Light-emitting element, light-emitting device, electronic device, and lighting device

Abstract

To provide a novel organic compound, that is, to provide a novel organic compound that is effective in improving device characteristics and reliability.SOLUTION: These organic compounds have a dibenzobenzofuroquinoxaline skeleton or a dibenzobenzothienoquinoxaline skeleton and are represented by the following general formula (G1). (In the formula, Q represents O or S, and R1 to R12 represent specific groups.)SELECTED DRAWING: None

Description

[Technical Field]

[0001] One aspect of the present invention relates to organic compounds, light-emitting devices, light-emitting devices, electronic devices, and lighting devices. However, one aspect of the present invention is not limited to these. That is, one aspect of the present invention is a material The present invention relates to a method, a manufacturing method, or a driving method. Alternatively, one aspect of the present invention relates to a process, Relating to synes, manufactures, or compositions of matter. Furthermore, specific examples include semiconductor devices, display devices, and liquid crystal display devices. can. [Background technology]

[0002] A light-emitting element (also called an organic EL element) consisting of an EL layer sandwiched between a pair of electrodes is thin, lightweight, and Because it possesses characteristics such as fast response to force signals and low power consumption, it was applied. The display is attracting attention as a next-generation flat-panel display.

[0003] A light-emitting element works by applying a voltage between a pair of electrodes, thereby emitting electrons injected from each electrode. Holes recombine in the EL layer, and the light-emitting material (organic compound) contained in the EL layer becomes excited. It enters a state, and emits light when that excited state returns to the ground state. The types of excited states are as follows: , singlet excited state (S * ) and triplet excited state (T * ) and, from the singlet excited state Light emission is called fluorescence, and light emission from a triplet excited state is called phosphorescence. The statistical generation ratios for these are S * :T * It is thought that the ratio is 1:3. The resulting emission spectrum is unique to that particular luminescent material and emits different types of organic compounds. By using it as a light-emitting material, it is possible to obtain light-emitting elements with various emission colors.

[0004] Regarding such light-emitting elements, improvements to the element structure and material development are being made to enhance their element characteristics. Developments and other such activities are being actively carried out (see, for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2010-182699 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] In the development of light-emitting elements, the organic compounds used in the light-emitting elements enhance their properties and reliability. Therefore, it is extremely important. Thus, in one aspect of the present invention, a novel organic compound is provided. Furthermore, this invention provides novel organic compounds that are effective in improving device characteristics and reliability. In one embodiment, a novel organic compound that can be used in a light-emitting element is provided. In one embodiment, a novel organic compound is provided that can be used in the EL layer of a light-emitting element. Furthermore, a novel invention using a novel organic compound, which is one aspect of the present invention, is a highly efficient and reliable novel invention. We provide optical elements. We also provide novel light-emitting devices, novel electronic devices, or novel lighting devices. Provided. Note that the description of these issues does not preclude the existence of other issues. One aspect of the invention does not necessarily have to solve all of these problems. External issues will naturally become clear from the descriptions in the specification, drawings, claims, etc. It is possible to extract other issues from the descriptions in the detailed specifications, drawings, and claims. [Means for solving the problem]

[0007] One aspect of the present invention is an organic compound represented by the following general formula (G1).

[0008] [ka]

[0009] However, in the general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of them is a ring The fused aromatic ring or fused heteroaromatic ring formed has 3 to 30 carbon atoms, either substituted or unsubstituted. The first group has either of the following, and the others are independently hydrogen, a halogen group, and a hydroxyl group. It represents one of the following: a group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0010] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0011] [ka]

[0012] However, in the general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of them is a ring The first group has a hole-transporting skeleton with 3 to 30 substituted or unsubstituted carbon atoms. Yes, and the others are each independently hydrogen, halogen group, hydroxyl group, amino group, nitro group, and "T" represents one of the groups with 1 to 50 carbon atoms.

[0013] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0014] [ka]

[0015] Provided that in the general formula (G1), Q represents O or S, and R 1 to R 12 at least one of which is a fluo orene skeleton, a phenanthrene skeleton, a triphenylene skeleton, a naphthalene skeleton, a dibenzothio phene skeleton, a dibenzofuran skeleton, or a first group having any one of a carbazole skeleton and the others each independently represent any one of hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

[0016] In addition, in each of the above configurations, the total number of carbon atoms in the first group is preferably 3 to 100.

[0017] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0018]

Chemical Formula

[0019] Provided that in the general formula (G1), Q represents O or S, and R 1 to R 12 at least one of which is a group that is a substituted or unsubstituted arylene group having 6 to 24 ring-forming carbon atoms, or a carbon forming a ring via a substituted or unsubstituted heteroarylene group having 3 to 24 ring-forming atoms, a structure represented by any one of the following general formulas (A-1 ) to (A-21) is bonded to form the first group, and the others are each independently any one of hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms .

[0020]

Chemical Formula

[0021] However, in general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 teeth Each of these can be independently: hydrogen, an alkyl group with 1 to 6 carbon atoms, and a substituted group with 5 to 7 carbon atoms forming a ring. Alternatively, an unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or The character く represents one of the unsubstituted carbazolyl groups.

[0022] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0023] [ka]

[0024] However, in the general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of the following is The first base is represented by one of the general formulas (A-1) to (A-21), and the others are as follows: Independently, hydrogen, halogeno group, hydroxyl group, amino group, nitro group, or carbon atoms numbering 1 to 50 It represents one of the bases.

[0025] [ka]

[0026] However, in general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 teeth Each of these can be independently: hydrogen, an alkyl group with 1 to 6 carbon atoms, and a substituted group with 5 to 7 carbon atoms forming a ring. Alternatively, an unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or The character く represents one of the unsubstituted carbazolyl groups.

[0027] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0028] [ka]

[0029] However, in the general formula (G1), Q represents O or S, and R 3 The number of carbon atoms forming the ring is 3 to 3 The first having either a substituted or unsubstituted condensed aromatic ring or a condensed heteroaromatic ring It is a base, R 1 , R 2 and R 4 ~R 12 Each of these independently consists of hydrogen, a halogen group, and a hydro This represents one of the following: a xy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0030] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0031] [ka]

[0032] However, in the general formula (G1), Q represents O or S, and R 3 The number of carbon atoms forming the ring is 3 to 3 The first group has a hole-transporting skeleton with substitution or unsubstituted R 1 , R 2 and R 4 ~R 12 Each of these independently consists of a hydrogen group, a halogen group, a hydroxyl group, an amino group, and a nitro group. It represents either a group with 1 to 50 carbon atoms, or any other group with 1 to 50 carbon atoms.

[0033] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0034] [ka]

[0035] However, in the general formula (G1), Q represents O or S, and R 3 is a fluorene skeleton, phenant Lenolen skeleton, triphenylene skeleton, naphthalene skeleton, dibenzothiophene skeleton, dibenzof The first group is having either a ran skeleton or a carbazole skeleton, R 1 , R 2 Oh biR 4 ~R 12 Each of these is independently a hydrogen, halogen group, hydroxyl group, amino group, and nitro group. It represents either a group or a group with 1 to 50 carbon atoms.

[0036] In each of the above configurations, R 3 The total number of carbon atoms is preferably 3 to 100.

[0037] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0038] [ka]

[0039] However, in the general formula (G1), Q represents O or S, and R 3 The number of carbon atoms forming the ring is 6 to 2 4 substituted or unsubstituted arylene groups, or substituted groups with 3 to 24 carbon atoms forming the ring. Alternatively, via an unsubstituted heteroarylene group, any of the following general formulas (A-1) to (A-21) The first group to which the structure shown by one is bonded is R 1 , R 2 and R 4 ~R 12 That Each of these independently consists of hydrogen, a halogen group, a hydroxyl group, an amino group, a nitro group, or a carbon atom with 1 or more carbon atoms. It represents one of the 50 bases.

[0040] [ka]

[0041] However, in general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 teeth Each of these can be independently: hydrogen, an alkyl group with 1 to 6 carbon atoms, and a substituted group with 5 to 7 carbon atoms forming a ring. Alternatively, an unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or The character く represents one of the unsubstituted carbazolyl groups.

[0042] Another aspect of the present invention is an organic compound represented by the following general formula (G1).

[0043] [ka]

[0044] However, in the general formula (G1), Q represents O or S, and R 3 The following general formula (A-1)~(A The first base is represented by one of the following: R 1 , R 2 and R 4 ~R 12 That Each of these independently consists of hydrogen, a halogen group, a hydroxyl group, an amino group, a nitro group, or a carbon atom with 1 or more carbon atoms. It represents one of the 50 bases.

[0045] [ka]

[0046] However, in general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 teeth Each of these can be independently: hydrogen, an alkyl group with 1 to 6 carbon atoms, and a substituted group with 5 to 7 carbon atoms forming a ring. Alternatively, an unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or a substituted or The character く represents one of the unsubstituted carbazolyl groups.

[0047] In each of the above configurations, the group having 1 to 50 carbon atoms is an alkyloxy group, an aryloxy group, and amino groups substituted with aryl groups, amino groups substituted with aryl groups, cyano groups, carboxy Substituted with syl groups, alkyloxycarbonyl groups, aryloxycarbonyl groups, or alkyl groups. Silyl groups substituted with aryl groups, alkyl groups, cycloalkyl groups, he It is either a teloaryl group or an aryl group.

[0048] Another aspect of the present invention relates to an organic represented by structural formula (100) or structural formula (125). It is a compound.

[0049] [ka]

[0050] Another aspect of the present invention relates to a benzofloxaline skeleton or benzothienoxa This is a light-emitting element using an organic compound having a phosphorus skeleton. Furthermore, dibenzo[f,h][1 ]Benzoflo[2,3-b]quinoxaline skeleton or dibenzo[f,h][1]benzoth Furthermore, it is a light-emitting element that uses an organic compound having an eno[2,3-b]quinoxaline skeleton. Preferred. In addition to the above organic compounds, a substance that converts triplet excitation energy into light emission, for example. For example, a light-emitting element having a phosphorescent material or TADF material containing an organometallic complex is also one embodiment of the present invention. include.

[0051] Another aspect of the present invention is a light-emitting element using an organic compound which is an aspect of the present invention described above. It is a child. Furthermore, the EL layer between the pair of electrodes and the light-emitting layer contained in the EL layer are part of the present invention. A light-emitting element formed using an organic compound is also included as one embodiment of the present invention. Furthermore, in addition to light-emitting elements, light-emitting devices having transistors, substrates, etc., are also within the scope of the invention. Include. In addition to these light-emitting devices, a microphone, camera, control buttons, and external connections. Electronic devices and lighting devices having components, housings, covers, support bases, or speakers are also within the scope of the invention. Include it.

[0052] An organic compound according to one aspect of the present invention can be used as a luminescent substance, but it emits phosphorescence. It can be used in combination with a light-emitting material (phosphorescent compound) as the light-emitting layer of a light-emitting device. In other words, it is possible to obtain light emission from the triplet excited state in the light emission layer, This enables high efficiency of the element and is extremely effective. Therefore, one aspect of the present invention is A light-emitting device that uses a combination of an organic compound and a phosphorescent compound in its light-emitting layer is one embodiment of the present invention. It shall be included in the above. Furthermore, a configuration in which a third substance is added to the light-emitting layer in addition to the above. good.

[0053] Furthermore, one aspect of the present invention includes a light-emitting device having an element-emitting element, and further includes a light-emitting device having a light Light-emitting devices are also included in this category. Therefore, in this specification, light-emitting devices refer to image display devices. This refers to a device or light source (including lighting equipment). It also refers to a connector on a light-emitting device, for example, F PC (Flexible printed circuit) or TCP (Tape A module with a Carrier Package attached, and a printer at the end of the TCP connection. A module equipped with a circuit board, or a light-emitting element with COG (Chip On Glass) s) All modules with ICs (integrated circuits) directly mounted using this method are also included as light-emitting devices. Let's assume that. [Effects of the Invention]

[0054] One aspect of the present invention can provide a novel organic compound, namely, device characteristics and signal This invention can provide novel organic compounds that are effective in enhancing reliability. In this way, we can provide novel organic compounds that can be used in light-emitting devices. In one aspect of the present invention, a novel organic compound is proposed that can be used in the EL layer of a light-emitting element. It can be provided. Furthermore, a novel organic compound, which is one aspect of the present invention, can be used to provide high efficiency and reliability. This technology can provide highly reliable novel light-emitting devices. Furthermore, it can provide novel light-emitting devices and novel electronic devices. We can provide equipment or novel lighting devices. Note that the effects of these are described elsewhere. This does not preclude the existence of these effects. Furthermore, one aspect of the present invention does not necessarily imply these effects. It is not necessary to have all of these. Furthermore, any effects other than those described above are described in the specification, drawings, claims, etc. This will become clear from the description, and from the description in the specification, drawings, claims, etc. It is possible to extract effects other than those mentioned above. [Brief explanation of the drawing]

[0055] [Figure 1] A diagram illustrating the structure of a light-emitting element. [Figure 2] A diagram illustrating a light-emitting device. [Figure 3] A diagram illustrating a light-emitting device. [Figure 4] A diagram explaining electronic devices. [Figure 5] A diagram explaining electronic devices. [Figure 6] A diagram explaining automobiles. [Figure 7] A diagram illustrating a lighting device. [Figure 8] 1H-NMR chart of the organic compound shown in structural formula (100). [Figure 9] Ultraviolet-visible absorption spectrum and emission spectrum of the organic compound shown in structural formula (100). [Figure 10] A diagram explaining light-emitting elements. [Figure 11] This figure shows the current density-luminance characteristics of light-emitting element 1 and comparative light-emitting element 2. [Figure 12] A diagram showing the voltage-luminance characteristics of light-emitting element 1 and comparison light-emitting element 2. [Figure 13] This figure shows the brightness-current efficiency characteristics of light-emitting element 1 and comparative light-emitting element 2. [Figure 14] A diagram showing the voltage-current characteristics of light-emitting element 1 and comparison light-emitting element 2. [Figure 15] A figure showing the emission spectra of light-emitting element 1 and comparative light-emitting element 2. [Figure 16] A diagram showing the reliability of light-emitting element 1 and comparison light-emitting element 2. [Figure 17] 1H-NMR chart of the organic compound shown in structural formula (125). [Modes for carrying out the invention]

[0056] 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. It is possible to modify it in various ways. Therefore, the present invention is described in the following embodiments. It should not be interpreted in this way only.

[0057] Note that the position, size, and scope of each component shown in the drawings, etc., are for ease of understanding. The position, size, and range of the edges may not be shown. Therefore, the disclosed invention is not necessarily However, this is not limited to the location, size, and scope disclosed in drawings, etc.

[0058] Furthermore, in this specification and other documents, when describing the structure of the invention using drawings, the same thing may be referred to as The symbols used are consistent across different drawings.

[0059] (Embodiment 1) This embodiment describes an organic compound that is one aspect of the present invention.

[0060] An organic compound according to one aspect of the present invention is a dibenzobenzofloxacin skeleton or diben A structure having a zobenzothienoxaline skeleton represented by the following general formula (G1) It is an organic compound.

[0061] [ka]

[0062] In general formula (G1), Q represents O or S, and R 1 ~R 12 At least one of them , fused aromatic rings or fused heteroatomic rings with 3 to 30 substituted or unsubstituted carbon atoms forming the ring. The first group has either a ring or a hydrogen atom, while the others are independently hydrogen, a halogen group, and a hydrogen atom. This represents one of the following: a roxy group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0063] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R 1 ~R 12At least one of them is a substitution or The first group has an unsubstituted hole-transporting skeleton, while the others are independently hydrogen and halogen. It represents one of the following: a hydroxyl group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms. You can also write ".".

[0064] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R 1 ~R 12 At least one of them is a fluorene skeleton, a phenanthrene skeleton, and a truffle phenylene skeleton, naphthalene skeleton, dibenzothiophene skeleton, dibenzofuran skeleton, or The first group has one of the carbazole skeletons, and the others are each independently hydrogen, halo The character represents one of the following: a geno group, a hydroxyl group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms. You can also write, "Yes."

[0065] Furthermore, the first group in each of the above-mentioned configurations preferably has a total carbon number of 3 to 100. stomach.

[0066] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R 1 ~R 12 At least one of them is a substitution or Unsubstituted arylene groups, or substituted or unsubstituted helium groups with 3 to 24 carbon atoms forming the ring. The teloarylene group is represented by one of the following general formulas (A-1) to (A-21). The structure is bonded to the first group, while the others are independently hydrogen, a halogen group, and a hydroxyl group. It can also be written as: , represents an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0067] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R 1 ~R 12 At least one of the following general formulas (A-1) to (A-21) The first group is represented by 1, and the others are independently hydrogen, a halogen group, and a hydroxyl group. It can also be written as: , represents an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

[0068] [ka]

[0069] In general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 Each of these independently consists of hydrogen, an alkyl group with 1 to 6 carbon atoms, and a ring-forming atom with 5 to 7 carbon atoms. A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or This represents either a substituted or unsubstituted carbazolyl group.

[0070] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R 3 These are fused aromatic rings with 3 to 30 substituted or unsubstituted carbon atoms forming the ring. The first group is having either a condensed heteroaromatic ring, R 1 , R 2 and R 4 ~R 12 Each of these independently consists of hydrogen, a halogen group, a hydroxyl group, an amino group, a nitro group, or carbon. It can also be written as "It represents one of the bases from 1 to 50."

[0071] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R3 These are hole-transporting bones with 3 to 30 substituted or unsubstituted carbon atoms forming a ring. It is the first base which has a case, R 1 , R 2 and R 4 ~R 12 Each of them independently produces hydrogen and ha A rogeno group, hydroxyl group, amino group, nitro group, or any of the groups with 1 to 50 carbon atoms. It can also be written as "to represent."

[0072] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R 3 These are fluorene skeleton, phenanthrene skeleton, triphenylene skeleton, naphthalene The carbazole skeleton, dibenzothiophene skeleton, dibenzofuran skeleton, or carbazole skeleton The first group having either R 1 , R 2 and R 4 ~R 12 Each of them independently produces hydrogen, A halogen group, hydroxyl group, amino group, nitro group, or any group with 1 to 50 carbon atoms. It can also be written as "This represents..."

