbon groups (alkyl groups and alicyclic groups) that form bonds in hybrid orbitals. In this case (i.e., when a fused ring is not included), the refractive index becomes lower, and the carrier (electron) transport... This is preferable because it also improves fertilization.

[0111] Furthermore, in the organic compound represented by the above general formula (G1), A is a pyridine ring, Limidine rings, pyrazine rings, pyridazine rings, and triazine rings can be used. When using an organic compound represented by the general formula (G1) in a layer in contact with the luminescent layer or active layer, Triazine rings, pyrazine rings, and pyrazine rings are readily injected into these layers and have good electron transport properties. A methyl ring is preferred, and a triazine ring is particularly preferred.

[0112] Furthermore, in the organic compound represented by the above general formula (G1), substituents (alkyl group and alicyclic group) The total number of (substances) per molecule should be between 4 and 10, taking synthesis costs into consideration. It is preferable, and even more preferable if the refractive index is 6 or higher to lower it further. Similarly, Using larger substituents (alkyl groups or alicyclic groups) allows for refraction even with fewer substituents. It effectively reduces the rate, and considering the synthesis cost, the number of carbon atoms in the alkyl group is 4. It is more preferable that the number of carbon atoms in the alicyclic group be 6 or more.

[0113] Furthermore, in the organic compound represented by the above general formula (G1), the number of carbon atoms forming the ring is 6 The aromatic hydrocarbon groups up to 14 include substituted or unsubstituted phenyl groups, naphthyl groups, and phenyl groups. Phenanthryl groups and fluorenyl groups can be used. In particular, phenyl groups have a low refractive index. It is preferable because it can be done. Also, the naphthyl group, phenanthryl group, and fluorenyl group are gal This is preferable because it can raise the transition temperature. Also, the number of carbon atoms that form these rings The aromatic hydrocarbon group has 6 to 14 carbon atoms, and the branched alkyl group has 3 to 5 carbon atoms or Substitution with a chloroalkyl group increases the glass transition temperature while simultaneously increasing the refractive index. This is preferable because it provides the effect of maintaining a low refractive index. From the viewpoint of reduction, aromatic hydrocarbon groups having 6 to 14 carbon atoms that form the above ring are carbon Alkyl groups with 1 to 6 elementary atoms, alicyclic groups with 3 to 10 carbon atoms, and groups with 1 to 6 carbon atoms. A carbon source that forms a ring substituted with an alkyl group or an alicyclic group having 3 to 10 carbon atoms. It is preferable that the group is substituted with any aromatic hydrocarbon group having 6 to 14 atoms. For example, the 1,3-di(t-butyl)phenyl group and the 1,3-dicyclohexylphenyl group Sea urchin, with an alkyl group having 1 to 6 carbon atoms, or an alicyclic group having 3 to 10 carbon atoms. A substituted phenyl group is preferred. Also, 3-t-butyl-5-[1,3-di(t-butyl )phenyl]phenyl group, or 3-cyclohexyl-5-[1,3-dicyclohexylphenyl [Nyl]phenyl group, such as an alkyl group having 1 to 6 carbon atoms or a group having 3 to 6 carbon atoms Phenyl groups substituted with 10 alicyclic groups are preferred. When rings are used and the number of fused rings is three or more, if the other six-membered rings are a When the ring is fused only at positions c and e, the refractive index can be lower compared to polyacene. Therefore, it is preferable. For example, the phenanthrene ring has a higher refractive index than the anthracene ring. It can be lowered.

[0114] Furthermore, the number of carbon atoms forming the ring in the organic compound represented by the above general formula (G1) is 3. The heteroaromatic ring groups up to 9 include pyridyl group, pyrimidinyl group, pyrazinyl group, and triazinyl group. The following can be used: quinolyl group, quinozolinyl group, quinoxalinyl group, etc.

[0115] Furthermore, in the organic compound represented by the above general formula (G1), alkyl groups having 1 to 6 carbon atoms The propyl group can be a methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group. Groups such as butyl, tert-butyl, pentyl, and hexyl can be used. Examples of alicyclic groups having 3 to 10 carbon atoms include cyclopropyl group, cyclohexyl group, and cyclo Rhodecanyl groups, bicyclooctyl groups, adamantyl groups, etc., can be used.

[0116] Another aspect of the present invention is an organic compound represented by the general formula (G2).

[0117] [ka]

[0118] In general formula (G2), A represents a six-membered heteroaromatic ring containing one to three nitrogen atoms. Also R 0 These are hydrogen, alkyl groups having 1 to 6 carbon atoms, and alicyclic groups having 3 to 10 carbon atoms. It represents either a substituent represented by formula (G2-1), or R 2 , R 4 , R 7 , R 9 , R 12 , R 14 At least one of them is a substituted phenyl group, The others are, independently, hydrogen, alkyl groups having 1 to 6 carbon atoms, and alicyclic groups having 3 to 10 carbon atoms. Formula group, aromatic hydrocarbon group having 6 to 14 carbon atoms forming a substituted or unsubstituted ring, Represents either a substituted or unsubstituted pyridyl group. A substituted phenyl group can have one or more substitutions. It has two substituents, each of which substituents is independently an alkyl group having 1 to 6 carbon atoms, and a carbon atom. Alicyclic groups with 3 to 10 elementary atoms, and 6 to 1 carbon atoms forming a substituted or unsubstituted ring. 4 aromatic hydrocarbon groups, substituted or unsubstituted ring-forming complex aromatic groups with 3 to 9 carbon atoms. It is one of the following: a ring group. Note that the organic compound represented by the above general formula (G2) is a carbon source Hydrocarbons selected from alkyl groups having 1 to 6 carbon atoms and alicyclic groups having 3 to 10 carbon atoms. Total carbon atoms have multiple groups and form bonds with sp3 hybrid orbitals relative to the total number of carbon atoms in the molecule. The proportion of elementary atoms is between 10% and 60%.

[0119] Furthermore, in the structure of the organic compound represented by the general formula (G2) above, the bonds are formed by sp3 hybrid orbitals. The proportion of the total number of carbon atoms forming a compound affects the refractive index of the organic compound. That is, As the total number of carbon atoms forming bonds in sp3 hybrid orbitals increases, the refractive index decreases. This can improve the light extraction efficiency of light-emitting devices using this technology. As the total number of carbon atoms forming bonds in the orbitals increases, heat resistance, such as the glass transition temperature, improves. And it is preferable. However, the total number of carbon atoms forming bonds in sp3 hybrid orbitals becomes large. If this is excessive, the overlap of LUMO orbitals between adjacent molecules in organic compounds is inhibited. As a result, carrier transportability (such as electron transportability and injectionability) decreases, and the total amount within the molecule The ratio of the total number of carbon atoms to the total number of carbon atoms that form bonds with sp3 hybrid orbitals is 10%. Preferably, the above is 60% or less, and more preferably 20% to 50%. Furthermore, the total within the molecule The ratio of the total number of carbon atoms to the total number of carbon atoms that form bonds with sp3 hybrid orbitals should be 20% or less. It is preferable to keep it below 40%.

[0120] Furthermore, the organic compound represented by the above general formula (G2) is a six-membered ring containing one to three nitrogen atoms. A heteroaromatic ring and a six-membered aromatic ring (i.e., a substituted or unsubstituted phenyl group), and sp3 It is formed only from hydrocarbon groups (alkyl groups and alicyclic groups) that form bonds in hybrid orbitals. In this case (i.e., when a fused ring is not included), the refractive index becomes lower, and the carrier (electron) transport... This is preferable because it also improves fertilization.

[0121] Furthermore, in the organic compound represented by the above general formula (G2), A is a pyridine ring, Limidine rings, pyrazine rings, pyridazine rings, and triazine rings can be used. When using an organic compound represented by the general formula (G2) in a layer in contact with the luminescent layer or active layer, Triazine rings, pyrazine rings, and pyrazine rings are readily injected into these layers and have good electron transport properties. A methyl ring is preferred, and a triazine ring is particularly preferred.

[0122] Furthermore, in the organic compound represented by the above general formula (G2), substituents (alkyl group and alicyclic group) The total number of (substances) per molecule should be between 4 and 10, taking synthesis costs into consideration. It is preferable, and even more preferable if the refractive index is 6 or higher to lower it further. Similarly, Using larger substituents (alkyl groups or alicyclic groups) allows for refraction even with fewer substituents. It effectively reduces the rate, and considering the synthesis cost, the number of carbon atoms in the alkyl group is 4. It is more preferable that the number of carbon atoms in the alicyclic group be 6 or more.

[0123] Furthermore, in the organic compound represented by the above general formula (G2), the number of carbon atoms forming the ring is 6 The aromatic hydrocarbon groups up to 14 include substituted or unsubstituted phenyl groups, naphthyl groups, and phenyl groups. Phenanthryl groups and fluorenyl groups can be used. In particular, phenyl groups have a low refractive index. It is preferable because it can be done. Also, the naphthyl group, phenanthryl group, and fluorenyl group are gal This is preferable because it can raise the transition temperature. Also, the number of carbon atoms that form these rings The aromatic hydrocarbon group has 6 to 14 carbon atoms, and the branched alkyl group has 3 to 5 carbon atoms or Substitution with a chloroalkyl group increases the glass transition temperature while simultaneously increasing the refractive index. This is preferable because it provides the effect of maintaining a low refractive index. From the viewpoint of reduction, aromatic hydrocarbon groups having 6 to 14 carbon atoms that form the above ring are carbon Alkyl groups with 1 to 6 elementary atoms, alicyclic groups with 3 to 10 carbon atoms, and groups with 1 to 6 carbon atoms. A carbon source that forms a ring substituted with an alkyl group or an alicyclic group having 3 to 10 carbon atoms. It is preferable that the group is substituted with any aromatic hydrocarbon group having 6 to 14 atoms. For example, the 1,3-di(t-butyl)phenyl group and the 1,3-dicyclohexylphenyl group Sea urchin, with an alkyl group having 1 to 6 carbon atoms, or an alicyclic group having 3 to 10 carbon atoms. A substituted phenyl group is preferred. Also, 3-t-butyl-5-[1,3-di(t-butyl )phenyl]phenyl group, or 3-cyclohexyl-5-[1,3-dicyclohexylphenyl [Nyl]phenyl group, such as an alkyl group having 1 to 6 carbon atoms or a group having 3 to 6 carbon atoms Phenyl groups substituted with 10 alicyclic groups are preferred. When rings are used and the number of fused rings is three or more, if the other six-membered rings are a When the ring is fused only at positions c and e, the refractive index can be lower compared to polyacene. Therefore, it is preferable. For example, the phenanthrene ring has a higher refractive index than the anthracene ring. It can be lowered.

[0124] Furthermore, the number of carbon atoms forming the ring in the organic compound represented by the above general formula (G2) is 3. The heteroaromatic ring groups up to 9 include pyridyl group, pyrimidinyl group, pyrazinyl group, and triazinyl group. The following can be used: quinolyl group, quinozolinyl group, quinoxalinyl group, etc.

[0125] Furthermore, in the organic compound represented by the above general formula (G2), alkyl groups having 1 to 6 carbon atoms The propyl group can be a methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group. Groups such as butyl, tert-butyl, pentyl, and hexyl can be used. Examples of alicyclic groups having 3 to 10 carbon atoms include cyclopropyl group, cyclohexyl group, and cyclo Rhodecanyl groups, bicyclooctyl groups, adamantyl groups, etc., can be used.

[0126] R 2 , R 4 , R 7 , R 9 , R 12 , R 14 As shown, the substituent is attached at the meta position of the phenyl group. Having this feature is preferable because it allows for a lower film density and thus a lower refractive index.

[0127] Note R 2 , R 4 , R 7 , R 9 , R 12 , R 14 Of these, at least two are hydrogen. However, the steric hindrance around A can be reduced (where LUMO orbitals are mainly distributed). This reduces the steric hindrance of its substituents, improves electron transport, and reduces the drive voltage. This is possible and desirable.

[0128] Another aspect of the present invention is an organic compound represented by the general formula (G3).

[0129] [ka]

[0130] In general formula (G3), Q 1 to Q 3 Among them, 2 or 3 represent N, and Q 1 to Q 3 Among them When 2 of them are N, the remaining 1 represents CH. Also, R 1 to R 15 At least one of is a phenyl group having a substituent, and the others are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms , an alicyclic group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 14 carbon atoms forming a substituted or unsubstituted ring , or a substituted or unsubstituted pyridyl group. The phenyl group having a substituent has 1 or 2 substituents, and each of the substituents is independently , an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 14 carbon atoms forming a substituted or unsubstituted ring , or a heteroaromatic ring group having 3 to 9 carbon atoms forming a substituted or unsubstituted ring. In addition, the organic compound represented by the above general formula (G3) has a plurality of hydrocarbon groups selected from an alkyl group having 1 to 6 carbon atoms and an alicyclic group having 3 to 10 carbon atoms, and the ratio of the total number of carbon atoms forming bonds with sp3 hybrid orbitals to the total number of carbon atoms in the molecule is 10% or more and 60% or less . . Note that in the structure of the organic compound represented by the above general formula (G3), the ratio of the total number of carbon atoms forming bonds with sp3 hybrid orbitals affects the refractive index of the organic compound. That is , when the total number of carbon atoms forming bonds with sp3 hybrid orbitals increases, the refractive index decreases, so the light extraction efficiency of a light-emitting device using this can be improved. Also, sp3 hybrid .

[0131] Note that in the structure of the organic compound represented by the above general formula (G3), the ratio of the total number of carbon atoms forming bonds with sp3 hybrid orbitals affects the refractive index of the organic compound. That is, when the total number of carbon atoms forming bonds with sp3 hybrid orbitals increases, the refractive index decreases, so the light extraction efficiency of a light-emitting device using this can be improved. Also, sp3 hybrid ​​​When the total number of carbon atoms forming bonds in the orbital increases, the heat resistance such as the glass transition point is improved and is preferable. However, if the total number of carbon atoms forming bonds in the sp3 hybrid orbital becomes too large the overlap of the LUMO orbitals with adjacent molecules among the molecules of the organic compound is inhibited and the carrier transport property (such as electron transport property and injection property) decreases. Therefore, the ratio of the total number of carbon atoms forming bonds in the sp3 hybrid orbital to the total number of carbon atoms in the molecule is preferably 10% or more and 60% or less, and more preferably 20% or more and 50% or less. Furthermore, it is preferable that the ratio of the total number of carbon atoms forming bonds in the sp3 hybrid orbital to the total number of carbon atoms in the molecule is 20% or more and 40% or less. Furthermore, it is preferable that the ratio of the total number of carbon atoms forming bonds in the sp3 hybrid orbital to the total number of carbon atoms in the molecule is 20% or more and 40% or less. Furthermore, it is preferable that the ratio of the total number of carbon atoms forming bonds in the sp3 hybrid orbital to the total number of carbon atoms in the molecule is 20% or more and 40% or less.

[0132] In addition, when the organic compound represented by the general formula (G3) is composed only of a 6-membered heteroaromatic ring containing Q 1 to Q 3 , a 6-membered aromatic ring (that is, a substituted or unsubstituted phenyl group), and a hydrocarbon group (alkyl group or alicyclic group) forming a bond in the sp3 hybrid orbital ( that is, when it does not contain a condensed ring), the refractive index is low and the carrier (electron) transport property is also high so it is preferable.

[0133] In addition, in the organic compound represented by the general formula (G3), for the 6-membered ring containing Q 1 to Q 3 , a pyridine ring or a triazine ring can be used. When the organic compound represented by the general formula (G3 ) is used in a layer adjacent to the light-emitting layer or the active layer, a triazine ring, a pyrazine ring, or a pyrimidine ring that can easily inject electrons into these layers and has good electron transport property is preferable and a triazine ring is particularly preferable.

[0134] ​​​​​ Furthermore, in the organic compound represented by the above general formula (G3), substituents (alkyl group and alicyclic group) The total number of (substances) per molecule should be between 4 and 10, taking synthesis costs into consideration. It is preferable, and even more preferable if the refractive index is 6 or higher to lower it further. Similarly, Using larger substituents (alkyl groups or alicyclic groups) allows for refraction even with fewer substituents. It effectively reduces the rate, and considering the synthesis cost, the number of carbon atoms in the alkyl group is 4. It is more preferable that the number of carbon atoms in the alicyclic group be 6 or more.

[0135] Furthermore, in the organic compound represented by the above general formula (G3), the number of carbon atoms forming the ring is 6 The aromatic hydrocarbon groups up to 14 include substituted or unsubstituted phenyl groups, naphthyl groups, and phenyl groups. Phenanthryl groups and fluorenyl groups can be used. In particular, phenyl groups have a low refractive index. It is preferable because it can be done. Also, the naphthyl group, phenanthryl group, and fluorenyl group are gal This is preferable because it can raise the transition temperature. Also, the number of carbon atoms that form these rings The aromatic hydrocarbon group has 6 to 14 carbon atoms, and the branched alkyl group has 3 to 5 carbon atoms or Substitution with a chloroalkyl group increases the glass transition temperature while simultaneously increasing the refractive index. This is preferable because it provides the effect of maintaining a low refractive index. From the viewpoint of reduction, aromatic hydrocarbon groups having 6 to 14 carbon atoms that form the above ring are carbon Alkyl groups with 1 to 6 elementary atoms, alicyclic groups with 3 to 10 carbon atoms, and groups with 1 to 6 carbon atoms. A carbon source that forms a ring substituted with an alkyl group or an alicyclic group having 3 to 10 carbon atoms. It is preferable that the group is substituted with any aromatic hydrocarbon group having 6 to 14 atoms. For example, the 1,3-di(t-butyl)phenyl group and the 1,3-dicyclohexylphenyl group Sea urchin, with an alkyl group having 1 to 6 carbon atoms, or an alicyclic group having 3 to 10 carbon atoms. A substituted phenyl group is preferred. Also, 3-t-butyl-5-[1,3-di(t-butyl )phenyl]phenyl group, or 3-cyclohexyl-5-[1,3-dicyclohexylphenyl [Nyl]phenyl group, such as an alkyl group having 1 to 6 carbon atoms or a group having 3 to 6 carbon atoms Phenyl groups substituted with 10 alicyclic groups are preferred. When rings are used and the number of fused rings is three or more, if the other six-membered rings are a When the ring is fused only at positions c and e, the refractive index can be lower compared to polyacene. Therefore, it is preferable. For example, the phenanthrene ring has a higher refractive index than the anthracene ring. It can be lowered.

[0136] Furthermore, the number of carbon atoms forming the ring in the organic compound represented by the above general formula (G3) is 3. The heteroaromatic ring groups up to 9 include pyridyl group, pyrimidinyl group, pyrazinyl group, and triazinyl group. The following can be used: quinolyl group, quinozolinyl group, quinoxalinyl group, etc.

[0137] Furthermore, in the organic compound represented by the above general formula (G3), alkyl groups having 1 to 6 carbon atoms The propyl group can be a methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group. Groups such as butyl, tert-butyl, pentyl, and hexyl can be used. Examples of alicyclic groups having 3 to 10 carbon atoms include cyclopropyl group, cyclohexyl group, and cyclo Rhodecanyl groups, bicyclooctyl groups, adamantyl groups, etc., can be used.

[0138] Another aspect of the present invention is an organic compound represented by the general formula (G4).

[0139] [ka]

[0140] In the above general formula (G4), Q 1 ~Q 3 Of these, 2 or 3 represent N, and Q 1 ~Q 3 If 2 of them are N, the remaining 1 represents CH. Also, R 2 , R 4 , R 7 , R 9 , R 12 , R 14 At least one of them is a substituted phenyl group, and the others are each a phenyl group. In addition, hydrogen, alkyl groups having 1 to 6 carbon atoms, alicyclic groups having 3 to 10 carbon atoms, substitution Alternatively, aromatic hydrocarbon groups with 6 to 14 carbon atoms forming an unsubstituted ring, substituted or unsubstituted. Represents one of the substituted pyridyl groups. A substituted phenyl group can have one or two substitutions. It has a substitution group, and each substituent is independently an alkyl group having 1 to 6 carbon atoms, and a alkyl group having 3 carbon atoms. Aromatic groups having 6 to 14 carbon atoms forming alicyclic groups of up to 10 alicyclic groups, or substituted or unsubstituted rings. Hydrocarbon groups, heteroaromatic ring groups with 3 to 9 carbon atoms forming a substituted or unsubstituted ring, It is one of the following. Note that the organic compound represented by the above general formula (G4) has 1 to 1 carbon atoms. It has multiple hydrocarbon groups selected from 6 alkyl groups and alicyclic groups having 3 to 10 carbon atoms. And the total number of carbon atoms in the molecule that form bonds with sp3 hybrid orbitals The percentage is between 10% and 60%.

[0141] Furthermore, in the structure of the organic compound represented by the above general formula (G4), the bonds are formed by sp3 hybrid orbitals. The proportion of the total number of carbon atoms forming a compound affects the refractive index of the organic compound. That is, As the total number of carbon atoms forming bonds in sp3 hybrid orbitals increases, the refractive index decreases. This can improve the light extraction efficiency of light-emitting devices using this technology. As the total number of carbon atoms forming bonds in the orbitals increases, heat resistance, such as the glass transition temperature, improves. And it is preferable. However, the total number of carbon atoms forming bonds in sp3 hybrid orbitals becomes large. If this is excessive, the overlap of LUMO orbitals between adjacent molecules in organic compounds is inhibited. As a result, carrier transportability (such as electron transportability and injectionability) decreases, and the total amount within the molecule The ratio of the total number of carbon atoms to the total number of carbon atoms that form bonds with sp3 hybrid orbitals is 10%. Preferably, the above is 60% or less, and more preferably 20% to 50%. Furthermore, the total within the molecule The ratio of the total number of carbon atoms to the total number of carbon atoms that form bonds with sp3 hybrid orbitals should be 20% or less. It is preferable to keep it below 40%.

[0142] Furthermore, the organic compound represented by the above general formula (G4) is Q 1 ~Q 3 A 6-membered ring complex aromatic compound containing A fragrance ring, a 6-membered aromatic ring (i.e., a substituted or unsubstituted phenyl group), and sp3 hybrid orbitals. When it is formed only by hydrocarbon groups (alkyl groups or alicyclic groups) that form bonds ( In other words, if a fused ring is not included, the refractive index becomes lower, and the carrier (electron) transport properties also become higher. Therefore, it is preferable.

[0143] Furthermore, in the organic compound represented by the above general formula (G4), Q 1 ~Q 3 A 6-membered ring including For this purpose, a pyridine ring or a triazine ring can be used. Note that the above general formula (G4 When using an organic compound represented by ) in a layer in contact with the light-emitting layer or active layer, electrons are present in these layers. Triazine rings, pyrazine rings, and pyrimidine rings are preferred because they are easy to inject and have good electron transport properties. A triazine ring is particularly preferred.

[0144] Furthermore, in the organic compound represented by the above general formula (G4), substituents (alkyl group and alicyclic group) The total number of (substances) per molecule should be between 4 and 10, taking synthesis costs into consideration. It is preferable, and even more preferable if the refractive index is 6 or higher to lower it further. Similarly, Using larger substituents (alkyl groups or alicyclic groups) allows for refraction even with fewer substituents. It effectively reduces the rate, and considering the synthesis cost, the number of carbon atoms in the alkyl group is 4. It is more preferable that the number of carbon atoms in the alicyclic group be 6 or more.

