Organic electroluminescent elements and compounds

Abstract

To provide an organic electroluminescent element with excellent durability. [Solution] The anode, cathode, and at least one layer of organic matter between the anode and cathode are provided. In an organic electroluminescent element, one of the organic layers comprises three or more types. The luminescent material contains compounds, and each of the two or more of these compounds has a deuterium atom. Structure it as layers.

Description

[Technical Field]

[0001] This invention relates to organic electroluminescent elements and compounds. [Background technology]

[0002] Research and development of materials for use in organic electroluminescent devices is actively underway. In addition, the host and dopant used in the light-emitting layer that constitutes the organic electroluminescent element There are various attempts to improve the characteristics of the elements by developing and combining new components. It has been done in various ways.

[0003] Regarding the host used in the light-emitting layer, those having structures such as the following have been useful to date. It is known as a compound. [ka]

[0004] Regarding dopants used in the light-emitting layer, those having the following structures, for example, have been used so far. It is known as a useful compound (see, for example, Patent Document 1). [ka] [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] WO2022 / 270354 [Overview of the project] [Problems that the invention aims to solve]

[0006] However, the proposed organic electroluminescent elements have improved durability. There is room for improvement. Therefore, to provide organic electroluminescent elements with superior durability... The inventors conducted studies with the objective of achieving this. [Means for solving the problem]

[0007] As a result of diligent research, the inventors have found that the compound contained in the light-emitting layer satisfies certain conditions. By doing so, the durability of organic electroluminescent elements can be improved. We have found that the present invention is based on these findings and specifically follows It has a structure. [1] Having an anode, a cathode, and at least one organic layer between the anode and the cathode An organic electroluminescent element, One of the organic layers consists of three or more compounds, and two or more of these compounds An organic electroluminescent element in which each light-emitting layer contains a deuterium atom. [2] Each of the three or more compounds constituting the light-emitting layer has a deuterium atom, The organic electroluminescent element described in [1]. [3] The organic electroluminescent layer comprising three compounds as described in [1] or [2] Lorluminescence element. [4] The organic electroluminescent layer comprising four compounds as described in [1] or [2] Lorluminescence element. [5] None of the three or more compounds constituting the light-emitting layer contain heavy metal elements. An organic electroluminescent element as described in any one of [1] to [4]. [6] The light-emitting layer comprises at least one host and at least one assist dopant It includes the at least one host and the at least one assist dopant. An organic electroluminescence device according to any one of [1] to [5], wherein each of the tos has a deuterium atom. Troluminescent element. [7] The light-emitting layer contains at least one host, at least one assist dopant, and at least one dopant, wherein each of the at least one host, the at least one assist dopant, and the at least one dopant has a deuterium atom, and the organic electroluminescence device according to any one of [1] to [6]. [8] The organic electroluminescence device according to any one of [1] to 7], wherein the light-emitting layer contains at least one dopant having a boron atom. [9] The organic electroluminescence device according to [8], wherein the dopant is a compound represented by the following general formula (1). General formula (1) [Chemical formula] [In general formula (1), R and R 2 each independently represents a hydrogen atom, a deuterium atom or a substituent. R 3 to R 26 each independently represents a hydrogen atom, a deuterium atom or a substituent, or other R 3 to R 26 are bonded to each other to form a cyclic structure. Among R 3 to R 26 , the combinations that can form a cyclic structure are R and R 3 , R 4 and R 4 , R 5 and R 5 , R <​​​​​​​​​​​9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 However, R 1 ~R 26 At least one of them contains a deuterium atom.