[0073] Furthermore, R in each of the above configurations 3 Preferably, the total number of carbon atoms is between 3 and 100.

[0074] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R 3 These are substituted or unsubstituted arylene groups with 6 to 24 carbon atoms forming a ring. Alternatively, via substituted or unsubstituted heteroarylene groups having 3 to 24 carbon atoms forming a ring The first base to which a structure represented by any one of the following general formulas (A-1) to (A-21) is bonded And R 1 , R 2 and R 4~R 12 Each of these independently consists of hydrogen, a halogen group, and a hydroxygen group. It can also be written as: "It represents one of the following: a C group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms." stomach.

[0075] Furthermore, the general formula (G1) described above has the following configuration in addition to the above: "In general formula (G1), Q is O or S Represents R 3 The first base is represented by one of the following general formulas (A-1) to (A-21). And R 1 , R 2 and R 4 ~R 12 Each of these independently consists of hydrogen, a halogen group, and a hydroxygen group. It can also be written as: "It represents one of the following: a C group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms." stomach.

[0076] [ka]

[0077] In general formulas (A-1) to (A-21), Q' represents O or S, and R 13 ~R 24 Each of these independently consists of hydrogen, an alkyl group with 1 to 6 carbon atoms, and a ring-forming atom with 5 to 7 carbon atoms. A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted phenyl group, or This represents either a substituted or unsubstituted carbazolyl group.

[0078] In each of the above configurations, the groups having 1 to 50 carbon atoms are alkyloxy groups and aryloxy groups. amino groups, alkyl groups substituted with amino groups, aryl groups substituted with amino groups, cyano groups, Ruboxyl group, alkyloxycarbonyl group, aryloxycarbonyl group, alkyl group Silyl groups substituted with aryl groups, silyl groups substituted with alkyl groups, cycloalkyl groups It is preferable that it be a group, a heteroaryl group, or an aryl group. Specific examples include methoxy group, ethoxy group, propoxy group, tert-butoxy group, Phenoxy group, 4-methylphenoxy group, 3,5-dimethylphenoxy group, 1-naphthoxy 1-C group, 2-naphthoxy group, methylamino group, ethylamino group, dimethylamino group, 1-C group methylamino group, methylethylamino group, phenylmethylamino group, phenylamino group, dif Phenylamino group, 1-naphthylamino group, 2-naphthylamino group, N-1-naphthyl-N -Phenylamino group, N-2-naphthyl-N-phenylamino group, bis(biphenyl-4) -yl)amino group, N,N-bis(p-terphenyl)amino group, methoxycarbonyl group , ethoxycarbonyl group, phenoxycarbonyl group, trimethylsilyl group, triphenyl Silyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group tert-butyl group, n-hexyl group, benzyl group, cyclopropyl group, cyclobutyl Group, cyclopentyl group, cyclohexyl group, phenyl group, 1-naphthyl group, 2-naphthyl group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group, phenantrenyl group, riphenylenyl group, 9,9-dimethylfluorenyl group, pyridyl group, quinolyl group, 9- Rubazolyl group, 9-phenyl-2-carbazolyl group, 9-phenyl-3-carbazolyl group Examples include the dibenzofuranyl group and the dibenzothiophenyl group. In addition, spiroflu Groups such as the olenyl group and the N,N-bis(p-biphenylyl)amino group, which have 25 or fewer carbon atoms, Groups with 1 to 25 carbon atoms are preferred when considering sublimation properties.

[0079] In the organic compound according to one aspect of the present invention, hydrogen contained in the skeleton is deuterium may be used.

[0080] In addition, in each of the above structures, in general formula (G1) or general formulas (A-1) to (A-21), the substitution is preferably substitution with a group having carbon atoms such as methyl group, ethyl group, n-propyl group, isopropyl group, s ec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group 1 to 6 alkyl groups, and phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 1- naphthyl group, 2-naphthyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group refers to substitution by a substituent such as an aryl group having 6 to 12 carbon atoms. In addition, these substituents may be bonded to each other to form a ring. For example, when the arylene group is a substituent which is a 2,7-fluorenylene group having two phenyl groups at the 9-position, the pheny l groups may be bonded to each other to form a spiro-9,9'-bifluorene-2,7-diyl group .

[0081] In addition, in each of the above structures, R in general formula (G1) 1 to R 12 represents a carbon forming a ring Specific examples of the condensed aromatic ring or condensed heteroaromatic ring having 3 to 30 carbon atoms include a quinoline ring, an isoqui noline ring, quinazoline ring, quinoxaline ring, naphthalene ring, benzothiophene ring, benzo furan ring, indole ring, fluorene ring, phenanthrene ring, triphenylene ring, diben zothiophene ring, benzonaphthothiophene ring, dibenzofuran ring, benzonaphthofuran ring , carbazole ring, benzocarbazole ring, or dibenzocarbazole ring, etc. .

[0082] Furthermore, in each of the above configurations, R in general formula (G1) 1 ~R 12 The carbon atoms that form the ring, represented by Examples of hole-transporting skeletons with 3 to 30 holes include naphthalene rings and benzothiophene rings. benzofuran ring, indole ring, fluorene ring, phenanthrene ring, triphenylene ring , dibenzothiophene ring, benzonaphthothiophene ring, dibenzofuran ring, benzonaphth Examples include furan rings, carbazole rings, benzocarbazole rings, or dibenzocarbazole rings. It can be done.

[0083] Furthermore, in each of the above configurations, R in general formula (G1) 1 ~R 12 The carbon atoms that form the ring, represented by Specific examples of arylene groups with a number between 6 and 24 include phenylene groups, naphthalene groups, and phenylene groups. Phenyldiyl group, terphenyldiyl group, fluoroorangeyl group, phenantradiyl Examples include the triphenylenediyl group and others.

[0084] Furthermore, in each of the above configurations, R in general formula (G1) 1 ~R 12 The carbon atoms that form the ring, represented by Specific examples of heteroarylene groups with 3 to 24 members include pyridinediyl groups and pyrazinediyl groups. yl group, pyrimidinediyl group, triazinediyl group, triazolediyl group, oxadiazo Diyl group, thiadiazole diyl group, oxazole diyl group, thiazole diyl group, Thiofendiyl group, pyrrolediyl group, franziyl group, selenofendiyl group, ben Zothiophene diyl group, benzopyrrole diyl group, benzofranziyl group, quinoline diyl Diyl group, isoquinoline diyl group, dibenzothiophene diyl group, carbazole diyl group, di Examples include benzofranzyl groups.

[0085] Further, in each of the above configurations, R in general formulas (A-1) to (A-21) 13 to R 24 represented by , specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an iso propyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a penty l group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, a neohexy l group, a 3-methylpentyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 1,2-di methylbutyl group, a 2,3-dimethylbutyl group, and the like.

[0086] Further, in each of the above configurations, R in general formulas (A-1) to (A-21) 13 to R 24 represented by , specific examples of the cycloalkyl group having 5 to 7 carbon atoms forming the ring include a cyclopentyl group , a cyclohexyl group, a cycloheptyl group, and the like.

[0087] Next, specific structural formulas of the organic compound which is one aspect of the present invention described above are shown below.

[0088]

Chemical Formula

[0089]

Chemical Formula

[0090]

Chemical Formula

[0091]

Chemical Formula

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] Furthermore, the organic compounds represented by the above structural formulas (100) to (175) are the same as those represented by the above general formula (G1). An example of an organic compound represented by this is an organic compound that is one aspect of the present invention. It is not limited to that.

[0096] Next, an example of a method for synthesizing an organic compound, which is one aspect of the present invention and is represented by the general formula (G1), is given. I will explain about that.

[0097] First, the organic compound represented by the following general formula (G1), dibenzobenzofloxaline derivative An example of a method for synthesizing dibenzobenzothienoquinoxaline derivatives is described below. .

[0098] [ka]

[0099] In general formula (G1), Q represents O or S, and R 1 ~R 12 Each is independently of hydrogen , or represents a substituent, and R 1 ~R 12 At least one of them has 3 carbon atoms forming a ring. 30 represents either a substituted or unsubstituted condensed aromatic ring or a condensed heteroaromatic ring.

[0100] ≪Synthesis method for halogen compounds represented by general formula (G0)≫ First, a dibenzobenzofloxaline derivative represented by the above general formula (G1), or A halogen compound (general formula (G) used in the synthesis of dibenzobenzothienoxaline derivatives The method for synthesizing 0)) will be explained.

[0101] The halogen compound represented by the general formula (G0) below can be synthesized, for example, by the synthesis method shown below. It can be synthesized in feces. Here, we show the first and second synthesis methods.

[0102] [ka]

[0103] In the above general formula (G0), Q represents O or S, and R 31 ~R 42 Each is independent , represents hydrogen, or substituent, and R 31 ~R 42 At least one of them represents a halogen.

[0104] <First synthesis method> The halogen compound represented by the above general formula (G0) is synthesized as shown in the synthesis scheme (A-1) below. Sea urchin, having a phenyl group substituted with a hydroxyl group or a sulfanyl group, halogenated The dibenzoquinoxaline derivative (A1) is reacted with a base such as potassium carbonate (A2). This can be obtained by [method].

[0105] [ka]

[0106] In the synthesis scheme (A-1), Q represents O or S, X represents halogen, R 31 to R 42 each independently represent hydrogen or a substituent, and R 31 to R 42 at least one of of which represents halogen.

[0107] <Second Synthesis Method> The halogen compound represented by the above general formula (G0) can be obtained as shown in the following synthesis scheme (A-1') by reacting a phenyl group substituted with a methyloxy group or a methylsulfanyl group, a dibenzoquinoxaline derivative (A1') having an amino group, and tert-butyl nitrite to obtain the same.

[0108]

Chem

[0109] In the synthesis scheme (A-1'), Q represents O or S, R 31 to R 42 each independently represent hydrogen or a substituent, and at least one of R 31 to R 42 represents halo gen.

[0110] <<Method for Synthesizing Organic Compound Represented by General Formula (G1)>> Next, a method for synthesizing a dibenzobenzofuroquinoxaline derivative or a dibenzobenzothienoquinoxaline derivative represented by the above general formula (G1) will be described.

[0111] The dibenzobenzofuroquinoxaline derivative or dibenzo benzothienoquinoxaline derivative represented by the above general formula (G1) can be produced as shown in the following synthesis scheme (A-2) by the above The halogen compound (G0) obtained in scheme (A-1) or (A-1'), and boron It is obtained by coupling an acid compound (B1) with another compound.

[0112] [ka]

[0113] In addition, in the synthesis scheme (A-2), Q represents O or S, and R 1 ~R 12 , and R 31 ~R 42 Each of these independently represents either hydrogen or a substituent, and R 1 ~R 12 few One is a fused aromatic ring or a ring formed by substituted or unsubstituted carbon atoms with 3 to 30 carbon atoms. It has one of the condensed heteroaromatic rings. Also, B 1 is boronic acid or boronic acid ester or This represents cyclic triol borate salts, etc.

[0114] The compounds (A1) and (A1') mentioned above are commercially available in various forms, or are compounded. Because it is possible, it is represented by the general formula (G1), and is one aspect of the present invention, dibenzobenzofloxacin. Quinoxaline derivatives, or dibenzobenzothienoquinoxaline derivatives, come in many varieties. It can be synthesized. Therefore, one embodiment of the present invention is an organic compound that can be varied. It is characterized by being rich in [something].

[0115] Furthermore, the specific structural formula of the compound (G0) mentioned above is shown below.

[0116] [ka]

[0117]

Chem.

[0118] Note that the organic compounds represented by the above structural formulas (200) to (223) are encompassed by the above general formula (G0) and are merely examples of halogen compounds represented thereby, and are not limited thereto.

[0119] Heretofore, one embodiment of the present invention has been described with respect to an example of a method for synthesizing an organic compound which is one aspect of the present invention, a dibenzobenzofuroquinoxaline derivative, and a dibenzobenzothienoquinoxaline derivative; however, the present invention is not limited thereto, and synthesis may be performed by any other synthesis method.

[0120] Note that the organic compound described in the present embodiment can be used in appropriate combination with the structures described in other embodiments.

[0121] Note that the organic compound which is one aspect of the present invention described above has an electron-transporting property and a hole-transporting property. Therefore, it can be used as a host material for a light-emitting layer, or also for an electron-transporting layer and a hole-transporting layer. In addition, the organic compound which is one aspect of the present invention can maintain a relatively high T1 energy level. Therefore, it is preferably used as a host material in combination with a phosphorescent substance (phosphorescent material). Furthermore, since the organic compound exhibits fluorescence emission, it can itself be used as a light-emitting substance in a light-emitting element as well. Accordingly, light-emitting elements including these organic compounds are also included in one aspect of the present invention .

[0122] Furthermore, the organic compound which is one aspect of the present invention has a low LUMO level, and is a compound that readily accepts electrons and is therefore suitable. Accordingly, it is preferably used as a host material for an electron-transporting layer or a light-emitting layer This allows for a reduction in the driving voltage of the light-emitting element.

[0123] Furthermore, an organic compound according to one aspect of the present invention has a high HOMO level (specifically -5.7e). By combining an organic compound that readily accepts holes (V or higher), an excited complex can be formed. This allows for the efficient transfer of excitation energy from the excited complex to the luminescent material. This invention can improve the efficiency, reliability, and drive voltage of phosphorescent light-emitting devices. Organic compounds combined with other organic compounds (hole transport materials and electron transport materials) For specific examples of materials, the materials shown in Embodiment 2 can be used as appropriate.

[0124] Furthermore, by using an organic compound according to one aspect of the present invention, a light-emitting element with high luminescence efficiency and light emission can be obtained. Devices, electronic equipment, or lighting devices can be realized. Furthermore, low-power light-emitting elements can be used. This can be used to realize a child, a light-emitting device, an electronic device, or a lighting device.

[0125] In this embodiment, one aspect of the present invention has been described. Now, let's describe one aspect of the present invention. However, this aspect of the present invention is not limited to these. No. In other words, various aspects of the invention are described in this embodiment and other embodiments. Therefore, one aspect of the present invention is not limited to a specific aspect. For example, one aspect of the present invention is An example of its application to a light-emitting element has been shown, but the present invention is not limited thereto. Furthermore, depending on the circumstances, one aspect of the present invention may be applied to something other than a light-emitting element. Depending on the circumstances, one aspect of the present invention may not be applied to a light-emitting element.

[0126] The configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments. It is possible.

[0127] (Embodiment 2) In this embodiment, a light-emitting element, which is one aspect of the present invention, will be described. An organic compound, which is one embodiment of the present invention, can be used in the light-emitting element described in the present invention.

[0128] ≪Basic Structure of Light-Emitting Devices≫ Figure 1(A) shows a light-emitting element formed by sandwiching an EL layer between a pair of electrodes. Specifically, the first The structure has an EL layer 103, which includes a light-emitting layer, sandwiched between the first electrode 101 and the second electrode 102. do.

[0129] Figure 1(B) shows multiple (2 layers in Figure 1(B)) EL layers (103a, 1 A laminated structure (tandem structure) having 03b) with a charge generation layer 104 sandwiched between EL layers. This shows a light-emitting element. Such a tandem-structured light-emitting element can be driven at low voltage and consumes low power. This makes it possible to realize a light-emitting device with low power consumption.

[0130] Furthermore, when a voltage is applied to the first electrode 101 and the second electrode 102, the charge generation layer 104 is generated. Then, electrons are injected into one EL layer (103a or 103b), and the other EL layer (103b Alternatively, it has the function of injecting holes into 103a). Therefore, in Figure 1(B), the first When a voltage is applied to electrode 101 such that its potential is higher than that of the second electrode 102, charge generation occurs. Electrons are injected from layer 104 into EL layer 103a, and holes are injected into EL layer 103b.

[0131] The charge generation layer 104 has light transmission to visible light in terms of light extraction efficiency (specifically In particular, it is preferable that the transmittance of visible light to the charge generation layer 104 is 40% or more. Furthermore, the charge generation layer 104 had a lower conductivity than the first electrode 101 and the second electrode 102. It works even then.

[0132] Figure 1(C) shows the laminated structure of the EL layer 103. In Figure 1(C), the first electric When electrode 101 functions as an anode, the EL layer 103 has holes (H) on the first electrode 101. (Role) injection layer 111, hole transport layer 112, light-emitting layer 113, electron transport layer 114, The electron injection layers 115 are sequentially stacked in a structure as shown in Figure 1(B), which is a tandem structure. Even when there are multiple EL layers, as shown in Figure 1(D), each EL layer is as described above from the anode side. The structure is such that the electrodes are stacked sequentially. The first electrode 101 is the cathode, and the second electrode 102 If the anode is the first electrode, the stacking order is reversed.

[0133] Furthermore, in the configuration in which multiple EL layers are stacked, as shown in Figure 1(E), the EL layers are charged Three layers are stacked (103a, 103b, 103) via generation layers (104a, 104b) respectively. c) The configuration may also be as described. However, the number of layers is not limited to 2 or 3 layers. It is not necessary, and a configuration with four or more layers stacked is also acceptable. Also, the EL layer (103, 103a, 1 The light-emitting layers (113, 113a, 113b, 113c) included in 03b, 103c) are Each material contains a luminescent substance or a combination of multiple substances as appropriate, exhibiting fluorescence that produces a desired emission color. A configuration can be made that produces light emission or phosphorescence. Also, the light-emitting layer 113 (113a, 1 If there are multiple units of 13b and 113c), the light-emitting color of each light-emitting layer may be different. In this case, the light-emitting materials and other materials used in each stacked light-emitting layer are different. Any material can be used. For example, the light-emitting layer 113a can be blue, and the light-emitting layer 113b can be red, green, Alternatively, the light-emitting layer 113c can be either yellow or blue, but the light-emitting layer 113a can be blue. The light-emitting layer 113b is red, and the light-emitting layer 113c is red. It is also possible to consider the brightness and color characteristics of multiple light sources and, as appropriate, add other light colors. A combination of these can be used.