[0145] Furthermore, in the organic compound represented by the above general formula (G4), the number of carbon atoms forming the ring is 6 The aromatic hydrocarbon groups up to 14 include substituted or unsubstituted phenyl groups, naphthyl groups, and phenyl groups. Phenanthryl groups and fluorenyl groups can be used. In particular, phenyl groups have a low refractive index. It is preferable because it can be done. Also, the naphthyl group, phenanthryl group, and fluorenyl group are gal This is preferable because it can raise the transition temperature. Also, the number of carbon atoms that form these rings The aromatic hydrocarbon group has 6 to 14 carbon atoms, and the branched alkyl group has 3 to 5 carbon atoms or Substitution with a chloroalkyl group increases the glass transition temperature while simultaneously increasing the refractive index. This is preferable because it provides the effect of maintaining a low refractive index. From the viewpoint of reduction, aromatic hydrocarbon groups having 6 to 14 carbon atoms that form the above ring are carbon Alkyl groups with 1 to 6 elementary atoms, alicyclic groups with 3 to 10 carbon atoms, and groups with 1 to 6 carbon atoms. A carbon source that forms a ring substituted with an alkyl group or an alicyclic group having 3 to 10 carbon atoms. It is preferable that the group is substituted with any aromatic hydrocarbon group having 6 to 14 atoms. For example, the 1,3-di(t-butyl)phenyl group and the 1,3-dicyclohexylphenyl group Sea urchin, with an alkyl group having 1 to 6 carbon atoms, or an alicyclic group having 3 to 10 carbon atoms. A substituted phenyl group is preferred. Also, 3-t-butyl-5-[1,3-di(t-butyl )phenyl]phenyl group, or 3-cyclohexyl-5-[1,3-dicyclohexylphenyl [Nyl]phenyl group, such as an alkyl group having 1 to 6 carbon atoms or a group having 3 to 6 carbon atoms Phenyl groups substituted with 10 alicyclic groups are preferred. When rings are used and the number of fused rings is three or more, if the other six-membered rings are a When the ring is fused only at positions c and e, the refractive index can be lower compared to polyacene. Therefore, it is preferable. For example, the phenanthrene ring has a higher refractive index than the anthracene ring. It can be lowered.

[0146] Furthermore, the number of carbon atoms forming the ring in the organic compound represented by the above general formula (G4) is 3. The heteroaromatic ring groups up to 9 include pyridyl group, pyrimidinyl group, pyrazinyl group, and triazinyl group. The following can be used: quinolyl group, quinozolinyl group, quinoxalinyl group, etc.

[0147] Furthermore, in the organic compound represented by the above general formula (G4), alkyl groups having 1 to 6 carbon atoms The propyl group can be a methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group. Groups such as butyl, tert-butyl, pentyl, and hexyl can be used. Examples of alicyclic groups having 3 to 10 carbon atoms include cyclopropyl group, cyclohexyl group, and cyclo Rhodecanyl groups, bicyclooctyl groups, adamantyl groups, etc., can be used.

[0148] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), the substituted phenyl group is represented by the following general formula (G1- It is preferable to represent it as in 2).

[0149] [ka]

[0150] In the above general formula (G1-2), α represents a substituted or unsubstituted phenylene group. Also, R 20 This includes alkyl groups having 1 to 6 carbon atoms, alicyclic groups having 3 to 10 carbon atoms, or Aromatic hydrocarbon groups with 6 to 14 carbon atoms forming a substituted or unsubstituted ring, substituted or m represents a heteroaromatic ring group with 3 to 9 carbon atoms forming an unsubstituted ring. n represents a value between 1 and 2. Note that when m is 2, the multiple αs may be the same or different. Also, if n is 2, multiple R 20 These can be the same or different.

[0151] In the above configuration, the phenyl group having substituents represented by the above general formula (G1-2) is one Organic compounds represented by general formulas (G1), (G2), (G3), and (G4) R in compounds 2 and R 4It is preferable that either one or both of these be the case (however The group represented by the general formula (G1-2) is R 2 and R 4 If both are true, then the above general formula (G The two bases represented in 1-2) may be the same or different.

[0152] Furthermore, in a phenyl group having substituents represented by the above general formula (G1-2), the carbon atoms Examples of alkyl groups with a number of 1 to 6 include methyl group, ethyl group, propyl group, isopropyl group, By using butyl groups, isobutyl groups, tert-butyl groups, pentyl groups, hexyl groups, etc. This is possible. In addition, as alicyclic groups having 3 to 10 carbon atoms, cyclopropyl group, cyclopropyl group, By using lohexyl groups, cyclodecanyl groups, bicyclooctyl groups, adamantyl groups, etc. It is possible.

[0153] Furthermore, in a phenyl group having substituents represented by the above general formula (G1-2), a ring is formed. Aromatic hydrocarbon groups with 6 to 14 carbon atoms include substituted or unsubstituted phenyl A naphthyl group, a phenanthryl group, or a fluorenyl group can be used. In particular, a naphthyl group can be used. The flu group is preferred because it allows for a lower refractive index. Also preferred are the naphthyl group, phenanthryl group, and flu group. The olen group is preferred because it can raise the glass transition temperature. The aromatic hydrocarbon group formed has 6 to 14 carbon atoms, and the branched group has 3 to 14 carbon atoms. Substitution with alkyl or cycloalkyl groups increases the glass transition temperature simultaneously This is preferable because it prevents the refractive index from increasing (i.e., maintains a low refractive index). Furthermore, from the viewpoint of reducing the refractive index, fragrances with 6 to 14 carbon atoms forming the above ring are available. Group hydrocarbons include alkyl groups having 1 to 6 carbon atoms, and alicyclic groups having 3 to 10 carbon atoms. Substituted with an alkyl group having 1 to 6 carbon atoms or an alicyclic group having 3 to 10 carbon atoms It is substituted with any of the aromatic hydrocarbon groups having 6 to 14 carbon atoms forming a ring. Preferably, a 1,3-di(t-butyl)phenyl group, a 1,3-dicyclohex group Alkyl groups with 1 to 6 carbon atoms, such as silphenyl groups, or groups with 3 to 6 carbon atoms Phenyl groups substituted with 10 alicyclic groups are preferred. Also, 3-t-butyl-5-[1, 3-di(t-butyl)phenyl]phenyl group, or 3-cyclohexyl-5-[1,3-di [Cyclohexylphenyl] A phenyl group, or an alkyl group having 1 to 6 carbon atoms A phenyl group substituted with a phenyl group substituted with an alicyclic group having 3 to 10 carbon atoms is preferred. It is also the case that when fused rings are used, and the number of fused rings is three or more, the six-membered ring is... And when the other six-membered rings are fused only at positions a, c, and e, the refractive index is compared to polyacene. This is preferable because it can lower the value. For example, the phenanthrene ring is preferable to anthracene. The refractive index can be lowered compared to a ring.

[0154] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), the substituted phenyl group is represented by the following general formula (G1- It is preferable that it be represented as in 3).

[0155] [ka]

[0156] In the above general formula (G1-3), R 21 hydrogen, alkyl groups having 1 to 6 carbon atoms, carbon Alicyclic groups having 3 to 10 elementary atoms, or substituents represented by the general formula (G1-3-1), It represents a difference of 1. Also, R 22 This represents a substituent represented by the general formula (G1-3-1). In general formula (G1-3-1), R 23 and R 24 These are hydrogen and alkyl groups having 1 to 6 carbon atoms. R represents either a group or an alicyclic group having 3 to 10 carbon atoms. 23 and R 24 At least one of them is an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 3 to 10 carbon atoms. It is an alicyclic group. 23 and R 24 Both are alkyl groups having 1 to 6 carbon atoms. It is more preferable that n is an alicyclic group having 3 to 10 carbon atoms. Also, n is 0 to 2 This represents multiple R. 21 These may be the same or different. Note that if n is 0, R 23 and R 24 At least one of them has 1 to 6 carbon atoms It shall be either an alkyl group or an alicyclic group having 3 to 10 carbon atoms.

[0157] Furthermore, the phenyl group having substituents represented by the above general formula (G1-3) is general formula (G1) ~(G4) R 2 and R 4 It is preferable that it be either one or both of the following: However, the group represented by the general formula (G1-3) is R 2 and R 4 If both are true, then the above general The two bases represented by formula (G1-3) may be the same or different.

[0158] Furthermore, in the phenyl group having substituents represented by the general formula (G1-3) above, the carbon atoms Examples of alkyl groups with a number of 1 to 6 include methyl group, ethyl group, propyl group, isopropyl group, By using butyl groups, isobutyl groups, tert-butyl groups, pentyl groups, hexyl groups, etc. This is possible. In addition, as alicyclic groups having 3 to 10 carbon atoms, cyclopropyl group, cyclopropyl group, By using lohexyl groups, cyclodecanyl groups, bicyclooctyl groups, adamantyl groups, etc. It is possible.

[0159] Furthermore, in a phenyl group having substituents represented by the above general formula (G1-3), a ring is formed. Aromatic hydrocarbon groups with 6 to 14 carbon atoms include substituted or unsubstituted phenyl A naphthyl group, a phenanthryl group, or a fluorenyl group can be used. In particular, a naphthyl group can be used. The flu group is preferred because it allows for a lower refractive index. Also preferred are the naphthyl group, phenanthryl group, and flu group. The olen group is preferred because it can raise the glass transition temperature. The aromatic hydrocarbon group formed has 6 to 14 carbon atoms, and the branched group has 3 to 14 carbon atoms. Substitution with alkyl or cycloalkyl groups increases the glass transition temperature simultaneously This is preferable because it prevents the refractive index from increasing (i.e., maintains a low refractive index). Furthermore, from the viewpoint of reducing the refractive index, fragrances with 6 to 14 carbon atoms forming the above ring are available. Group hydrocarbons include alkyl groups having 1 to 6 carbon atoms, and alicyclic groups having 3 to 10 carbon atoms. Substituted with an alkyl group having 1 to 6 carbon atoms or an alicyclic group having 3 to 10 carbon atoms It is substituted with any of the aromatic hydrocarbon groups having 6 to 14 carbon atoms forming a ring. Preferably, a 1,3-di(t-butyl)phenyl group, a 1,3-dicyclohex group Alkyl groups with 1 to 6 carbon atoms, such as silphenyl groups, or groups with 3 to 6 carbon atoms Phenyl groups substituted with 10 alicyclic groups are preferred. Also, 3-t-butyl-5-[1, 3-di(t-butyl)phenyl]phenyl group, or 3-cyclohexyl-5-[1,3-di [Cyclohexylphenyl] A phenyl group, or an alkyl group having 1 to 6 carbon atoms A phenyl group substituted with a phenyl group substituted with an alicyclic group having 3 to 10 carbon atoms is preferred. It is also the case that when fused rings are used, and the number of fused rings is three or more, the six-membered ring is... And when the other six-membered rings are fused only at positions a, c, and e, the refractive index is compared to polyacene. This is preferable because it can lower the value. For example, the phenanthrene ring is preferable to anthracene. The refractive index can be lowered compared to a ring.

[0160] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), the aromatic compound has 6 to 14 carbon atoms forming a ring. A hydrocarbon group or a heteroaromatic ring group having 3 to 9 carbon atoms forming a ring has substituents. In addition, the substituents are alkyl groups having 1 to 6 carbon atoms, and alicyclic groups having 3 to 10 carbon atoms. unsubstituted aromatic hydrocarbon groups having 6 to 14 carbon atoms, alkyl groups having 1 to 6 carbon atoms A ring formed by a group or an alicyclic group having 3 to 10 carbon atoms, with 6 carbon atoms. Preferably, it is one of the 14 aromatic hydrocarbon groups. The alkyl groups include methyl, ethyl, propyl, isopropyl, and butyl groups. Isobutyl groups, tert-butyl groups, pentyl groups, hexyl groups, etc., can be used. Furthermore, as alicyclic groups having 3 to 10 carbon atoms, cyclopropyl group, cyclohexyl Groups such as cyclodecanyl, bicyclooctyl, and adamantyl can be used. Furthermore, aromatic hydrocarbon groups with 6 to 14 carbon atoms include the phenyl group and the naphthyl group. Phenanthryl groups and fluorenyl groups can be used. In particular, the phenyl group has a refractive index. It is preferable because it can be made low. Also, the naphthyl group, phenanthryl group, and fluorenyl group are This is preferable because it can raise the glass transition temperature. Also, the carbon atoms that form these rings A branched alkyl group with 3 to 5 carbon atoms, which contains an aromatic hydrocarbon group with 6 to 14 carbon atoms. Substitution with cycloalkyl groups increases the glass transition temperature and simultaneously raises the refractive index. This is preferable because it results in the effect of not refraction (i.e., maintaining a low refractive index). From the viewpoint of reducing the rate, aromatic hydrocarbon groups having 6 to 14 carbon atoms forming the above ring are alkyl groups having 1 to 6 carbon atoms, alicyclic groups having 3 to 10 carbon atoms, and groups having 1 carbon atom Carbons forming a ring substituted with alkyl groups up to 6 or alicyclic groups having 3 to 10 carbon atoms. It is preferable that the group is substituted with any aromatic hydrocarbon group having 6 to 14 elementary atoms. For example, the 1,3-di(t-butyl)phenyl group and the 1,3-dicyclohexylphenyl group. As shown, alkyl groups having 1 to 6 carbon atoms, or alicyclic groups having 3 to 10 carbon atoms. A phenyl group substituted with is preferred. Also, 3-t-butyl-5-[1,3-di(t-butyl [Tyl)phenyl]phenyl group, or 3-cyclohexyl-5-[1,3-dicyclohexyl [Phenyl] A phenyl group, such as an alkyl group with 1 to 6 carbon atoms or a group with 3 carbon atoms. Phenyl groups substituted with phenyl groups substituted with 10 alicyclic groups are preferred. When fused rings are used, if the number of fused rings is three or more, one six-membered ring is paired with another six-membered ring. When the ring is fused only at positions a, c, and e, the refractive index is lower compared to polyacene. This is preferable because it allows for refraction. For example, the phenanthrene ring is more refraction-dependent than the anthracene ring. The rate can be lowered.

[0161] Furthermore, in each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and Organic compounds represented by general formula (G4), and the above general formulas (G1-2) and ( In a phenyl group having substituents represented by G1-3), the number of carbon atoms forming the ring is 6 Aromatic hydrocarbon groups 1 through 14 are represented by one of the following formulas (ra-1) to (ra-15). It is preferable that this be done.

[0162] [ka]

[0163] In each of the above configurations, general formula (G1), general formula (G2), general formula (G3), and general formula In the organic compound represented by (G4), the substituted or unsubstituted pyridyl group is an unsubstituted pyridyl group. A lysyl group, or a pyridyl group substituted with one or more methyl groups, is preferred. stomach.

[0164] Another aspect of the present invention is an organic compound represented by the general formula (G4').

[0165] [ka]

[0166] In the above general formula (G4'), Q 1 ~Q 3 Of these, 2 or 3 represent N, and Q 1 ~Q 3If two of them are N, the remaining one represents CH. Also, R 2 This is expressed by the following formula (R 2 -1 ) is represented as R 4 , R 7 , R 9 , R 12 , R 14 Each of these is independent of the following equation (r-1)~(r It represents one of the following (R 2 -1) In this case, β is substituted or unsubstituted phenyl R represents a len group, or a substituted or unsubstituted biphenyldiyl group. 25 is, equation (r-1 ) represents one of the following: (r-20), where n is either 1 or 2. Note that the above general formula (G4 The organic compounds represented by ') are alkyl groups having 1 to 6 carbon atoms and alkyl groups having 3 to 6 carbon atoms. It has multiple hydrocarbon groups selected from 10 alicyclic groups, and the sp ratio is relative to the total number of carbon atoms in the molecule. The proportion of total carbon atoms forming bonds in three hybrid orbitals is between 10% and 60%.

[0167] Furthermore, in the structure of the organic compound represented by the general formula (G4') above, sp3 hybrid orbitals are bonded together. The proportion of the total number of carbon atoms forming a compound affects the refractive index of the organic compound. As the total number of carbon atoms forming bonds in sp3 hybrid orbitals increases, the refractive index decreases. Therefore, it is possible to improve the light extraction efficiency of light-emitting devices using this. Also, sp3 As the total number of carbon atoms forming bonds in hybrid orbitals increases, the heat resistance, such as the glass transition temperature, improves. This is preferable. However, the total number of carbon atoms forming bonds in sp3 hybrid orbitals increases. If this is excessive, the overlap of LUMO orbitals between adjacent molecules in organic compounds is inhibited. As a result, carrier transport properties (such as electron transport and injection properties) decrease, within the molecule The ratio of the total number of carbon atoms that form bonds in sp3 hybrid orbitals to the total number of carbon atoms is 10 A percentage of % or more and 60% or less is preferred, and a percentage of 20% or more and 50% or less is more preferred. Furthermore, within the molecule The ratio of the total number of carbon atoms that form bonds with sp3 hybrid orbitals to the total number of carbon atoms is 20%. It is preferable that the percentage be 40% or less.

[0168] Furthermore, the organic compound represented by the above general formula (G4') is Q 1 ~Q 3 A complex 6-membered ring containing Aromatic rings, six-membered aromatic rings (i.e., substituted or unsubstituted phenyl groups), and sp3 hybrid orbitals. When formed only by hydrocarbon groups (alkyl groups or alicyclic groups) that form bonds in the road. (In other words, if it does not contain a fused ring), the refractive index will be lower, and the carrier (electron) transport properties will also be lower. This is preferable because it increases the price.

[0169] Furthermore, in the organic compound represented by the above general formula (G4'), Q 1 ~Q 3 A 6-membered ring including A pyridine ring or a triazine ring can be used as the above general formula (G When using the organic compound represented in 4') in a layer in contact with the luminescent layer or the active layer, these layers Triazine rings, pyrazine rings, and pyrimidine rings, which readily accept electrons and have good electron transport properties, A triazine ring is preferred, and a triazine ring is particularly preferred.

[0170] [ka]

[0171] The above formula (R 2 -1) The β in is a substituted or unsubstituted phenylene group, a biphenylene group, or a benzene group. A ¹-triyl group can be used. If substituents are present, a group having 1 to 6 carbon atoms can be used. Lukyl groups and alicyclic groups having 3 to 10 carbon atoms can be used.

[0172] Furthermore, (R in the organic compound represented by the above general formula (G4') 2 The above formula (R 2 - 1) R in the middle 25 is expressed by one of the following equations (r-1) to (r-20), where β is as follows It can be expressed as one of the equations (β-1) to (β-14).

[0173] [ka]

[0174] [ka]

[0175] Next, specific examples of organic compounds having the above-described configurations, which represent one aspect of the present invention, are shown below. .

[0176] [ka]

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] [ka]

[0181]

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[0182]

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[0183]

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[0184]

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[0185]

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[0186]

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[0187]

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[0188]

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[0189]

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[0190]

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[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] In the above general formula (G1), the one that consists only of a six-membered ring, an alkyl group, and an alicyclic group is It can have a low refractive index and absorption rate in the visible range, and can be used as an electron transport material for optical devices. In this case, it is preferable to be able to maintain a low drive voltage.

[0197] In the above general formula (G1), A is substituted with three substituted or unsubstituted phenyl groups. In that case, it is preferable that at least one of the phenyl groups does not contain substituents of an alkyl group or an alicyclic group. When used as an electron transport material in electronic devices, it is preferable because it allows the drive voltage to be kept low. For example, structural formulas (103), (107), (111), and (116) )~(129), Structural formula (212)~(215), Structural formula (218)~(221), Structure Formulas (311)~(316), Structural formulas (412)~(417), Structural formulas (600)~(60 5) are some examples.

[0198] Note that the above structural formulas (100) to (129), structural formulas (200) to (223), and structural formula (3 Structural formulas (00) to (317), structural formulas (400) to (435), structural formulas (500) to (506) Organic compounds represented by structural formulas (600) to (605) are represented by the general formula (G1) above. This is just one example of an organic compound, but the organic compounds that are part of this embodiment of the present invention are not limited to this. .

[0199] Next, according to one aspect of the present invention, a method for synthesizing an organic compound represented by the following general formula (G1) I will explain.

[0200] [ka]

[0201] In the general formula (G1) above, A represents a six-membered heteroaromatic ring containing one to three nitrogen atoms. Yes. Also, R 0 These are hydrogen, alkyl groups having 1 to 6 carbon atoms, and alicyclic groups having 3 to 10 carbon atoms. Represents either a formula group or a substituent represented by formula (G1-1). 1 ~R 15 few At least one of them is a substituted phenyl group, and the others are independently hydrogen and carbon. Alkyl groups with 1 to 6 atoms, alicyclic groups with 3 to 10 carbon atoms, substituted or unsubstituted rings Aromatic hydrocarbon groups having 6 to 14 carbon atoms, substituted or unsubstituted pyridyl groups that form the compound. It represents either of the following. A substituted phenyl group has one or two substituents, and Each substituent can independently be an alkyl group having 1 to 6 carbon atoms or an alicyclic group having 3 to 10 carbon atoms. Aromatic hydrocarbon groups with 6 to 14 carbon atoms forming a ring, substituted or unsubstituted, substituted Alternatively, it may be a heteroaromatic ring group with 3 to 9 carbon atoms forming an unsubstituted ring. Furthermore, the organic compound represented by the above general formula (G1) is an alkyl group having 1 to 6 carbon atoms. It has multiple hydrocarbon groups selected from alicyclic groups having 3 to 10 carbon atoms, and the total carbon in the molecule The ratio of the total number of carbon atoms forming bonds with sp3 hybrid orbitals to the number of elementary atoms is less than 10%. It is below 60%.

[0202] ≪Synthesis method for organic compounds represented by general formula (G1)≫ The following describes an example of a synthesis method for an organic compound represented by general formula (G1). Various reactions can be applied to the synthesis of these organic compounds. For example, the synthesis scheme As shown in (A-1), aryl halide (a1) and aryl halide (a2) Compound (a4) can be obtained by reacting (a3) ​​with (a4). In the above reaction, aryl halides (a2) and (a3) ​​are mixed with a Grignard reagent or a ly By using a thium compound and reacting it with an aryl halide (a1) in an ether solvent, This yields compound (a4).

[0203] [ka]

[0204] In the formula, A represents a six-membered heteroaromatic ring containing one to three nitrogen atoms. Also, R 1 ~R 1 0 At least one of them is a substituted phenyl group, and the others are each independently hydrogen , alkyl groups having 1 to 6 carbon atoms, alicyclic groups having 3 to 10 carbon atoms, substituted or absent Aromatic hydrocarbon groups with 6 to 14 carbon atoms forming a substitution ring, substituted or unsubstituted pyri It represents either a zyl group or any of the other. A phenyl group with substituents has one or two substituents. Each substituent is independently an alkyl group having 1 to 6 carbon atoms, or an alkyl group having 3 to 10 carbon atoms. Alicyclic groups, aromatic hydrocarbon groups having 6 to 14 carbon atoms that form substituted or unsubstituted rings. Either a substituted or unsubstituted heteroaromatic ring group with 3 to 9 carbon atoms forming a ring. Yes. Also, X 1 ~X 5 Each of these independently represents either chlorine, bromine, or iodine. .

[0205] In the above reaction, aryl halides (a2) and (a3) ​​are assumed to have the same structure. This is preferable as it increases the yield of aryl halides (a4). However, If the structures of reels (a2) and (a3) ​​are different, halogenation is performed in the first step. After reacting aryl (a1) with aryl halide (a2), in the second step, the obtained The synthesis step is completed in two steps by reacting the resulting product with an aryl halide (a3), for example. By dividing it into more than two parts, the yield of compound (a4) can be increased.

[0206] Note that R in the general formula (G1) 0 If it is hydrogen, X 3 By using hydrogen, the synthesis scheme Organic compounds represented by general formula (G1) can be synthesized using (A-1).

[0207] Next, as shown in the synthesis scheme (A-2) below, aryl halide (a4) and aryl By coupling it with the boron compound (a5), the target compound (G1) is formed. This can be achieved. This reaction uses a synthesis method that employs a metal catalyst in the presence of a base. This is possible, and for example, the Suzuki-Miyaura reaction can be used.