[10] The light-emitting layer includes a host represented by the following general formula (2) or the following general formula (3) The organic electroluminescent element described in any one of [1] to [9]. General formula (2) [ka] [In general formulas (2) and (3), R 31 ~R 41 and R 51 ~R 61 teeth, Each independently consists of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or R represents an unsubstituted alkyl group. 42 ~R 49 Each is independently a hydrogen atom, a deuterium atom, and Represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group, or other R 42 ~R 49 are combined with each other to form a cyclic structure. R 42 ~R 49 Among them, the combinations that can form a cyclic structure are R and R 42 R 43 and R 43 R 44 and R 44 R 45 and R 4 6 and R 47 R and R 47 R 48 and R 48 R 49 and R 62 R 69 ~R 62 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted al kyl group, or are combined with other R ~R 69 to form a cyclic structure. R 6 2 69 Among them, the combinations that can form a cyclic structure are R 62 and R 63 63 R 64 and R 64 65 R 66 and R 67 R 67 and R 68 68 R 69 and R 31 49 R 51 and R 69 42 R 43 and R 43 44 R 31 ~R 49 At least one of them contains a deuterium atom, and at least one of R 51 ~R 69 contains a deuterium atom.]

[11] R and R 42 R [[ID=9*]] 43 and R 43 R 44 and R <0*000101> R 45 and R 46 4746 and R 47 , R 47 and R 48 , R 48 and R 49 At least one pair of these are joined together to form a ring structure, R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 66 and R 67 , R 67 and R 68 , R 68 and R 69 At least one pair of these are joined together to form a ring structure, as described in

[10] . Organic electroluminescent element.

[12] The organic electroluminescent element according to any one of [1] to

[0011] , wherein the light-emitting layer comprises an assist dopant which is a delayed fluorescence material.

[13] The assist dopant is a substitution having at least one deuterium atom It consists of an unsubstituted carbazolyl group and a substituted or unsubstituted group having at least one deuterium atom. The organic electroluminescent device described in

[12] having a triazinyl group or a cyano group. Element.

[14] The organic ether described in any one of [1] to

[13] , further comprising an electron barrier layer. Lectroluminescent element.

[15] Compounds represented by the following general formula (1). General formula (1) [ka] [In general formula (1), R 1 and R 2 Each of these independently consists of a hydrogen atom, a deuterium atom, or Represents a substituent. 3 ~R 26 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. , other R 3 ~R 26 They are bonded to each other to form a ring structure. 3 ~R 26 Among them, ring The combinations that can form a morphological structure are R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 However, R 1 ~R 26 At least one of them contains a deuterium atom.

[16] The compound described in

[15] having one of the following structures. [ka] [Effects of the Invention]

[0008] The present invention provides an organic electroluminescent element with excellent durability. It is possible. [Modes for carrying out the invention]

[0009] The details of the present invention will be described below. Description of the constituent elements is as follows: This may be done based on typical embodiments and specific examples of the present invention, but the present invention is This specification is not limited to such embodiments or specific examples. The numerical range expressed includes the numbers before and after the "~" as the lower and upper limits. It means the range. In the chemical structural formulas of this specification, hydrogen atoms are represented as H or in the table. The indications are omitted. For example, the indications of atoms bonded to carbon atoms in the ring skeleton of a benzene ring are omitted. When this is the case, in the parts where the display is omitted, H is bonded to the carbon atoms that make up the ring skeleton. In this specification, the term "substituent" refers to atoms other than hydrogen and deuterium atoms. It means a child or a group of atoms.

[0010] [Emitting layer of an organic electroluminescent element] The organic electroluminescent element comprises an anode, a cathode, and between the anode and the cathode. It has at least one organic layer, and at least one of the organic layers is a light-emitting layer. The present invention provides an organic electroluminescent element in which the light-emitting layer comprises three or more compounds And, of the three or more compounds contained in the light-emitting layer, two or more compounds (for example, two, For example, each of the three types (for example, four types) has a deuterium atom. Some embodiments of the present invention So, organic electroluminescent elements are compounds of three or more types (for example, three types, for example, four types) It has a light-emitting layer made of materials, and all three or more compounds contained in the light-emitting layer are heavy water. It has elementary atoms. In some embodiments of the present invention, it is an organic electroluminescent element It has a light-emitting layer made of three types of compounds, and of the three compounds contained in that light-emitting layer Two or three of these have a deuterium atom. In some embodiments of the present invention, organic electro The trollluminescent element has a light-emitting layer made of four types of compounds, and the light-emitting layer contains Two, three, or four of the four compounds have a deuterium atom (preferably three). (or four types, more preferably four types having deuterium atoms). Note that the organic electrochemical The compounds constituting the light-emitting layer of the trollluminescent element are organic compounds. In several embodiments, the compound constituting the light-emitting layer of the organic electroluminescent element is Neither of them contains heavy metal elements.