[0134] Furthermore, in a light-emitting element according to one aspect of the present invention, the EL layer (103, 103a, 103b) This configuration also allows for strengthening the resulting light emission by causing resonance between the two electrodes. Good. For example, in Figure 1(C), the first electrode 101 is a reflective electrode, and the second electrode 10 By using a semi-transmissive / semi-reflective electrode for component 2, a micro-optical resonator (microcavity) structure is formed. This allows for an increase in the light emission obtained from the EL layer 103.

[0135] Furthermore, the first electrode 101 of the light-emitting element is made of a reflective conductive material and a light-transmitting conductive material. In the case of a reflective electrode consisting of a laminated structure with a transparent conductive film, the thickness of the transparent conductive film can be controlled. Optical adjustment can be performed by controlling it. Specifically, the light obtained from the light-emitting layer 113 With respect to the wavelength λ of light, the distance between the first electrode 101 and the second electrode 102 is mλ / 2 (where m is a natural number) It is preferable to adjust it so that it is in a neighborhood.

[0136] Furthermore, in order to amplify the desired light (wavelength: λ) obtained from the light-emitting layer 113, the first electrode The optical distance from 101 to the region (emission region) where the desired light from the light-emitting layer 113 can be obtained, and the second The optical distance from electrode 102 to the region of the light-emitting layer 113 where the desired light is obtained (light-emitting region) and Adjust them so that they are in the vicinity of (2m'+1)λ / 4 (where m' is a natural number). It is preferable that... This shows the region where electrons recombine.

[0137] By performing such optical adjustments, the spectrum of a specific monochromatic light obtained from the light-emitting layer 113 can be adjusted. By narrowing the torque curve, it is possible to obtain luminescence with good color purity.

[0138] However, in the above case, the optical distance between the first electrode 101 and the second electrode 102 is strictly speaking the first The total thickness from the reflection region at electrode 101 to the reflection region at the second electrode 102 is This is possible. However, the reflection regions at the first electrode 101 and the second electrode 102 must be precisely defined. Since it is difficult to determine, any position of the first electrode 101 and the second electrode 102 is reversed. Assuming it is a morphic domain, the above effects can be sufficiently obtained. Also, the first The optical distance between electrode 101 and the light-emitting layer from which the desired light is obtained is, strictly speaking, the distance between the first electrode 101 and the light-emitting layer. This is the optical distance between the reflective region and the light-emitting region in the light-emitting layer from which the desired light is obtained. This is possible. However, the reflection region at the first electrode 101 and the emission of the desired light are important. Since it is difficult to precisely determine the light-emitting region in the light layer, the first electrode 101 is arbitrary By assuming that the position is the reflection region and any position on the light-emitting layer where the desired light is obtained is the light-emitting region, It is assumed that the above-mentioned effects can be fully obtained.

[0139] When the light-emitting element shown in Figure 1(C) has a microcavity structure, the EL layer is common. By doing so, it is possible to extract light of different wavelengths (monochromatic light). Therefore, different emission colors can be obtained. This eliminates the need for color separation (e.g., RGB), enabling higher resolution. It can also be used in combination with (color filters). Furthermore, the emission intensity in the front direction at a specific wavelength can be adjusted. Because it is possible to strengthen this, power consumption can be reduced.

[0140] In addition, in the light-emitting element according to one aspect of the present invention described above, the first electrode 101 and the second electrode At least one of 102 is a light-transmitting electrode (such as a transparent electrode, a semi-transparent / semi-reflective electrode, etc.) Assuming that the light-transmitting electrode is a transparent electrode, the visible light transmittance of the transparent electrode is 40% or less. The above applies. Also, in the case of semi-transparent and semi-reflective electrodes, the reflectance of visible light of the semi-transparent and semi-reflective electrodes is The ratio shall be 20% to 80%, preferably 40% to 70%. Furthermore, these electrodes , resistivity is 1 × 10 -2 It is preferable to keep it below Ωcm.

[0141] Furthermore, in the light-emitting element according to one aspect of the present invention described above, the first electrode 101 and the second electrode If one of the electrodes 102 is a reflective electrode (reflective electrode), the reflective electrode can The reflectance of visible light shall be 40% to 100%, preferably 70% to 100%. Furthermore, this electrode has a resistivity of 1 × 10⁻⁶. -2 It is preferable to keep it below Ωcm.

[0142] ≪Specific structure and fabrication method of light-emitting element≫ Next, a specific structure and manufacturing method of a light-emitting element according to one aspect of the present invention will be described. In Figures 1(A) to 1(D), if the symbols are the same, the explanations will also be the same.

[0143] <First electrode and second electrode> As the material for forming the first electrode 101 and the second electrode 102, the element structure described above is If the functions of both electrodes can be satisfied, the following materials can be used in appropriate combinations. This can be done. For example, metals, alloys, electrically conductive compounds, and mixtures thereof can be used as appropriate. It can be used. Specifically, In-Sn oxide (also called ITO), In-Si- Examples include Sn oxide (also known as ITSO), In-Zn oxide, and In-W-Zn oxide. Other materials include aluminum (Al), titanium (Ti), chromium (Cr), and manganese (Mn). ), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), gallium (Ga) Zinc (Zn), indium (In), tin (Sn), molybdenum (Mo), tantalum ( Ta), tungsten (W), palladium (Pd), gold (Au), platinum (Pt), silver (A) g) Metals such as yttrium (Y), neodymium (Nd), and combinations thereof as appropriate. Alloys containing these elements can also be used. In addition, other elements from Group 1 of the periodic table not exemplified above or Elements belonging to Group 2 (for example, lithium (Li), cesium (Cs), calcium (Ca) ), strontium (Sr), europium (Eu), ytterbium (Yb), etc. Rare earth metals and alloys containing them in appropriate combinations, as well as graphene and other materials, are used. It is possible.

[0144] The light-emitting element shown in Figure 1 has an EL layer 103 having a stacked structure as shown in Figure 1(C). When the first electrode 101 is the anode, the hole injection layer of the EL layer 103 is placed on the first electrode 101. Layers 111 and 112 are sequentially formed by vacuum deposition. Also, Figure 1(D) As shown, multiple EL layers (103a, 103b) having a stacked structure sandwich the charge generation layer 104. When the first electrode 101 is the anode, the EL layer 103 is placed on the first electrode 101. The hole injection layer 111a and hole transport layer 112a of a are sequentially laminated and formed by vacuum deposition. Furthermore, after the EL layer 103a and the charge generation layer 104 are sequentially stacked, the charge generation layer 10 On top of 4, the hole injection layer 111b and hole transport layer 112b of the EL layer 103b are similarly sequentially laminated. It will be done.

[0145] <Hole injection layer and hole transport layer> The hole injection layers (111, 111a, 111b) are the first electrode 101 which is the anode and charge generation A layer in which holes are injected from layer (104) into the EL layer (103, 103a, 103b). It is a layer containing a material with high hole injection potential.

[0146] Materials with high hole injection potential include molybdenum oxide, vanadium oxide, and ruthenium oxide. Examples include transition metal oxides such as tungsten oxide and manganese oxide. In addition, Phthalocyanines such as thalocyanine (abbreviated as H2Pc) and copper phthalocyanine (abbreviated as CuPc) Nin-based compounds, etc., can be used.

[0147] Furthermore, the low molecular weight compound, 4,4',4''-tris(N,N-diphenylamino) Riphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methyl Phenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4 '-Bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl( Abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N' -phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD) , 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino] Benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)- N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6- Bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenyl Nilcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9- Phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCz) Aromatic amine compounds such as PCN1 can be used.

[0148] Furthermore, polymer compounds (oligomers, dendrimers, polymers, etc.), such as poly(N-vinyl) Lucarbazole (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: P VTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl] [Nyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), Poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine Poly(TPD), etc., can be used. Alternatively, poly(3,4-ethylene) Dioxythiophene / poly(styrene sulfonic acid) (abbreviation: PEDOT / PSS), Add an acid such as polyaniline / poly(styrene sulfonic acid) (abbreviation: PAni / PSS). Polymeric compounds, etc., can also be used.

[0149] Furthermore, materials with high hole injection potential include hole transport materials and acceptor materials (electron acceptors). Composite materials containing (accepting materials) can also be used. In this case, the acceptor material provides a positive result. Electrons are extracted from the pore-transporting material and holes are created in the hole injection layers (111, 111a, 111b). This occurs, and the light-emitting layer (113, 113) is transmitted through the hole transport layer (112, 112a, 112b). Holes are injected into the hole injection layer (a, 113b, 113c). Note that the hole injection layer (111, 111a, 111b) is a composite material containing a hole transport material and an acceptor material (electron-accepting material). It may be formed as a single layer consisting of a hole transport material and an acceptor material (electron-accepting material). The material and the other material may be formed by laminating them in separate layers.

[0150] The hole transport layer (112, 112a, 112b) is a hole injection layer (111, 111a, 111 b) The holes injected from the first electrode 101 and the charge generation layer 104 are released into the light-emitting layer (11 3, 113a, 113b, 113c) are transport layers. Note that hole transport layers (112, 112a, 112b) are layers containing hole transport material. Hole transport layer (112, 112 The hole transport material used in a, 112b) is particularly suitable for the hole injection layer (111, 111a, 111 It is preferable to use a device that has the same or a similar HOMO level as the HOMO level in b). It's nice.

[0151] Acceptor material used in hole injection layers (111, 111a, 111b) is element Oxides of metals belonging to groups 4 through 8 of the periodic table can be used. Specifically These are molybdenum oxide, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, and tartary oxide. Examples include rhomboids, manganese oxide, and rhenium oxide. Among these, molybdenum oxide is particularly noteworthy. It is preferable because it is stable in the atmosphere, has low hygroscopicity, and is easy to handle. Other examples include quinodymethane. Organic acceptors such as derivatives, chloranil derivatives, and hexaazatriphenylene derivatives It can be used. Specifically, 7,7,8,8-tetracyano-2,3,5,6 Trafluoroquinodimethane (abbreviation: F4-TCNQ), chloranil, 2,3,6,7,1 0,11-Hexacyano-1,4,5,8,9,12-Hexazatriphenylene (abbreviation) Examples such as HAT-CN can be used. In particular, multiple complex atoms can be used, such as HAT-CN. Compounds in which an electron-withdrawing group is bonded to a condensed aromatic ring are thermally stable and therefore preferred. Furthermore, radians having electron-withdrawing groups (especially halogen groups such as fluoro groups or cyano groups) [3] Len derivatives are preferred because they have very high electron-accepting properties, specifically α,α',α''-1 ,2,3-cyclopropanetriylidentris[4-cyano-2,3,5,6-tetraph [Luolobenzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetri Iridentris[2,6-dichloro-3,5-difluoro-4-(trifluoromethyl) [Benzeneacetonitrile], α,α',α''-1,2,3-cyclopropanetriylide Examples include pentris [2,3,4,5,6-pentafluorobenzeneacetonitrile]. It can be done.

[0152] Hole injection layer (111, 111a, 111b) and hole transport layer (112, 112a, 11 The hole transport material used in 2b) is 1 × 10 -6 cm 2 Hole mobility of / Vs or greater A substance having this property is preferred. However, any substance that has higher hole transport than electron transport is also acceptable. You can use the following.

[0153] Examples of hole-transporting materials include π-electron-rich heteroaromatic compounds (for example, those with a carbazole skeleton). Hole vessels in compounds such as compounds with a furan skeleton or compounds with an aromatic amine skeleton Materials with high feedability are preferred.

[0154] A specific example of a hole-transporting material is 4,4'-bis[N-(1-naphthyl)-N-pheni [Luaminobiphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methyl) Phenyl)-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-phenyl Phenylfluoren-9-yl)triphenylamine (abbreviation: BPAFLP), 4-phenyl Lu-3'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: mBPA) FLP), N-(9,9-dimethyl-9H-fluoren-2-yl)-N-{9,9-di Methyl-2-[N'-phenyl-N'-(9,9-dimethyl-9H-fluorene-2-I [Lu)amino]-9H-fluoren-7-yl}phenylamine (abbreviation: DFLADFL) N-(9,9-dimethyl-2-diphenylamino-9H-fluoren-7-yl)diph Phenylamine (abbreviation: DPNF), 2-[N-(4-diphenylaminophenyl)-N- Phenylamino]spiro-9,9'-bifluorene (abbreviation: DPASF), 4-phenyl -4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBA1BP), 3-[4-(9-phenanthryl)-phenyl]-9-phenyl-9 H-carbazole (abbreviation: PCPPn), N-(4-biphenyl)-N-(9,9-dimethyl (Tyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazole-3-amine (Abbreviation: PCBiF), N-(1,1'-biphenyl-4-yl)-N-[4-(9-yl) [phenyl-9H-carbazole-3-yl)phenyl]-9,9-dimethyl-9H-fluor Len-2-amine (abbreviation: PCBBiF), 4,4'-diphenyl-4''-(9-phenyl Nyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBBi1BP) , 4-(1-naphthyl)-4'-(9-phenyl-9H-carbazole-3-yl)tri Phenylamine (abbreviation: PCBANB), 4,4'-di(1-naphthyl)-4''-(9 -phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBNBB) ), 4-phenyldiphenyl-(9-phenyl-9H-carbazole-3-yl)amine (Abbreviation: PCA1BP), N,N'-bis(9-phenylcarbazole-3-yl)-N ,N'-diphenylbenzene-1,3-diamine (abbreviation: PCA2B), N,N',N' '-Triphenyl-N,N',N''-Tris(9-phenylcarbazole-3-yl) Benzene-1,3,5-triamine (abbreviation: PCA3B), 9,9-dimethyl-N-phenyl Nyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]fluore N-2-amine (abbreviation: PCBAF), N-phenyl-N-[4-(9-phenyl-9H -carbazole-3-yl)phenyl]spiro-9,9'-bifluoren-2amine( Abbreviation: PCBASF), 2-[N-(9-phenylcarbazole-3-yl)-N-phenylcarbazole-3-yl) [Nylamino]spiro-9,9'-bifluorene (abbreviation: PCASF), 2,7-bis[N -(4-diphenylaminophenyl)-N-phenylamino]spiro-9,9'-biflu Oren (abbreviation: DPA2SF), N-[4-(9H-carbazole-9-yl)phenyl ]-N-(4-phenyl)phenylaniline (abbreviation: YGA1BP), N,N'-bis[ 4-(carbazole-9-yl)phenyl]-N,N'-diphenyl-9,9-dimethyl Using aromatic amine compounds such as fluorene-2,7-diamine (abbreviation: YGA2F) It is possible to do so. Also, 3-[4-(1-naphthyl)-phenyl]-9-phenyl-9H -Carbazole (abbreviation: PCPN), 4,4',4''-Tris(carbazole-9-I) Triphenylamine (abbreviation: TCTA), 4,4',4''-tris[N-(1-na Phthyl)-N-phenylamino]triphenylamine (abbreviation: 1'-TNATA), 4, 4',4''-Tris(N,N-diphenylamino)triphenylamine (abbreviation: TDA) TA), 4,4',4''-Tris[N-(3-methylphenyl)-N-phenylamino ] Triphenylamine (abbreviation: m-MTDATA), N,N'-di(p-tolyl)-N, N'-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4'-bis[ N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DP) AB), N,N'-bis{4-[bis(3-methylphenyl)amino]phenyl}-N, N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviation: DNTPD) ), 1,3,5-Tris[N-(4-diphenylaminophenyl)-N-phenylamino Compounds having an aromatic amine skeleton such as benzene (abbreviation: DPA3B), 1,3-bis( N-carbazolyl)benzene (abbreviation: mCP), 4,4'-di(N-carbazolyl)bif Phenyl (abbreviation: CBP), 3,6-bis(3,5-diphenylphenyl)-9-phenyl Carbazole (abbreviation: CzTP), 3,3'-bis(9-phenyl-9H-carbazole) ) (abbreviation: PCCP), 3-[N-(4-diphenylaminophenyl)-N-phenyl Mino]-9-phenylcarbazole (abbreviation: PCzDPA1), 3,6-bis[N-(4 -diphenylaminophenyl)-N-phenylamino]-9-phenylcarbazole (abbreviated) Name: PCzDPA2), 3,6-bis[N-(4-diphenylaminophenyl)-N-( 1-Naphthyl)amino]-9-phenylcarbazole (abbreviation: PCzTPN2), 3-[ N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole Luvazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole) -3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA) 2) 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amine [no]-9-phenylcarbazole (abbreviation: PCzPCN1), 1,3,5-tris[4- (N-carbazolyl)phenyl]benzene (abbreviation: TCPB), 9-[4-(10-phenyl]benzene [Nyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: CzPA), etc. Compounds having a ruvacole skeleton, 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-fluorene-9-I] Phenyl-6-phenyldibenzothiophene (abbreviation: DBTFLP-IV), etc. A compound having a thiophene skeleton, 4,4',4''-(benzene-1,3,5-triyl )tri(dibenzofuran) (abbreviation: DBF3P-II), 4-{3-[3-(9-pheni Lu-9H-fluoren-9-yl)phenyl]phenyl}dibenzofuran (abbreviation: mmD Examples include compounds having a furan skeleton, such as BFFLBi-II.

[0155] Furthermore, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphen Nylamine (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenyl [amino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide]( Abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis Using polymer compounds such as (phenyl)benzidine (abbreviation: Poly-TPD) It's also possible.

[0156] However, the hole transport material is not limited to the above, and may be one or more of various known materials. Combined as a hole transport material, the hole injection layer (111, 111a, 111b) and It can be used in the pore transport layer (112, 112a, 112b). Note that the hole transport layer (1 12, 112a, 112b) may each be formed from multiple layers. That is, for example, For example, the first hole transport layer and the second hole transport layer may be stacked on top of each other.