[0208] [ka]

[0209] In the formula, A represents a six-membered heteroaromatic ring containing one to three nitrogen atoms. Also, R 0 is, equation (G This represents the substituent shown in 1-1). Also, R 1 ~R 15 At least one of the following is It is a phenyl group with a conversion group, and the others are, independently, hydrogen and an alkyl group having 1 to 6 carbon atoms. A group, an alicyclic group having 3 to 10 carbon atoms, or a group with 6 carbon atoms forming a substituted or unsubstituted ring. Represents one of 14 aromatic hydrocarbon groups, substituted or unsubstituted pyridyl groups. A phenyl group having a group has one or two substituents, each substituent independently of a carbon Alkyl groups with 1 to 6 atoms, alicyclic groups with 3 to 10 carbon atoms, substituted or unsubstituted rings Aromatic hydrocarbon groups with 6 to 14 carbon atoms that form rings, substituted or unsubstituted rings. It is one of the heteroaromatic ring groups having 3 to 9 carbon atoms. 1 Boronic acid and pineapple This represents boronic acid esters such as ruboron. 3 is either chlorine, bromine, or iodine. Therefore, using the one with a larger atomic number is preferable because it increases reactivity. X 3 Boronic acid and boronic acid esters such as pinacol boron, Y 1 halogens and sulfon These can also be reacted to form a luoxy group.

[0210] Also R 0 However, alkyl groups having 1 to 6 carbon atoms, or alicyclic groups having 3 to 10 carbon atoms. In this case, the Grignard reagent or lithium compound of these alkyl or alicyclic groups , reacting with aryl halide (a4) in an ether solvent using a metal catalyst. Compound (a4) is obtained by this method. For example, using the Kumada-Tamao-Coliu coupling. It is possible.

[0211] In addition, in the above synthesis scheme (A-1), aryl halogen (a1) is arylho First, react with the um compound (a5), and then with the resulting compound and the aryl halide (a2) It is also acceptable to react (a3) ​​with the target product (G1). If all substitution groups have the same structure, these three substituents and halogenation in the first step X of aryl(a1) 1 ~X 3 When these are substituted and coupled, the synthetic cost This is preferable as it can suppress the problem.

[0212] Alternatively, as shown in the synthesis scheme (B-1) below, aryl halides ((b1) + ( b1-1)) is coupled with an arylboron compound (b2) to produce the target compound ( G1) can be synthesized. In this reaction, a metal catalyst is used in the presence of a base. It is possible to use a method, for example, the Suzuki-Miyaura reaction.

[0213] [ka]

[0214] In the formula, A represents a six-membered heteroaromatic ring containing one to three nitrogen atoms. Also, R 0 is hydrogen, Alkyl groups having 1 to 6 carbon atoms, alicyclic groups having 3 to 10 carbon atoms, or formula (G1- It represents any of the substituents shown in 1). Also, R 1 ~R 15 at least one of the following One is a phenyl group having substituents, and the others are each independently hydrogen and a carbon atom having 1 to 6 carbon atoms. Alkyl groups, alicyclic groups having 3 to 10 carbon atoms, carbon atoms forming substituted or unsubstituted rings This represents either an aromatic hydrocarbon group with 6 to 14 atoms, or a substituted or unsubstituted pyridyl group. A substituted phenyl group may have one or two substituents, and each substituent may be independent. The elements include alkyl groups with 1 to 6 carbon atoms, alicyclic groups with 3 to 10 carbon atoms, substitutions, or no substitutions. Aromatic hydrocarbon groups with 6 to 14 carbon atoms forming a substituted ring, or substituted or unsubstituted rings. It is one of the heteroaromatic ring groups having 3 to 9 carbon atoms. 2 is boronic acid and This represents boronic acid esters such as pinacolboron. 4 is chlorine, bromine, iodine, or Reactivity is determined by using the sulfonyloxy group with the larger atomic number. It is desirable because it increases. Also, X 4 Boronic acid treatments such as boronic acid and pinacol boron Ru, Y 2 These can also be reacted with halogens or sulfonyloxy groups.

[0215] In this synthesis scheme, the R of the arylboron compound (b2) 12 aryl halogens ( Y of substituent (b1) in (b1)+(b1-1) 2 An example of a reaction in which substitution is performed was shown, but The reaction is similar to that of aryl halides ((b1)+(b1-1)) 1 ~R 11 , R 13 ~R 15 You can also do it at the substitution position.

[0216] The above describes an example of a method for synthesizing an organic compound, which is one aspect of the present invention. This is not the only way to synthesize it; it may be synthesized by any other method.

[0217] The configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments. It is possible.

[0218] (Embodiment 2)

[0219] Figure 1(A) shows a diagram representing a light-emitting device according to one aspect of the present invention. The vice has a first electrode 101, a second electrode 102, and an EL layer 103, and the EL layer Using the electron transport layer material shown in Embodiment 1 or the organic compound shown in Embodiment 1 Yes, they are.

[0220] The EL layer 103 has an emissive layer 113, a hole injection layer 111 and / or hole transport layer. It may also have layer 112. The light-emitting layer 113 contains a light-emitting material, which is one embodiment of the present invention. The light-emitting device obtains light from the light-emitting material. The light-emitting layer 113 contains a host material, Other materials may be included. The electron transport layer material shown in Embodiment 1 is an electron transport layer The organic compounds shown in Embodiment 1 are included in the transport layer 114 and / or the electron injection layer 115. Whether the material is contained in the light-emitting layer 113 or the electron transport layer 114, the electron injection layer It doesn't matter if it's included in 115, or any of them.

[0221] In addition to these, Figure 1(A) also shows a hole injection layer 111 and a hole transport layer 112. However, the configuration of light-emitting devices is not limited to these. For example, hole transport layer 112 An electron blocking layer may be provided between the light-emitting layer 113 and the electron A hole block layer may be provided between the transport layer 114 and the other layer.

[0222] The electron transport layer material or organic compound has good electron transport properties, therefore electron transport layer 1 It is effective to use it in 14. Also, an electron transport layer material or organic material according to one aspect of the present invention The compound is mixed with an alkali metal organometallic complex to form electron transport layer 114 or / and electron injection The configuration used for layer 115 is preferable because it improves the driving voltage and luminous efficiency.

[0223] Furthermore, an organic compound according to one embodiment of the present invention can also be used as a host material. In this case, by co-depositing with the hole transport material, the organic compound and the hole transport material The configuration may also be one in which an excited complex is formed by [a specific method]. This enables effective energy transfer to the light-emitting material, resulting in high efficiency and a long lifespan. This makes it possible to provide a light-emitting device having the following characteristics.

[0224] The organic compound in one aspect of the present invention is an organic compound with a low refractive index, and therefore it is placed within the EL layer By using this in the part, a light-emitting device with good external quantum efficiency can be obtained.

[0225] Next, we will describe the detailed structure and materials of the light-emitting device mentioned above. One aspect of the present invention As described above, the light-emitting device has a pair of electrodes, the first electrode 101 and the second electrode 102, between them. It has an EL layer 103 consisting of multiple layers, and in any part of the EL layer 103, The material includes the electron transport layer material or organic compound disclosed in Embodiment 1.

[0226] The first electrode 101 is made of a metal, alloy, or conductive material with a large work function (specifically, 4.0 eV or more). It is preferable to form them using chemical compounds and mixtures thereof. Specifically, for example, For example, indium tin oxide (ITO), silica Indium oxide-tin oxide and indium oxide-zinc oxide containing silicon dioxide or silicon dioxide. Examples include indium oxide (IWZO) containing tungsten oxide and zinc oxide. These conductive metal oxide films are usually deposited by sputtering, but sol-ge It is also acceptable to use methods such as the Lu method for fabrication. An example of a fabrication method is indium oxide-oxide Zinc is used in a target where 1-20 wt% zinc oxide is added to indium oxide. Methods include forming by the puttering method. Additionally, tungsten oxide and zinc oxide are used. The contained indium oxide (IWZO) has a ratio of 0.5% to tungsten oxide relative to indium oxide. Sputtering is performed using a target containing 5-5 wt% zinc oxide and 0.1-1 wt% zinc oxide. It can also be formed by law. Other materials include gold (Au), platinum (Pt), and nickel (Ni). , tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt ( Co), copper (Cu), palladium (Pd), or nitrides of metallic materials (e.g., titanium nitride) Examples include (n). Graphene can also be used. Note that the composite material described later is EL By using it in the layer that is in contact with the first electrode 101 in layer 103, regardless of the work function, It will become possible to select the polar materials.

[0227] The EL layer 103 preferably has a laminated structure, but the laminated structure is not particularly limited. There is no fixed term, and it consists of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and a carrier block layer (positive Various layer structures such as pore-blocking layers, electron-blocking layers, exciton-blocking layers, and charge-generating layers are used. It can be applied. In this embodiment, as shown in Figure 1(A), the electron transport layer 114 In addition to the electron injection layer 115 and the light-emitting layer 113, the hole injection layer 111 and the hole transport layer 112 are also included. The configuration includes, as shown in Figure 1(B), an electron transport layer 114, an electron injection layer 115, and light emission. In addition to layer 113, hole injection layer 111, and hole transport layer 112, the structure has a charge generation layer 116. The two types of compositions will be explained below. The materials that make up each layer are specifically described below.

[0228] The hole injection layer 111 is a layer containing a substance having acceptor properties. Both organic and inorganic compounds can be used as materials.

[0229] Substances that exhibit acceptor properties include compounds containing electron-withdrawing groups (halogen groups or cyano groups). It is possible to use the substance, 7,7,8,8-tetracyano-2,3,5,6-tetrafluor Roquinodimethane (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) Examples include 10-octafluoro-7H-pyrene-2-ylidene)malononitrile. This is possible. In particular, electron-withdrawing groups can be found in condensed aromatic rings that have multiple complex atoms, such as HAT-CN. The bonded compound is preferably thermally stable. Also, electron-withdrawing groups (especially fluorogroups) are preferable. Radialene derivatives having halogen groups or cyano groups, such as [3] are very electron-accepting. It is preferable because it is high, specifically α,α',α''-1,2,3-cyclopropane Redentris [4-Cyano-2,3,5,6-Tetrafluorobenzeneacetonitrile] α,α',α''-1,2,3-cyclopropanetriylidentris[2,6-diclo [Ro-3,5-difluoro-4-(trifluoromethyl)benzeneacetonitrile], α, α',α''-1,2,3-cyclopropanetriylidentris[2,3,4,5,6- Examples include pentafluorobenzeneacetonitrile. Substances with acceptor properties. In addition to the organic compounds mentioned above, other examples include molybdenum oxide, vanadium oxide, and lutein. Nium oxides, tungsten oxides, manganese oxides, etc. can be used. In addition, Phthalocyanines such as phthalocyanine (abbreviated as H2Pc) and copper phthalocyanine (CuPc) The complex compound of the system, 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl [Diamino]biphenyl (abbreviation: DPAB), N,N'-bis{4-[bis(3-methylf [phenyl)amino]phenyl}-N,N'-diphenyl-(1,1'-biphenyl)-4, Aromatic amine compounds such as 4'-diamine (abbreviation: DNTPD), or poly(3,4-) (Thilydioxythiophene) / Poly(styrene sulfonate) (PEDOT / PSS), etc. The hole injection layer 111 can also be formed using polymers or the like. The material attracts electrons from adjacent hole transport layers (or hole transport materials) by applying an electric field. It can be removed.

[0230] Furthermore, the hole injection layer 111 contains the above-mentioned acceptor substance in a material having hole transport properties. Composite materials can also be used that have been modified to include acceptor properties. By using composite materials containing certain properties, the material used to form electrodes can be selected regardless of the work function. This means that, as the first electrode 101, not only materials with a large work function, but also... This allows us to use materials with small function values.

[0231] Examples of hole-transporting materials used in composite materials include aromatic amine compounds and carbazoles. Derivatives, aromatic hydrocarbons, polymer compounds (oligomers, dendrimers, polymers, etc.) Various organic compounds can be used. The materials are 1 x 10 -6 cm 2 It is preferable that the material has a hole mobility of / Vs or higher. It seems so. Below, we will discuss materials that can be used as hole transport materials in composite materials. List the organic compounds specifically.

[0232] Aromatic amine compounds that can be used in composite materials include N,N'-di(p-tolyl )-N,N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4' -Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated) 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 Examples include carbazole derivatives such as [Duaminobenzene] (abbreviation: DPA3B). Specifically, 3-[N-(9-phenylcarbazole-3-yl)-N-phenylcarbazole-3-yl] [Nylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N -(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole Bazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenyl Carbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) ), 4,4'-di(N-carbazolyl)biphenyl (abbreviation: CBP), 1,3,5-tri Su[4-(N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(1 0-phenylanthracene-9-yl)phenyl]-9H-carbazole (abbreviation: CzP) A) 1,4-bis[4-(N-carbazolyl)phenyl]-2,3,5,6-tetraph Phenylbenzene and the like can be used. As aromatic hydrocarbons, for example, 2-ter t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 2 -tert-butyl-9,10-di(1-naphthyl)anthracene, 9,10-bis(3 ,5-diphenylphenyl)anthracene (abbreviation: DPPA), 2-tert-butyl- 9,10-Bis(4-phenylphenyl)anthracene (abbreviation: t-BuDBA), 9, 10-di(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylant Helical (abbreviation: DPA Anth), 2-tert-butylanthracene (abbreviation: t-BuA nth), 9,10-bis(4-methyl-1-naphthyl)anthracene (abbreviation: DMNA) ), 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthra Sen, 9,10-bis[2-(1-naphthyl)phenyl]anthracene, 2,3,6,7 -Tetramethyl-9,10-di(1-naphthyl)anthracene, 2,3,6,7-tetra Methyl-9,10-di(2-naphthyl)anthracene, 9,9'-bianthryl, 10, 10'-Diphenyl-9,9'-biantryl, 10,10'-bis(2-phenylphenyl Nil)-9,9'-biantril, 10,10'-bis[(2,3,4,5,6-penta Phenyl)phenyl]-9,9'-bianthryl, anthracene, tetracene, rubrene Examples include perylene and 2,5,8,11-tetra(tert-butyl)perylene. In addition, pentacene, coronene, etc. can also be used. It has a vinyl skeleton. This is also good. Examples of aromatic hydrocarbons having a vinyl group include 4,4'-bis(2, 2-Diphenylvinyl)biphenyl (abbreviation: DPVBi), 9,10-bis[4-(2, Examples include 2-diphenylvinyl)phenyl]anthracene (abbreviated as DPVPA). Furthermore, an organic compound according to one embodiment of the present invention can also be used.

[0233] Also, poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenyl (Abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamine) [Phenylamino(N'-phenylamino)phenyl(N'-phenylamino)phenyl(methacrylamide) (abbreviated) Name: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis( High molecular weight compounds such as phenyl(benzidine) (abbreviated as Poly-TPD) can also be used. Cut.

[0234] Examples of hole-transporting materials used in composite materials include carbazole skeletons and dibenzof It must have one of the following skeletons: a ranic skeleton, a dibenzothiophene skeleton, or an anthracene skeleton. More preferably, having substituents including a dibenzofuran ring or a dibenzothiophene ring. Aromatic amines, aromatic monoamines having a naphthalene ring, or 9-fluorenyl group It may also be an aromatic monoamine to which the nitrogen of the amine is bonded via an arylene group. These organic compounds are substances that have an N,N-bis(4-biphenyl)amino group. This is preferable because it allows for the fabrication of light-emitting devices with a good lifespan. Specifically, the compound is N-(4-biphenyl)-6,N-diphenylbenzo[b] Naphtho[1,2-d]furan-8-amine (abbreviation: BnfABP), N,N-bis(4- Biphenyl)-6-phenylbenzo[b]naphtho[1,2-d]furan-8-amine (abbreviated) Name: BBABnf), 4,4'-bis(6-phenylbenzo[b]naphtho[1,2-d] furan-8-yl-4''-phenyltriphenylamine (abbreviation: 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-bis 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''-diphenyltri 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-Iltriphenylamine (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)tri 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 (Lu)-4''-phenyltriphenylamine (abbreviation: TPBiAβNB), 4-(3-Bi) Phenylyl)-4'-[4-(2-naphthyl)phenyl]-4''-phenyltriphenyl Luamine (abbreviation: mTPBiAβNBi), 4-(4-biphenylyl)-4'-[4-( 2-Naphthyl)phenyl]-4''-phenyltriphenylamine (abbreviation: TPBiAβ) NBi), 4-phenyl-4'-(1-naphthyl)triphenylamine (abbreviation: αNBA) 1BP), 4,4'-bis(1-naphthyl)triphenylamine (abbreviation: αNBB1BP) ), 4,4'-diphenyl-4''-[4'-(carbazole-9-yl)biphenyl- 4-yl]triphenylamine (abbreviation: YGTBi1BP), 4'-[4-(3-phenyl Lu-9H-carbazole-9-yl)phenyl]tris(1,1'-biphenyl-4-yl) (Abbreviation: YGTBi1BP-02), 4-[4'-(carbazole-9-yl) )biphenyl-4-yl]-4'-(2-naphthyl)-4''-phenyltriphenyl Min (abbreviation: YGTBiβNB), N-[4-(9-phenyl-9H-carbazole-3 -yl)phenyl]-N-[4-(1-naphthyl)phenyl]-9,9'-spirobio 9H-Fluorene)-2-amine (abbreviation: PCBNBSF), N,N-bis([1,1' -biphenyl]-4-yl)-9,9'-spirobio[9H-fluorene]-2-amine( Abbreviation: BBASF), N,N-bis(1,1'-biphenyl-4-yl)-9,9'-s Pyrobi[9H-fluorene]-4-amine (abbreviation: BBASF(4)), N-(1,1' -biphenyl-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)- 9,9'-Spirobi(9H-Fluorene)-4-amine (abbreviation: oFBiSF), N-( 4-biphenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo Ran-4-amine (abbreviation: FrBiF), N-[4-(1-naphthyl)phenyl]-N- [3-(6-phenyldibenzofuran-4-yl)phenyl]-1-naphthylamine (abbreviated) Name: mPDBfBNBN), 4-phenyl-4'-(9-phenylfluoren-9-yl) ) Triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenyl Luolen-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl-4 '-[4-(9-phenylfluoren-9-yl)phenyl]triphenylamine (abbreviation) :BPAFLBi), 4-phenyl-4'-(9-phenyl-9H-carbazole-3- Il)triphenylamine (abbreviation: PCBA1BP), 4,4'-diphenyl-4''- (9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBB) i1BP), 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3- Il)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4 ''-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: P CBNBB), N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-I [Phenyl]-9,9'-spirobio[9H-fluorene]-2-amine (abbreviated as PCB) ASF), N-(1,1'-biphenyl-4-yl)-9,9-dimethyl-N-[4-( 9-phenyl-9H-carbazole-3-yl)phenyl]-9H-fluoren-2-yl Min (abbreviation: PCBBiF), N,N-bis(9,9-dimethyl-9H-fluorene-2) -yl)-9,9'-spirobio-9H-fluorene-4-amine, N,N-bis(9,9 -dimethyl-9H-fluoren-2-yl)-9,9'-spirobio-9H-fluoren- 3-amine, N,N-bis(9,9-dimethyl-9H-fluoren-2-yl)-9,9 '-Spirobi-9H-fluoren-2-amine, N,N-bis(9,9-dimethyl-9H Examples include (-fluoren-2-yl)-9,9'-spirovi-9H-fluoren-1-amine. It is possible to do so.

[0235] Furthermore, hole-transporting materials used in composite materials have a highest occupied orbital (Highest The Occupied Molecular Orbital (HOMO) level is -5. Furthermore, the substance has a relatively deep HOMO level between 7 eV and -5.4 eV. Preferred. 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 improves the lifespan. This makes it easier to obtain light-emitting devices.

[0236] Furthermore, alkali metal or alkaline earth metal fluorides are preferably mixed into the above composite material. Alternatively, by increasing the atomic ratio of fluorine atoms in the layer to 20% or more, the refraction of the layer The ratio can be reduced. This also allows a layer with a lower refractive index to form inside the EL layer 103. This can be achieved, and the external quantum efficiency of light-emitting devices can be improved.

[0237] By forming the hole injection layer 111, the hole injection performance is improved, and the driving voltage is reduced. A light-emitting device can be obtained. In addition, organic compounds with acceptability can be deposited. Because it is easy to process and readily forms thin films, it is a user-friendly material.

[0238] The hole transport layer 112 is formed by including a material that has hole transport properties. The materials are 1 x 10 -6 cm 2 It is preferable to have a hole mobility of / Vs or higher. .

[0239] As a material having the above hole transport properties, 4,4'-bis[N-(1-naphthyl)-N-f [phenylamino]biphenyl (abbreviation: NPB), 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 [Luaminobiphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorine) Len-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-( 9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4 -phenyl-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (Abbreviation: PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H- Carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1- Naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl- 9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9- Dimethyl-N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl) Phenyl]fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-( 9-phenyl-9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H Chemical compounds having an aromatic amine skeleton such as -fluorene]-2-amine (abbreviated as PCBASF) Compounds, 1,3-bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di( N-carbazolyl)biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenyl) Phenyl)-9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl Compounds having a carbazole skeleton, such as ru-9H-carbazole (abbreviated as PCCP), and ,4,4',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (Abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H- Fluoren-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III) , 4-[4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyl Compounds containing a thiophene skeleton, such as dibenzothiophene (abbreviation: DBTFLP-IV) , or 4,4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran)( Abbreviation: DBF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9- [phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II), etc. Examples include compounds having a furan skeleton. Among those mentioned above, compounds having an aromatic amine skeleton Compounds containing composites or carbazole skeletons are highly reliable and exhibit high hole transport properties. Furthermore, it is preferable because it also contributes to reducing the driving voltage. The materials listed as having hole transport properties are also materials that constitute the hole transport layer 112. It can be used suitably.

[0240] The light-emitting layer 113 has a light-emitting substance and a host material. It is acceptable for the materials to be included simultaneously. Furthermore, it is also acceptable for it to be a laminate of two layers with different compositions.

[0241] Whether the luminescent material is a fluorescent material or a phosphorescent material, it exhibits thermally activated delayed fluorescence (T The substance may be any other luminescent substance, even if it exhibits ADF (Active Deposition Factor). One embodiment is a layer that exhibits fluorescence emission, particularly a layer that exhibits blue fluorescence emission. It can be suitably applied depending on the circumstances.

[0242] In the light-emitting layer 113, possible materials that can be used as fluorescent light-emitting materials include, for example, Examples include those listed below. Other fluorescent materials can also be used.

[0243] 5,6-Bis[4-(10-phenyl-9-antryl)phenyl]-2,2'-bipyri Zin (abbreviation: PAP2BPy), 5,6-bis[4'-(10-phenyl-9-antri [Lu)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2BPy), N, N'-diphenyl-N,N'-bis[4-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6FLPAPrn), N,N'-bi Su(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-carbazole-9-yl)phenyl]-N,N'-di Phenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazo (Abbreviated) 4'-(10-phenyl-9-anthryl)triphenylamine ( Name: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-dife Nyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-diphenyl Nyl-N-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole -3-amine (abbreviation: PCAPA), perylene, 2,5,8,11-tetra-tert- Butylperylene (abbreviation: TBP), 4-(10-phenyl-9-anthryl)-4'-( 9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAP) A) 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-carbazole-3-amine (abbreviation: 2PCAPPA), N-[4-(9,10-diphenyl-2-anthryl)phenyl]-N,N',N'-to Riphenyl-1,4-phenylenediamine (abbreviation: 2DPAPPA), N,N,N',N ',N'',N'',N''',N'''-Octaphenyldibenzo[g,p]chrysene -2,7,10,15-tetraamine (abbreviation: DBC1), coumarin 30, N-(9,1 0-Diphenyl-2-anthryl)-N,9-Diphenyl-9H-carbazole-3-A Min (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl] )-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N' -Triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10 -Bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-tri Phenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), 9,10-bis( 1,1'-biphenyl-2-yl)-N-[4-(9H-carbazole-9-yl) [Nyl]-N-phenylanthracene-2-amine (abbreviation: 2YGABPhA), N,N, 9-Triphenylanthracene-9-amine (abbreviation: DPhAPhA), Coumarin 545 T,N,N'-diphenylquinacridone (abbreviation: DPQd), rubren, 5,12-bis (1,1'-biphenyl-4-yl)-6,11-diphenyltetracene (abbreviation: BPT) ), 2-(2-{2-[4-(dimethylamino)phenyl]ethenyl}-6-methyl-4 H-pyran-4-ylidene)propanedinitrile (abbreviation: DCM1), 2-{2-methyl -6-[2-(2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidine] [-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: D CM2), N,N,N',N'-Tetrakis(4-methylphenyl)tetracene-5,1 1-Diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'- Tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluorantene-3,10 -Diamine (abbreviation: p-mPhAFD), 2-{2-isopropyl-6-[2-(1,1 ,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij] [Quinoridine-9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (Abbreviation: DCJTI), 2-{2-tert-butyl-6-[2-(1,1,7 Tramethyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolidine 9-yl)ethenyl]-4H-pyran-4-ylidene}propanedinitrile (abbreviation: DC JTB), 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-teto Lahydro-1H,5H-benzo[ij]quinoridine-9-yl)ethenyl]-4H-pyra N-4-ylidene propanedinitrile (abbreviation: BisDCJ™), N,N'-diphosphate Nyl-N,N'-(1,6-pyrene-diyl)bis[(6-phenylbenzo[b]naphthate [1,2-d]furan)-8-amine](abbreviation: 1,6BnfAPrn-03), 3,1 0-Bis[N-(9-phenyl-9H-carbazol-2-yl)-N-phenylamino ]Naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10PCA2Nb f(IV)-02), 3,10-bis[N-(dibenzofuran-3-yl)-N-phenyl Luamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3,10Fr Examples include A2Nbf(IV)-02). In particular, 1,6FLPAPrn and 1,6m Pyridine compounds such as MemFLPAPrn and 1,6BnfAPrn-03 can be substituted. The condensed aromatic diamine compounds shown exhibit high hole-trapping properties and excellent luminescence efficiency and reliability. This is preferable because it is well-maintained.