[0011] The light-emitting layer of an organic electroluminescent device contains at least a host and a dopant. It is preferable that the host contained in the light-emitting layer is more than the dopant contained in the light-emitting layer. The lowest excitation singlet energy is also high. Therefore, the emission from the light-emitting layer is mainly from the dopant. Although the light emission originates from the emitting layer, some of it may also come from the host. Preferably, more than 90% of the light is emitted from the dopant, for example, more than 95%, for example It is also acceptable if more than 99% of the light emission comes from the dopant. Concentration of the dopant in the light-emitting layer The amount is 30% by mass or less, preferably 20% by mass or less, for example, 10% by mass or less. For example, it may be 5% by mass or less, for example, 1% by mass or less, and 0.01% by mass or more (for example) Preferably, it is 0.1% by mass or more.

[0012] When an organic electroluminescent element has a light-emitting layer made of three types of compounds, The function of each of the three compounds is not limited. Preferably, at least the host and dopa This is the case where a dopant is included. In this case, the light-emitting layer contains two types of hosts and one type of dopant. It is also acceptable to use 90% or more of the light emitted from the light-emitting layer (for example, 95% or more, for example, 99%). The above) preferably involves light emission from a dopant. Also, the light-emitting layer consists of one host and two It may include two types of Dopants, in which case the light emitted will come from each of the two types of Dopants. It is preferable that this is more than 10% (e.g., more than 20%, or more than 30%) of the light emitted from the light-emitting layer. The combined light emission from the two types of dopants is 90% or more of the light emission from the light-emitting layer (example) It is preferable that the percentage is 95% or higher, for example, 99% or higher. For example, two types of dopants Therefore, compounds with different emission colors can be selected and used.