[0157] In the light-emitting element shown in Figure 1(D), the light-emitting layer 1 is placed on the hole transport layer 112a of the EL layer 103a. 13a is formed by vacuum deposition. Also, the EL layer 103a and the charge generation layer 104 After formation, the light-emitting layer 113b is deposited on the hole transport layer 112b of the EL layer 103b by vacuum deposition. It is formed from.

[0158] <Luminous layer> The light-emitting layers (113, 113a, 113b, 113c) are layers containing light-emitting material. Luminescent materials include those that emit light in colors such as blue, purple, blue-violet, green, yellow-green, yellow, orange, and red. A substance exhibiting the following characteristics is used as appropriate. In addition, multiple light-emitting layers (113a, 113b, 113c) are used. By using a luminescent material, a configuration can be created that exhibits different luminescent colors (for example, complementary colors). It can be made to produce white light emission obtained by combining different emission colors. Furthermore, one of the light-emitting layers It may also be a layered structure having different luminescent materials.

[0159] Furthermore, the light-emitting layers (113, 113a, 113b, 113c) contain a light-emitting material (guest material). In addition, it may contain one or more types of organic compounds (host material, assist material). i. In addition, one or more types of organic compounds may be hole transporters as described in this embodiment. Either or both of the material or the electron transport material can be used.

[0160] As a light-emitting material that can be used in the light-emitting layer (113, 113a, 113b, 113c) There are no particular limitations, and it refers to luminescent materials that convert singlet excitation energy into emission in the visible light region, This method utilizes a light-emitting material that converts the triplet excitation energy into visible light emission. In one aspect of the invention, an organic compound exhibits fluorescence emission, and the singlet excitation energy is set in the visible light region. It can be used as a light-emitting material that converts light emission into a specific range. For example, the following can be cited:

[0161] Examples of light-emitting materials that convert singlet excitation energy into light include fluorescent materials. Examples include pyrene derivatives, anthracene derivatives, triphenylene derivatives, and ful Orene derivatives, carbazole derivatives, dibenzothiophene derivatives, dibenzofuran derivatives Dibenzoquinoxaline derivatives, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives Examples include pyrene derivatives, phenanthrene derivatives, and naphthalene derivatives. In particular, pyrene derivatives are It is preferable because it has a high photon quantum yield. A specific example of a pyrene derivative is N,N'-bis(3- Methylphenyl)-N,N'-bis[3-(9-phenyl-9H-fluoren-9-yl] )phenyl]pyrene-1,6-diamine (abbreviation: 1,6mMemFLPAPrn), 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(dibenzofuran-2-yl)-N,N'-diphenylpyrene-1,6-diamine (abbreviated) Name: 1,6FrAPrn), N,N'-bis(dibenzothiophen-2-yl)-N,N '-diphenylpyrene-1,6-diamine (abbreviation: 1,6ThAPrn), N,N'-( Pyrene-1,6-diyl)bis[(N-phenylbenzo[b]naphtho[1,2-d]fura [N)-6-amine] (abbreviation: 1,6BnfAPrn), N,N'-(pyrene-1,6-di Il)bis[(N-phenylbenzo[b]naphtho[1,2-d]furan)-8-amine] (Abbreviation: 1,6BnfAPrn-02), N,N'-(pyrene-1,6-diyl)bis[ (6,N-diphenylbenzo[b]naphtho[1,2-d]furan)-8-amine) (abbreviation) Examples include :1,6BnfAPrn-03).

[0162] In addition, 5,6-bis[4-(10-phenyl-9-antryl)phenyl]-2, 2'-Bipyridine (abbreviation: PAP2BPy), 5,6-Bis[4'-(10-phenyl- 9-Anthryl)biphenyl-4-yl]-2,2'-bipyridine (abbreviation: PAPP2B) Py), N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N' -Diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-Cal Bazole-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (Abbreviation: YGAPA), 4-(9H-carbazole-9-yl)-4'-(9,10-di Phenyl-2-anthryl)triphenylamine (abbreviation: 2YGAPPA), N,9-di Phenyl-N-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazo 4-(10-phenyl-9-anthryl)-4 (abbreviation: PCAPA), 4-(10-phenyl-9-anthryl)-4 '-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PC) BAPA), 4-[4-(10-phenyl-9-antryl)phenyl]-4'-(9- Phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPBA) ), perylene, 2,5,8,11-tetra(tert-butyl)perylene (abbreviation: TBP) ), N,N''-(2-tert-butylanthracene-9,10-diyldi-4,1- Phenylene)bis[N,N',N'-triphenyl-1,4-phenylenediamine](abbreviated) Name: DPABPA), N,9-diphenyl-N-[4-(9,10-diphenyl-2-A Nantrillyl]phenyl]-9H-carbazole-3-amine (abbreviation: 2PCAPPA), N -[4-(9,10-diphenyl-2-antryl)phenyl]-N,N',N'-triphenyl Phenyl-1,4-phenylenediamine (abbreviated as 2DPAPPA), etc., can be used. ru.

[0163] Furthermore, examples of light-emitting materials that convert triplet excitation energy into light include phosphorescent materials. The quality (phosphorescent material) and thermally activated delayed fluorescence (Thermally activated delayed fluorescence) Examples include tivated delayed fluorescence (TADF) materials. It can be done.

[0164] Examples of phosphorescent materials include organometallic complexes, metal complexes (platinum complexes), and rare earth metal complexes. These exhibit different emission colors (emission peaks) depending on the substance, so select as appropriate as needed. Select and use.

[0165] It exhibits a blue or green color, and the peak wavelength of its emission spectrum is between 450 nm and 570 nm. Examples of phosphorescent materials include the following substances:

[0166] For example, 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) -Diphenyl-4H-1,2,4-Triazolat) Iridium(III) (Abbreviation: [Ir (Mptz)3]), Tris[4-(3-biphenyl)-5-isopropyl-3-phenyl Iridium(III) (abbreviation: [Ir(iPrp) Tris[3-(5-biphenyl)-5-isopropyl-4-phenyl]), Tris[3-(5-biphenyl)-5-isopropyl-4-phenyl Iridium(III) (abbreviation: [Ir(iPr5) Organometallic complexes having a 4H-triazole skeleton, such as btz)3]), Tris[3- Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazolate Iridium(III) (abbreviation: [Ir(Mptz1-mp)3]), Tris(1-methicone) Iridium(II) 5-phenyl-3-propyl-1H-1,2,4-triazolato) I) (abbreviation: [Ir(Prptz1-Me)3]) has a 1H-triazole skeleton The organometallic complex, fac-tris[1-(2,6-diisopropylphenyl)-2-f [Enyl-1H-imidazole] Iridium(III) (abbreviation: [Ir(iPrpmi)3 ]), Tris[3-(2,6-dimethylphenyl)-7-methylimidazo[1,2-f] Phenanthridine Iridium (III) (Abbreviation: Ir(dmpimpt-Me)3) Organometallic complexes having an imidazole skeleton such as ]), bis[2-(4',6'-diflu Olophenyl)pyridinato-N,C 2’ Iridium(III) tetrakis(1-pyrazo Lyl) Borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)p Riginato-N,C 2’ Iridium(III) picolinate (abbreviation: Firpic), S{2-[3',5'-bis(trifluoromethyl)phenyl]pyridinate-N,C 2’ Iridium(III) picolinate (abbreviation: [Ir(CF3ppy)2(pic)]) , bis[2-(4',6'-difluorophenyl)pyridinate-N,C 2’ ]iridium (III) Acetylacetonate (abbreviation: Fir(acac)) has an electron-withdrawing group Examples include organometallic complexes using phenylpyridine derivatives as ligands.

[0167] It exhibits a green or yellow color, and the peak wavelength of its emission spectrum is between 495 nm and 590 nm. Examples of phosphorescent materials include the following substances:

[0168] For example, Tris(4-methyl-6-phenylpyrimidinato)iridium(III) (abbreviation) :[Ir(mppm)3]), Tris(4-t-butyl-6-phenylpyrimidinato) Lydium(III) (abbreviation: [Ir(tBuppm)3]), (acetylacetonate) Iridium(III) (abbreviation: [Ir(m ppm)2(acac)]), (acetylacetonato)bis(6-tert-butyl-4) -Phenylpyrimidina) Iridium(III) (Abbreviation: [Ir(tBuppm)2(a (cac)), (acetylacetonato)bis[6-(2-norbornyl)-4-phenyl [Pyrimidinato] Iridium(III) (Abbreviation: [Ir(nbppm)2(acac)]) (acetylacetonato)bis[5-methyl-6-(2-methylphenyl)-4-phenyl [Lupyrimidinat] Iridium(III) (Abbreviation: [Ir(mpmppm)2(acac) ]), (acetylacetonato)bis{4,6-dimethyl-2-[6-(2,6-dimethyl Phenyl)-4-pyrimidinyl-κN 3 ]phenyl-κC}iridium(III) (abbreviation) :[Ir(dmppm-dmp)2(acac)]), (acetylacetonato)bis(4 ,6-diphenylpyrimidinato)iridium(III) (abbreviation: [Ir(dppm)2( Organometallic complexes having a pyrimidine skeleton such as (acac)), (acetylacetonate) Bis(3,5-dimethyl-2-phenylpyradinato)iridium(III) (abbreviation: [I r(mppr-Me)2(acac)]), (acetylacetonato)bis(5-isopropyl Iridium(III) (abbreviation: [Ir(m) Organometallic complexes having a pyrazine skeleton, such as ppr-iPr)2(acac)]), S(2-phenylpyridinato-N,C) 2’ ) Iridium(III) (Abbreviation: [Ir(pp y)3]), bis(2-phenylpyridinato-N,C 2’ Iridium(III) acetyl Luacetonate (abbreviation: [Ir(ppy)2(acac)]), bis(benzo[h]quinone) Iridium(III) acetylacetonate (abbreviation: [Ir(bzq)2(ac ac)]), Tris(benzo[h]quinolinato) iridium(III) (abbreviation: [Ir( bzq)3]), Tris(2-phenylquinolinato-N,C) 2’ Iridium (III) (Abbreviation: [Ir(pq)3]), bis(2-phenylquinolinato-N,C) 2’ ) Iridiu Mu(III)acetylacetonate (abbreviation: [Ir(pq)2(acac)]) Organometallic complexes having a pyridine skeleton, bis(2,4-diphenyl-1,3-oxazolate -N,C 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(dpo)2 (acac)]), bis{2-[4'-(perfluorophenyl)phenyl]pyridinate -N,C 2’ Iridium(III) acetylacetonate (abbreviation: [Ir(p-PF- (ph)2(acac)]), bis(2-phenylbenzothiazolat-N,C 2’ ) Iridi um(III)acetylacetonate (abbreviation: [Ir(bt)2(acac)]) and others In addition to organometallic complexes, tris(acetylacetonato)(monophenanthroline)terbium (III) (abbreviation: [Tb(acac)3(Phen)]) is an example of a rare earth metal complex. It can be done.

[0169] It exhibits a yellow or red color, and the peak wavelength of its emission spectrum is between 570 nm and 750 nm. Examples of phosphorescent materials include the following substances:

[0170] For example, (diisobutyrylmethanato)bis[4,6-bis(3-methylphenyl)pyrim [Dinato] Iridium(III) (abbreviation: [Ir(5mdppm)2(dibm)]), Su[4,6-bis(3-methylphenyl)pyrimidinato](dipivaloylmethanato)yl Zium(III) (abbreviation: [Ir(5mdppm)2(dpm)]), (Dipivaloylmethic acid) Thanato)bis[4,6-di(naphthalene-1-yl)pyrimidinato]iridium(III Organic compounds having a pyrimidine skeleton, such as (abbreviation: [Ir(d1npm)2(dpm)]) Metal complex, (acetylacetonato)bis(2,3,5-triphenylpyradinato)iridi Um(III) (abbreviation: [Ir(tppr)2(acac)]), Bis(2,3,5-) Iridium(III) (dipivaloylmethanato) (abbreviation: [Ir (tppr)2(dpm)]), (acetylacetonato)bis[2,3-bis(4-full) Olophenyl)quinoxalinato] Iridium(III) (abbreviation: [Ir(Fdpq)2( Organometallic complexes having a pyrazine skeleton, such as acac), and tris(1-phenylyl) Sokinolinato-N,C 2’ Iridium(III) (abbreviation: [Ir(piq)3]), S(1-phenylisoquinolinato-N,C) 2’ Iridium(III) acetylacetonate Organometallic compounds with a pyridine skeleton, such as t (abbreviation: [Ir(piq)2(acac)]). Group complex, 2,3,7,8,12,13,17,18-octaethyl-21H,23H-Po Platinum complexes such as rufiline platinum(II) (abbreviation: [PtOEP]), tris(1,3- Diphenyl-1,3-propanedionato)(monophenanthroline) europium(II) I) (Abbreviation: [Eu(DBM)3(Phen)]), Tris[1-(2-tenoyl)-3 ,3,3-trifluoroacetonate](monophenanthroline) europium(III) Examples include rare earth metal complexes such as (abbreviated as [Eu(TTA)3(Phen)]).

[0171] Organic compounds (host material, a) used in the light-emitting layer (113, 113a, 113b, 113c) As a cyst material, it has an energy gap larger than that of the luminescent material (guest material). One or more materials having a G-gap can be selected and used. Materials listed as hole transport materials, and materials listed as electron transport materials later, Such organic compounds (host material, assist material) can also be used. Organic compounds, which are one form of this phenomenon, have a low LUMO level and are therefore used as host or assist materials. This allows for a reduction in the drive voltage. The relatively high T1 level mentioned earlier is also a desirable characteristic. It is one of the combinations that forms an excited complex. Because it is low in rank, it can be combined with many other materials. By giving other materials as examples, this This section details the properties required for organic compounds such as host materials and assist materials.

[0172] When the light-emitting material is a fluorescent material, the host material has an energy level of singlet excited state. It is preferable to use organic compounds that are large and have low energy levels in their triplet excited states. In addition to the hole-transporting and electron-transporting materials shown in this embodiment, bipolar materials While it can be used as a host material, any substance that satisfies the above conditions is more preferable. For example, anthracene derivatives and tetracene derivatives are also suitable.

[0173] Therefore, as a host material to be combined with a fluorescent light-emitting substance, for example, 9-phenyl- 3-[4-(10-phenyl-9-antryl)phenyl]-9H-carbazole (abbreviation) :PCzPA), PCPN, CzPA, 7-[4-(10-phenyl-9-anthryl) Phenyl]-7H-dibenzo[c,g]carbazole (abbreviation: cgDBCzPA), 6- [3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1 ,2-d]furan (abbreviation: 2mBnfPPA), 9-phenyl-10-{4-(9-phenyl Nyl-9H-fluoren-9-yl)biphenyl-4'-yl}anthracene (abbreviation: F LPPA), 5,12-diphenyltetracene, 5,12-bis(biphenyl-2-yl) Examples include tetracene.

[0174] When the luminescent material is a phosphorescent material, the host material is the triplet excitation energy of the luminescent material ( Organic compounds where the triplet excitation energy is greater than the energy difference between the ground state and the triplet excited state. You just need to select a compound. Note that the hole-transporting and electron-transporting materials shown in this embodiment... In addition to the above, bipolar materials can be used as host materials, but the above conditions must be met. Substances that add to it are more preferable. For example, anthracene derivatives, phenanthrene derivatives. , condensed polycyclic aromatics such as pyrene derivatives, chrysene derivatives, and dibenzo[g,p]chrysene derivatives Group compounds are also suitable.

[0175] Therefore, as a host material to be combined with a phosphorescent light-emitting substance, for example, 9,10-diph Phenylanthracene (abbreviation: DPAnth), N,N-diphenyl-9-[4-(10- Phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine (abbreviation: Cz A1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DP) hPA), YGAPA, PCAPA, 9-(4-{4'-[N-phenyl-N-(N-f Phenyl-3-carbazolyl)amino}phenyl)phenyl-10-phenylanthrace N (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9- Diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), 6,12-dimethyl Toxy-5,11-diphenylchrysene, N,N,N',N',N'',N'',N'' ',N'''-Octaphenyldibenzo[g,p]chrysene-2,7,10,15-Tet Laamine (abbreviation: DBC1), CzPA, 3,6-diphenyl-9-[4-(10-phenyl Nyl-9-antryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9, 10-Bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10 -di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10 -di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-biantril (Abbreviation: BANT), 9,9'-(Stilben-3,3'-Diyl)Diphenanthrene( Abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated) (Name: DPNS2), 1,3,5-tri(1-pyrenyl)benzene (abbreviation: TPB3), etc. It can be listed.

[0176] Furthermore, when multiple organic compounds are used in the light-emitting layer (113, 113a, 113b, 113c) It is preferable to use a compound that forms an excitation complex mixed with a phosphorescent material. By using this configuration, the energy transfer from the excited complex to the luminescent material, called Ex, is achieved. Using TET (Exciplex-Triplet Energy Transfer) Luminescence can be obtained. In this case, various organic compounds can be used in appropriate combinations. However, in order to efficiently form an excited complex, a compound that readily accepts holes (holes) is needed. Combining an electron-transporting material with a compound that readily accepts electrons (an electron-transporting material) That is particularly preferable.

[0177] TADF materials are materials that can be converted from a triplet excited state to a singlet excited state by a small amount of thermal energy. It enables reverse intersystem crossing (op-conversion) and efficiently generates light (fluorescence) from the singlet excited state. It refers to materials that exhibit this phenomenon. Furthermore, the conditions under which thermally activated delayed fluorescence can be efficiently obtained are three The energy difference between the doublet excited level and the singlet excited level is 0 eV or more and 0.2 eV or less, preferably. One example is that the voltage is between 0 eV and 0.1 eV. Also, regarding delayed fluorescence in TADF materials... Light refers to emission that has a spectrum similar to ordinary fluorescence but with a significantly longer lifetime. The lifespan is 1 × 10 -6 For more than a second, preferably 1 × 10⁻⁶ seconds. -3 It is more than a second.