[0244] In the light-emitting layer 113, if a phosphorescent material is used as the light-emitting material, it is possible to use it. Examples of suitable materials include the following:

[0245] Tris{2-[5-(2-methylphenyl)-4-(2,6-dimethylphenyl)-4H -1,2,4-triazole-3-yl-κN2]phenyl-κC}iridium(III ) (abbreviation: [Ir(mpptz-dmp)3]), Tris(5-methyl-3,4-diphen) Iridium(III) (abbreviation: [Ir(Mpt) z)3]), Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl-4H -1,2,4-Triazolat] Iridium(III) (Abbreviation: [Ir(iPrptz-3 Organometallic iridium complexes having a 4H-triazole skeleton, such as b)3]), and Tris [3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-tria Zolato] Iridium (III) (abbreviation: [Ir(Mptz1-mp)3]), Tris (1 -Methyl-5-phenyl-3-propyl-1H-1,2,4-triazolato)iridium (III) (Abbreviation: [Ir(Prptz1-Me)3]) 1H-triazole bone iridium organometallic complexes with a specific classification, and fac-tris[(1-2,6-diisopropyl [Phenyl)-2-phenyl-1H-imidazole]iridium(III) (abbreviation: [Ir (iPrpmi)3]), Tris[3-(2,6-dimethylphenyl)-7-methylimi Dazo[1,2-f]phenantriginato]iridium(III) (abbreviation:[Ir(dmp Organometallic iridium complexes having an imidazole skeleton such as impt-Me)3]), Bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ ]iridium( III) Tetrakis(1-pyrazolyl)borate (abbreviation: Fir6), bis[2-(4' ,6'-Difluorophenyl)pyridinate-N,C 2’ Iridium(III) picolina Firpic (abbreviation: Firpic), bis{2-[3',5'-bis(trifluoromethyl) [enyl]pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: [Ir( CF3ppy)2(pic)]), bis[2-(4',6'-difluorophenyl)pyri Dinato-N,C 2’ Iridium(III) acetylacetonate (abbreviation: FIraca) organometallic iridium ligands having electron-withdrawing groups as shown in c) Examples include um complexes. These are compounds that exhibit blue phosphorescence, starting from 440 nm. This compound has an emission peak at 520 nm.

[0246] Also, tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato)yli Dium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonato)bis (6-methyl-4-phenylpyrimidinato)iridium(III) (abbreviation: [Ir(mp) pm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4- Phenylpyrimidina) Iridium(III) (Abbreviation: [Ir(tBuppm)2(ac (ac)), (acetylacetonate)bis[6-(2-norbornyl)-4-phenylp Limiginato Iridium(III) (abbreviation: [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)]) has a pyrimidine skeleton iridium metal complexes and (acetylacetonato)bis(3,5-dimethyl-2-phenyl Iridium(III) (abbreviation: Ir(mppr-Me)2(acac)) ]), (acetylacetonato)bis(5-isopropyl-3-methyl-2-phenylpyra) Dinato-iridium(III) (abbreviation: [Ir(mppr-iPr)2(acac)]) organometallic iridium complexes having a pyrazine skeleton, such as tris(2-phenylpyridium Nato-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]quinolinate) iridium (I II) Acetylacetonate (abbreviation: [Ir(bzq)2(acac)]), Tris(be 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) acetylated Setanate (abbreviation: [Ir(pq)2(acac)]) is a pyridine skeleton-containing substance In addition to iridium metal complexes, tris(acetylacetonate)(monophenanthroline) Rare earth metals such as rubium(III) (abbreviation: [Tb(acac)3(Phen)]) Examples include complexes. These are compounds that mainly exhibit green phosphorescence, with a wavelength of 500 nm to 6 It has an emission peak at 00 nm. Furthermore, it is an organometallic iridium complex with a pyrimidine skeleton. The body is particularly preferable because it is outstanding in terms of reliability and luminescence efficiency.

[0247] Also, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrimid Sodium iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), bis(Ir(5mdppm)2(dibm)]), [4,6-Bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)iridi Um(III) (abbreviation: [Ir(5mdppm)2(dpm)]), bis[4,6-di( Naphthalene-1-yl)pyrimidinato](dipivaloylmethanato)iridium(III) Organometallic gold with a pyrimidine skeleton, such as (abbreviation: [Ir(d1npm)2(dpm)]) Iridium complexes of the genus, and (acetylacetonato)bis(2,3,5-triphenylpyrazine Iridium(III) (abbreviation: [Ir(tppr)2(acac)]), bis(2, 3,5-Triphenylpyrazinate)(dipivaloylmethanato) Iridium(III) (abbreviated) Name: [Ir(tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis (4-Fluorophenyl)quinoxalinato] Iridium(III) (Abbreviation: [Ir(Fd Organometallic iridium complexes having a pyrazine skeleton such as pq)2(acac)]) and RIS(1-phenylisoquinolinato-N,C) 2’ Iridium(III) (abbreviation: [Ir (piq)3]), bis(1-phenylisoquinolinato-N,C 2’ Iridium (II) I) Pyridogenated acetylacetonate (abbreviation: [Ir(piq)2(acac)]) In addition to organometallic iridium complexes with a n skeleton, 2, 3, 7, 8, 12, 13, 17, 18 -Octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP) Platinum complex and Tris(1,3-diphenyl-1,3-propanedionato)(monophenate Nanthroline europium(III) (abbreviation: [Eu(DBM)3(Phen)]), Tris[1-(2-tenoyl)-3,3,3-trifluoroacetonate](monophenane) Like trolin europium(III) (abbreviation: [Eu(TTA)3(Phen)]) Examples include rare earth metal complexes. These are compounds that exhibit red phosphorescence, and 60 It has an emission peak from 0 nm to 700 nm. Furthermore, it is an organometallic compound with a pyrazine skeleton. The lydium complex yields a red emission with good chromaticity.

[0248] In addition to the phosphorescent compounds described above, other known phosphorescent substances may be selected and used. stomach.

[0249] TADF materials include fullerenes and their derivatives, acridines and their derivatives, and eosin. Derivatives can be used. Also, magnesium (Mg), zinc (Zn), cadmium (Cd), tin (Sn), platinum (Pt), indium (In), or palladium (P Examples of metal-containing porphyrins include those described in d). 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)), copropol Filinetetramethyl ester-tin fluoride complex (SnF2(Copro III-4M) e) Octaethylporphyrin-tin fluoride complex (SnF2(OEP)), ethio Rufirin-tin fluoride complex (SnF2(Etio I)), octaethylporphyrin Examples include platinum chloride complexes (PtCl2OEP), etc.

[0250] [ka]

[0251] Furthermore, the following structural formula shows 2-(biphenyl-4-yl)-4,6-bis(12-) Enylindoro[2,3-a]carbazole-11-yl)-1,3,5-triazine( Abbreviations: PIC-TRZ) and 9-(4,6-diphenyl-1,3,5-triazine-2- Il)-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzT) Zn), 9-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl [Lu]-9'-phenyl-9H,9'H-3,3'-bicarbazole (abbreviation: PCCzPT) Zn), 2-[4-(10H-phenoxazine-10-yl)phenyl]-4,6-diph Phenyl-1,3,5-triazine (abbreviation: PXZ-TRZ), 3-[4-(5-phenyl -5,10-dihydrophenazine-10-yl)phenyl]-4,5-diphenyl-1, 2,4-Triazole (abbreviation: PPZ-3TPT), 3-(9,9-dimethyl-9H-A Cryzin-10-yl)-9H-xanthen-9-one (abbreviation: ACRXTN), bis[ 4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,10'H-spiro[acridine-9,9 π-electron-rich heteroaromatic rings such as '-anthracene]-10'-one (abbreviated as ACRSA) Heterocyclic compounds having one or both of the π-electron-deficient heteroaromatic rings can also be used. The heterocyclic compound has a π-electron-rich heteroaromatic ring and a π-electron-deficient heteroaromatic ring. It is preferable because it has high electron transport and hole transport properties. In particular, the π-electron-deficient heteroaromatic ring is Among the skeletons it possesses, pyridine skeleton, diazine skeleton (pyrimidine skeleton, pyrazine skeleton, pyr The dazine skeleton and the triazine skeleton are preferred because they are stable and reliable. In particular, Benzoflopyrimidine skeleton, benzothienopyrimidine skeleton, benzoflopyrazine skeleton, ben The zothienopyrazine skeleton is preferred because it has high acceptability and good reliability. Also, π Among skeletons having electron-excess heteroaromatic rings, the acridine skeleton, the phenoxazine skeleton, and fu The phenothiazine skeleton, furan skeleton, thiophene skeleton, and pyrrole skeleton are stable and reliable. For the sake of being good, it is preferable to have at least one of the skeletons. The dibenzofuran skeleton is used for the thiophene skeleton, and the dibenzothiophene skeleton is used for the thiophene skeleton, respectively. Preferred. Also, as pyrrole skeletons, indole skeletons, carbazole skeletons, indole Carbazole skeleton, bicarbazole skeleton, 3-(9-phenyl-9H-carbazole-3) The -yl)-9H-carbazole skeleton is particularly preferred. Substances in which electron-deficient heteroaromatic rings are directly bonded to π-electron-rich heteroaromatic rings have electron-donating properties. The electron-accepting ability of π-electron-deficient heteroatomous rings increases, and the energies of the S1 and T1 levels change. This is particularly preferable because the difference becomes smaller, allowing for efficient acquisition of thermally activated delayed fluorescence. Instead of a π-electron-deficient heteroaromatic ring, an aromatic ring with an electron-withdrawing group such as a cyano group attached is used. It may also be used. In addition, aromatic amine skeletons, phenazine skeletons, etc. can be used as π-electron-rich skeletons. It can be used. In addition, xanthene skeletons and thioxanthene skeletons can be used as π-electron-deficient skeletons. Dioxide skeleton, oxadiazole skeleton, triazole skeleton, imidazole skeleton, Traquinone skeleton, boron-containing skeletons such as phenylborane and volanthrene, benzonitrile and These include aromatic rings or heteroaromatic rings having nitrile or cyano groups such as cyanobenzene, and benzobenzene. Carbonyl skeletons such as phenones, phosphine oxide skeletons, sulfone skeletons, etc. can be used. In this way, at least of the π-electron-deficient heteroaromatic ring and the π-electron-excess heteroaromatic ring Instead of one, a π-electron-deficient skeleton and a π-electron-excess skeleton can be used.

[0252] [ka]

[0253] TADF materials are characterized by a small difference between the S1 and T1 levels, and triple intersystem crossing occurs due to reverse intersystem crossing. A function that can convert energy from singlet excitation energy to singlet excitation energy. It is a material that possesses this property. Therefore, the triplet excitation energy is obtained by a small amount of thermal energy. Upconversion to the multiplet excitation energy (reverse intersystem crossing) is possible, and the singlet excited state can be efficiently converted. It can be generated easily. Furthermore, the triplet excitation energy can be converted into luminescence. .

[0254] Furthermore, an excited complex (exciplex) is formed by two different substances forming an excited state. Exciplex (also called 'x' or 'exciplex') is a state where the difference between the S1 level and the T1 level is extremely small. As a TADF material capable of converting triplet excitation energy to singlet excitation energy, It has the function of being functional.

[0255] Furthermore, the phosphorescence spectrum observed at low temperatures (e.g., 77K to 10K) can be used as an indicator of the T1 level. A cull can be used. As for TADF materials, the short-wavelength tail of its fluorescence spectrum is Draw a tangent line, and set the energy at the wavelength of the extrapolation line as the S1 level, and the short wave of the phosphorescence spectrum When a tangent line is drawn at the long side of the tail, and the energy of the wavelength of the extrapolation line is taken as the T1 level, Preferably, the difference between S1 and T1 is 0.3 eV or less, and preferably 0.2 eV or less. Even better.

[0256] Furthermore, when using TADF material as a light-emitting material, the S1 level of the host material is the TADF material. It is preferable that the T1 level of the host material is higher than the S1 level of the TADF material. A higher rank is preferable.

[0257] The host material for the light-emitting layer may be an electron-transporting material or a hole-transporting material, or the above Various carrier transport materials, such as TADF materials, can be used.

[0258] Materials with hole transport properties include those having an amine skeleton or a π-electron-rich heteroaromatic ring skeleton. A compound is preferred. For example, 4,4'-bis[N-(1-naphthyl)-N-phenyl Mino]biphenyl (abbreviation: NPB), 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-phenylamino ] Biphenyl (abbreviation: BSPB), 4-phenyl-4'-(9-phenylfluorene-9) -yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl-3'-(9-phenyl) Nylfluoren-9-yl)triphenylamine (abbreviation: mBPAFLP), 4-phenyl Lu-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated name) :PCBA1BP), 4,4'-diphenyl-4''-(9-phenyl-9H-carbazo (3-yl)triphenylamine (abbreviation: PCBBi1BP), 4-(1-naphthyl )-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation) :PCBANB), 4,4'-di(1-naphthyl)-4''-(9-phenyl-9H-ka Luvazole-3-yl)triphenylamine (abbreviation: PCBNBB), 9,9-dimethyl -N-phenyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl] Fluoren-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl [9H-carbazole-3-yl)phenyl]-9,9'-spirobio[9H-fluorine] Compounds having an aromatic amine skeleton such as len-2-amine (abbreviation: PCBASF), 1,3-Bis(N-carbazolyl)benzene (abbreviation: mCP), 4,4'-Di(N-carbazolyl)benzene Bazolyl biphenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl) -9-phenylcarbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H Compounds having a carbazole skeleton, such as (abbreviated as PCCP) -carbazole, and 4,4 ',4''-(benzene-1,3,5-triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II), 2,8-diphenyl-4-[4-(9-phenyl-9H-fluore] [-9-yl)phenyl]dibenzothiophene (abbreviation: DBTFLP-III), 4-[ 4-(9-phenyl-9H-fluoren-9-yl)phenyl]-6-phenyldibenzo Compounds containing a thiophene skeleton, such as thiophene (abbreviation: DBTFLP-IV), and 4, 4',4''-(benzene-1,3,5-triyl)tri(dibenzofuran) (abbreviation: D BF3P-II), 4-{3-[3-(9-phenyl-9H-fluorene-9-yl)f [phenyl]phenyl}dibenzofuran (abbreviation: mmDBFFLBi-II) and other furan bones Examples of compounds having a specific characteristic include compounds having an aromatic amine skeleton and Compounds with a rubazole skeleton are reliable, have high hole transport properties, and are drivable. It is preferable because it also contributes to voltage reduction. Furthermore, the hole transport layer 112 has hole transport properties. The organic compounds listed as examples of materials can also be used.

[0259] Examples of materials with electron transport properties include bis(10-hydroxybenzo[h]quinoli Sodium beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolate) )(4-phenylphenolate)aluminum(III) (abbreviation: BAlq), bis(8- Zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl) [Phenolate]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl) Metal complexes such as phenolate zinc(II) (abbreviated as ZnBTZ) and π-electron-deficient heteroatoms Organic compounds having a fragrant ring skeleton are preferred. Organic compounds having a π-electron-deficient hetero-aromatic ring skeleton. For example, 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 [Diazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1] ,3,4-Oxadiazole-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 having a polyazole skeleton such as -II), and 2-[3-(dibenzothioff) [phenyl-4-yl]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-carbazole-9-yl)biphenyl-3-yl]dibenzo[f,h]quinoxali n (abbreviation: 2mCzBPDBq), 4,6-bis[3-(phenanthrene-9-yl)f [enyl]pyrimidine (abbreviation: 4,6mPnP2Pm), 4,6-bis[3-(4-diben Dia, such as zothienyl(phenyl)pyrimidine (abbreviation: 4,6mDBTP2Pm-II) Heterocyclic compounds having a din skeleton, or 3,5-bis[3-(9H-carbazole-9-yl] )phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3-pyridine) Heterocyclization of pyridine skeletons such as [zyl]phenyl]benzene (abbreviation: TmPyPB) Compounds are one example. Among those mentioned above, heterocyclic compounds having a diazine skeleton and pyridine skeletons are examples. Heterocyclic compounds having are reliable and preferred. In particular, diazines (pyrimidines and Heterocyclic compounds with a pyrazine skeleton exhibit high electron transport properties and contribute to reducing the driving voltage. Furthermore, the organic compound described in Embodiment 1 is also a material that has electron transport properties, and the host and It can be used as follows. By using the organic compound described in Embodiment 1, EL A layer with a low refractive index can be formed inside layer 103, improving the external quantum efficiency of the light-emitting device. It can be raised.

[0260] As for TADF materials that can be used as host materials, the previously mentioned TADF materials are... The same material can be used. When TADF material is used as the host material, TA The triplet excitation energy generated in the DF material is converted to a singlet excitation energy through reverse intersystem crossing. It is converted into a substance, and then energy is transferred to the light-emitting material, thereby increasing the luminescence efficiency of the light-emitting device. This can be achieved. At this time, the TADF material functions as an energy donor, and the luminescent substance It functions as an energy acceptor.

[0261] This is very effective when the above-mentioned light-emitting material is a fluorescent material. In order to obtain high luminescence efficiency, the S1 level of the TADF material is 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. A high level is preferable. Therefore, the T1 level of the TADF material is the same as the T1 level of the fluorescent material. A higher value is preferable.

[0262] Furthermore, T exhibits emission that overlaps with the wavelength of the lowest energy absorption band of the fluorescent material. It is preferable to use ADF material. This allows the fluorescent material to be converted from TADF material. This is preferable because it allows for smoother transfer of excitation energy and efficient emission.

[0263] Furthermore, singlet excitation energy is efficiently generated from triplet excitation energy through reverse intersystem crossing. For this to occur, it is preferable that carrier recombination occurs in the TADF material. The triplet excitation energy generated by the DF material is transferred to the triplet excitation energy of the fluorescent material. It is preferable not to do so. To that end, the fluorescent material has a luminescent phosphodiolus ( It is preferable to have a protecting group around the skeleton that causes light emission. The protecting group is a π bond. Substituents that do not have a substituent are preferred, saturated hydrocarbons are preferred, specifically those having 3 or more carbon atoms. Alkyl alkyl groups with 0 or fewer carbon atoms, and substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms. Examples include trialkylsilyl groups with 3 to 10 carbon atoms, and when there are multiple protecting groups... Even more preferable. Substituents without π bonds have poor carrier transport capabilities, therefore, With minimal impact on carrier transport and carrier recombination, TADF materials and fluorescent materials This allows us to increase the distance from the luminescent phosphatid. Here, the luminescent phosphatid is the luminescent phosphatid in a fluorescent material. This refers to the atomic group (skeleton) that causes light. A luminescent phosphophore is preferably a skeleton with π bonds, and is aromatic. It is preferable that it contains a ring, and preferably has a condensed aromatic ring or a condensed heteroaromatic ring. Examples of aromatic rings or condensed heteroaromatic rings include the phenanthrene skeleton, stilbene skeleton, and acridone. Examples include skeletons, phenoxazine skeletons, phenothiazine skeletons, etc. In particular, naphthalene skeletons, Anthracene skeleton, fluorene skeleton, chrysene skeleton, triphenylene skeleton, tetracene skeleton Pyrene skeleton, perylene skeleton, coumarin skeleton, quinacridone skeleton, naphthobisbenzo Fluorescent materials having a ranic skeleton are preferred because they have a high fluorescence quantum yield.

[0264] When using a fluorescent material as the light-emitting material, the host material should have an anthracene skeleton. Materials that are suitable for this purpose are used as host materials for fluorescent materials. When used in this way, it is possible to realize a light-emitting layer with good luminescence efficiency and durability. Host material Substances having an anthracene skeleton that can be used as a material include diphenylanthracene skeletons, In particular, substances having a 9,10-diphenylanthracene skeleton are preferred because they are chemically stable. Furthermore, if the host material has a carbazole skeleton, hole injection and transport properties are enhanced. Therefore, it is preferable, but a benzocarbazole skeleton in which a benzene ring is further condensed on carbazole is preferable. When included, the HOMO becomes about 0.1 eV shallower than that of carbazole, making it easier for holes to enter. Therefore, it is preferable. In particular, when the host material contains a dibenzocarbazole skeleton, The HOMO becomes about 0.1 eV shallower than in zole, making it easier for holes to enter, and also for hole transport. It is also excellent in terms of properties and has high heat resistance, making it suitable. Therefore, it is even more suitable as a host material. What is interesting is the 9,10-diphenylanthracene skeleton and the carbazole skeleton (or It is a substance that simultaneously possesses a benzocarbazole skeleton or a dibenzocarbazole skeleton. From the viewpoint of hole injection and transport as described above, the carbazole skeleton was replaced with a benzofluorene skeleton. A dibenzofluorene skeleton may also be used. An example of such a substance is 9-phenyl Lu-3-[4-(10-phenyl-9-antryl)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}anthra Sen (abbreviation: FLPPA), 9-(1-naphthyl)-10-[4-(2-naphthyl)fe Examples include nylanthracene (abbreviation: αN-βNPAnth). In particular, CzPA, cgDBCzPA, 2mBnfPPA, and PCzPA exhibit very good properties and are therefore preferred. That's a good choice.

[0265] Furthermore, the host material may be a mixture of multiple substances, and the mixed host material When used, a mixture of electron-transporting material and hole-transporting material is used. Preferably, by mixing an electron-transporting material with a hole-transporting material. Furthermore, the transport properties of the light-emitting layer 113 can be easily adjusted, and the recombination region can be easily controlled. This is possible. The weight ratio of the content of hole-transporting material to electron-transporting material is positive. The ratio of materials with pore transport properties to materials with electron transport properties should be 1:19 to 19:1.

[0266] Furthermore, phosphorescent materials can be used as part of the above-mentioned mixed materials. When using a fluorescent material as a light-emitting material, excitation energy is supplied to the fluorescent material. It can be used as an energy donor.

[0267] Furthermore, these mixed materials may form excited complexes. These excited complexes are luminescent substances. It forms an excited complex that emits light that overlaps with the wavelength of the lowest energy absorption band. By selecting the right combination, energy transfer becomes smoother, and luminescence is obtained more efficiently. This is preferable because it allows for a reduction in the drive voltage.

[0268] Furthermore, at least one of the materials forming the excitation complex may be a phosphorescent material. By doing so, the triplet excitation energy is efficiently converted to the singlet excitation energy through reverse intersystem crossing. It can be converted to -.

[0269] As a combination of materials that efficiently form excited complexes, HO is a material with hole transport properties. It is preferable that the MO level is above the HOMO level of the electron-transporting material. If the LUMO level of a material with electron-transporting properties is higher than or equal to the LUMO level of a material with electron-transporting properties Preferred. Note that the LUMO and HOMO levels of the material are controlled by cyclic voltammetry. From the electrochemical properties (reduction potential and oxidation potential) of the material measured by CV (coefficient of variation) It can be derived.