[0013] When an organic electroluminescent element has a light-emitting layer made of three types of compounds, this generation In some preferred embodiments of the present invention, the three compounds are a host and an assist dopant. And it is a dopant. At this time, the maximum amount of light emitted from the organic electroluminescent element The minutes are the light emitted from the Dopant. The assist Dopant makes the Dopant more efficient. It functions to emit light. The host contained in the light-emitting layer, which consists of three types of compounds, The lowest excitation singlet energy is higher than that of the included assist dopants and dopants. In some embodiments of the light emission layer, the assist dopant included in the light emission layer is included in the light emission layer The lowest excitation singlet energy is higher than that of the dopant. In some embodiments of the present invention, The lowest excitation singlet energy of the assist dopant contained in the light-emitting layer is contained in the light-emitting layer Within ±0.20 eV of the lowest excitation singlet energy of the dopant (for example, ±0.15 eV) It is within (for example, within ±0.10 eV, for example, within ±0.07 eV). In the light-emitting layer, When excitation energy is generated by the recombination of electrons and atoms, each organic in the light-emitting layer The compound transitions from the ground state to the excited singlet state and the excited triplet state. Formation of an organic compound (singlet exciton) and an excited triplet state organic compound (triplet exciton). The probabilities are statistically 25% for singlet excitons and 75% for triplet excitons. Of these, the energy of the excited singlet state host and the assist dopant is transferred to the dopant. The dopant in the ground state transitions to an excited singlet state. The molecule then emits fluorescence when it returns to its ground state. At this time, the assist dopant is delayed. In the case of fluorescent materials, the assist dopant in the excited triplet state reverses the excited singlet state through inter-system interaction. Furthermore, this is preferable because the singlet excitation energy due to the reverse intersystem crossing is also transferred to the dopant. At this time, the energy of the assist dopant of the excited triplet state, which has a high abundance, is also indirectly Compared to a configuration in which the light-emitting layer does not contain an assist dopant, organic electroluminescence contributes more to light emission. This can dramatically improve the luminescence efficiency of luminescent elements. The light-emitting layer interacts with the host. If cystodopant and dopant are included, more than 90% of the emission from the luminescence layer (e.g., 9%) It is preferable that 5% or more (for example, 99% or more) of the light emission comes from the dopant. When two or more dopants are included, the luminescence from each dopant is 10% of the luminescence from the luminescence layer. It is preferable that the amount is greater than or equal to (for example, 20% or more, for example, 30% or more). There may be some light emission from the dopants or assist dopants, but it is preferable to have little. The concentration of the dopant is preferably lower than the concentration of the host or assist dopant. . The concentration of dopant in the luminescent layer (if it contains two or more types of dopants, the concentration of those dopants) The total concentration of the ions is 30% by mass or less, preferably 20% by mass or less, for example It may be 10% by mass or less, for example 5% by mass or less, for example 1% by mass or less, and 0.01 It is preferable that it be mass% or more (for example, 0.1 mass% or more). Assist in the light-emitting layer Dopant concentration (if it includes two or more assist dopants, then the concentration of those assist dopants) The total concentration of the ions is preferably 5% by mass or more, for example 10% by mass or more, for example 20% by mass or more, for example, 30% by mass or more, for example, 50% by mass or less, for example It may be 40% by mass or less. The host concentration in the luminescent layer is 40% by mass or more. Preferably, it may be 50% by mass or more, for example 60% by mass or more, for example 9 It may be 5% by mass or less, 90% by mass or less, or 80% by mass or less.

[0014] When an organic electroluminescent element has a light-emitting layer made of four types of compounds, for example For example, two types of hosts, one type of assist dopant, and one type of dopant could be employed, or This involves employing one type of host, two types of assist dopants, and one dopant. It is possible. In some embodiments of the present invention, a delayed fluorescence material is used as an assist dopant. This uses one type of host, two types of assist dopants which are delayed fluorescence materials, and 1 You can use different types of Dopants.

[0015] Regarding the concentrations of each compound in the light-emitting layer composed of four types of compounds, from three of the compounds... You can refer to the above description regarding the concentrations of various compounds in the light-emitting layer. When using two or more specific compounds, the reading should be based on the total concentration of those two or more compounds. It can be replaced and referenced. That is, for example, if you use two or more types of assist dopants The concentration of the assist dopant in the light-emitting layer consisting of three compounds is described in the above 2 This can be interpreted and referenced as the total concentration of dopants of type 1 or more.

[0016] Even when the organic electroluminescent element has a light-emitting layer made of five or more compounds , use multiple types of hosts, multiple types of assist dopants, and multiple types of dopants as appropriate. This allows for the formation of a light-emitting layer.