[0178] Examples of TADF materials include fullerenes and their derivatives, and acridines such as proflavin. Examples include derivatives and eosin. Also, magnesium (Mg), zinc (Zn), cadmium Um (Cd), tin (Sn), platinum (Pt), indium (In), or palladium Examples of metal-containing porphyrins include those containing (Pd), etc. For example, protoporphyrin-tin fluoride complex (abbreviation: SnF2 (Proto IX)) Mesoporphyrin-tin fluoride complex (abbreviation: SnF2 (Meso IX)), hematopo Rufirin-tin fluoride complex (abbreviation: SnF2(Hemato IX)), copropolph Fluorine tetramethyl ester-tin fluoride complex (abbreviation: SnF2(Copro III- 4Me)), Octaethylporphyrin-tin fluoride complex (abbreviation: SnF2(OEP)) , Ethioporphyrin-tin fluoride complex (abbreviation: SnF2(Etio I)), Octae Examples include tilporphyrin-platinum chloride complex (abbreviated as PtCl2OEP).

[0179] Other TADF materials include 2-(biphenyl-4-yl)-4,6-bis(12- Phenylindoro[2,3-a]carbazole-11-yl)-1,3,5-triazine (Abbreviation: PIC-TRZ), 2-{4-[3-(N-phenyl-9H-carbazole-3) -yl)-9H-carbazole-9-yl]phenyl}-4,6-diphenyl-1,3, 5-Triazine (abbreviation: PCCzPTzn), 2-[4-(10H-phenoxazine-1 0-yl)phenyl]-4,6-diphenyl-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-acrylidine-10-yl)-9H-xanthene-9- ONE (abbreviation: ACRXTN), bis[4-(9,9-dimethyl-9,10-dihydroac Lysine)phenyl]sulfone (abbreviation: DMAC-DPS), 10-phenyl-10H,1 0'H-Spiro[acridine-9,9'-anthracene]-10'-one (abbreviation: ACR) Heterocyclic compounds having π-electron-rich heteroaromatic rings and π-electron-deficient heteroaromatic rings such as SA) It can be used. Furthermore, π-electron-rich heteroaromatic rings and π-electron-deficient heteroaromatic rings can be directly used. The bonded substance acts as a donor for π-electron-rich heteroaromatic rings and as an accessory for π-electron-deficient heteroaromatic rings. Both ptarian properties become stronger, and the energy difference between the singlet and triplet excited states decreases. Therefore, it is particularly preferable.

[0180] Furthermore, when using TADF materials, they can also be used in combination with other organic compounds.

[0181] By using the above materials appropriately, the light-emitting layer (113, 113a, 113b, 113c) It is possible to form the above materials. Furthermore, the above materials can be combined with low molecular weight materials and high molecular weight materials. This allows it to be used for forming the light-emitting layers (113, 113a, 113b, 113c). ru.

[0182] In the light-emitting element shown in Figure 1(D), an electron transport layer is located on the light-emitting layer 113a of the EL layer 103a. 114a is formed. Also, after the EL layer 103a and the charge generation layer 104 are formed, An electron transport layer 114b is formed on the light-emitting layer 113b of the EL layer 103b.

[0183] <Electron transport layer> The electron transport layer (114, 114a, 114b) is an electron injection layer (115, 115a, 115 b) The electrons injected from the second electrode 102 are directed to the light-emitting layer (113, 113a, 11 These are the layers that transport electrons to (3b, 113c). Note that electron transport layers (114, 114a, 114b) ) is a layer containing an electron transport material. Used in the electron transport layer (114, 114a, 114b) The electron transport material is 1 × 10 -6 cm 2 Materials with an electron mobility of / Vs or higher are preferred. It is possible to use materials other than those mentioned above, provided they have higher electron transport capabilities than holes. This can be achieved. An organic compound, which is one aspect of the present invention, satisfies these requirements. In addition, LUMO A lower energy level leads to a lower driving voltage, therefore, in one aspect of the present invention, the electron transport layer The use of organic compounds is preferable. Other usable materials are listed below.

[0184] Examples of electron transport materials include metal complexes having a quinoline skeleton and those having a benzoquinoline skeleton. Other metal complexes, metal complexes with an oxazole skeleton, metal complexes with a thiazole skeleton, etc. , oxadiazole derivatives, triazole derivatives, imidazole derivatives, oxazole derivatives Conductors, thiazole derivatives, phenanthroline derivatives, quinoline ligands having quinoline ligands Conductors, benzoquinoline derivatives, quinoxaline derivatives, dibenzoquinoline derivatives, pyr Contains din derivatives, bipyridine derivatives, pyrimidine derivatives, and other nitrogen-containing heteroaromatic compounds. Materials with high electron transport capabilities, such as π-electron-deficient heteroaromatic compounds, can be used.

[0185] A specific example of an electron-transporting material is tris(8-quinolinolato)aluminum(III). (Abbreviation: Alq3), Tris(4-methyl-8-quinolinolato)aluminum(III) (Abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium ( II) (Abbreviation: BeBq2), bis(2-methyl-8-quinolinolate)(4-phenyl Aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc (II) Metal complexes having a quinoline skeleton or benzoquinoline skeleton, such as (Znq) , bis[2-(2-benzoxazolyl)phenolate]zinc(II) (abbreviation: ZnPBO ), bis[2-(2-benzothiazolyl)phenolate]zinc(II) (abbreviation: ZnBTZ) ), bis[2-(2-hydroxyphenyl)benzothiazolat]zinc(II) (abbreviation: Z Examples include metal complexes having an oxazole or thiazole skeleton, such as n(BTZ)2). It is possible.

[0186] In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl (Lu)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-te rt-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 9-[4-(5-phenyl-1,3,4-oxadiazole-2-yl) Oxadiazole derivatives such as phenyl]-9H-carbazole (abbreviation: CO11), 3- (4'-tert-butylphenyl)-4-phenyl-5-(4''-biphenyl)-1 ,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4 -(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated) Triazole derivatives such as p-EtTAZ, 2,2',2''-(1,3,5-ben (Zentriyl) Tris(1-phenyl-1H-benzoimidazole) (abbreviation: TPBI) , 2-[3-(dibenzothiophen-4-yl)phenyl]-1-phenyl-1H-ben Imidazole derivatives such as zoimidazole (abbreviation: mDBTBIm-II) (benzimidazole) (including zole derivatives) and 4,4'-bis(5-methylbenzoxazole-2-yl) Oxazole derivatives such as stilbene (abbreviation: BzOS), vasophenanthroline (abbreviation :Bphen), vasocuproine (abbreviation: BCP), 2,9-bis(naphthalene-2- Examples include yl-4,7-diphenyl-1,10-phenanthroline (abbreviation: NBphen), etc. Phenanthroline derivatives, 2-[3-(dibenzothiophen-4-yl)phenyl]di Benzo[f,h]quinoxaline (abbreviation: 2mDBTPDBq-II), 2-[3'-(di [Benzothiophene-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (Abbreviation: 2mDBTBPDBq-II), 2-[3'-(9H-carbazole-9-yl) )biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mCzBPDBq) ), 2-[4-(3,6-diphenyl-9H-carbazole-9-yl)phenyl]diphenyl Nzo[f,h]quinoxaline (abbreviation: 2CzPDBq-III), 7-[3-(dibenzo Thiofen-4-yl)phenyl]dibenzo[f,h]quinoxaline (abbreviation: 7mDBT) PDBq-II), and 6-[3-(dibenzothiophen-4-yl)phenyl]dibenzothiophene Quinoxaline inducers such as nzzo[f,h]quinoxaline (abbreviation: 6mDBTPDBq-II) The body, or dibenzoquinoxaline derivatives, 3,5-bis[3-(9H-carbazole-9 -yl)phenyl]pyridine (abbreviation: 35DCzPPy), 1,3,5-tri[3-(3 Pyridine derivatives such as -pyridyl)phenyl]benzene (abbreviation: TmPyPB), 4,6- Bis[3-(phenanthrene-9-yl)phenyl]pyrimidine (abbreviation: 4,6mPnP) 2Pm), 4,6-bis[3-(4-dibenzothienyl)phenyl]pyrimidine (abbreviation: 4,6mDBTP2Pm-II), 4,6-bis[3-(9H-carbazole-9-yl) Pyrimidine derivatives such as phenyl]pyrimidine (abbreviation: 4,6mCzP2Pm), 2-{ 4-[3-(N-phenyl-9H-carbazol-3-yl)-9H-carbazol-9 -yl]phenyl}-4,6-diphenyl-1,3,5-triazine (abbreviation: PCCzP) Tzn), 9-[3-(4,6-diphenyl-1,3,5-triazine-2-yl)fer [nyl]-9'-phenyl-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTz) Triazine derivatives such as n-02) can be used.

[0187] Also, poly(2,5-pyridinediyl) (abbreviation: PPy), poly[(9,9-dihexyl Fluorene-2,7-diyl)-co-(pyridine-3,5-diyl)(abbreviation: PF- Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2' Using polymer compounds such as (-bipyridine-6,6'-diyl) (abbreviation: PF-BPy) It is possible to stay there.

[0188] Furthermore, the electron transport layers (114, 114a, 114b) are not only single-layered but also made of the above material. The structure may consist of two or more layers stacked together.

[0189] Next, in the light-emitting element shown in Figure 1(D), electrons are transported on the electron transport layer 114a of the EL layer 103a. The sub-injection layer 115a is formed by vacuum deposition. Subsequently, the EL layer 103a and charge generation After the raw layer 104 is formed and the electron transport layer 114b of the EL layer 103b is formed, The sub-injection layer 115b is formed by vacuum deposition.

[0190] <Electron injection layer> The electron injection layers (115, 115a, 115b) are layers containing materials with high electron injection potential. The electron injection layers (115, 115a, 115b) contain lithium fluoride (LiF) and fluoride. Cium (CsF), calcium fluoride (CaF2), lithium oxide (LiO2) x ) etc. Alkali metals, alkaline earth metals, or compounds thereof can be used. Furthermore, rare earth metal compounds such as erbium fluoride (ErF3) can be used. Alternatively, an electride may be used in the electron injection layers (115, 115a, 115b). As for ctrides, for example, a mixed oxide of calcium and aluminum with a high concentration of electrons added. Examples of added substances include the electron transport layers (114, 114a, 114b) mentioned above. It is also possible to use the materials that make up the structure.

[0191] Furthermore, the electron injection layers (115, 115a, 115b) contain organic compounds and electron donors. A composite material made by mixing ) and may be used. Such a composite material is made by an electron donor Because electrons are generated in the organic compound, it exhibits excellent electron injection and electron transport properties. Preferably, the organic compound is a material that is excellent at transporting the generated electrons, and specifically Specifically, for example, the electron transport properties used in the electron transport layers (114, 114a, 114b) described above. Materials (such as metal complexes and heteroaromatic compounds) can be used. As electron donors, Any substance that exhibits electron-donating properties to the compound will suffice. Specifically, alkali metals and alkalis Lithium-earth metals and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, Examples include erbium and ytterbium. Also, alkali metal oxides and alkaline earth elements. Metal oxides are preferred, including lithium oxide, calcium oxide, and barium oxide. It can also be used. Furthermore, Lewis bases such as magnesium oxide can be used. Organic compounds such as thiafulvalene (abbreviated as TTF) can also be used.

[0192] Furthermore, in the light-emitting element shown in Figure 1(D), the light obtained from the light-emitting layer 113b is amplified. In this case, the optical distance between the second electrode 102 and the light-emitting layer 113b is such that the light-emitting layer 113b exhibits It is preferable to form it such that the wavelength λ of the light is less than 1 / 4. In this case, electron transport layer 1 This can be adjusted by changing the film thickness of 14b or the electron injection layer 115b.

[0193] <Charge generation layer> In the light-emitting element shown in Figure 1(D), the charge generation layer 104 is connected to the first electrode (anode) 101. When a voltage is applied between the second electrode (cathode) 102 and the EL layer 103a, electrons are injected into the EL layer 103a. Furthermore, it has the function of injecting holes into the EL layer 103b. The charge generation layer 104 has the function of injecting holes Even if the electron-transporting material has an electron acceptor added to it, the electron-transporting material The configuration may also include an electron donor. Furthermore, both of these configurations may be combined. It may be layered. Furthermore, by forming the charge generation layer 104 using the materials described above... This makes it possible to suppress the increase in driving voltage when EL layers are stacked.

[0194] In the charge generation layer 104, if an electron acceptor is added to the hole transport material, As the hole transport material, the material shown in this embodiment can be used. As a receptor, 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinone Examples include dimethane (abbreviated as F4-TCNQ) and chloranil. Examples of metal oxides belonging to groups 4 through 8 in the table can be listed. Specifically, Vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide Examples include stainless steel, manganese oxide, and rhenium oxide.

[0195] In the charge generation layer 104, if an electron donor is added to the electron transport material, As the electron transport material, the material shown in this embodiment can be used. The donors include alkali metals, alkaline earth metals, rare earth metals, or periodic elements. Metals belonging to groups 2 and 13 in the table, as well as their oxides and carbonates, can be used. Specifically, lithium (Li), cesium (Cs), magnesium (Mg), calcium Calcium (Ca), Ytterbium (Yb), Indium (In), Lithium Oxide, Cesium Carbonate It is preferable to use materials such as 'mu'. Also, an organic compound such as tetratianaphthalene is electron It may also be used as a donor.

[0196] <Circuit board> The light-emitting element shown in this embodiment can be formed on various substrates. The types are not limited to specific ones. An example of a substrate is a semiconductor substrate (for example) Single crystal substrates or silicon substrates), SOI substrates, glass substrates, quartz substrates, plastic substrates Metal substrates, stainless steel substrates, substrates with stainless steel foil, tan Tungsten substrate, substrate having tungsten foil, flexible substrate, laminated film, Examples include paper containing fibrous materials, or base films.

[0197] Examples of glass substrates include barium borosilicate glass and aluminoborosilicate glass. Examples include soda-lime glass or other materials. Also, flexible substrates and laminated films. Examples of base films include polyethylene terephthalate (PET) and polyethylene Plasti Acrylic resin and other synthetic resins, polypropylene, polyester, polyvinyl fluoride, Polyvinyl chloride, polyamide, polyimide, aramid resin, epoxy resin, inorganic vapor deposition film Examples include film or paper products.

[0198] The light-emitting element shown in this embodiment requires a vacuum process such as evaporation, or a spin-coil process. Solution processes such as the vapor deposition method and inkjet method can be used. For example, sputtering, ion plating, ion beam deposition, molecular beam deposition, and Physical vapor deposition (PVD) methods such as empty vapor deposition and chemical vapor deposition (CVD) methods can be used. It is possible. In particular, the functional layer (hole injection layer (111, 111a, 111) included in the EL layer of the light-emitting element. b) Hole transport layer (112, 112a, 112b), light-emitting layer (113, 113a, 113 b, 113c), electron transport layer (114, 114a, 114b), electron injection layer (115, 1 15a, 115b)), and the charge generation layers (104, 104a, 104b), Vapor deposition methods (vacuum deposition, etc.), coating methods (dip coating, die coating, bar coating, etc.) (Pin coat method, spray coat method, etc.), printing method (inkjet method, screen printing (stencil printing)) Printing methods include offset (lithographic) printing, flexographic (letterpress) printing, gravure printing, and micro-printing. It can be formed by methods such as contact printing and nanoimprint printing.

[0199] The EL layers (103, 103a, 103b) of the light-emitting element shown in this embodiment are composed of Each functional layer (hole injection layer (111, 111a, 111b), hole transport layer (112, 112a) , 112b), light-emitting layer (113, 113a, 113b, 113c), electron transport layer (114 , 114a, 114b), electron injection layer (115, 115a, 115b)) and charge generation layer ( 104, 104a, 104b) are not limited to the materials mentioned above, but also include other materials However, if they can fulfill the functions of each layer, they can be used in combination. For example, For example, high molecular weight compounds (oligomers, dendrimers, polymers, etc.), medium molecular weight compounds (low molecular weight compounds) Compounds in the intermediate region between polymers and macromolecules (molecular weight 400-4000), inorganic compounds (quantum dot materials) Materials such as colloidal quantum dots can be used. Materials, alloy-type quantum dot materials, core-shell type quantum dot materials, core-type quantum dot materials, etc. You can use these.

[0200] The configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments. It is assumed that this is possible.

[0201] (Embodiment 3) This embodiment describes a light-emitting device that is one aspect of the present invention. Note that Figure 2(A) The light-emitting device shown consists of a transistor (FET) 202 on the first substrate 201 and a light-emitting element (2 Active matrix formed by electrically connecting 03R, 203G, 203B, 203W It is a type of light-emitting device, and multiple light-emitting elements (203R, 203G, 203B, 203W) It has a common EL layer 204, and depending on the light emission color of each light-emitting element, between the electrodes of each light-emitting element It has a microcavity structure in which the optical distance is adjusted. Also obtained from the EL layer 204 The emitted light is formed on the second substrate 205, creating a color filter (206R, 206G, 206 This is a top-emission type light-emitting device that is emitted via B).

[0202] The light-emitting device shown in Figure 2(A) is configured such that the first electrode 207 functions as a reflective electrode. Furthermore, the second electrode 208 is formed to function as a semi-transmissive / semi-reflective electrode. Other embodiments include: Refer to the description and use it as appropriate.

[0203] Furthermore, in Figure 2(A), for example, the light-emitting element 203R is a red light-emitting element, and the light-emitting element 203 G is a green light-emitting element, light-emitting element 203B is a blue light-emitting element, and light-emitting element 203W is a white light-emitting element. In this case, as shown in Figure 2(B), the light-emitting element 203R has a first electrode 207 and a second electrode The light-emitting element 203G is adjusted so that the distance between it and pole 208 is 200R, and the first light The distance between electrode 207 and the second electrode 208 is adjusted to an optical distance of 200G, and the light-emitting element 2 03B is such that the optical distance between the first electrode 207 and the second electrode 208 is 200B. Adjust. Note that, as shown in Figure 2(B), the conductive layer 210R in the light-emitting element 203R The first electrode 207 is laminated, and the conductive layer 210G is laminated on the light-emitting element 203G. This allows for more precise optical adjustments.