[0270] Furthermore, the formation of excited complexes is related to, for example, the emission spectrum of hole-transporting materials and electron-transporting properties. The emission spectrum of a material having the above properties, and the emission spectrum of a mixed film obtained by mixing these materials. In comparison, the emission spectrum of the mixed film is shifted to longer wavelengths than the emission spectra of each individual material. Alternatively, this can be confirmed by observing a phenomenon (which has a new peak on the longer wavelength side). Alternatively, transient photoluminescence (PL) and electron transport of materials with hole transport properties. The transient PL of materials possessing certain properties and the transient PL of a mixed film obtained by mixing these materials are compared, and the mixing The transient PL lifetime of the film has a longer lifetime component than the transient PL lifetime of each material, or a delayed lifetime component. This can be confirmed by observing differences in transient responses, such as an increase in the proportion of the time. Furthermore, the transient PL mentioned above can be interpreted as transient electroluminescence (EL). No. That is, transient EL for hole-transporting materials, transient E for electron-transporting materials. By comparing the transient EL of L and mixed films and observing the differences in transient response, Excitation complex formation can be confirmed.

[0271] The electron transport layer 114 is a layer containing a material that has electron transport properties. For example, 10 nm or more, and 50 nm or less, preferably 15 nm or more, and 35 nm or less. It is preferable to form it as a film thickness. As for materials having electron transport properties, disclosed in Embodiment 1 It is preferable to use an electron transport layer material or organic compound. By using the electron transport layer material or organic compound disclosed in Form 1, the EL layer 1 03 A layer with a low refractive index can be formed inside, improving the external quantum efficiency of the light-emitting device. It becomes possible to do so.

[0272] In Embodiment 1, materials other than the electron transport layer material or organic compound disclosed are used in the electron transport layer 114. If present, the above-mentioned substances are listed as electron-transporting materials that can be used as host materials. It is possible to use things.

[0273] Furthermore, the electron transport layer 114 is made of an electron transport material and an alkali metal or alkaline earth element. It is preferable that the mixture contains elemental metals, compounds, or complexes of metals. In particular, it contains alkali metal organometallic compounds. A complex is preferred, and a lithium organometallic complex is even more preferred. Ligand of the organometallic complex As such, ligands having an 8-quinolinolato structure are particularly preferred, and 8-quinolinolato It is more preferable that it be thium or 6-methyl-8-quinolinolatolithium. The electron transport layer 114 having this configuration may also serve as the electron injection layer 115.

[0274] Furthermore, the electron transport layer 114 has an electron mobility at which the square root of the electric field strength [V / cm] is 600. 1 x 10 -7 cm2 / Vs or more 5×10 -5 cm 2 It is preferable that it is less than or equal to / Vs. The amount of electrons injected into the light-emitting layer is controlled by reducing the electron transportability in the electron transport layer 114. This allows the light-emitting layer to avoid an electron-excess state. This configuration allows for In particular, a hole injection layer is formed as a composite material, and the composite material has hole transport properties. The HOMO level is relatively deep, between -5.7eV and -5.4eV. It is particularly preferable when it is a material because it has a good lifespan. In this case, it has electron transport properties. The material used is preferably one whose HOMO level is -6.0 eV or higher. The material having the ability to transport molecules is preferably an organic compound having an anthracene skeleton, It is more preferable that the organic compound contains both a transene skeleton and a heterocyclic skeleton. As the elementary ring skeleton, a nitrogen-containing 5-membered ring skeleton or a nitrogen-containing 6-membered ring skeleton is preferred, and these heterocycles The skeletal structure consists of a pyrazole ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazi Nitrogen-containing five-membered rings, such as pyrimidine rings and pyridazine rings, contain two complex atoms in the ring. It is particularly preferable that it has a skeleton or a nitrogen-containing 6-membered ring skeleton. Also, alkali metals or As elements, compounds, or complexes of earth metals, the 8-hydroxyquinolinate structure is used. It is preferable to include it. Specifically, for example, 8-hydroxyquinolinatolithium (abbreviation: Examples include Liq, 8-hydroxyquinolinato-sodium (abbreviated as Naq), etc. Yes, it is possible. In particular, monovalent metal ion complexes, especially lithium complexes, are preferred, and Liq is good. It is preferable. Furthermore, if it contains an 8-hydroxyquinolinate structure, its methyl-substituted form (for example) (For example, 2-methyl substituted or 5-methyl substituted compounds can also be used.) Among them, alkali metals or alkaline earth metals in elemental form, compound, or complex form, their thickness It is preferable that a concentration difference (including cases where it is zero) exists in the opposite direction.

[0275] The electron transport layer 114 is provided between the light-emitting layer 113 and the second electrode 102. Between the transport layer 114 and the second electrode 102, lithium fluoride is used as the electron injection layer 115. LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxy Alkali metals or alkaline earth metals such as quinolinatolithium (abbreviation: Liq) The electron injection layer 115 may be provided with a layer containing those compounds. A layer made of alkali metals or alkaline earth metals or compounds thereof is contained within it. Alternatively, an electride may be used. Examples of electrides include calcium and Examples include materials obtained by adding a high concentration of electrons to a mixed oxide of aluminum.

[0276] Furthermore, materials with electron transport properties and elements or compounds of alkali metals or alkaline earth metals are also included. Alternatively, a material mixed with a complex may be used as the electron injection layer 115. As for materials, we will also list the materials that can be used in the electron transport layer 114. It can be used. Furthermore, the electron injection layer 115 having this configuration also serves as the electron transport layer 114. Sometimes I sleep.

[0277] Furthermore, the electron injection layer 115 is made of a substance having electron transport properties (preferably a bipyridine skeleton). (An organic compound containing) the above alkali metal or alkaline earth metal fluoride in a microcrystalline state It is also possible to use a layer containing a concentration of 50 wt% or more. This layer is refraction Because it is a low-efficiency layer, it is possible to provide a light-emitting device with better external quantum efficiency. It becomes Noh.

[0278] Alternatively, a charge generation layer 116 may be provided instead of the electron injection layer 115 (Figure 1(B)). The charge generation layer 116 generates holes in the layer in contact with the cathode side of the layer when an electric potential is applied, and in the anode side. This refers to a layer that can inject electrons into the adjacent layer. The charge generation layer 116 has a small amount of At the very 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 it using the composite materials listed as materials that can be used. Also, the P-type layer 1 17 is a composite material comprising a film containing the acceptor material described above and a hole transport material It may also be constructed by stacking films containing the P-type layer 117. 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, and the light-emitting device It works.

[0279] In addition to the P-type layer 117, the charge generation layer 116 also includes an electron relay layer 118 and an electron injection buffer. It is preferable that one or both of the layers 119 are provided.

[0280] The electron relay layer 118 contains at least an electron-transporting material, and the electron injection buffer layer 1 It has the function of preventing interaction between 19 and the P-type layer 117, thereby enabling smooth electron transfer. The LUMO level of the electron-transporting material contained in the relay layer 118 is in the P-type layer 117. The LUMO level of the acceptor material and the charge generation layer 116 in the electron transport layer 114 It is preferable that the LUMO level is between the LUMO level of the material contained in the contacting layer. Electron relay layer 11 Specific energy levels of the LUMO level in electron-transporting materials used in 8 The voltage should be -5.0 eV or higher, preferably -5.0 eV to -3.0 eV. As for electron-transporting materials used in the electron relay layer 118, phthalocyanine-based materials are used. It is preferable to use a material or a metal complex having a metal-oxygen bond and an aromatic ligand.

[0281] The electron injection buffer layer 119 contains alkali metals, alkaline earth metals, rare earth metals, and These compounds (alkali metal compounds (oxides such as lithium oxide, halides, and carbonates) (including carbonates such as thium and cesium carbonate), alkaline earth metal compounds (oxides, halogens) Compounds of rare earth metals (including oxides, halides, and carbonates), or compounds of rare earth metals (including oxides, halides, and carbonates) It is possible to use materials with high electron injection capabilities, such as (m)).

[0282] Furthermore, the electron injection buffer layer 119 contains an electron transporting substance and a donor substance, and If performed, alkali metals, alkaline earth metals, and rare earth metals will be used as donor substances. , and these compounds (alkali metal compounds (oxides and halides such as lithium oxide) , including carbonates such as lithium carbonate and cesium carbonate), alkaline earth metal compounds (oxides, (including halides and carbonates), or compounds of rare earth metals (oxides, halides, carbon In addition to salts, tetratianaphthacene (abbreviated as TTN), nickerosene, decametine Organic compounds such as runicerosene can also be used. Therefore, it is formed using the same material as the material that constitutes the electron transport layer 114 described earlier. This can be done. Furthermore, the organic compound in one aspect of the present invention is an organic compound with a low refractive index. Furthermore, by using it in the electron injection buffer layer 119, a light emission device with good external quantum efficiency can be achieved. You can obtain S.

[0283] The material forming the second electrode 102 has a small work function (specifically, 3.8 eV or less). (Below) Metals, alloys, electrically conductive compounds, and mixtures thereof can be used. Specific examples of such cathode materials include alkaline materials such as lithium (Li) and cesium (Cs). Metallic compounds, as well as magnesium (Mg), calcium (Ca), strontium (Sr), etc. Elements belonging to Group 1 or Group 2 of the periodic table, and alloys containing these elements (MgAg, Rare earth metals such as AlLi, europium (Eu), ytterbium (Yb), and this Examples include alloys containing these. However, between the second electrode 102 and the electron transport layer, By providing an electron injection layer, regardless of the magnitude of the work function, Al, Ag, ITO, and silica can be used. Various conductive materials such as indium oxide-tin oxide containing silicon dioxide or silicon dioxide are used as the second... It can be used as electrode 102. These conductive materials are produced using dry methods such as vacuum deposition and sputtering, as well as inkjet methods. It is possible to deposit films using methods such as spin coating. Furthermore, wet deposition can be performed using the sol-gel method. It may be formed by a mold, or by a wet process using a paste of a metallic material.

[0284] Furthermore, various methods can be used to form the EL layer 103, regardless of whether they are dry or wet methods. This can be done using methods such as vacuum deposition, gravure printing, offset printing, and screen printing. You may use methods such as printing, inkjet printing, or spin coating.

[0285] Furthermore, each electrode or layer described above may be formed using different film deposition methods.

[0286] The configuration of the layer provided between the first electrode 101 and the second electrode 102 is as described above. It is not limited to this. However, if the light-emitting region and the metal used in the electrodes or carrier injection layer are in close proximity To suppress the quenching that occurs as a result, the first electrode 101 and the second electrode 1 A configuration is preferred in which a light-emitting region is provided at a location away from O2 where holes and electrons recombine.

[0287] Furthermore, the hole transport layer and electron transport layer in contact with the light-emitting layer 113, and especially the recombination in the light-emitting layer 113, The carrier transport layer near the region suppresses energy transfer from excitons generated in the light-emitting layer. Therefore, the band gap is the light-emitting material that makes up the light-emitting layer or the light contained in the light-emitting layer. It is preferable to use materials with a band gap larger than the band gap of the material itself. It seems so.

[0288] Next, we have a light-emitting device (multilayer element, tandem element) with a configuration in which multiple light-emitting units are stacked. The form of the (also called the child) will be explained with reference to Figure 1(C). This light-emitting device is positive This is a light-emitting device having multiple light-emitting units between the electrode and the cathode. The EL layer 103 has a configuration almost identical to that shown in Figure 1(A). That is, Figure 1(C) The light-emitting device shown is a light-emitting device having multiple light-emitting units, as shown in Figure 1(A) or The light-emitting device shown in Figure 1(B) is a light-emitting device having one light-emitting unit. It can be said that.

[0289] In Figure 1(C), a first light-emitting unit 511 and a cathode 502 are located between the anode 501 and the cathode 502. A second light-emitting unit 512 is stacked with the first light-emitting unit 511 and the second light-emitting unit A charge generation layer 513 is provided between the knit 512 and the cathode 502. These correspond to the first electrode 101 and the second electrode 102 in Figure 1(A), respectively. The same thing described in the explanation can be applied. Also, the first light-emitting unit 51 The first and second light-emitting units 512 may have the same configuration or different configurations.

[0290] When a voltage is applied to the anode 501 and cathode 502, the charge generation layer 513 generates a light from one of the light-emitting units. It has the function of injecting electrons into one unit and holes into the other light-emitting unit. That is, Figure In 1(C), when a voltage is applied such that the potential of the anode is higher than the potential of the cathode... In addition, the charge generation layer 513 injects electrons into the first light-emitting unit 511 and the second light-emitting unit Any method that injects a hole into T512 will suffice.

[0291] The charge generation layer 513 is formed with the same configuration as the charge generation layer 116 described in Figure 1(B). Preferably, composite materials of organic compounds and metal oxides have good carrier implantation and carrier transport properties. Due to its superior performance, it can achieve low-voltage and low-current operation. If the anode side of the net is in contact with the charge generation layer 513, the charge generation layer 513 will light up the unit. Since it can also serve as the hole injection layer of the net, the light-emitting unit does not require a hole injection layer. That's fine.

[0292] Furthermore, if an electron injection buffer layer 119 is provided in the charge generation layer 513, the electron injection buffer Since layer 119 plays the role of an electron injection layer in the anode-side light-emitting unit, the anode-side light emission The unit does not necessarily need to have an electron injection layer.

[0293] Figure 1(C) illustrates a light-emitting device having two light-emitting units, but there are also devices with three or more units. The same method can be applied to light-emitting devices that stack the above light-emitting units. As in the light-emitting device according to this embodiment, multiple light-emitting units are charged between a pair of electrodes. By separating and arranging the elements with the generation layer 513, high-brightness light emission is possible while maintaining a low current density. This enables the realization of even longer-lasting elements. Furthermore, it allows for low-voltage operation and low power consumption of light-emitting elements. The device can be realized.

[0294] Furthermore, by making the light-emitting color of each light-emitting unit different, the entire light-emitting device... This allows you to obtain light emission of the desired color. For example, a light emission device having two light emission units In the vise, the first light-emitting unit emits red and green light, and the second light-emitting unit emits blue light. By obtaining color, it is also possible to obtain a light-emitting device that emits white light as a whole. be.

[0295] Furthermore, the EL layer 103, the first light-emitting unit 511, the second light-emitting unit 512 and Each layer, such as the charge generation layer, and the electrodes are, for example, deposited by methods such as vapor deposition (including vacuum deposition) and droplet ejection ( It can be formed using methods such as inkjet printing, coating, and gravure printing. They can be used. Also, they include low molecular weight materials, medium molecular weight materials (including oligomers and dendrimers), and Alternatively, it may contain polymer materials.

[0296] (Embodiment 3) This embodiment describes a light-emitting device using the light-emitting device described in Embodiment 2. ru.

[0297] In this embodiment, a light-emitting device made using the light-emitting device described in Embodiment 2 is used. Let's explain using Figure 2. Figure 2(A) is a top view showing the light-emitting device, and Figure 2(B) is Figure 2(A) is a cross-sectional view taken at AB and CD. This light-emitting device is a light-emitting device The drive circuit section (source line drive circuit) 601, indicated by the dotted line, controls the emission of light. It includes a pixel section 602 and a drive circuit section (gate line drive circuit) 603. Also, 604 The sealing substrate, 605 is a sealing material, and the area inside the sealing material 605 is a space 607. It is.

[0298] The routing wire 608 is input to the source line drive circuit 601 and the gate line drive circuit 603. FPC (Flexible Printed Circuit) is a wiring system for transmitting signals and serves as an external input terminal. (Input circuit) 609 receives video signals, clock signals, start signals, reset signals, etc. Receive. Note that only the FPC is shown in the diagram here, but this FPC has a print distribution A wire substrate (PWB) may be attached. The light-emitting device in this specification is a light-emitting device This includes not only the main unit but also the state in which the FPC or PWB is attached to it. ru.

[0299] Next, the cross-sectional structure will be explained using Figure 2(B). The drive circuit section is located on the element substrate 610. And a pixel section is formed, but here, the source line drive circuit 601 which is the drive circuit section and One pixel in the pixel section 602 is shown.

[0300] The element substrate 610 is a substrate made of glass, quartz, organic resin, metal, alloy, semiconductor, etc. FRP (Fiber Reinforced Plastics), PVF (Polyvinyl Fiber) Made using a plastic substrate made of fluoride, polyester, or acrylic resin. Just make it.

[0301] The structure of transistors used in pixels and driving circuits is not particularly limited. For example, inverse staggered It can be a type of transistor or a staggered transistor. Also, top Either a gate-type transistor or a bottom-gate transistor is acceptable. The semiconductor material is not particularly limited, and examples include silicon, germanium, silicon carbide, nitride Gallium can be used, or an In-Ga-Zn metal oxide can be used. An oxide semiconductor containing at least one of the elements, such as zinc, gallium, and zinc, may also be used.

[0302] The crystallinity of semiconductor materials used in transistors is not particularly limited; amorphous semiconductors, Crystalline semiconductors (microcrystalline semiconductors, polycrystalline semiconductors, single-crystal semiconductors, or semiconductors with a crystalline region in part) Any semiconductor having the properties of [the semiconductor material] may be used. If a semiconductor having crystalline properties is used, transients may occur. This is preferable because it suppresses the deterioration of the stanic characteristics.

[0303] Here, in addition to the transistors provided in the pixels and driving circuits mentioned above, the touch sensors and the like described later are also included. It is preferable to use oxide semiconductors for semiconductor devices such as transistors. It is particularly preferable to use oxide semiconductors with a wider band gap than silicon. By using an oxide semiconductor with a wider band gap than Ricon, the off state of the transistor can be controlled. The current in this state can be reduced.

[0304] The above oxide semiconductor preferably contains at least indium (In) or zinc (Zn). It is also In-M-Zn oxides (where M is Al, Ti, Ga, Ge, Y, Zr, Sn, It is an oxide semiconductor containing an oxide (such as a metal like La, Ce, or Hf). It is preferable.

[0305] In particular, the semiconductor layer has multiple crystalline portions, and the c-axis of the crystalline portion is the surface on which the semiconductor layer is formed. Alternatively, an acid oriented perpendicular to the upper surface of the semiconductor layer and having no grain boundaries between adjacent crystalline regions. It is preferable to use a crystalline semiconductor film.

[0306] By using such materials as semiconductor layers, fluctuations in electrical properties are suppressed, resulting in high reliability. This makes it possible to create a transistor.

[0307] Furthermore, due to its low off-current, the transistor having the aforementioned semiconductor layer can be used to... This makes it possible to retain the charge stored in the capacity over a long period of time. By applying a generator to each pixel, the gradation of the image displayed in each display area is maintained while driving It also becomes possible to shut down the circuit. As a result, it is possible to realize electronic devices with extremely reduced power consumption. It can be expressed.

[0308] It is preferable to provide an undercoat to stabilize the characteristics of the transistor. The undercoat may be: Inorganic silicon oxide films, silicon nitride films, silicon oxide-nitride films, silicon nitride-oxide films, etc. It can be fabricated using an insulating film, either as a single layer or in a multilayer configuration. The underlayer is fabricated by sputtering. CVD (Chemical Vapor Deposition) method (Plasma CVD method) , thermal CVD method, MOCVD (Metal Organic CVD) method, ALD ( Formed using methods such as Atomic Layer Deposition, coating, and printing. Yes, it is possible. However, a base coat does not need to be applied unless necessary.

[0309] Note that FET623 is one of the transistors formed in the drive circuit section 601. Furthermore, the drive circuit is formed using various CMOS, PMOS, or NMOS circuits. This is sufficient. Furthermore, this embodiment shows a driver-integrated type in which the drive circuit is formed on the substrate. However, this is not always necessary, and the drive circuit can be formed externally rather than on the circuit board. .

[0310] Furthermore, the pixel section 602 includes a switching FET 611 and a current control FET 612 and its drive It is formed by a plurality of pixels, each including a first electrode 613 electrically connected to the rain. However, it is not limited to this, and can also be used as a pixel unit combining three or more FETs and a capacitive element. good.

[0311] Furthermore, an insulator 614 is formed covering the end of the first electrode 613. Here, positive It can be formed by using a photosensitive acrylic resin film of a mold.

[0312] Furthermore, in order to ensure good coverage of the EL layer and other layers formed later, the upper end of the insulator 614 is Alternatively, a curved surface with curvature is formed at the lower end. For example, the material of the insulator 614 and When a positive-type photosensitive acrylic resin is used, the radius of curvature is only at the upper end of the insulator 614. It is preferable to have a curved surface having a thickness of 0.2 μm to 3 μm. Also, the insulating material 614 is used. Therefore, either a negative-type or positive-type photosensitive resin can be used.

[0313] An EL layer 616 and a second electrode 617 are formed on the first electrode 613, respectively. Here, the material used for the first electrode 613 which functions as an anode is a material with a work function of It is desirable to use large materials. For example, ITO film or silicon-containing indigo Indium oxide film, indium oxide film containing 2-20 wt% zinc oxide, titanium nitride film, In addition to monolayer films such as chromium films, tungsten films, zinc films, and Pt films, titanium nitride films and aluminum films are also available. Lamination with a film mainly composed of aluminum, titanium nitride film and aluminum film and titanium nitride A three-layer structure with a film can be used. Furthermore, a laminated structure can be used as a wiring resistor. It has low noise levels, provides good ohmic contact, and can even function as an anode. .

[0314] Furthermore, the EL layer 616 was coated using a vapor deposition method with a vapor deposition mask, an inkjet method, and a spin coating method. It is formed by various methods such as those described in Embodiment 2. The EL layer 616 is formed by the structure described in Embodiment 2. It contains the following: In addition, other materials constituting the EL layer 616 include low molecular weight compounds, This may be a high-molecular-weight compound (including oligomers and dendrimers).

[0315] Furthermore, the material used for the second electrode 617, which is formed on the EL layer 616 and functions as a cathode. Examples include materials with a low work function (Al, Mg, Li, Ca, or alloys and compounds thereof) It is preferable to use materials (MgAg, MgIn, AlLi, etc.). Note that the EL layer 61 If the light generated in 6 passes through the second electrode 617, the second electrode 617 is defined as the film thickness. A thin metal film and a transparent conductive film (ITO, zinc oxide containing 2-20 wt%). Using a lamination process with indium tin oxide containing zinc and silicon (zinc oxide (ZnO), etc.) That would be good.

[0316] Furthermore, the first electrode 613, the EL layer 616, and the second electrode 617 form the shape of the light-emitting device. This has been achieved. The light-emitting device is the light-emitting device described in Embodiment 2. The element is made up of multiple light-emitting devices, but in the light-emitting device of this embodiment This includes both the light-emitting device described in Embodiment 2 and light-emitting devices having other configurations. It's okay if they're mixed together.

[0317] Furthermore, by bonding the sealing substrate 604 to the element substrate 610 with the sealing material 605, A light-emitting device is placed in the space 607 surrounded by the sub-substrate 610, the sealing substrate 604, and the sealing material 605. The structure is equipped with chair 618. Furthermore, the space 607 is filled with filler material. In addition to cases where inert gases (such as nitrogen or argon) are used for filling, there are also cases where sealing materials are used for filling. There are also cases where a recess is formed in the sealing substrate and a desiccant is placed there to prevent deterioration due to moisture. This configuration is preferable because it can suppress oxidation.

[0318] Furthermore, it is preferable to use epoxy resin or glass frit for the sealing material 605. These materials should ideally be as impermeable to moisture and oxygen as possible. In addition to glass substrates and quartz substrates, other materials can be used for the encapsulating substrate 604, such as FRP (Fiber Reinforced Plastic). reinforced plastics, PVF (polyvinyl fluoride), polyester A plastic substrate made of tel or acrylic resin can be used.

[0319] Although not shown in Figure 2, a protective film may be provided on the second electrode. The protective film is an organic resin film. It can be formed with an inorganic insulating film. Also, the exposed portion of the sealing material 605 can be covered with A protective film may be formed. Furthermore, the protective film may be on the surface and sides of the pair of substrates, a sealing layer, and an insulating layer. It can be installed to cover exposed surfaces such as the margin layer.