[0204] The second substrate 205 has color filters (206R, 206G, 206B) formed on it. Color filters allow a specific wavelength range of visible light to pass through, and also allow a specific wavelength range to pass through. This is a blocking filter. Therefore, as shown in Figure 2(A), it overlaps with the light-emitting element 203R. By placing a color filter 206R that allows only the red wavelength range to pass through at this position, the light-emitting element Red light can be obtained from sub-unit 203R. Also, green light can be obtained in a position that overlaps with the light-emitting element 203G. By providing a color filter 206G that allows only the wavelength range to pass through, the light-emitting element 203 Green light can be obtained from G. In addition, the blue wavelength range is located at a position that overlaps with the light-emitting element 203B. By providing a color filter 206B that only allows blue light to pass through, the light-emitting element 203B can be filtered to emit blue light. Color emission can be obtained. However, the light-emitting element 203W does not require a color filter. White light emission can be obtained. Note that the edges of one type of color filter have a black layer (black). A color matrix (209) may also be provided. Furthermore, a color filter (206R The black layers (206G, 206B) and 209 are covered with an overcoat layer made of a transparent material. It's okay if it's included.

[0205] Figure 2(A) shows a structure (top emission type) that extracts light from the second substrate 205 side. The light-emitting device is shown, and as shown in Figure 2(C), the first substrate on which the FET202 is formed It can also be used as a light-emitting device with a structure that extracts light from the 201 side (bottom emission type). In the case of a bottom-emission type light-emitting device, the first electrode 207 is a semi-transmissive / semi-reflective electrode. The first electrode is formed to function as such, and the second electrode 208 is formed to function as a reflective electrode. Furthermore, the first substrate 201 shall be at least a light-transmitting substrate. (206R', 206G', 206B') are light-emitting elements (203 It is sufficient to place it on the side of the first substrate 201 (rather than R, 203G, and 203B).

[0206] Furthermore, in Figure 2(A), the light-emitting elements are a red light-emitting element, a green light-emitting element, a blue light-emitting element, Although the case of a white light-emitting element has been shown, the light-emitting element in one aspect of the present invention is not limited to that configuration. It does not need to be, and the configuration may also include yellow or orange light-emitting elements. To fabricate these light-emitting devices, an EL layer (light-emitting layer, hole injection layer, hole transport layer, electron transport layer) is used. For materials used in layers (such as electron injection layers and charge generation layers), please refer to the descriptions in other embodiments. It can be used as appropriate. In that case, the color filter will also be used according to the light emission color of the light-emitting element. You need to select the appropriate Ruta.

[0207] By using the above configuration, a light-emitting device equipped with light-emitting elements that emit multiple colors of light can be created. It can be obtained.

[0208] The configuration shown in this embodiment may be used in appropriate combination with the configurations shown in other embodiments. It shall be possible.

[0209] (Embodiment 4) This embodiment describes a light-emitting device that is one aspect of the present invention.

[0210] By applying the element configuration of a light-emitting element according to one aspect of the present invention, an active matrix type It is possible to fabricate light-emitting devices and passive matrix type light-emitting devices. A matrix-type light-emitting device has a configuration that combines light-emitting elements and transistors (FETs). Possesses. Therefore, passive matrix type light-emitting device, active matrix type light-emitting device These are all included in one aspect of the present invention. Note that the light-emitting device shown in this embodiment may also include other It is possible to apply the light-emitting element described in the embodiment.

[0211] In this embodiment, an active matrix type light-emitting device will be described using Figure 3.

[0212] Figure 3(A) is a top view showing the light-emitting device 21, and Figure 3(B) is a top view of Figure 3(A) with the dashed line A -This is a cross-sectional view taken at line A'. The active matrix type light-emitting device is a first substrate 30 1 A pixel section 302, a drive circuit section (source line drive circuit) 303 provided on, and a drive circuit section (Gate line driving circuit) (304a, 304b) is included. Pixel section 302 and driving circuit section (303, 304a, 304b) are sealed by the sealing material 305 between the first substrate 301 and the second It is sealed between the substrate 306.

[0213] Furthermore, routing wiring 307 is provided on the first substrate 301. It is electrically connected to the external input terminal, FPC308. Note that FPC308 is a drive The dynamic circuit section (303, 304a, 304b) receives an external signal (for example, a video signal, a crossover signal). It transmits signals such as the clock signal, start signal, and reset signal, as well as electrical potential. The FPC308 also has Printed circuit boards (PWBs) may be attached. The state in which B is attached is included in the light-emitting device.

[0214] Next, Figure 3(B) shows the cross-sectional structure of the light-emitting device.

[0215] The pixel section 302 includes an FET (switching FET) 311 and an FET (current control FET). Multiple pixels having 312 and a first electrode 313 electrically connected to the FET 312. It is formed by [this]. The number of FETs in each pixel is not particularly limited and is not necessarily [limited]. It can be established as needed.

[0216] FET309, 310, 311, 312 are not particularly limited, for example, staggered Transistors such as type 1 and reverse staggered transistors can be applied. Also, top-gate and bo A transistor structure such as a Tomgate type may also be acceptable.

[0217] Furthermore, the semiconductors that can be used in these FETs 309, 310, 311, and 312 are The crystallinity is not particularly limited; amorphous semiconductors, crystalline semiconductors (microcrystalline semiconductors, Whether using a polycrystalline semiconductor, a single-crystal semiconductor, or a semiconductor having a crystalline region in part, Good. Furthermore, by using a crystalline semiconductor, the degradation of transistor characteristics can be suppressed. Therefore, it is preferable.

[0218] Furthermore, these semiconductors include, for example, elements of Group 14, compound semiconductors, and oxide semiconductors. Organic semiconductors can be used, such as silicon-based semiconductors and gallium Semiconductors containing arsenic, oxide semiconductors containing indium, and other materials can be applied.

[0219] The drive circuit section 303 includes FET 309 and FET 310. The ET310 is a circuit containing a unipolar (either N-type or P-type) transistor. It may be formed as follows, or as a CMOS circuit including N-type and P-type transistors. It may be formed in this way. Alternatively, it may be configured to have an external drive circuit.

[0220] The end of the first electrode 313 is covered with an insulator 314. Organic compounds such as negative-type photosensitive resins and positive-type photosensitive resins (acrylic resins), and acids Inorganic compounds such as silicon oxide, silicon nitride, and silicon nitride can be used. Preferably, the upper or lower end of the edge 314 has a curved surface with curvature. This allows for better coverage of the film formed on the upper layer of the insulator 314.

[0221] An EL layer 315 and a second electrode 316 are laminated on the first electrode 313. 315 includes a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. To possess.

[0222] Note that the configuration of the light-emitting element 317 shown in this embodiment is different from the configuration and materials described in other embodiments. A fee can be applied. Although not shown in the diagram, the second electrode 316 is an external input. It is electrically connected to the FPC308 terminal.

[0223] Furthermore, although only one light-emitting element 317 is shown in the cross-sectional view in Figure 3(B), the pixel section 3 In 02, multiple light-emitting elements are arranged in a matrix. Pixel section 30 In 2, light-emitting elements that can produce three types of light (R, G, B) are selectively formed, and It is possible to form a light-emitting device capable of multi-color display. In addition, three types of light (R, G, B) can be emitted. In addition to light-emitting elements that produce light, for example, white (W), yellow (Y), magenta (M) ), a light-emitting element that can emit cyan (C), etc. may be formed. For example, three types (R, Add the aforementioned light-emitting elements to the light-emitting elements that produce light G and B). This allows for improvements in color purity and reduced power consumption. By combining it with a filter, it can also be used as a light-emitting device capable of full-color display. The types of color filters include red (R), green (G), blue (B), cyan (C), and magenta. Colors such as black (M) and yellow (Y) can be used.

[0224] The FETs (309, 310, 311, 312) on the first substrate 301 and the light-emitting element 317 are By bonding the second substrate 306 and the first substrate 301 together with the sealing material 305, The space 318 is surrounded by the first substrate 301, the second substrate 306, and the sealing material 305. It has a structure provided for this. In addition, the space 318 contains an inert gas (such as nitrogen or argon) It may be filled with organic material (including sealant 305).

[0225] Epoxy resin or glass frit can be used for the sealant 305. It is preferable to use a material that does not permeate moisture or oxygen as much as possible for the 305 material. The second substrate 306 is similar to the one that can be used for the first substrate 301. Therefore, various substrates described in other embodiments can be used as appropriate. In addition to glass substrates and quartz substrates, FRP (Fiber-Reinforced Plastic) is also used as a substrate. d Plastics), PVF (polyvinyl fluoride), polyester or acrylic A plastic substrate made of resin or the like can be used. Glass frit can be used as a sealing material. When using glass, the first substrate 301 and the second substrate 306 are glass from the viewpoint of adhesion. A substrate is preferred.

[0226] As described above, an active matrix type light-emitting device can be obtained.

[0227] Furthermore, when forming an active matrix type light-emitting device on a flexible substrate, The FET and light-emitting element may be formed directly, but the FET and light-emitting element may be formed on a separate substrate having a release layer. After forming the element, the FET and light-emitting element are separated by applying heat, force, laser irradiation, etc. The material may also be peeled off and then transferred to a flexible substrate for fabrication. For example, the peeling layer could be... Lamination of inorganic films such as tungsten films and silicon oxide films, and organic resin films such as polyimide, etc. It can be used. Furthermore, as a flexible substrate, it is possible to form transistors on it. In addition to boards, paper substrates, cellophane substrates, aramid film substrates, polyimide film substrates, Fabric substrate (natural fibers (silk, cotton, linen), synthetic fibers (nylon, polyurethane, polyester)) (or includes regenerated fibers such as acetate, cupro, rayon, and recycled polyester.) Examples include leather substrates or rubber substrates. By using these substrates, durability It offers excellent heat resistance and allows for weight reduction and thinning.

[0228] Note that the configuration shown in this embodiment can be used in combination with the configurations shown in other embodiments as appropriate. It is possible.

[0229] (Embodiment 5) In this embodiment, a light-emitting element according to one aspect of the present invention, and a light-emitting element according to one aspect of the present invention This section describes various electronic devices and automobiles that have been completed by applying this light-emitting device. Furthermore, the light-emitting device is mainly applied to the display unit in the electronic device described in this embodiment. It is possible.

[0230] The electronic equipment shown in Figures 4(A) to 4(C) consists of a housing 7000, a display unit 7001, and a speaker. 7003, LED lamp 7004, operation key 7005 (power switch or operation switch) (including), connection terminal 7006, sensor 7007 (force, displacement, position, velocity, acceleration, angular velocity) Rotation speed, distance, light, liquid, magnetism, temperature, chemicals, sound, time, hardness, electric field, current, voltage , including functions for measuring power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation. It may have a microphone 7008, etc.

[0231] Figure 4(A) shows a mobile computer, and in addition to the above, it includes a switch 7009, red It may have external port 7010, etc.

[0232] Figure 4(B) shows a portable image playback device equipped with a recording medium (for example, a DVD player). In addition to the above, it also has a second display unit 7002, a recording medium reading unit 7011, etc. It is possible.

[0233] Figure 4(C) shows a digital camera with television receiving capabilities, and in addition to the above, it has an antenna. It may have components such as 7014, a shutter button 7015, an image receiving unit 7016, etc.

[0234] Figure 4(D) shows a personal digital information terminal. The personal digital information terminal displays information on three or more sides of the display unit 7001. It has the function of displaying. Here, information 7052, information 7053, and information 7054 are respectively This shows an example of display on different surfaces. For example, a user might have a mobile device in the breast pocket of their clothing. Information 7053 displayed in a position visible from above the mobile device with the end retracted. It is also possible to check this. Users can view it without taking their mobile device out of their pocket. This allows you to check and, for example, decide whether or not to answer the phone.

[0235] Figure 4(E) shows a portable information terminal (including a smartphone), with a housing 7000 and a display unit 7 It may have 001, operation keys 7005, etc. Furthermore, the portable information terminal may have a speaker. They may also be provided with connection terminals, sensors, etc. Furthermore, the portable information terminal may provide text and image information in multiple quantities. It can be displayed on the number surface. Here is an example showing three icons, 7050. It is also possible to display the information 7051, indicated by the dashed rectangle, on another surface of the display unit 7001. Yes, it is possible. An example of information 7051 is notifications of incoming messages such as email, SNS, and phone calls. Subject line of emails and social media messages, sender name, date, time, battery level, antenna reception. There are strengths and so on. Alternatively, at the location where information 7051 is displayed, there is icon 7050. Any of these can be displayed.

[0236] Figure 4(F) shows a large television system (also called a television or television receiver). It may have a housing 7000, a display unit 7001, etc. Also, here, This shows a configuration in which the housing 7000 is supported by the 7018. Also, a television device. The operation can be performed using a separate remote control unit 7111, etc. Note that the display unit 7 001 may be equipped with a touch sensor, and can be operated by touching the display unit 7001 with a finger or the like. It is also acceptable. The remote control operator 7111 outputs information from the remote control operator 7111. It may have a display unit. The remote control unit 7111 may have operation keys or buttons. The control panel allows you to operate the channel and volume, and the display unit 7001 displays the information. The image can be manipulated.

[0237] The electronic devices shown in Figures 4(A) to 4(F) can have a variety of functions. For example, , a function to display various information (still images, videos, text images, etc.) on the display unit, touch panel Features include a calendar, a function to display the date or time, and various software (programs). Functions that control processing by (M), wireless communication function, and various computers using wireless communication function It has the function of connecting to a data network and transmitting or receiving various types of data using wireless communication. The function to be performed is to read the program or data recorded on the recording medium and display it on the display unit. It can have functions such as, One display unit primarily shows image information, while the other display unit primarily shows text information. A function that displays images that take parallax into account on multiple display units to create a three-dimensional image. It can have a display function, etc. Furthermore, in an electronic device having an image receiving unit, Features for taking still images, recording videos, and automatically or manually correcting captured images. Functions, functions to save captured images to a recording medium (external or built into the camera), captured images It can have a function to display on the display unit, etc. Note that Figures 4(A) to 4(F) The functions that the electronic devices shown may have are not limited to these, and may have a variety of functions. It is possible.

[0238] Figure 4(G) shows a wristwatch-type personal information terminal, which can be used, for example, as a smartwatch. This watch-type portable information terminal consists of a casing 7000, a display unit 7001, and an operating button. Tan 7022, 7023, connector 7024, band 7025, microphone 7026 It has a sensor 7029, a speaker 7030, etc. The display unit 7001 has a curved display surface. It is designed to display images along a curved surface. Furthermore, this portable information terminal... For example, hands-free calls are possible through mutual communication with a wireless headset. Yes. Furthermore, the connection terminal 7024 allows for mutual data transmission with other information terminals, It can also be charged. Charging can be done via wireless power transfer.

[0239] The display unit 7001, mounted on the housing 7000 which also serves as the bezel, has a non-rectangular display area. It has. The display unit 7001 has an icon 7027 that represents the time, and other icons 702 It can display numbers such as 8. Furthermore, the display unit 7001 is equipped with a touch sensor (input device). It may also be a touch panel (input / output device).

[0240] Furthermore, the smartwatch shown in Figure 4(G) can have a variety of functions. For example, , a function to display various information (still images, videos, text images, etc.) on the display unit, touch panel Features include a calendar, a function to display the date or time, and various software (programs). Functions that control processing by (M), wireless communication function, and various computers using wireless communication function It has the function of connecting to a data network and transmitting or receiving various types of data using wireless communication. The function to be performed is to read the program or data recorded on the recording medium and display it on the display unit. It can have functions such as [specific functions].

[0241] Furthermore, the 7000 housing contains a speaker and sensors (force, displacement, position, velocity, acceleration, angular velocity). Degrees, rotation speed, distance, light, liquid, magnetism, temperature, chemical substances, sound, time, hardness, electric field, electric current, electricity Includes functions for measuring pressure, power, radiation, flow rate, humidity, gradient, vibration, odor, or infrared radiation. It may have a microphone, etc.

[0242] Furthermore, a light-emitting device according to one aspect of the present invention and a display having a light-emitting element according to one aspect of the present invention The device can be used in each display unit of the electronic device shown in this embodiment, and is a long-life electronic device. This can be achieved.

[0243] Furthermore, as an electronic device to which a light-emitting device is applied, the foldable device shown in Figures 5(A) to (C) A portable information terminal that can be used is shown. Figure 5(A) shows a portable information terminal 93 in its unfolded state. Figure 10 is shown. Also, Figure 5(B) shows the unfolded state and the folded state from one to the other. Figure 5(C) shows the mobile information terminal 9310 in an intermediate state of transformation. Furthermore, Figure 5(C) shows the folded The image shows the folded state of the personal digital assistant (PDA) 9310. It offers excellent portability, and when unfolded, the seamless, wide display area provides a clear overview of the information displayed. To be excellent.

[0244] The display unit 9311 is supported by three housings 9315 connected by hinges 9313. The display unit 9311 is a touch panel (input / output) equipped with a touch sensor (input device). It may also be a force device. In addition, the display unit 9311 is connected to the two housings via the hinge 9313. By bending the 9315, the mobile information terminal 9310 can be folded from its unfolded state. It can be reversibly deformed into a fixed state. Furthermore, the light-emitting device according to one aspect of the present invention is a display It can be used in part 9311. Furthermore, it enables the realization of long-life electronic devices. Display unit 931 The display area 9312 in 1 is located on the side of the folded portable information terminal 9310. This is the display area. Display area 9312 contains information icons and frequently used apps and programs. It can display shortcuts to Gram, allowing you to check information and launch apps. It can be done smoothly.

[0245] Furthermore, Figures 6(A) and 6(B) show automobiles to which light-emitting devices are applied. The unit can be installed as an integral part of the vehicle. Specifically, as shown in Figure 6(A) of the vehicle... Exterior lights 5101 (including rear of the vehicle), tire wheels 5102, doors 5103 It can be applied to part or the whole. Also, the interior of the automobile shown in Figure 6(B) Display unit 5104, steering wheel 5105, shift lever 5106, seat 5107, inner - Can be applied to rearview mirrors 5108, etc. Also applicable to parts of glass windows. You may do so.

[0246] As described above, electronic devices and automatic devices to which a light-emitting device or display device according to one aspect of the present invention is applied. A car can be obtained. Furthermore, in that case, long-lasting electronic devices can be realized. The electronic devices and automobiles that can be used are not limited to those shown in this embodiment, but can be used in any field. It is possible to apply it.

[0247] The configuration shown in this embodiment may be used in appropriate combination with the configurations shown in other embodiments. It is possible.

[0248] (Embodiment 6) In this embodiment, a light-emitting device, or a light-emitting element that is a part thereof, which is an embodiment of the present invention, is used The configuration of the lighting device manufactured using this method will be explained with reference to Figure 7.

[0249] Figures 7(A) and 7(B) show an example of a cross-sectional view of a lighting device. Note that Figure 7(A) shows the light on the substrate side. This is a bottom-emission type lighting device that extracts light from the sealed substrate side, and Figure 7(B) shows that the light is extracted from the sealed substrate side. It is a top-emission type lighting device.

[0250] The lighting device 4000 shown in Figure 7(A) has a light-emitting element 4002 on a substrate 4001. Furthermore, the substrate 4003 has irregularities on the outside of the substrate 4001. The light-emitting element 4002 is It has one electrode 4004, an EL layer 4005, and a second electrode 4006.

[0251] The first electrode 4004 is electrically connected to electrode 4007, and the second electrode 4006 is connected to electrode 4 It is electrically connected to 008. It is also an auxiliary wiring that is electrically connected to the first electrode 4004. 4009 may be provided. Furthermore, an insulating layer 4010 is formed on the auxiliary wiring 4009. Yes, they are.

[0252] Furthermore, substrate 4001 and encapsulating substrate 4011 are bonded together with sealing material 4012. A desiccant 4013 is provided between the sealing substrate 4011 and the light-emitting element 4002. Preferred. Note that the substrate 4003 has irregularities as shown in Figure 7(A), so the light-emitting element 40 This can improve the efficiency of extracting the light generated in step 02.

[0253] The lighting device 4200 in Figure 7(B) has a light-emitting element 4202 on a substrate 4201. Sub-electrode 4202 has a first electrode 4204, an EL layer 4205, and a second electrode 4206. .

[0254] The first electrode 4204 is electrically connected to electrode 4207, and the second electrode 4206 is connected to electrode 4 It is electrically connected to 208. Also, auxiliary wiring 4 is electrically connected to the second electrode 4206. 209 may be provided. Also, an insulating layer 4210 may be provided below the auxiliary wiring 4209. stomach.

[0255] The substrate 4201 and the uneven sealing substrate 4211 are bonded together with a sealing material 4212. Furthermore, a barrier film 4213 and a planarization film 421 are placed between the sealing substrate 4211 and the light-emitting element 4202. 4 may be provided. Note that the sealing substrate 4211 has irregularities as shown in Figure 7(B), This improves the efficiency of extracting light generated by the light-emitting element 4202.

[0256] Furthermore, an example of the application of these lighting devices is ceiling lights used for indoor lighting. Ceiling lights come in various types, such as surface-mounted and recessed. A lighting device is constructed by combining a light-emitting device with a housing or cover.

[0257] Other applications include footlights that illuminate the floor surface to enhance safety underfoot. It is also possible. Footlights are effective for use in places such as bedrooms, stairwells, and hallways. In this case, the size and shape can be changed as appropriate depending on the size and structure of the room. It is also possible to create a stationary lighting device by combining the device and a support base. .

[0258] Furthermore, it can also be applied as a sheet-shaped lighting device (sheet-shaped lighting). Because the lighting fixtures are mounted on the wall, they don't take up much space and can be used for a wide range of applications. Furthermore, it can be easily scaled up to cover a large area. It can also be used on curved walls and enclosures.

[0259] In addition to the above, a light-emitting device according to one aspect of the present invention may be installed in some of the furniture in the room, By applying a light-emitting element, which is part of it, it can be made into a lighting device that also functions as furniture. Cut.

[0260] As described above, various lighting devices can be obtained by applying light-emitting devices. This is included in one aspect of the present invention.

[0261] Furthermore, the configuration shown in this embodiment can be used in appropriate combination with the configurations shown in other embodiments. It is possible. [Examples]

[0262] <<Synthesis Example 1>> In this embodiment, an organic compound represented by structural formula (100) of Embodiment 1 is used. Compound, 13-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f,h][ 1) Synthesis of benzoflo[2,3-b]quinoxaline (abbreviation: 13mDBtPBfdbq) The method will be explained below. The structure of 13mDBtPBfdbq is shown below.

[0263] [ka]

[0264] <Step 1: 1,4-dihydrophenanthr[9,10-b]pyrazine-2,3 Synthesis of n> Phenanthrene-9,10-diamine hydrochloride 5.97g and sodium bicarbonate 16.5g g, 230 mL of diethyl oxalate, is placed in a three-necked flask fitted with a reflux condenser, and the inside is filled with nitrogen. It was changed. Then, the reaction was carried out by stirring at 130°C for 23 hours. After the predetermined time had elapsed, Add 1 liter of water and stir at room temperature for 30 minutes. Then, the resulting mixture was filtered by suction and ethanol was removed. By washing with a solvent, the desired pyrazine derivative was obtained (yellowish-brown powder, yield 3.91g). , yield 61%). The synthesis scheme for Step 1 is shown in the following formula (a-1).

[0265] [ka]

[0266] <Step 2: Synthesis of 2,3-dichlorodibenzo[f,h]quinoxaline> Next, we obtain 1,4-dihydrophenanthr[9,10-b]pyrazine obtained in step 1 above. Place 3.91 g of -2,3-dione and 60 mL of anhydrous DMF into a three-necked flask fitted with a reflux tubing. Then, the inside was purged with nitrogen. After cooling the flask with ice, 5.4 mL of phosphoryl chloride was added, and 1 The mixture was stirred at 0°C for 7.5 hours. After the predetermined time had elapsed, the resulting mixture was heated with 1M sodium hydroxide solution. After pouring into 130 mL of solution, it was filtered by suction. The resulting solid was then washed with water and ethanol. It was dissolved in toluene and filtered through Celite. The resulting filtrate was concentrated to obtain The desired quinoxaline derivative was obtained (yellowish-white powder, yield 1.00 g, yield 22%). The synthesis scheme for P2 is shown in the following equation (a-2).

[0267] [ka]

[0268] <Step 3: 2-chloro-3-(5-chloro-2-methoxyphenyl)quinoxaline Synthesis> Next, the 2,3-dichlorodibenzo[f,h]quinoxaline 1.8 obtained in step 2 above. 5g, 5-chloro-2-methoxyphenylboronic acid 1.16g, sodium carbonate 0.66g g, ethylene glycol dimethyl ether (abbreviation: DME) 27 mL, water 27 mL, The mixture was placed in a three-necked flask fitted with a flow tube, and the inside was purged with nitrogen. The contents of the flask were then stirred under reduced pressure. After degassing, tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(P) Add 0.48g of pH3)4) and stir at 100°C for 20.5 hours to allow the reaction to proceed. Afterward, water is added, and the solid obtained by suction filtration is dissolved in dichloromethane and filtered. The filtrate was then concentrated. The resulting solid was then used as the developing solvent in a toluene:hexane = 1:2 mixture. The desired quinoxaline derivative was obtained by purification using silica gel column chromatography. White powder, yield 1.86 g, yield 74%. The synthesis scheme for Step 3 is shown in formula (a-3) below. ) is shown.

[0269] [ka]

[0270] Step 4: 2-Chloro-3-(5-Chloro-2-hydroxyphenyl)quinoxaline Synthesis of > Next, the 2-chloro-3-(5-chloro-2-methoxyphenyl) obtained in step 3 above Place 2.56 g of quinoxaline and 70 mL of anhydrous dichloromethane into a three-necked flask and nitrate the inside. Sublimation was performed. After cooling the flask to -20°C, boron tribromide (1M dichloromethane solution) was added. ) 13 mL was added dropwise and stirred at room temperature for 16 hours. After the specified time had elapsed, water was added and dichloromethyl Extraction was performed using tung. The solid obtained by this procedure was then treated with dichloromethane as the developing solvent. The desired quinoxaline derivative was obtained by purification using silica gel column chromatography. (Yellow powder, yield 2.12g, yield 84%). The synthesis scheme for step 4 is given by the following formula (a As shown in -4).

[0271] [ka]

[0272] <Step 5: 13-Chlorodibenzo[f,h][1]benzofloxacin[2,3-b]quini Sarin synthesis > Next, the 2-chloro-3-(5-chloro-2-hydroxyphenyl) obtained in step 4 above 2.12 g of quinoxaline and 27 mL of anhydrous N-methyl-2-pyrrolidone (abbreviation: NMP) Then, it was placed in a three-necked flask fitted with a reflux condenser, and the inside was purged with nitrogen. 1.5g of potassium carbonate was added to it. After adding 1g, the mixture was stirred at 120°C for 8 hours. After the specified time had elapsed, water was added, and the resulting mixture was... The material was filtered by suction. The resulting solid was washed with ethanol to obtain the desired Kinokisari. A derivative was obtained (pale yellow powder, yield 1.56 g, yield 84%). Step 5 Synthesizing ski The value of 'Mu' is shown in the following formula (a-5).

[0273] [ka]

[0274] <Step 6: 13-[3-(dibenzothiophen-4-yl)phenyl]dibenzo[f [1]Benzoflo[2,3-b]quinoxaline (abbreviation: 13mDBtPBfdbq) ) synthesis > Furthermore, the 13-chlorodibenzo[f,h][1]benzofl[2, obtained in step 5 above 3-b]Quinoxaline 0.78g, (dibenzothiophen-4-yl)phenyl-3-b 1.10 g of chloric acid, 1.26 g of cesium fluoride, and 44 mL of mesitylene were added to a reflux tubing. The contents were placed in a three-necked flask and the inside was purged with nitrogen. The contents of the flask were then agitated under reduced pressure to remove air. Afterwards, Tris(dibenzylideneacetone)dipalladium(0) (abbreviation: Pd2(dba)) 3) 0.075g, 2'-(dicyclohexylphosphino)acetophenone ethylene ketase 0.059g of the compound was added and stirred at 120°C for 17 and a half hours. After the predetermined time had elapsed, the resulting mixture was... Ethanol was added to the mixture and filtered by suction, then washed with water and ethanol. The resulting solid was then treated with a suction filter. The material is dissolved in ene and filtered through a filtration aid consisting of layers of Celite, alumina, and Celite in that order. After concentrating and drying, the target product was obtained by recrystallizing with toluene (yellowish-white powder, yield). 0.71 g, yield 56%. 0.70 g of the obtained yellowish-white powder was subjected to train sublimation. The substance was purified by sublimation using the argon method. The sublimation purification conditions were: pressure 2.7 Pa, argon gas flow rate 10. The solid was heated at 330°C while flowing 5 mL / min. After sublimation purification, the target product was yellowish-white. The solid was obtained in a yield of 0.56 g and 80%. The synthesis scheme for Step 6 is shown in the following formula (a-6 ) is shown.

[0275] [ka]

[0276] Nuclear magnetic resonance spectroscopy of the yellowish-white solid obtained in step 6 above ( 1 Analysis results by H-NMR The results are shown below. Also, 1 The H-NMR chart is shown in Figure 8. From these results, it can be concluded that in this example... In this context, an organic compound, 13mD, which is one embodiment of the present invention represented by the above-mentioned structural formula (100), is used. It was found that BtPBfdbq was obtained.

[0277] 1 H-NMR.δ(CDCl3):7.49-7.51(m,2H),7.63-7.6 4(m,2H),7.71(t,1H),7.80-7.89(m,8H),8.06( d,1H),8.16(s,1H),8.22-8.25(m,2H),8.70-8. 74(m,3H),9.36(d,1H),9.49-9.51(m,1H).

[0278] Next, the ultraviolet-visible absorption spectrum of a toluene solution of 13 mDBtPBfdbq and a solid thin film was measured. The absorption spectrum (hereinafter simply referred to as the "absorption spectrum") and emission spectrum were measured.

[0279] For measuring the absorption spectrum in a toluene solution, use a UV-Vis spectrophotometer (manufactured by JASCO Corporation). A V550 model was used. A fluorometer was also used to measure the emission spectrum in the toluene solution. (FS920, manufactured by Hamamatsu Photonics Ltd.) was used. The absorption spectrum of the obtained toluene solution was measured. The measurement results for the tor and emission spectra are shown in Figure 9(A). The horizontal axis represents wavelength, and the vertical axis represents absorption intensity. And it represents the luminescence intensity.

[0280] From the results in Figure 9(A), in a toluene solution of 13 mDBtPBfdbq, approximately 281 nm An absorption peak is observed around 397 nm, and emission occurs around 405 nm (excitation wavelength 372 nm). A peak in wavelength was observed.

[0281] For measuring the absorption spectrum of solid thin films, solid thin films fabricated by vacuum deposition on a quartz substrate are used. The measurements were taken using a UV-Vis spectrophotometer (Hitachi High-Technologies U4100 model). Furthermore, to measure the emission spectrum of a solid thin film, the same solid thin film as described above was used, and the fluorescence spectroscopy was measured. The absorption of the obtained solid thin film was measured using a meter (FS920, Hamamatsu Photonics Ltd.). The measurement results of the spectrum and emission spectrum are shown in Figure 9(B). The horizontal axis represents wavelength, and the vertical axis represents absorption. This represents the intensity of light and the intensity of light emission.

[0282] From the results in Figure 9(B), in the solid thin film of 13mDBtPBfdbq, 383nm and 40 An absorption peak is observed around 3 nm, and an emission wavelength is observed around 511 nm (excitation wavelength 380 nm). A peak was observed.

[0283] In addition, differential scanning calorimetry was performed on 13mDBtPBfdbq. A constant measurement device (Pyris 1, manufactured by PerkinElmer Japan Co., Ltd.) was used. Measurements were performed as follows: The temperature was increased from 10°C to 350°C at a rate of 40°C / min, and then it was heated to 350°C for 1 minute. Hold the temperature for a while, then cool it down from 350°C to -10°C at a rate of 100°C / min. This constituted one cycle. In this embodiment, measurements were taken over three cycles. Based on the results from the heating cycle in the second cycle, the glass transition temperature (Tg) is 141°C. This was found. Therefore, the 13mDBtPBfdbq synthesized in this example is extremely heat resistant. It was found to be a material with excellent properties. [Examples]

[0284] In this embodiment, as a light-emitting element according to one aspect of the present invention, the 13-[3- (dibenzothiophen-4-yl)phenyl]dibenzo[f,h][1]benzofl[2 [3-b]Quinoxaline (abbreviation: 13mDBtPBfdbq) (structural formula (100)) The light-emitting element 1 used in the optical layer, and 2-[3-(3'-gibe] as a light-emitting element for comparison, [Nzothiophen-4-yl]biphenyl]dibenzo[f,h]quinoxaline (abbreviation: 2m Regarding the comparative light-emitting element 2 using DBTBPDBq-II (structural formula (200)) as the light-emitting layer... Next, the element structure, manufacturing method, and characteristics will be described. The element structure of the element is shown in Figure 10, and the specific configuration is shown in Table 1. Furthermore, the element used in this embodiment The chemical formulas of the materials are shown below.

[0285] [Table 1]

[0286] [ka]

[0287] <<Fabrication of light-emitting elements>> The light-emitting element shown in this embodiment has a first electrode 9 formed on a substrate 900 as shown in Figure 10. On top of 01 are a hole injection layer 911, a hole transport layer 912, an emissive layer 913, an electron transport layer 914, and an electron The structure is such that injection layers 915 are sequentially stacked, and a second electrode 903 is stacked on top of the electron injection layer 915. It holds.

[0288] First, a first electrode 901 was formed on the substrate 900. The electrode area was 4 mm². 2 (2mm x 2 The thickness was set to mm. A glass substrate was used for the substrate 900. The first electrode 901 was Indium tin oxide (ITSO) containing silicon dioxide is sputtered to 70 nm It was formed by depositing a film with the specified thickness.

[0289] Here, as a pretreatment, the surface of the substrate is washed with water, then fired at 200°C for 1 hour, followed by UV spectroscopy. The zoning process was performed for 370 seconds. After that, 10 -4 Vacuum deposition equipment with internal pressure reduced to approximately Pa The substrate is placed in the vacuum deposition apparatus and vacuum firing is performed at 170°C for 30 minutes in the heating chamber of the vacuum deposition apparatus. Afterward, I let the circuit board cool for about 30 minutes.

[0290] Next, a hole injection layer 911 was formed on the first electrode 901. The hole injection layer 911 was formed using vacuum vapor 1 × 10 inside the attachment device -4 After reducing the pressure to Pa, 4,4',4''-(benzene-1,3,5 -Triyl)tri(dibenzothiophene) (abbreviation: DBT3P-II) and molybdenum oxide The ratio of DBT3P-II to molybdenum oxide is 2:1 (mass ratio), and the film thickness is 70 nm. It was formed by co-depositing in this manner.

[0291] Next, a hole transport layer 912 was formed on the hole injection layer 911. The hole transport layer 912 consisted of 4,4 '-Diphenyl-4''-(9-phenyl-9H-carbazole-3-yl)triphenyl Luamine (abbreviated as PCBBi1BP) is used and deposited to form a film thickness of 20 nm. did.

[0292] Next, a light-emitting layer 913 was formed on the hole transport layer 912.

[0293] In the case of the light-emitting element 1, the light-emitting layer 913 is an organic compound according to one aspect of the present invention as a host material. Using material 13mDBtPBfdbq, PCBBiF as assist material, guest material ( As a phosphorescent material, bis[4,6-dimethyl-2-(2-quinolinyl-κN)phenyl- κC](2,4-pentanedionato-κ 2 O,O') Iridium(III) (Abbreviation: [I Using r(dmpqn)2(acac)]), the weight ratio is 13mDBtPBfdbq:PC BBiF:[Ir(dmpqn)2(acac)]=0.75:0.25:0.1 The coating was co-deposited as shown. The film thickness was set to 40 nm.