[0320] The protective film can be made of a material that is impermeable to impurities such as water. This effectively suppresses the diffusion of impurities such as these from the outside to the inside.

[0321] Materials that make up the protective film include oxides, nitrides, fluorides, sulfides, ternary compounds, and metals. Alternatively, polymers can be used, for example, aluminum oxide, hafnium oxide, etc. Phenium silicate, lanthanum oxide, silicon oxide, strontium titanate, tantalum oxide Titanium dioxide, zinc oxide, niobium oxide, zirconium oxide, tin oxide, yttrium oxide cerium oxide, scandium oxide, erbium oxide, vanadium oxide, or indi oxide Materials containing um, etc., as well as aluminum nitride, hafnium nitride, silicon nitride, tantalum nitride, nitrogen Includes titanium dioxide, 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 oxides Strontium-containing sulfides, erbium and aluminum-containing oxides, and Materials containing oxides, etc., including lium and zirconium can be used.

[0322] The protective film can be formed using a film deposition method that provides good step coverage. This is preferable. One such method is atomic layer deposition (ALD). There is a deposition method. Protecting materials that can be formed using the ALD method. It is preferable to use it for membranes. By using the ALD method, a dense membrane can be created with cracks and pinholes. A protective film can be formed with reduced defects or with a uniform thickness. Also, This reduces the damage inflicted on the processed material when forming a protective film.

[0323] For example, by forming a protective film using the ALD method, surfaces with complex uneven shapes, or taps can be formed. A uniform and low-defect protective film can be formed on the top, sides, and back surfaces of the panel. .

[0324] As described above, a light-emitting device fabricated using the light-emitting device described in Embodiment 2 is obtained. It is possible.

[0325] The light-emitting device in this embodiment uses the light-emitting device described in Embodiment 2. This makes it possible to obtain a light-emitting device with good characteristics. Specifically, the method described in Embodiment 2. Because light-emitting devices have good luminous efficiency, it is possible to create light-emitting devices with low power consumption. ru.

[0326] Figure 3 shows a light-emitting device that emits white light, with a colored layer (color filter) provided. This shows an example of a light-emitting device that has been made full-color. Figure 3(A) shows substrate 1001, base Insulating film 1002, gate insulating film 1003, gate electrodes 1006, 1007, 1008, Interlayer insulating film 1020, second interlayer insulating film 1021, peripheral portion 1042, pixel portion 1040 , drive circuit section 1041, first electrodes 1024W, 1024R, 1024G of the light-emitting device , 1024B, partition wall 1025, EL layer 1028, second electrode 1029 of light-emitting device, seal The stopper plate 1031, sealing material 1032, etc. are shown in the diagram.

[0327] Furthermore, Figure 3(A) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue). The colored layer 1034B is provided on a transparent substrate 1033. Also, the black matrix 1 A 035 layer may be further provided. Transparent substrate 1 provided with a colored layer and a black matrix. 033 is aligned and fixed to substrate 1001. Note that the colored layer and black matrix Kus 1035 is covered with an overcoat layer 1036. Also, in Figure 3(A) This consists of a light-emitting layer that allows light to escape to the outside without passing through the colored layers, and a layer that allows light to escape to the outside by passing through the colored layers of each color. There is a light-emitting layer, and light that does not pass through the colored layer is white, while light that passes through the colored layer is red, green, and blue. Therefore, images can be represented using four colored pixels.

[0328] Figure 3(B) shows the colored layers (red colored layer 1034R, green colored layer 1034G, blue colored layer Example of forming layer 1034B) between the gate insulating film 1003 and the first interlayer insulating film 1020. This was shown. Thus, the colored layer is provided between the substrate 1001 and the sealing substrate 1031. That's good too.

[0329] Furthermore, in the light-emitting device described above, light is taken to the substrate 1001 side on which the FET is formed. Although a light-emitting device with a bottom-emission structure was used, the light emission was taken from the sealing substrate 1031 side. It can also be used as a light-emitting device with a projection structure (top emission type). A cross-sectional view of the light-emitting device is shown in Figure 4. In this case, the substrate 1001 is a substrate that does not transmit light. This can be done. Until the connecting electrode that connects the FET and the anode of the light-emitting device is fabricated, the bottle It is formed in the same way as a muemission-type light-emitting device. Then, the third interlayer insulating film 1037 is electrically... It is formed covering pole 1022. This insulating film may also play a planarization role. Third layer 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.

[0330] The first electrodes of the light-emitting device, 1024W, 1024R, 1024G, and 1024B, are located here. It is designated as the anode, but it can also be the cathode. Also, a top-emission type generator as shown in Figure 4. In the case of an optical device, it is preferable that the first electrode be a reflective electrode. Configuration of EL layer 1028 The configuration is as described in Embodiment 2 as the EL layer 103, and the white light The device structure is designed to allow light to be obtained.

[0331] In the top emission structure shown in Figure 4, the colored layer (red colored layer 1034R, green colored layer) The sealing is performed using a sealing substrate 1031 having a color layer 1034G and a blue colored layer 1034B. This can be done. The encapsulation substrate 1031 has a black matrix positioned between the pixels. 1035 may be provided. Colored layer (red colored layer 1034R, green colored layer 1034G, The blue colored layer (1034B) and the black matrix are formed by the overcoat layer (1036). It may be covered. The sealing substrate 1031 shall be a light-transmitting substrate. Furthermore, while we have shown an example of full-color display using four colors—red, green, blue, and white—this is not particularly limited. Alternatively, full-color display may be performed using four colors: red, yellow, green, and blue, or three colors: red, green, and blue.

[0332] In top-emission type light-emitting devices, a microcavity structure can be suitably applied. A light-emitting device having a microcavity structure has a first electrode as a reflective electrode and a second electrode as This is obtained by using semi-transparent and semi-reflective electrodes. Between the reflective electrode and the semi-transparent and semi-reflective electrode It has at least an EL layer and at least an emissive layer that forms an emissive region.

[0333] The reflective electrode has a visible light reflectance of 40% to 100%, preferably 70% to 100%. It is %, and its resistivity is 1 × 10⁻⁶. -2 Assume the membrane is less than Ωcm in diameter. Also, semipermeable... The semi-reflective electrode has a visible light reflectance of 20% to 80%, preferably 40% to 70%. , and its resistivity is 1 × 10 -2 Assume the membrane is less than Ωcm in diameter.

[0334] The light emitted from the light-emitting layer contained in the EL layer is reflected by the reflective electrode and the semi-transmitting / semi-reflective electrode. It is reflected and resonates.

[0335] The light-emitting device changes the thickness of the transparent conductive film, the aforementioned composite material, the carrier transport material, etc. This allows us to change the optical distance between the reflective electrode and the semitransmissive / semi-reflective electrode. Furthermore, the light of the resonant wavelength is amplified between the reflective electrode and the semitransmissive / semi-reflective electrode, causing resonance. It can attenuate light of wavelengths that are not present.

[0336] Furthermore, the light reflected back by the reflective electrode (the first reflected light) is semi-transmitted from the light-emitting layer. • Because it causes significant interference with the light (first incident light) that directly enters the semi-reflecting electrode, the reflective electrode and 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 amplified). It is preferable to adjust the wavelength of the emitted light. By adjusting the optical distance, the first By aligning the phase of the reflected light and the first incident light, the light emitted from the light-emitting layer can be further amplified. ru.

[0337] Furthermore, even if the EL layer in the above configuration has a structure with multiple light-emitting layers, it may still be a single light-emitting layer The structure may also have the following characteristics, for example, in combination with the configuration of the tandem light-emitting device described above. Furthermore, multiple EL layers are provided in a single light-emitting device with a charge generation layer in between, and each EL layer This may also be applied to a configuration in which one or more light-emitting layers are formed.

[0338] Having a microcavity structure enhances the emission intensity in the front direction at specific wavelengths. This makes it possible to reduce power consumption. Furthermore, the four sub-colors red, yellow, green, and blue are used. In the case of a light-emitting device that displays images as is, in addition to the brightness enhancement effect of yellow light emission, all sub-pixels By applying a microcavity structure tailored to the wavelength of each color, a light-emitting device with excellent characteristics can be produced. It can be placed there.

[0339] The light-emitting device in this embodiment uses the light-emitting device described in Embodiment 2. This makes it possible to obtain a light-emitting device with good characteristics. Specifically, the method described in Embodiment 2. Because light-emitting devices have good luminous efficiency, it is possible to create light-emitting devices with low power consumption. ru.

[0340] Up to this point, we have explained active-matrix light-emitting devices, but from here on we will discuss passive devices. A matrix-type light-emitting device will be described. Figure 5 shows a passive light-emitting device fabricated by applying the present invention. This shows a matrix-type light-emitting device. Note that Figure 5(A) is a perspective view showing the light-emitting device, Figure 5( B) is a cross-sectional view obtained by cutting Figure 5(A) along the XY line. In Figure 5, on the substrate 951, An EL layer 955 is provided between electrode 952 and electrode 956. The end of electrode 952 is It is covered with an insulating layer 953. And a partition layer 954 is provided on top of the insulating layer 953. The side walls of the partition layer 954, as they approach the substrate surface, have a gap between one side wall and the other side wall. It has a slope that narrows as the partition becomes narrower. In other words, the cross-section of the partition wall layer 954 in the short-side direction is It is a shape, and the bottom edge (which 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 edge (the edge that faces the same direction as the surface direction of the insulating layer 953 and does not come into contact with the insulating layer 953). It is shorter than that. In this way, by providing the partition layer 954, light emission devices caused by static electricity, etc. This can prevent defects in the system. Furthermore, it can also be implemented in passive matrix type light-emitting devices. It uses the light-emitting device described in Form 2, and is a reliable light-emitting device, or has low power consumption. It can be made into a small light-emitting device.

[0341] The light-emitting device described above consists of numerous tiny light-emitting devices arranged in a matrix. Because these can be controlled, it can be suitably used as a display device for representing images. It is a light-emitting device.

[0342] Furthermore, this embodiment can be freely combined with other embodiments.

[0343] (Embodiment 4) In this embodiment, Figure 6 shows an example in which the light-emitting device described in Embodiment 2 is used as an illumination device. I will explain while referring to Figure 6(B). Figure 6(B) is a top view of the lighting device, and Figure 6(A) is a top view of Figure 6(B). This is a cross-sectional view.

[0344] The lighting device in this embodiment has a light-transmitting substrate 400 which is a support, and a first An electrode 401 is formed. The first electrode 401 is the first electrode 10 in Embodiment 2. This corresponds to 1. When light is extracted from the first electrode 401 side, the first electrode 401 is light-transmitting. It is formed from a material having [a certain characteristic].

[0345] A pad 412 for supplying voltage to the second electrode 404 is formed on the substrate 400.

[0346] An EL layer 403 is formed on the first electrode 401. The EL layer 403 is in Embodiment 2. The configuration of the EL layer 103 in the light-emitting units 511, 512 and the charge generation layer 513 This corresponds to a combined configuration, etc. Please refer to the relevant description for details on these configurations.

[0347] The EL layer 403 is covered to form the second electrode 404. The second electrode 404 is in Embodiment 2. This corresponds to the second electrode 102. When light emission is taken from the first electrode 401 side, the second The electrode 404 is formed of a highly reflective material. The second electrode 404 is pad 412 Voltage is supplied by connecting it to it.

[0348] The above describes a light-emitting device having a first electrode 401, an EL layer 403, and a second electrode 404. The lighting device shown in this embodiment has a light-emitting device with high luminous efficiency. Since it is a chair, the lighting device in this embodiment is a lighting device with low power consumption. It is possible.

[0349] The substrate 400 on which the light-emitting device having the above configuration is formed and the sealing substrate 407 are sealed The lighting device is completed by fixing and sealing it using materials 405 and 406. Either 405 or 406 is acceptable. Also, the inner sealing material 406 (Figure 6 (B) (Not shown) A desiccant can also be mixed in, which allows it to absorb moisture. This leads to improved reliability.

[0350] Furthermore, the pad 412 and a portion of the first electrode 401 are extended outside the sealing materials 405 and 406. By providing it, it can be used as an external input terminal. Also, a converter can be placed on top of it. An IC chip 420 or similar, which incorporates such features, may also be provided.

[0351] As described above, the lighting device described in this embodiment has an EL element and the light-emitting device described in Embodiment 2. This allows for a light-emitting device with low power consumption.

[0352] (Embodiment 5) In this embodiment, an example of an electronic device that includes the light-emitting device described in Embodiment 2 as a part thereof is provided. This will be explained. The light-emitting device described in Embodiment 2 has good luminous efficiency and low power consumption. It is a small light-emitting device. As a result, the electronic device described in this embodiment has low power consumption. It is possible to create an electronic device that has a small light-emitting part.

[0353] Examples of electronic devices to which the above-mentioned light-emitting device is applied include television equipment (televisions, and (Also called a television receiver), monitors for computers, digital cameras, digital cameras Digital video cameras, digital photo frames, mobile phones (both mobile phones and mobile phone devices) (Examples include) portable game consoles, personal digital assistants, audio playback devices, and large game machines such as pachinko machines. These are some examples. Specific examples of these electronic devices are shown below.

[0354] Figure 7(A) shows an example of a television system. The television system is housed in a 710 enclosure. The display unit 7103 is incorporated into part 1. Also, the housing is connected by the stand 7105. This shows the configuration supporting 7101. The display unit 7103 can display video. The display unit 7103 is capable of arranging the light-emitting devices described in Embodiment 2 in a matrix. It is composed of the following.

[0355] The television equipment can be operated using the control switches on the housing 7101 or a separate remote control. This can be done using the device 7110. The remote control device 7110 has an operation key 7109. This allows you to control the channel and volume, and the video displayed on the display unit 7103 It can be operated. Also, the remote control unit 7110 A display unit 7107 that displays the information output from the unit may also be provided.

[0356] The television system shall consist of a receiver, modem, etc. It can receive television broadcasts, and also communicate via wired or wireless connection through a modem. By connecting to a network, one-way (sender to receiver) or two-way (sender to receiver) communication is possible. It is also possible to communicate information between recipients, or between recipients themselves.

[0357] Figure 7(B1) is a computer, consisting of the main unit 7201, the casing 7202, the display unit 7203, and a key - Includes board 7204, external connection port 7205, pointing device 7206, etc. Furthermore, this computer arranges the light-emitting devices described in Embodiment 2 in a matrix. It is manufactured by using it in the display unit 7203. The computer in Figure 7(B1) is It may also be in a form like 7(B2). The computer in Figure 7(B2) has a keyboard 7 204, a second display unit 7210 is provided instead of the pointing device 7206. The second display unit 7210 is a touch panel, and the second display unit 7210 displays Input can be performed by operating the displayed input indicator with your finger or a special pen. Furthermore, the second display unit 7210 can display not only input information but also other images. It is possible. The display unit 7203 may also be a touch panel. The two screens are hinged. Because it is connected, the screen may be scratched or damaged when stored or transported. This can also prevent problems from occurring.

[0358] Figure 7(C) shows an example of a mobile terminal. The mobile phone is incorporated into the housing 7401. In addition to the display unit 7402, there are operation buttons 7403, an external connection port 7404, and a speaker 740 5. It is equipped with a microphone 7406, etc. The mobile phone is the light-emitting device described in Embodiment 2. It has a display unit 7402 made by arranging devices in a matrix.

[0359] The mobile terminal shown in Figure 7(C) allows users to input information by touching the display unit 7402 with their fingers or other objects. It can also be configured to allow for making phone calls or composing emails. Operations such as this can be performed by touching the display unit 7402 with a finger or the like.

[0360] The display unit 7402 has three main modes. The first is a display that primarily displays images. The first mode is display mode, the second is input mode which is mainly for inputting information such as characters. The third is display mode. This is a display + input mode, which is a combination of two modes: display mode and input mode.

[0361] For example, when making a phone call or composing an email, the display unit 7402 is used for text input. In this case, the primary text input mode should be used, and you should perform the input operation for the characters displayed on the screen. It is preferable to display a keyboard or number buttons on most of the screen of the display unit 7402. It seems so.

[0362] Furthermore, the mobile device has sensors inside that detect tilt, such as a gyroscope and an accelerometer. By installing the device, the orientation of the mobile terminal (portrait or landscape) is determined, and the screen display of the display unit 7402 is displayed accordingly. The display can be set to switch automatically.

[0363] Furthermore, screen modes can be switched by touching the display unit 7402 or by operating the housing 7401. This is done by operating button 7403. Also, the type of image displayed on display unit 7402 Therefore, it is also possible to switch between them. For example, the image signal displayed on the display unit is a video signal. Switch to display mode if it's data, or to input mode if it's text data.

[0364] Furthermore, in input mode, the signal detected by the optical sensor of the display unit 7402 is detected and displayed If there is no input via touch operation on unit 7402 for a certain period of time, the screen mode will be changed to input mode. You may also control the system to switch from that display mode to a different mode.

[0365] The display unit 7402 can also function as an image sensor. For example, the display unit 74 By touching device 02 with the palm or fingers, the user can be authenticated by capturing images of their palm print, fingerprints, etc. Furthermore, the display unit may have a backlight that emits near-infrared light or a sensing light that emits near-infrared light. Using the appropriate source, it is also possible to image finger veins, palmar veins, and other veins.

[0366] The configuration shown in this embodiment is a combination of the configurations shown in Embodiments 1 to 4 as appropriate. They can be used together.

[0367] As described above, the application range of the light-emitting device equipped with the light-emitting device described in Embodiment 2 is extremely broad. This light-emitting device can be applied to electronic devices in all fields. Embodiment 2 By using the described light-emitting device, it is possible to obtain electronic devices with low power consumption.

[0368] Figure 8(A) is a schematic diagram showing an example of a cleaning robot.

[0369] The cleaning robot 5100 has a display 5101 located on the top and multiple displays located on the sides. It has several cameras 5102, brushes 5103, and operation buttons 5104. However, the underside of the 5100 cleaning robot is equipped with wheels, a suction port, etc. The 5100 robot also includes an infrared sensor, ultrasonic sensor, acceleration sensor, and piezo sensor. It is equipped with various sensors such as optical sensors and gyro sensors. Also, the cleaning robot 5 Unit 100 is equipped with wireless communication means.

[0370] The cleaning robot 5100 moves autonomously, detects the dirt 5120, and uses the suction port located on its underside to... It can then vacuum up the dust.

[0371] Furthermore, the cleaning robot 5100 analyzes images captured by the camera 5102, and detects walls, furniture, or It can determine the presence or absence of obstacles such as steps. Furthermore, image analysis can detect wiring and other obstacles. If an object that may become entangled in brush 5103 is detected, the rotation of brush 5103 will be stopped. can.

[0372] The display 5101 displays information such as the battery level and the amount of dust collected. This is possible. The path taken by the cleaning robot 5100 can be displayed on the display 5101. Good. Also, the display 5101 is a touch panel, and the operation buttons 5104 are on the display. It may also be provided at Ray 5101.

[0373] The cleaning robot 5100 can communicate with portable electronic devices 5140 such as smartphones. Yes, it is possible. Images captured by camera 5102 can be displayed on the portable electronic device 5140. Therefore, the owner of the 5100 cleaning robot can know what's happening in the room even when they're away from home. It is possible to display the information on the display 5101 on portable electronic devices such as smartphones. You can also check it there.

[0374] A light-emitting device according to one aspect of the present invention can be used in a display 5101.

[0375] The robot 2100 shown in Figure 8(B) consists of a computing unit 2110, an illuminance sensor 2101, and a microphone. Lophone 2102, upper camera 2103, speaker 2104, display 2105, bottom It is equipped with a camera 2106, an obstacle sensor 2107, and a moving mechanism 2108.

[0376] Microphone 2102 has the function of detecting the user's voice and ambient sounds, etc. Speaker 2104 has the function of emitting sound. Robot 2100 has a microphone Using the 2102 and speaker 2104, communication with the user is possible. It is possible.

[0377] The display 2105 has the function of displaying various information. The robot 2100 is The user can display the desired information on the display 2105. The 2105 may have a touch panel. Also, the display 2105 is removable. It can be any information terminal capable of charging, and by installing it in a fixed position on the robot 2100, And it enables the transfer of data.

[0378] The upper camera 2103 and lower camera 2106 are used to image the area around the robot 2100. It has the ability to detect obstacles. Furthermore, the obstacle sensor 2107 uses the moving mechanism 2108 to detect robot 210 Robot 21 can detect the presence or absence of obstacles in the direction of travel as it moves forward. 00 uses the upper camera 2103, the lower camera 2106 and the obstacle sensor 2107 The light-emitting device according to one aspect of the present invention can recognize its surroundings and move safely. It can be used in display 2105.

[0379] Figure 8(C) shows an example of a goggle-type display. For example, the housing 5000, the display unit 5001, the speaker 5003, the LED lamp 5004, Connection terminal 5006, sensor 5007 (force, displacement, position, velocity, acceleration, angular velocity, rotational speed, Distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, electric current, voltage, power, radiation (including functions for measuring radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation), It includes a crossphone 5008, a second display unit 5002, a support unit 5012, an earphone 5013, etc. do.

[0380] A light-emitting device according to one aspect of the present invention is used in a display unit 5001 and a second display unit 5002. can.

[0381] Figure 9 shows an example in which the light-emitting device described in Embodiment 2 is used in a desk lamp, which is a lighting device. The desk lamp shown in Figure 9 has a housing 2001 and a light source 2002. As for the second example, the lighting device described in Embodiment 3 may be used.

[0382] Figure 10 shows the light-emitting device described in Embodiment 2 used as an indoor lighting device 3001. This is an example. The light-emitting device described in Embodiment 2 is a light-emitting device with high luminous efficiency. This allows for a lighting device with low power consumption. Also, the light-emitting device described in Embodiment 2 Because chairs can be made to cover a large area, they can be used as large-area lighting devices. The light-emitting device described in Embodiment 2 is thin and can therefore be used as a thinned lighting device. This becomes possible.

[0383] The light-emitting device described in Embodiment 2 can also be mounted on the windshield or dashboard of an automobile. It can be mounted. Figure 11 shows the light-emitting device described in Embodiment 2 mounted on the front of an automobile. This shows one embodiment for use in a display or dashboard. Display areas 5200 to 5203 are This is a display provided using the light-emitting device described in Embodiment 2.

[0384] Display area 5200 and display area 5201 are in an embodiment provided on the windshield of an automobile. A display device equipped with the light-emitting device described in 2. The light-emitting device described in Embodiment 2. This is achieved by fabricating the first and second electrodes with translucent electrodes, so that the opposite side is transparent. It can be used as a display device that is visible through a transparent, so-called see-through state. If it's a display, even if it's installed on the windshield of a car, it won't obstruct the view. It can be installed. Furthermore, if transistors or other components for driving are to be installed, organic semiconductors may be used. Organic transistors made of conductive materials, and transistors using oxide semiconductors, etc., have light transmission properties. It is best to use a transistor that has one.

[0385] The display area 5202 is equipped with the light-emitting device described in Embodiment 2, which is provided in the pillar portion. This is a display device. The display area 5202 displays images from an imaging device installed on the vehicle body. By extending it, the view obstructed by the pillar can be compensated for. Also, similarly, The display area 5203 provided on the shoeboard section allows the view obstructed by the vehicle body to be seen by the car. By displaying images from externally mounted imaging devices, blind spots are compensated for, and safety is enhanced. It can be done by projecting images that complement the parts that are not visible, making it more natural. Safety checks can be performed without any sense of unease.

[0386] Display area 5203 also displays navigation information, speedometer, tachometer, air conditioning settings, etc. By displaying this information, various types of information can be provided. The display can be adjusted to suit the user's preferences. The displayed items and layout can be changed. Note that this information is displayed in area 520. It can also be provided in display areas 0 to 5202. The 5203 can also be used as a lighting device.