[0294] In the case of comparative light-emitting element 2, the light-emitting layer 913 uses 2mDBTBPDBq-I as the host material. Using I, PCBBiF is used as the assisting material, and [Ir(d) is used as the guest material (phosphorescent material). Using mpqn)2(acac)], the weight ratio is 2mDBTBPDBq-II:PCBBi F:[Ir(dmpqn)2(acac)]=0.75:0.25:0.1 Co-deposition was performed. The film thickness was set to 40 nm.

[0295] Next, an electron transport layer 914 was formed on the light-emitting layer 913. The electron transport layer 914 is 9-[3- (4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl The film thickness of ru-2,3'-bi-9H-carbazole (abbreviation: mPCCzPTzn-02) is 3 0 nm, 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenyl Nanthroline (abbreviated as NBphen) is sequentially deposited to form a film thickness of 15 nm. Ta.

[0296] Next, an electron injection layer 915 was formed on the electron transport layer 914. The electron injection layer 915 is fluorinated It was formed by depositing lithium (LiF) to a film thickness of 1 nm.

[0297] Next, a second electrode 903 was formed on the electron injection layer 915. The second electrode 903 was made of aluminum. A layer of nium was formed by vapor deposition to a thickness of 200 nm. The second electrode 903 functions as the cathode.

[0298] Through the above process, a light-emitting element is formed on the substrate 900, with an EL layer sandwiched between a pair of electrodes. Furthermore, the hole injection layer 911, hole transport layer 912, light-emitting layer 913, and electric field described in the above process are also used. The child transport layer 914 and the electron injection layer 915 are functional layers constituting the EL layer in one aspect of the present invention. Furthermore, in the deposition process of the above-described manufacturing method, the deposition method is entirely performed using the resistance heating method. Used.

[0299] Furthermore, the light-emitting element fabricated as described above is sealed with another substrate (not shown). When sealing using a different substrate (not shown), place it in a glove box under a nitrogen atmosphere. Next, another substrate (not shown) coated with a sealant that hardens when exposed to ultraviolet light is placed on substrate 900. The substrates are fixed in place so that the sealant adheres to the area around the light-emitting element formed on the substrate 900. The parts were bonded together. During sealing, 365nm ultraviolet light was applied at 6 J / cm². 2 Irradiate to solidify the sealant, The sealant was stabilized by heat treatment at 80°C for 1 hour.

[0300] <<Operating characteristics of light-emitting elements>> The operating characteristics of each fabricated light-emitting element were measured. The measurements were taken at room temperature (maintained at 25°C). The experiment was conducted based on the atmosphere. The results are shown in Figures 11 to 14.

[0301] Table 2 below shows 1000 cd / m² 2 The main initial characteristic values ​​of each light-emitting element in the vicinity are shown.

[0302] [Table 2]

[0303] Furthermore, in the results above, the light-emitting element 1 fabricated in this embodiment is better than the comparative light-emitting element 2. It can be seen that it exhibits good current-voltage characteristics. This indicates that the light-emitting layer of the light-emitting element 1 is used In one aspect of the present invention, 13mDBtPBfdbq is fused with an oxygen-containing five-membered ring. This can be attributed to the deep LUMO levels resulting from the structure. Reduction potential measurement by luminometry (CV) revealed that LU of 2mDBTBPDBq-II The MO level is -2.94eV, while the LUMO level of 13mDBtPBfdbq The voltage was -3.17 eV.

[0304] Furthermore, 2.5 mA / cm² is supplied to both light-emitting element 1 and comparison light-emitting element 2. 2 A current was passed at the current density. The emission spectra at that time are shown in Figure 15. As shown in Figure 15, the light-emitting element 1 and the comparative light-emitting element The emission spectrum of sub-substrate 2 has a peak around 628 nm, and both are located in the emissive layer 913. This is due to the luminescence of the organometallic complex [Ir(dmpqn)2(acac)] contained within. This suggests that...

[0305] Next, reliability tests were performed on light-emitting element 1 and comparative light-emitting element 2. The results of the reliability tests were as follows: This is shown in Figure 16. In Figure 16, the vertical axis represents the normalized luminance (%) when the initial luminance is set to 100%. The graph shows the current density, with the horizontal axis representing the device's operating time (h). The reliability test was conducted with a current density of 75m. A / cm 2 The setting was changed, and the light-emitting element was driven.

[0306] Based on the reliability test results, light-emitting element 1 exhibits higher reliability compared to comparative light-emitting element 2. This was discovered. This is an organic compound, 13mDBtPBfdbq(composition), which is one embodiment of the present invention. This can be seen as an effect of using the formula (100)) in the light-emitting layer of the light-emitting element 1. In other words, 13mDBtPBfdbq is a dibenzoquinate as described in Embodiment 1. The sarin skeleton has a structure in which the 2nd and 3rd positions are condensed, and a five-membered ring containing oxygen is formed by ring fusion. Therefore, as shown in 2mDBTBPDBq-II (structural formula (200)), dibenzoquinoxali The substituted phenylene group at position 2 of the skeleton twists due to steric repulsion with the hydrogen at position 3. It has the characteristic of being absent and having improved molecular robustness and stability. Note that in Table 2... The fact that light-emitting element 1 showed better current-voltage characteristics than comparative light-emitting element 2 indicates that the light-emitting layer This suggests that the device structure has a narrow carrier recombination region, making it prone to localized degradation. However, as shown in Figure 16, reliability could be improved in one aspect of the present invention. In addition to having low steric hindrance, a certain organic compound exhibits good robustness. This can be understood as being due to having properties and stability. That is, in one aspect of the present invention A certain organic compound, when the driving voltage decreases, also suffers from reduced reliability, which is not ideal for light-emitting devices. It can be said that this material overcomes the trade-off phenomenon that is often encountered.

[0307] Furthermore, an organic compound, 13mDBtPBfdbq, which is one embodiment of the present invention, is the same as the molecule described above. This structure not only improves reliability, but also involves ring fusion with a five-membered ring containing oxygen. Having a structure minimizes the T1 level drop that becomes a problem when forming a polycyclic condensed molecular structure. This made it possible to suppress it to that extent. Specifically, the T1 level was observed at the liquid nitrogen temperature (77K). When determined to correspond to the short-wavelength peak of the phosphorescence spectrum, it was found to be 2mDBTBPDB While the T1 level of q-II is 515 nm, the T1 level of 13 mDBtPBfdbq This was suppressed to a long wavelength shift of approximately 20 nm, to 538 nm. Therefore, one aspect of the present invention The organic compound, 13mDBtPBfdbq (structural formula (100)), is used in the EL layer of the light-emitting element. Using this not only improves the reliability of the light-emitting element, but also maintains the T1 level to some extent. It can be said to be useful in that it allows you to do so. [Examples]

[0308] ≪Synthesis Example 2≫ In this embodiment, an organic compound represented by structural formula (101) of Embodiment 1 is used. Compound, 13-[3-(dibenzofuran-4-yl)phenyl]dibenzo[f,h][1] Synthesis method of benzoflo[2,3-b]quinoxaline (abbreviation: 13mDBfPBfdbq) This will be explained. The structure of 13mDBfPBfdbq is shown below.

[0309] [ka]

[0310] <Synthesis of 13mDBfPBfdbq> The 13mDBfPBfdbq shown in this example is the same as the 13mDBtPBfd described in Example 1. Similar to the synthesis method for bq, it is synthesized using the method shown in the synthesis scheme (b-1) below.

[0311] [ka]

[0312] Based on the above, an organic compound, 13mDBfPBfdbq, which is one aspect of the present invention, can be obtained. can. [Examples]

[0313] ≪Synthesis Example 3≫ In this embodiment, an organic compound represented by structural formula (102) of Embodiment 1 is used. Compound, 13-[3-(9H-carbazole-9-yl)phenyl]dibenzo[f,h][ 1) Synthesis method of benzoflo[2,3-b]quinoxaline (abbreviation: 13mCzPBfdbq) The law will be explained. The structure of 13mCzPBfdbq is shown below.

[0314] [ka]

[0315] <Synthesis of 13mCzPBfdbq> The 13mCzPBfdbq shown in this example is the same as the 13mDBtPBfdb described in Example 1. Similar to the method for synthesizing q, it is synthesized using the method shown in the synthesis scheme (c-1) below.

[0316] [ka]

[0317] Based on the above, an organic compound, 13mCzPBfdbq, which is one aspect of the present invention, can be obtained. Cut. [Examples]

[0318] <<Synthesis Example 4>> In this embodiment, an organic compound represented by structural formula (110) of Embodiment 1 is used. Compound, 13-[3-(triphenylene-2-yl)phenyl]dibenzo[f,h][1] The synthesis method for benzoflo[2,3-b]quinoxaline (abbreviation: 13mTpPBfdbq) I will explain this further. The structure of 13mTpPBfdbq is shown below.

[0319] [ka]

[0320] <Synthesis of 13mTpPBfdbq> The 13mTpPBfdbq shown in this example is the same as the 13mDBtPBfdb described in Example 1. Similar to the synthesis method for q, it is synthesized using the method shown in the synthesis scheme (d-1) below.

[0321] [ka]

[0322] Based on the above, an organic compound, 13mTpPBfdbq, which is one embodiment of the present invention, can be obtained. Cut. [Examples]

[0323] ≪Synthesis Example 5≫ In this embodiment, an organic compound represented by structural formula (123) of Embodiment 1 is used. Compound, 13-[3-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl) [Phenyl]dibenzo[f,h][1]benzoflof[2,3-b]quinoxaline (abbreviation: 1 The synthesis method for 3mPCCzPBfdbq) will be explained. Note that 13mPCCzPBf The structure of dbq is shown below.

[0324] [ka]

[0325] <Synthesis of 13mPCCzPBfdbq> The 13mPCCzPBfdbq shown in this example is the same as the 13mDBtPBf described in Example 1. Similar to the synthesis method for dbq, the synthesis is performed using the method shown in the synthesis scheme (e-1) below.

[0326] [ka]

[0327] Based on the above, we obtain an organic compound, 13mPCCzPBfdbq, which is one embodiment of the present invention. It is possible. [Examples]

[0328] ≪Synthesis Example 6≫ In this embodiment, an organic compound represented by structural formula (125) of Embodiment 1 is used. Compound, 13-(9'-phenyl-3,3'-bi-9H-carbazole-9-yl)diben Zo[f,h][1]benzofl[2,3-b]quinoxaline (abbreviation: 13PCCzBfd) The synthesis method for bq) will be explained. The structure of 13PCCzBfdbq is shown below. .

[0329] [ka]

[0330] <Synthesis of 13PCCzBfdbq> The 13-chlorodibenzo[f,h][1]benzofl[2, 3-b]Quinoxaline 0.78g, 9'-phenyl-3,3'-bi-9H-carbazole Place 0.90 g of mesitylene and 22 mL of mesitylene into a three-necked flask fitted with a reflux condenser, and fill the inside with nitrogen. The mixture was changed. After degassing by stirring the flask under reduced pressure, sodium tert-butoxy was added. 0.42g of bis(dibenzylideneacetone)palladium(0) (abbreviation: Pd(db) a)2) 0.013g, 2-dicyclohexylphosphino-2',6'-dimethoxybiph 0.018g of phenyl (abbreviated as S-Phos) was added and the mixture was stirred at 150°C for 13 hours.

[0331] After a predetermined time has elapsed, ethanol is added to the resulting mixture and filtered by suction, then washed with water and ethanol. The sample was purified. The resulting solid was subjected to silica gel column chromatography using toluene as the developing solvent. After purification by -, the target product was obtained by recrystallization with toluene (yellow solid, yield) 0.56 g, yield 35%). The synthesis scheme of the synthesis method shown in this example is given by the following formula (f-1) This will be shown.

[0332] [ka]

[0333] Furthermore, nuclear magnetic resonance spectroscopy of the yellow solid obtained above (1 The results of the analysis using H-NMR are shown below. As shown below. Also, 1 The H-NMR chart is shown in Figure 17. From these results, it can be seen that in this example... Therefore, an organic compound, 13PCCz, which is one embodiment of the present invention represented by the above-mentioned structural formula (125), It was found that Bfdbq was obtained.

[0334] 1 H-NMR.δ(CDCl3):7.33(t,1H),7.39(t,1H),7. 45-7.56(m,6H),7.62-7.69(m,5H),7.79-7.90( m,6H),7.95(d,1H),8.06(d,1H),8.27(d,1H),8 .32(d,1H),8.56(d,2H),8.70-8.76(m,3H),9.3 6(d,1H), 9.44(d,1H). [Explanation of Symbols]

[0335] 101 First electrode 102 Second electrode 103 EL layer 103a, 103b EL layer 104 Charge generation layer 111, 111a, 111b Hole injection layer 112, 112a, 112b Hole transport layer 113, 113a, 113b Emitting layer 114, 114a, 114b electron transport layer 115, 115a, 115b electron injection layer 200R, 200G, 200B optical distance 201 First substrate 202 Transistors (FETs) 203R, 203G, 203B, 203W Light-emitting element 204 EL layer 205 Second substrate 206R, 206G, 206B color filters 206R', 206G', 206B' color filters 207 First electrode 208 Second electrode 209 Black Matrix 210R, 210G conductive layer 301 First substrate 302 pixel section 303 Drive circuit section (source line drive circuit) 304a, 304b Drive circuit section (gate line drive circuit) 305 sealant 306 Second substrate 307 Wiring 308 FPC 309 FET 310 FET 311 FET 312 FET 313 First electrode 314 Insulators 315 EL layer 316 Second electrode 317 Light-emitting element 318 Space 900 circuit boards 901 First electrode 902 EL layer 903 Second electrode 911 Hole injection layer 912 Hole transport layer 913 Emitting layer 914 Electron transport layer 915 Electron injection layer 4000 Lighting devices 4001 circuit board 4002 Light-emitting element 4003 circuit board 4004 First electrode 4005 EL layer 4006 Second electrode 4007 Electrode 4008 Electrode 4009 Auxiliary wiring 4010 Insulating layer 4011 Sealing substrate 4012 Sealant 4013 Desiccant 4015 Diffuser 4200 Lighting equipment 4201 circuit board 4202 Light-emitting element 4204 First electrode 4205 EL layer 4206 Second electrode 4207 Electrode 4208 Electrode 4209 Auxiliary wiring 4210 Insulating layer 4211 Sealing substrate 4212 Sealant 4213 Barrier film 4214 Planarization film 4215 Diffuser 5101 Light 5102 Wheel 5103 Door 5104 Display section 5105 Handle 5106 Shift lever 5107 Seat 5108 Inner Rearview Mirror 7000 cabinets 7001 Display section 7002 2nd display section 7003 Speaker 7004 LED Lamp 7005 Operation Keys 7006 Connection terminal 7007 Recovery 7008 Microphone 7009 Switch 7010 Infrared Port 7011 Recording medium reading unit 7012 Support part 7013 Earphones 7014 Antenna 7015 Shutter button 7016 Image receiving unit 7018 Stand 7020 Camera 7021 External connection section 7022, 7023 Operation Buttons 7024 Connection terminal 7025 band, 7026 Microphone 7027 Icon representing the time 7028 Other icons 7029 Sensor 7030 speaker Information 7052, 7053, 7054 9310 Mobile Information Terminal 9311 Display section 9312 Display area 9313 Hinge 9315 enclosure

Claims

1. A light-emitting element having an organic compound represented by general formula (G1) between a pair of electrodes. 【Chemistry 1】 (In the formula, Q represents O, and R １ ~R １２ At least one of the groups is a first group having a substituted or unsubstituted condensed aromatic ring with 3 to 30 carbon atoms forming a ring, or a substituted or unsubstituted condensed heteroaromatic ring with 3 to 30 carbon atoms forming a ring, and the others each independently represent hydrogen, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a group with 1 to 50 carbon atoms.

2. A light-emitting element having an organic compound represented by general formula (G1) between a pair of electrodes. 【Chemistry 2】 (In the formula, Q represents O, and R １ ~R １２ At least one of the components is a first group having one of the following skeletons: fluorene, phenanthrene, triphenylene, naphthalene, dibenzothiophene, dibenzofuran, or carbazole; the others each independently represent one of the following: hydrogen, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.

3. In claim 1 or claim 2, A light-emitting element having a total carbon number of 3 to 100 in the first group.

4. A light-emitting element having an organic compound represented by general formula (G1) between a pair of electrodes. 【Transformation 3】 (In the formula, Q represents O, and R １ ~R １２ At least one of the groups is a first group to which a structure represented by any one of the following general formulas (A-1) to (A-21) is bonded via a substituted or unsubstituted arylene group having 6 to 24 carbon atoms forming a ring, or a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms forming a ring, while the others independently represent hydrogen, a halogeno group, a hydroxyl group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms. 【Chemistry 4】 (In the formula, Q' represents O or S, and R １３ ~R ２４ Each of these independently represents one of the following: hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

5. A light-emitting element having an organic compound represented by general formula (G1) between a pair of electrodes. 【Transformation 5】 (wherein Q represents O, R １ to R １２ at least one of which is a first group represented by any one of the following general formulas (A-1) to (A-21), and the others each independently represent any one of hydrogen, a halogeno group, a hydroxy group, an amino group, a nitro group, or a group having 1 to 50 carbon atoms.) 【Transformation 6】 (In the formula, Q' represents O or S, and R １３ ~R ２４ Each of these independently represents one of the following: hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 7 carbon atoms forming a ring, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

6. In any one of claims 1 to 5, R ３ This is the first light-emitting element.

7. A light-emitting element according to any one of claims 1 to 6, A transistor or at least one substrate, A light-emitting device having the following features.

8. The light-emitting device according to claim 7, At least one of the following: microphone, camera, control buttons, external connection port, or speaker, A powerful electronic device.

9. The light-emitting device according to claim 7, At least one of the housing, cover, or support base, A lighting device having the following features.

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