[0387] Figures 12(A) and (B) also show a foldable portable information terminal 5150. The portable information terminal 5150 consists of a housing 5151, a display area 5152, and a bendable portion 515 It has 3. Figure 12(A) shows the portable information terminal 5150 in its unfolded state. Figure 12( B) shows the portable information terminal in its folded state. The portable information terminal 5150 has a large display area Despite having a 5152mm field of view, it folds up compactly and is highly portable.

[0388] The display area 5152 can be folded in half by the bending portion 5153. Bending portion 515 3 consists of an expandable member and multiple support members, and when folded, the expandable The member stretches. The bent portion 5153 has a radius of curvature of 2 mm or more, preferably 3 mm or more. It folds up.

[0389] Note that the display area 5152 is a touch panel (input / output) equipped with a touch sensor (input device). It may also be a device. The light-emitting device according to one aspect of the present invention can be used in the display area 5152. Cut.

[0390] Figures 13(A) to (C) also show a foldable portable information terminal 9310. Figure 13 (A) shows the portable information terminal 9310 in its unfolded state. Figure 13(B) shows the unfolded state or This shows the portable information terminal 9310 in an intermediate state, transitioning from one folded state to the other. Figure 13(C) shows the folded state of the personal digital assistant 9310. Personal digital assistant 9310 It offers excellent portability when folded and a seamless, wide display area when unfolded. This provides excellent readability in the display.

[0391] 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). It may also be an input / output device. In addition, the display panel 9311 is connected via the hinge 9313. By bending the two housings 9315, the mobile information terminal 9310 is unfolded. It can be reversibly transformed from a folded state. A light-emitting device according to one aspect of the present invention It can be used with the display panel 9311. [Examples]

[0392] <<Synthesis Example 1>> In this embodiment, the organic compound shown as structural formula (100) in Embodiment 1, 2-{ (3',5'-di-tert-butyl)-1,1'-biphenyl-3-yl}-4,6- Bis(3,5-di-tert-butylphenyl)-1,3,5-triazine (abbreviation: mm) This document explains the synthesis method for tBumBP (dmmtBuPTzn). The structural formula for -dmmtBuPTzn is shown below.

[0393] [ka]

[0394] <Step 1: Synthesis of 3-bromo-3',5'-di-tert-butylbiphenyl> 1.0 g (4.3 mmol) of 3,5-di-t-butylphenylboronic acid in a three-necked flask. 1-Bromo-3-iodobenzene 1.5g (5.2 mmol), 2 mol / L potassium carbonate Add 4.5 mL of aqueous solution, 20 mL of toluene, and 3 mL of ethanol, and stir under reduced pressure. Degassing was performed by [method]. Furthermore, tris(2-methylphenyl)phosphine 52 mg (0 Add 0.17 mmol) and 10 mg (0.043 mmol) of palladium(II) acetate, and nitrate. The reaction was carried out at 80°C for 14 hours under an ambient atmosphere. After the reaction was complete, extraction with toluene was performed to obtain the result. The prepared organic layer was dried with magnesium sulfate. This mixture was naturally filtered, and the resulting filtrate... By purifying it using silica gel column chromatography (eluent: hexane) 1.0 g of the target white solid was obtained (yield: 68%). The synthesis scheme for Step 1 is shown in the following formula ( As shown in a-1).

[0395] [ka]

[0396] <Step 2: 2-(3',5'-di-tert-butylbiphenyl-3-yl)-4, Synthesis of 4,5,5-tetramethyl-1,3,2-dioxaborolane 1.0 g of 3-bromo-3',5'-di-tert-butylbiphenyl in a three-necked flask (2 0.9 mmol), Bis(pinacolate) diboron 0.96 g (3.8 mmol), Ca acetate Add 0.94 g (9.6 mmol) of lium and 30 mL of 1,4-dioxane, and stir under reduced pressure. Degassing was performed by mixing. Furthermore, 2-dicyclohexylphosphin-2',6' was added. -Dimethoxybiphenyl 0.12g (0.30 mmol), [1,1'-Bis(diphenyl [Luphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct 0. 12 g (0.15 mmol) was added and the reaction was carried out under a nitrogen atmosphere at 110°C for 24 hours. After the reaction is complete, extraction with toluene is performed, and the resulting organic layer is dried with magnesium sulfate. The mixture was allowed to breathe naturally. The resulting filtrate was subjected to silica gel column chromatography. By purification with toluene (eluent), 0.89 g of the target yellow oil was obtained. (Yield: 78%). The synthesis scheme for Step 2 is shown in the following formula (a-2).

[0397] [ka]

[0398] <Step 3: Synthesis of mmtBumBP-dmmtBuPTzn> In a three-necked flask, add 4,6-bis(3,5-di-tert-butylphenyl)-2-chloro -1,3,5-triazine 0.8g (1.6 mmol), 2-(3',5'-di-ter t-butylbiphenyl-3-yl)-4,4,5,5-tetramethyl-1,3,2-diole Xaborolane 0.89g (2.3 mmol), Tripotassium phosphate 0.68g (3.2 mg) Add 3 mL of water, 8 mL of toluene, and 3 mL of 1,4-dioxane, and stir under reduced pressure. Degassing was performed by doing so. Furthermore, palladium(II) acetate 3.5 mg (0.016 m) was added to this. (mol), Tris(2-methylphenyl)phosphine 10 mg (0.032 mmol) In addition, the mixture was heated under a nitrogen atmosphere under reflux for 12 hours. After the reaction was complete, extraction with ethyl acetate was performed. The resulting organic layer was dried over magnesium sulfate. This mixture was then naturally filtered. The filtrate was concentrated and subjected to silica gel column chromatography (eluent: ethyl acetate:hexa The solid was purified using a 1:20 ratio of ions to obtain a solid. This solid was then subjected to silica gel column chromatography. - Purified using (eluent chloroform:hexane = changed from 5:1 to 1:0). The obtained solid was recrystallized in hexane to obtain 0.88 g of the desired white solid (yield :76% was obtained. The synthesis scheme for Step 3 is shown in equation (a-3) below.

[0399] [ka]

[0400] The obtained white solid 0.87 g was subjected to argon gas flow by the train sublimation method. However, the substance was purified by sublimation under conditions of 230°C and a pressure of 5.8 Pa. After sublimation purification, the target substance was obtained as a white solid. The body was obtained in 0.82g with a recovery rate of 95%.

[0401] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 above (1 (H-NMR) The analysis results are shown below. From these results, in this embodiment, the structure represented by the above-mentioned structural formula (100) An organic compound, mmtBumBP-dmmtBuPTzn, which is one embodiment of the present invention, is obtained. It was discovered that...

[0402] H 1 NMR(CDCl3,300MHz):δ=1.42-1.49(m,54H), 7.50(s,1H),7.61-7.70(m,5H),7.87(d,1H),8. 68-8.69(m,4H),8.78(d,1H),9.06(s,1H).

[0403] Furthermore, the absorption spectrum of mmtBumBP-dmmtBuPTzn was measured using a UV-Vis spectrophotometer. Measurements were taken using a JASCO V550 (manufactured by JASCO Corporation). mmtBumBP-dmmtBu The absorption spectrum of PTzn is obtained from the absorption spectrum of a dichloromethane solution. The spectrum was obtained by subtracting the spectrum measured by placing only the sample in a quartz cell. As a result, at 267 nm An absorption peak is observed, but there is no absorption in the visible region, specifically between 440 nm and 700 nm. I found out.

[0404] Next, the mmtBumBP-dmmtBuPTzn obtained in this example was subjected to liquid chromatography. Liquid Chromatography Mass Spectro The analysis was performed using metry (abbreviated as LC / MS analysis).

[0405] LC / MS analysis was performed using a Thermo Fisher Scientific Ultimate30. LC (liquid chromatography) separation was performed using 00, and Thermo Fisher Science Mass spectrometry (MS) analysis was performed using Q Exactive from IFIC.

[0406] LC separation is performed using any column at a column temperature of 40°C, with appropriate solvent selection for the liquid delivery conditions. The sample is prepared by dissolving mmtBumBP-dmmtBuPTzn at any concentration in an organic solvent. The solution was prepared and injected in a volume of 5.0 μL.

[0407] The PRM method is used to determine the exact mass of mmtBumBP-dmmtBuPTzn. MS / MS measurement was performed at m / z 721.53. The PRM setting was: Target IO The mass range of m / z is 721.53±2.0 (isolation window=4 Detection was performed in positive mode. The target ion was accelerated within the collision cell. The energy NCE (Normalized Collision Energy) The measurement was performed with a value of 50. The MS spectrum obtained from the MS / MS measurement is shown in Figure 14.

[0408] Fragment ions with m / z 216.17 and m / z 292.21 were detected. These consist of one of the substituents bonded to triazine and carbon and nitrogen atoms derived from triazine. It is thought to be a fragment that has been made. For example, m / z 216.17 is tarsi A phenyl group with two butyl groups bonded to it has one carbon and one nitrogen atom derived from triazine. It is thought to be a combined fragment. Also, m / z 292.21 is tertiary. A biphenyl group, to which two butyl groups are bonded, is then bonded to one carbon and one nitrogen atom derived from triazine. These fragments are thought to be fragments that possess a triazine skeleton. This can be considered one of the characteristics of the compound.

[0409] Next, regarding the glass transition temperature, we will discuss differential scanning calorimetry (DSC), PerkinElmer. The study was conducted using a Pyris 1 DSC. The measurement results indicated that the glass transition temperature was 112°C. It was °C. Thus, the organic compound according to one embodiment of the present invention exhibits a high glass transition temperature. It was found to have good heat resistance.

[0410] Furthermore, Figure 15 shows the refractive index of mmtBumBP-dmmtBuPTzn using a spectroscopic ellipsometer. The results measured using the M-2000U (manufactured by J.A. Woolam Japan Co., Ltd.) are shown below. For the measurement, a film was used in which each layer of material was deposited on a quartz substrate by vacuum deposition, with a thickness of approximately 50 nm. The figure shows the refractive index of ordinary light (n, Ordinary) and the refractive index of extraordinary light. A certain n, Extra-ordinary, was described.

[0411] From this figure, mmtBumBP-dmmtBuPTzn is in the blue emission region (above 455nm). The ordinary refractive index is in the range of 1.50 to 1.75 throughout the entire range (below 465nm), and also 6 The ordinary refractive index at 33 nm is also in the range of 1.45 to 1.70, and the material has a low refractive index. It turned out to be a food.

[0412] Furthermore, light-emitting devices fabricated using this organic compound as an electron transport material exhibit good light emission. I was able to obtain it. [Examples]

[0413] ≪Synthesis Example 2≫ In this embodiment, the organic compound shown as structural formula (120) in Embodiment 1, 2-{ (3',5'-di-tert-butyl)-1,1'-biphenyl-3-yl}-4,6- Regarding the synthesis method of diphenyl-1,3,5-triazine (abbreviation: mmtBumBPTzn) Let me explain. The structure of mmtBumBPTzn is shown below.

[0414] [ka]

[0415] <Step 1: Synthesis of 3-bromo-3',5'-di-tert-butylbiphenyl> The synthesis was performed in the same manner as in step 1 of synthesis example 1.

[0416] <Step 2: 2-(3',5'-di-tert-butylbiphenyl-3-yl)-4, Synthesis of 4,5,5-tetramethyl-1,3,2-dioxaborolane The synthesis was performed in the same manner as in step 2 of synthesis example 1.

[0417] <Step 3: Synthesis of mmtBumBPTzn> 1.5g of 4,6-diphenyl-2-chloro-1,3,5-triazine in a three-necked flask (5 0.6 mmol), 2-(3',5'-di-tert-butylbiphenyl-3-yl)-4 4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2.4g (6.2 mmol) ), tripotassium phosphate 2.4g (11 mmol), water 10mL, toluene 28mL, 1, 10 mL of 4-dioxane was added and the mixture was stirred under reduced pressure to remove air. Then vinegar was added. Palladium(II) acid 13 mg (0.056 mmol), Tris(2-methylphenyl) Add 34 mg (0.11 mmol) of phosphine, heat under a nitrogen atmosphere for 14 hours under reflux, and then reverse the reaction. The reaction was carried out. After the reaction was complete, extraction was performed with ethyl acetate, and the water of the resulting organic layer was converted to magnesium sulfate. The solution was removed with citric acid. The filtrate obtained by natural filtration of this mixture was then subjected to silica gel column chromatography. To tography (developing solvent changed from chloroform:hexane = 1:5 to 1:3) After purification, 2.0 g of the desired white solid was obtained by recrystallization in hexane. Rate: 51%). The synthesis scheme for Step 3 is shown in equation (b-1) below.

[0418] [ka]

[0419] The obtained white solid 2.0 g was subjected to the train sublimation method under an argon gas stream. Sublimation purification was performed under conditions of 3.4 Pa pressure and 220°C. The solid was heated. After sublimation purification, the target product was obtained. A white solid of 1.8 g was obtained with a recovery rate of 80%.

[0420] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 3 above ( 1 (H-NMR) The analysis results are shown below. From these results, it can be seen that in this embodiment, the structure represented by the above-mentioned structural formula (120) It was found that an organic compound, mmtBumBPTzn, which is one embodiment of the present invention, was obtained. Ta.

[0421] H 1 NMR(CDCl3,300MHz):δ=1.44(s,18H),7.51- 7.68(m,10H),7.83(d,1H),8.73-8.81(m,5H),9 .01(s,1H).

[0422] Next, the absorption spectrum of mmtBumBPTzn was measured using a UV-Vis spectrophotometer (JASCO Corporation). The measurement was performed using a V550 model. The absorption spectrum of mmtBumBPTzn is shown. From the absorption spectrum of a lolomethane solution, only dichloromethane was measured by placing it in a quartz cell. The result was obtained by subtracting the Pectol. As a result, the dichloromethane solution of mmtBumBPTzn is An absorption peak was observed at 271 nm. This corresponds to the visible region, from 440 nm to 700 nm. Since there is no absorption in this range, it is understood that it has good absorption properties as a display material. It was.

[0423] Next, the mmtBumBPTzn obtained in this example was subjected to liquid chromatography-mass spectrometry (L iquid chromatography mass spectrometry The analysis was performed using LC / MS analysis.

[0424] LC / MS analysis was performed using a Thermo Fisher Scientific Ultimate30. LC (liquid chromatography) separation was performed using 00, and Thermo Fisher Science Mass spectrometry (MS) analysis was performed using Q Exactive from IFIC.

[0425] LC separation is performed using any column at a column temperature of 40°C, with appropriate solvent selection for the liquid delivery conditions. The sample was prepared by dissolving mmtBumBPTzn of any concentration in an organic solvent and then injected. The volume was set to 5.0 μL.

[0426] According to the PRM method, the Exact Mass of mmtBumBPTzn is m / z 497 MS / MS measurements were performed at 0.28. The PRM setting was configured to define the mass range of the target ion as m Set / z 497.28±2.0 (isolation window=4), and detection is performed by P The procedure was performed in activative mode. The energy N required to accelerate the target ion within the collision cell was determined. Measured with CE (Normalized Collision Energy) set to 50. The MS spectrum obtained from the MS / MS measurement is shown in Figure 16.

[0427] Fragment ions with m / z 104.05 and m / z 292.21 were detected. These consist of one of the substituents bonded to triazine and carbon and nitrogen atoms derived from triazine. It is thought to be a fragment that has been formed. For example, m / z 104.05 is phenyl It is thought to be a fragment in which one carbon and one nitrogen atom derived from triazine are bonded to the t-group. It is. m / z 292.21 has substituents other than the phenyl group that are carbon and nitrogen derived from triazine. These fragments are thought to be fragments formed by the combination of individual elements. This can be considered one of the characteristics of compounds with an azine skeleton.

[0428] Furthermore, Figure 17 shows the refractive index of mmtBumBPTzn measured with a spectroscopic ellipsometer (J.A. The results of measurements using the M-2000U (manufactured by Woolam Japan) are shown. A film was used in which each layer of material was deposited on a British substrate by vacuum deposition, with a thickness of approximately 50 nm. n,Ordinary is the refractive index of ordinary light rays, and n,Extr is the refractive index of extraordinary light rays. I wrote "a-ordinary".

[0429] From this figure, mmtBumBPTzn is in the blue emission region (455nm to 465nm). The refractive index is in the range of 1.50 to 1.75 throughout the entire region, and at 633 nm... The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. It was.

[0430] Furthermore, light-emitting devices fabricated using this organic compound as an electron transport material exhibit good light emission. I was able to obtain it. [Examples]

[0431] ≪Synthesis Example 3≫ In this embodiment, the organic compound shown as structural formula (121) in Embodiment 1, 2-( 3,3'',5,5''-Tetra-tert-butyl-1,1':3',1''-Turf Phenyl-5'-yl)-4,6-diphenyl-1,3,5-triazine (abbreviation: mmtB) The synthesis method for mmtBumTPTzn is described below. The structure of mmtBumTPTzn is shown below. show.

[0432] [ka]

[0433] <Step 1: Synthesis of mmtBumTPTzn> 0.67g of 4,6-diphenyl-2-chloro-1,3,5-triazine in a three-necked flask. 2.5 mmol), 2-3,5-bis(3,5-di-tert-butylphenyl)benz 1.6g of 1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.8 mmol), tripotassium phosphate 1.1 g (5.0 mmol), water 5 mL, toluene 14 mL of 1,4-dioxane and 5 mL of 1,4-dioxane were added, and the mixture was stirred under reduced pressure to remove air. Furthermore, palladium(II) acetate 5.6 mg (0.025 mmol), Tris(2- Add 15 mg (0.050 mmol) of methylphenylphosphine and, under a nitrogen atmosphere, 19 The mixture was heated under reflux for a specified time. After the reaction was complete, the reaction solution was filtered and separated into filtrate and filtrate (1). The filtrate was extracted with ethyl acetate, and the resulting organic layer was dried with magnesium sulfate. This mixture was filtered, the resulting filtrate was concentrated, and filtered again to obtain filtrate (2).

[0434] The obtained filtrates (1) and (2) were combined and subjected to silica gel column chromatography (development). After purification with solvent chloroform:hexane (1:5), the desired result was obtained by recrystallizing with toluene. 1.2 g of a white solid was obtained (yield: 71%). The synthesis scheme of Step 1 is shown in the following formula (c- As shown in 1).

[0435] [ka]

[0436] The obtained white solid 1.2 g was subjected to the train sublimation method under an argon gas stream. The solution was purified by sublimation at a pressure of 3.4 Pa and a temperature of 285°C. After sublimation purification, 1.1 g of the target substance was obtained as a white solid. It was obtained with a recovery rate of 89%.

[0437] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 1 above ( 1 (H-NMR) The analysis results are shown below. From these results, it can be seen that in this embodiment, the structure represented by the above-mentioned structural formula (121) It was found that an organic compound, mmtBumTPTzn, which is one embodiment of the present invention, was obtained. Ta.

[0438] H 1 NMR(CDCl3,300MHz):δ=1.44(s,36H),7.54- 7.62(m,12H),7.99(t,1H),8.79(d,4H),8.92(d ,2H).

[0439] Next, the absorption spectrum of mmtBumTPTzn was measured using a UV-Vis spectrophotometer (JASCO Corporation). The measurement was performed using a V550 model. The absorption spectrum of mmtBumTPTzn is shown. From the absorption spectrum of a lolomethane solution, only dichloromethane was measured by placing it in a quartz cell. The result was obtained by subtracting the vector. As a result, an absorption peak was observed at 265 nm, in the visible region. It was found that there is no absorption in the range of 440 nm to 700 nm.

[0440] Next, the mmtBumTPTzn obtained in this example was subjected to liquid chromatography-mass spectrometry (L iquid chromatography mass spectrometry The analysis was performed using LC / MS analysis.

[0441] LC / MS analysis was performed using a Thermo Fisher Scientific Ultimate30. LC (liquid chromatography) separation was performed using 00, and Thermo Fisher Science Mass spectrometry (MS) analysis was performed using Q Exactive from IFIC.

[0442] LC separation is performed using any column at a column temperature of 40°C, with appropriate solvent selection for the liquid delivery conditions. The sample was prepared by dissolving mmtBumTPTzn of any concentration in an organic solvent and then injected. The volume was set to 5.0 μL.

[0443] According to the PRM method, the Exact Mass of mmtBumTPTzn is m / z 685 MS / MS measurements were performed at 0.44. The PRM setting was set to the mass range of the target ion m Set / z to 685.44±2.0 (isolation window=4), and detection is performed by P The procedure was performed in activative mode. The energy N required to accelerate the target ion within the collision cell was determined. Measured with CE (Normalized Collision Energy) set to 50. The MS spectrum obtained from the MS / MS measurement is shown in Figure 18.

[0444] Fragment ions with m / z 104.05 and m / z 480.36 were detected. These consist of one of the substituents bonded to triazine and carbon and nitrogen atoms derived from triazine. It is thought to be a fragment that has been formed. For example, m / z 104.05 is phenyl It is thought to be a fragment in which one carbon and one nitrogen atom derived from triazine are bonded to the t-group. It is. m / z 480.36 has substituents other than the phenyl group that are carbon and nitrogen derived from triazine. These fragments are thought to be fragments formed by the combination of individual elements. This can be considered one of the characteristics of compounds with an azine skeleton.

[0445] Furthermore, Figure 19 shows the refractive index of mmtBumTPTzn measured with a spectroscopic ellipsometer (J.A. The results of measurements using the M-2000U (manufactured by Woolam Japan) are shown. A film was used in which each layer of material was deposited on a British substrate by vacuum deposition, with a thickness of approximately 50 nm. n,Ordinary is the refractive index of ordinary light rays, and n,Extr is the refractive index of extraordinary light rays. I wrote "a-ordinary".

[0446] From this figure, mmtBumTPTzn is in the blue emission region (455nm to 465nm). The refractive index is in the range of 1.50 to 1.75 throughout the entire region, and at 633 nm... The refractive index is also in the range of 1.45 to 1.70, indicating that it is a material with a low refractive index. It was.

[0447] Furthermore, light-emitting devices fabricated using this organic compound as an electron transport material exhibit good light emission. I was able to obtain it. [Examples]

[0448] <<Synthesis Example 4>> In this embodiment, the organic compound shown as structural formula (200) in Embodiment 1, 2-( 3',5'-di-tert-butylbiphenyl-3-yl)-4,6-bis(3,5-di -tert-butylphenyl)pyrimidine (abbreviation: mmtBumBP-dmmtBuPP) The synthesis method for m) will be explained below. The structure of mmtBumBP-dmmtBuPPm is as follows: This will be shown.

[0449] [ka]

[0450] <Step 1: 4,6-bis(3,5-ditert-butylphenyl)-2-chloro- Synthesis of 1,3-pyrimidines 1.4 g (7.8 mmol) of 2,4,6-trichloropyrimidine in a three-necked flask, acetone 40 mL nitrile, 16 mL water, 3,5-di-tert-butylphenylboronic acid 3.8 Add g (16 mmol) and 4.3 g (31 mmol) of potassium carbonate, and stir under reduced pressure. Degassing was performed by this. Here, bis(triphenylphosphine)palladium(II) dichloro 0.22 g (0.31 mmol) of lyd was added, and the mixture was stirred at 50°C for 4 hours under a nitrogen atmosphere. After the reaction is complete, toluene is added to the reaction mixture and washed with water and saturated saline solution to obtain the organic layer. The water was removed with magnesium sulfate. This mixture was naturally filtered. The resulting filtrate was concentrated. Shrinkage, silica gel column chromatography (eluent: hexane:toluene = 1:1) The product was purified by [method], yielding 2.7 g of the target white solid in a yield of 71%. Step 1 synthesis skim The formula is shown in equation (d-1) below.

[0451] [ka]

[0452] <Step 2: Synthesis of 3-bromo-3',5'-di-tert-butylbiphenyl> The synthesis was performed in the same manner as in step 1 of synthesis example 1.

[0453] <Step 3: 2-(3',5'-di-tert-butylbiphenyl-3-yl)-4, Synthesis of 4,5,5-tetramethyl-1,3,2-dioxaborolane The synthesis was performed in the same manner as in step 2 of synthesis example 1.

[0454] <Step 4: Synthesis of mmtBumBP-dmmtBuPPm> The 4,6-bis(3,5-di-tert-butyl) synthesized in Step 1 is placed in a three-necked flask. Enyl)-2-chloro-1,3-pyrimidine 0.93g (1.9 mmol) and step 3 2-(3',5'-di-tert-butylbiphenyl-3-yl)-4,4, synthesized 5,5-Tetramethyl-1,3,2-Dioxaborolane 0.92g (2.3 mmol), Potassium carbonate 0.53g (3.8 mmol), tetrahydrofuran (abbreviation: THF) 20 Add 4 mL of water and stir under reduced pressure to remove air. Then, add the tri-tert- Butylphosphonium tetrafluoroborate 17 mg (0.057 mmol) and Tris ( Add dibenzylideneacetone) dipalladium(0) 17 mg (0.019 mmol), This solution was stirred under a nitrogen atmosphere at 80°C for 17 hours. After the reaction was complete, toluene was added to the reaction mixture. Add water and saturated saline solution, then remove the water from the resulting organic layer with magnesium sulfate. The mixture was then filtered naturally. The resulting filtrate was subjected to silica gel column chromatography. The target product was purified using a developing solvent (hexane:toluene = 4:1) and obtained as a white solid of approximately 1.3 g was obtained (yield approximately 95%). The synthesis scheme for step 4 is shown in the following formula (d-2).

[0455] [ka]

[0456] Furthermore, nuclear magnetic resonance spectroscopy of the white solid obtained in step 4 above ( 1 (H-NMR) The analysis results are shown below. From these results, it can be seen that in this embodiment, the structure represented by the above-mentioned structural formula (200) An organic compound, mmtBumBP-dmmtBuPPm, which is one embodiment of the present invention, is obtained. I found out that...

[0457] H 1 NMR(CDCl3,300MHz):δ=1.39-1.45(m,54H), 7.47(t,1H),7.59-7.65(m,5H),7.76(d,1H),7. 95(s,1H),8.06(d,4H),8.73(d,1H),8.99(s,1H ).

[0458] Next, the absorption spectrum of mmtBumBP-dmmtBuPPm was measured using a UV-Vis spectrophotometer. Measurements were taken using a JASCO V550 (manufactured by JASCO Corporation). mmtBumBP-dmmtBuP The absorption spectrum of Pm is derived from the absorption spectrum of a dichloromethane solution, showing only dichloromethane. The spectrum was obtained by subtracting the spectrum measured in a quartz cell. As a result, absorption occurred at 267 nm. A peak is observed, and there is no absorption in the visible region, specifically in the range from 440 nm to 700 nm. I found out.

[0459] Next, the mmtBumBP-dmmtBuPPm obtained in this example was subjected to liquid chromatography. Liquid Chromatography Mass Spectro The analysis was performed using metry (abbreviated as LC / MS analysis).

[0460] LC / MS analysis was performed using a Thermo Fisher Scientific Ultimate30. LC (liquid chromatography) separation was performed using 00, and Thermo Fisher Science Mass spectrometry (MS) analysis was performed using Q Exactive from IFIC.

[0461] LC separation is performed using any column at a column temperature of 40°C, with appropriate solvent selection for the liquid delivery conditions. The sample is prepared by dissolving mmtBumBP-dmmtBuPPm at any concentration in an organic solvent. The solution was prepared and injected in a volume of 5.0 μL.

[0462] The exact mass of mmtBumBP-dmmtBuPPm is obtained by the PRM method. MS / MS measurements were performed at m / z 720.54. The PRM settings were as follows: Target ion The mass range is m / z 720.54±2.0 (isolation window=4) The detection was performed in positive mode. The target ions were accelerated within the collision cell. The energy NCE (Normalized Collision Energy) is 7 The measurement was performed with the value set to 0. The MS spectrum obtained from the MS / MS measurement is shown in Figure 20.

[0463] A fragment ion with a frequency of 216.17 m / z was detected. This ion was bound to triazine. A fragment composed of one of the substituents and carbon and nitrogen derived from triazine. It is thought that this is the case. For example, m / z 216.17 is a phenyl group with pyrimidine-derived carbon It is thought to be a fragment in which one element and one nitrogen are bonded together. This can be considered one of the characteristics of compounds that have a pyrimidine skeleton.

[0464] Furthermore, Figure 21 shows the refractive index of mmtBumBP-dmmtBuPPm using a spectroscopic ellipsometer. The results measured using the M-2000U (manufactured by J.A. Woolam Japan Co., Ltd.) are shown below. For the measurement, a film was used in which each layer of material was deposited on a quartz substrate by vacuum deposition, with a thickness of approximately 50 nm. The diagram shows n, the refractive index of ordinary light and n, the refractive index of extraordinary light. I wrote "n, Extra-ordinary".

[0465] From this figure, mmtBumBP-dmmtBuPPm is in the blue emission region (455nm and above). (Below 65nm) The ordinary refractive index is in the range of 1.50 to 1.75 throughout the entire range, and also 63 The ordinary refractive index at 3 nm is also in the range of 1.45 to 1.70, indicating a low refractive index material. It was found that...

[0466] Furthermore, light-emitting devices fabricated using this organic compound as an electron transport material exhibit good light emission. I was able to obtain it. [Examples]

[0467] In this embodiment, the light-emitting device 1 and comparative light-emitting device according to one embodiment of the present invention described in the embodiment Vice 1 will now be explained. The structural formulas of the organic compounds used in this example are shown below.

[0468] [ka]

[0469] (Method for fabricating light-emitting device 1) First, on a glass substrate, silver (Ag), palladium (Pd), and copper (Cu) are used as reflective electrodes. A 100 nm thick alloy film (Ag-Pd-Cu(APC) film) is formed by sputtering. After forming a thick film, indium tin oxide (ITSO) containing silicon oxide is spat as a transparent electrode. The first electrode 101 was formed by depositing a film with a thickness of 85 nm using the tarring method. The electrode area is 4 mm². 2 (2mm x 2mm)

[0470] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0471] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0472] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, N-(1,1'-biphenyl-4-yl)-N, represented by the above structural formula (i), obtained by vapor deposition. -[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethicone Lu-9H-fluorene-2-amine (abbreviation: PCBBiF) and electron acceptor material (OC The weight ratio of HD-001 to OCHD-001 is 1:0.05 (=PCBBiF:OCHD-001). A hole injection layer 111 was formed by co-depositing a 10 nm layer in this manner.

[0473] After depositing PCBBiF at a density of 20 nm on the hole injection layer 111, the structure represented by the above structural formula (ii) is obtained. N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p- - Phenyl (abbreviation: DBfBB1TP) is deposited to a thickness of 10 nm to form a hole transport layer 11 Formed 2.

[0474] Next, on the hole transport layer 112, 3,3'-(naphthalene-) represented by structural formula (iii) is added. 1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) An electron-blocking layer was formed by depositing a material to a wavelength of 0 nm.

[0475] Subsequently, 2-(10-phenyl-9-anthracenyl)bene, represented by structural formula (iv), is shown. Zo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA) and structural formula (v) Represented by 3,10-bis[N-(9-phenyl-9H-carbazol-2-yl)-N -phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviation: 3, 10PCA2Nbf(IV)-02) and Bnf(II) are used in a weight ratio of 1:0.015. The PhA:3,10PCA2Nbf(IV)-02) was co-deposited at 25 nm to produce light. Layer 113 was formed.

[0476] Next, we have a low refractive index material, 2-{(3',5'-di}, which is one embodiment of the present invention described in Example 1. (-tert-butyl)-1,1'-biphenyl-3-yl}-4,6-bis(3,5-di) -tert-butylphenyl)-1,3,5-triazine (abbreviation: mmtBumBP-d mmtBuPTzn) (structural formula (100)) is deposited to a size of 10 nm to form a hole block. After forming the layer, it is represented by the structural formula (vii) mmtBumBP-dmmtBuPTzn 6-methyl-8-quinolinolato-lithium (abbreviation: Li-6mq) and 1 by weight ratio 20n such that :1(=mmtBumBP-dmmtBuPTzn:Li-6mq) An electron transport layer 114 was formed by co-deposition.

[0477] After the formation of the electron transport layer 114, Li-6mq is deposited to a thickness of 1 nm to form the electron injection layer 11 Form 5, and finally, set the volume ratio of silver (Ag) to magnesium (Mg) to 1:0.1, and the film thickness By co-depositing to a size of 15 nm, a second electrode 102 is formed to create the light-emitting device 1. The second electrode 102 is semipermeable, having both the function of reflecting light and the function of transmitting light. These are hyper- and semi-reflective electrodes, and the light-emitting device in this embodiment extracts light from the second electrode 102. It is a hop-emission type element. Furthermore, on the second electrode 102, the structure is represented by structural formula (x). 1,3,5-tri(dibenzothiophen-4-yl)-benzene (abbreviation: DBT3P- II) is deposited at 70 nm to improve extraction efficiency.

[0478] (Method for fabricating comparative light-emitting device 1) Comparative light-emitting device 1 has a hole transport layer 112 thickness of 15 nm. Instead of mmtBumBP-dmmtBuPTzn used in the hole block layer, the structural formula ( Represented by vi), 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)- 1,1'-biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine (abbreviated) Using the name mFBPTzn, mmtBumBP-dmmtB was used in the electron transport layer 114. Instead of uPTzn, 2-[3-(2,6-dimethyl -3-pyridinyl)-5-(9-phenantrenyl)phenyl]-4,6-diphenyl- Using 1,3,5-triazine (abbreviation: mPn-mDMePyPTzn), electron transport layer 1 Instead of Li-6mq used in 14 and electron injection layer 115, the structure is represented by (ix). Using 8-quinolinolatolithium (abbreviated as Liq), the device was fabricated in the same manner as light-emitting device 1. Ta.

[0479] The element structures of light-emitting device 1 and comparative light-emitting device 1 are summarized in Table 1 below.

[0480] [Table 1]

[0481] Also, mmtBumBP-dmmtBuPTzn, mPn-mDMePyPTzn, Li Figure 22 shows the refractive indices of -6mq and Liq, respectively, and the refractive index at 456nm is shown. As shown in 2, the refractive index is measured using a spectroscopic ellipsometer (J.A. Woolam Japan). The procedure was performed using the company's M-2000U. The sample used for measurement consisted of each layer of material on a quartz substrate. A film with a thickness of approximately 50 nm was deposited by vacuum deposition. Note that the figure shows the refractive index of ordinary light. n, Ordinary and n, Extra-ordinary, which is the refractive index of an extraordinary ray. It was written as follows.

[0482] [Table 2]

[0483] Each of the above light-emitting devices was placed inside a glove box in a nitrogen atmosphere, and the light-emitting device was large The process of sealing the element with a glass substrate to prevent exposure to the elements (applying a sealing material around the element, After UV treatment and heat treatment at 80°C for 1 hour during sealing, the initial characteristics of these light-emitting devices are... Measurements were taken regarding the properties. Furthermore, the sealed glass substrate was treated with special measures to improve extraction efficiency. No other measures have been taken.

[0484] Figure 23 shows the luminance-current density characteristics of light-emitting device 1 and comparative light-emitting device 1, and the current efficiency- Brightness characteristics are shown in Figure 24, brightness-voltage characteristics in Figure 25, and current-voltage characteristics in Figure 26. The INDEX-luminance characteristics are shown in Figure 27, and the emission spectrum is shown in Figure 28. Device 1 and comparison light-emitting device 1: 1000 cd / m² 2 Table 3 shows the main characteristics of the vicinity. As shown below. Note that a spectroradiometer (Topcon) is used to measure luminance, CIE chromaticity, and emission spectrum. Measurements were taken at room temperature using a (SR-UL1R) device manufactured by the company.

[0485] The Blue Index (BI) is calculated by dividing the current efficiency (cd / A) by the y-chromaticity. This value is one of the indicators that represents the emission characteristics of blue light emission. Blue light emission is more luminous when the y chromaticity is small. It tends to produce light with high color purity. High-color-purity blue light emission even with a small luminance component. It is possible to represent a wide range of blue colors, and by using blue light emission with high color purity, blue Since the required brightness for color reproduction is reduced, a reduction in power consumption can be achieved. Therefore, BI, which takes into account y-chromaticity, one of the indicators of blue purity, is used as a means of representing the efficiency of blue light emission. The blue light-emitting device is more suitable for use in displays, and the higher the BI of the light-emitting device, the better the blue light-emitting device used in displays. It can be said that it is highly efficient as a chair.

[0486] [Table 3]

[0487] The results shown in Figures 23 to 28 and Table 3 indicate that a low refractive index material, which is one embodiment of the present invention, is used. Light-emitting device 1 exhibits almost the same emission spectrum as comparative light-emitting device 1, while the comparative emission It was found to be an EL device with better current efficiency than optical device 1.

[0488] Furthermore, the light-emitting device 1 and the comparative light-emitting device 1 have a luminescence of 1000 cd / m². 2 Bull in the vicinity The indices (BI) are 153 (cd / A / y) and 148 (cd / A / y), respectively. The maximum values ​​for BI were 161 (cd / A / y) and 149 (cd / A / y), respectively. Thus, light-emitting device 1 can be said to be a particularly good light-emitting device for BI. Therefore, One aspect of the present invention is suitable for light-emitting devices used in displays. [Examples]

[0489] In this embodiment, a light-emitting device 2 and a comparative light-emitting device 2, which are aspects of the present invention, are described below. Let me explain. The structural formulas of the organic compounds used in this example are shown below.

[0490] [ka]

[0491] (Method for fabricating light-emitting device 2) First, on a glass substrate, silver (Ag), palladium (Pd), and copper (Cu) are used as reflective electrodes. A 100 nm thick alloy film (Ag-Pd-Cu(APC) film) is formed by sputtering. After forming a thick film, indium tin oxide (ITSO) containing silicon oxide is spat as a transparent electrode. The first electrode 101 was formed by depositing a film with a thickness of 85 nm using the tarring method. The electrode area is 4 mm². 2 (2mm x 2mm)

[0492] Next, as a pretreatment for forming a light-emitting device on the substrate, the substrate surface is washed with water, and 2 After firing at 0°C for 1 hour, UV ozone treatment was performed for 370 seconds.

[0493] Then, 10 -4 A substrate is introduced into a vacuum deposition apparatus where the internal pressure is reduced to approximately Pa, and then vacuum deposition is performed. After vacuum firing at 170°C for 30 minutes in the heating chamber of the apparatus, the substrate is left for approximately 30 minutes. It was allowed to cool.

[0494] Next, the first electrode 101 is formed such that the surface on which the first electrode 101 is formed faces downwards. The prepared substrate is fixed to a substrate holder provided inside the vacuum deposition apparatus, and on the first electrode 101, N-(1,1'-biphenyl-4-yl)-N, represented by the above structural formula (i), obtained by vapor deposition. -[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethicone Lu-9H-fluorene-2-amine (abbreviation: PCBBiF) and electron acceptor material (OC The weight ratio of HD-001 to OCHD-001 is 1:0.05 (=PCBBiF:OCHD-001). A hole injection layer 111 was formed by co-depositing a 10 nm layer in this manner.

[0495] After depositing PCBBiF at a density of 20 nm on the hole injection layer 111, the structure represented by the above structural formula (ii) is obtained. N,N-bis[4-(dibenzofuran-4-yl)phenyl]-4-amino-p- - Phenyl (abbreviation: DBfBB1TP) is deposited to a thickness of 10 nm to form a hole transport layer 11 Formed 2.

[0496] Next, on the hole transport layer 112, 3,3'-(naphthalate represented by the above structural formula (iii) is added. n-1,4-diyl)bis(9-phenyl-9H-carbazole) (abbreviation: PCzN2) An electron blocking layer was formed by depositing a material to a thickness of 10 nm.

[0497] Subsequently, the 2-(10-phenyl-9-anthracenyl)- represented by the above structural formula (iv) Benzo[b]naphtho[2,3-d]furan (abbreviation: Bnf(II)PhA) and the above structure Represented by formula (v), 3,10-bis[N-(9-phenyl-9H-carbazole-2-I [Lu)-N-phenylamino]naphtho[2,3-b;6,7-b']bisbenzofuran (abbreviated) Name: 3,10PCA2Nbf(IV)-02) and Bnf, in a weight ratio of 1:0.015 (=Bnf (II) PhA:3,10PCA2Nbf(IV)-02) Co-deposited at 25nm Then the light-emitting layer 113 was formed.

[0498] Next, we have the low refractive index material, 2-{(3',5'-di}, which is one embodiment of the present invention described in Example 2. -tert-butyl)-1,1'-biphenyl-3-yl}-4,6-diphenyl-1, 3,5-triazine (abbreviation: mmtBumBPTzn) (structural formula (120)) at 10 nm After depositing in such a manner to form a hole block layer, mmtBumBPTzn and the above structure 8-Quinolinolato-lithium (abbreviated as Liq), represented by formula (ix), in a weight ratio of 1: A 20nm co-deposited electron transport layer 1 is created so that it becomes 1 (=mmtBumBPTzn:Liq). Formed 14.

[0499] After the formation of the electron transport layer 114, a film of Liq is deposited to a thickness of 1 nm to form the electron injection layer 115. Finally, the volume ratio of silver (Ag) to magnesium (Mg) was set to 1:0.1, and the film thickness was 15n. The second electrode 102 was formed by co-deposition so that the value was m, and the light-emitting device 2 was fabricated. Furthermore, the second electrode 102 has both the function of reflecting light and the function of transmitting light, and is semi-transparent / semi-transparent. The reflective electrode, and the light-emitting device in this embodiment, extracts light from the second electrode 102. It is a mission-type element. Furthermore, the second electrode 102 is represented by the above structural formula (x). 1,3,5-tri(dibenzothiophen-4-yl)-benzene (abbreviation: DBT3P-I) I) is deposited at a 70nm layer to improve extraction efficiency.

[0500] (Method for fabricating comparative light-emitting device 2) Comparative light-emitting device 2 has a hole transport layer 112 thickness of 15 nm. The mmtBumBPTzn used in the hole block layer is represented by the above structural formula (vi) 2-[ 3'-(9,9-dimethyl-9H-fluoren-2-yl)-1,1'-biphenyl-3 -yl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mFBPTzn), The mmtBumBPTzn used in the electron transport layer 114 is represented by the above structural formula (viii). 2-[3-(2,6-dimethyl-3-pyridinyl)-5-(9-phenantrenyl)fe [nyl]-4,6-diphenyl-1,3,5-triazine (abbreviation: mPn-mDMePyP The device was fabricated in the same way as light-emitting device 2, except that the Tzn was changed accordingly.

[0501] The element structures of light-emitting device 2 and comparative light-emitting device 2 are summarized in Table 4 below.

[0502] [Table 4]

[0503] Furthermore, the refractive indices of mmtBumBPTzn and mPn-mDMePyPTzn are shown in Figure 29. Furthermore, the refractive index at 456 nm is shown in Table 5. The measurement was performed using a spectroscopic ellipsometer (J-1). The procedure was performed using an A. Woolam Japan M-2000U. The sample used for measurement was stone. A film was used in which each layer of material was deposited on a British substrate by vacuum deposition, with a thickness of approximately 50 nm. n,Ordinary is the refractive index of ordinary light rays, and n,Extr is the refractive index of extraordinary light rays. I wrote "a-ordinary".

[0504] [Table 5]

[0505] The above-mentioned light-emitting device and comparative light-emitting device were placed in a glove box under a nitrogen atmosphere. , the process of sealing the light-emitting device with a glass substrate so that it is not exposed to the atmosphere (using a sealing material) After applying it around the child, UV treatment and heat treatment at 80°C for 1 hour are performed during sealing, these The initial characteristics of the optical device were measured. The glass substrate was sealed and then removed. No special measures have been taken to improve efficiency.

[0506] Figure 30 shows the luminance-current density characteristics of light-emitting device 2 and comparative light-emitting device 2, and the current efficiency- Brightness characteristics are shown in Figure 31, brightness-voltage characteristics in Figure 32, and current-voltage characteristics in Figure 33. The index-luminance characteristics are shown in Figure 34, and the emission spectrum is shown in Figure 35. Furthermore, the light-emitting device... 2 and the comparative light-emitting device 2: 1000 cd / m² 2 Table 6 shows the main characteristics of the vicinity. For measuring luminance, CIE chromaticity, and emission spectrum, a spectroradiometer (Topcon, S) is used. Measurements were taken at room temperature using R-UL1R.

[0507] [Table 6]

[0508] Figures 30 to 35 and Table 6 show a light-emitting device using a low refractive index material according to one embodiment of the present invention. It exhibits an emission spectrum that is almost the same as that of comparative light-emitting device 2, but is different from that of comparative light-emitting device 2. It was found to be an EL device with good current efficiency.

[0509] Furthermore, the maximum BI values ​​for light-emitting device 2 and comparison light-emitting device 2 are 159 (cd / A), respectively. The values ​​were 144 (cd / A / y) and 144 (cd / A / y). Thus, the light-emitting device 2 had particularly good BI. It can be said to be a light-emitting device. Therefore, one aspect of the present invention is used in a display. It is suitable for light-emitting devices. [Examples]

[0510] ≪Synthesis Example 5≫ In this embodiment, the organic compound shown as structural formula (123) in Embodiment 1, 2-( 3,3'',5',5''-Tetra-tert-butyl-1,1':3',1''-Ter Phenyl-5-yl)-4,6-diphenyl-1,3,5-triazine (abbreviation: mmtB) This explains the synthesis method of mmtBumTPTzn-02. The structure is shown below.

[0511] [ka]

[0512] <Step 1: 3,3'', 5',5''-Tetra-t-butyl-1,1':3',1' '-Terphenyl-5-yl-4,4,5,5-tetramethyl-1,3,2-dioxabond Roland's synthesis > In a three-necked flask, add 5-bromo-3,3'',5',5''-tetra-t-butyl-1,1' :3',1''-Terphenyl 1.0g (1.9mmol), Bis(pinacolate) dibo 0.62g (2.4 mmol) of chlorine, 0.61g (6.2 mmol) of potassium acetate, 1, 18 mL of 4-dioxane was added and the mixture was degassed. To this, [1,1'-bis(diphenylphosphine) [Ferrocene] Palladium(II) dichloride dichloromethane adduct 0.077g (0 (0.094 mmol) was added, and the reaction was carried out at 110°C under a nitrogen atmosphere for 24 hours.

[0513] After the reaction is complete, extraction with toluene is performed, and the resulting organic layer is dried with magnesium sulfate. It was dried. This mixture was filtered naturally, and the resulting filtrate was concentrated. This was then mixed with toluene:hexa Silica gel column chromatography was performed by varying the developing solvent from 2:1 fluorine to toluene only. By purification using a filtration system, 0.78 g of the target white solid (yield: 72%) was obtained. The synthesis scheme for step 1 is shown in the following equation (e-1).

[0514] [ka]

[0515] <Step 2: Synthesis of mmtBumTPTzn-02> 0.33g of 4,6-diphenyl-2-chloro-1,3,5-triazine in a three-necked flask. 1.2 mmol), 3,3'', 5',5''-tetra-t-butyl-1,1':3', 1''-Terphenyl-5-yl-4,4,5,5-tetramethyl-1,3,2-dioxy Saborolan 0.78g (1.3 mmol), Tripotassium phosphate 0.57g (2.7 mmol) l) Add 3 mL of water, 7 mL of toluene, and 3 mL of 1,4-dioxane and degas. This contains palladium(II) acetate 3 mg (0.013 mmol), tris(2-methylphenicol) Add 8 mg (0.027 mmol) of phosphine and ...

Claims

[Claim 1] The organic compound includes at least one six-membered heteroaromatic ring containing one to three nitrogen atoms, and a plurality of aromatic hydrocarbon rings having six to fourteen carbon atoms forming the ring, wherein at least two of the plurality of aromatic hydrocarbon rings are benzene rings, and the plurality of hydrocarbon groups are bonded in sp3 hybrid orbitals. A material for light-emitting devices, wherein the ordinary refractive index of the layer made of the organic compound for light of any wavelength in the range of 455 nm to 465 nm is 1.5 to 1.75.

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