[0017] In some embodiments of the present invention, the organic electroluminescent element comprises a light-emitting layer. Each of the three or more compounds that make up the group has a deuterium atom. That is, three or more compounds All three or more compounds constituting the light-emitting layer have a deuterium atom. For example, when the light-emitting layer consists of a host, an assist dopant, and a dopant, the host is small It contains at least one deuterium atom, and the assist dopant contains at least one deuterium atom The dopant contains at least one deuterium atom. The number is one or more, but preferably two or more, and more preferably three or more. It is preferable to have four or more, for example five or more, for example six or more, for example It may be 7 or more. The number of deuterium atoms contained in the host may be, for example, 10 or more. There may be 15 or more, for example, 20 or more. Deuterium contained in the assist dopant The number of atoms is, for example, 10 or more, for example, 15 or more, for example, 20 or more, for example, 25 or more For example, there may be 30 or more, or for example, 35 or more. Deuterium source contained in the dopant The number of offspring may be, for example, 5 or more, for example, 10 or more, for example, 15 or more. In some embodiments, the number of deuterium atoms contained in the assist dopant is included in the host. The number of deuterium atoms in the host is greater than the number of deuterium atoms in the dopant. More than the number of deuterium atoms present. In some embodiments of the present invention, the assist dopant The number of deuterium atoms contained in is greater than or equal to the number of deuterium atoms contained in the dopant, for example. Five or more, for example, 10 or more, for example, 15 or more is too many. In some embodiments of the present invention The number of deuterium atoms contained in the assist dopant is equal to the number of deuterium atoms contained in the dopant. The number is less than or equal to, for example, 5 or more, for example, 10 or more, for example, 15 or more less. In some embodiments, the number of deuterium atoms contained in the assist dopant is such that the host contains There are five or more deuterium atoms than the number of deuterium atoms present, for example, ten or more, for example, fifteen or more. In some embodiments of the invention, the number of deuterium atoms contained in the host is the number of deuterium atoms contained in the dopant. There are five or more deuterium atoms than the number of deuterium atoms present, for example, eight or more.

[0018] The compounds contained in the light-emitting layer include at least one ring (e.g., benzyl) that constitutes the compound. All hydrogen atoms bonded to the ring skeleton constituent atoms of the (N-ring) are replaced by deuterium atoms. Preferably (i.e., the ring skeleton constituent atoms include hydrogen atoms) 1 H) is not bonded. For example, when the compound contained in the light-emitting layer contains a carbazole structure, all of the hydrogen atoms bonded to the ring skeleton constituent atoms constituting the carbazole structure can be exemplified by the case where they are all substituted with deuterium atoms. When the compound contains a plurality of carbazole structures, all of the hydrogen atoms bonded to the ring skeleton constituent atoms constituting one or more of those carbazoles may be substituted with deuterium atoms (that is, it may also contain a carbazole structure to which a hydrogen atom ( H) is bonded). In some embodiments of the present invention, when the compound contained in the light-emitting layer has an alkyl group, at least one of the alkyl groups (for example, all of the alkyl groups ) has at least one deuterium atom, and may be, for example, a perdeuterated alkyl group. 1 When determining whether or not "each of three or more compounds constituting the light-emitting layer has a deuterium atom", trace amounts of compounds contained in the light-emitting layer are not considered. That is, even if a trace amount of a compound having no deuterium atom is contained in the light-emitting layer, it may fall under the category of "all of three or more compounds constituting the light-emitting layer have a deuterium atom". Examples of trace amounts of compounds include compounds that are mixed as impurities during the manufacturing process, non-deuterated compounds mixed in deuterated compounds, and synthetic by-products contained in deuterated compounds. The abundance of these trace amounts of compounds is preferably less than 0.01% by mass of the light-emitting layer , more preferably less than 0.001% by mass, and even more preferably less than 0.0001% by mass. In some embodiments of the present invention, the organic electroluminescence device has a single light-emitting layer .

[0019] Here, when determining whether or not "each of three or more compounds constituting the light-emitting layer has a deuterium atom", trace amounts of compounds contained in the light-emitting layer are not considered. That is, even if a trace amount of a compound having no deuterium atom is contained in the light-emitting layer, it may fall under the category of "all of three or more compounds constituting the light-emitting layer have a deuterium atom". Examples of trace amounts of compounds include compounds that are mixed as impurities during the manufacturing process, non-deuterated compounds mixed in deuterated compounds, and synthetic by-products contained in deuterated compounds. The abundance of these trace amounts of compounds is preferably less than 0.01% by mass of the light-emitting layer , more preferably less than 0.001% by mass, and even more preferably less than 0.0001% by mass. Examples of trace amounts of compounds include compounds that are mixed as impurities during the manufacturing process, non-deuterated compounds mixed in deuterated compounds, and synthetic by-products contained in deuterated compounds. The abundance of these trace amounts of compounds is preferably less than 0.01% by mass of the light-emitting layer , more preferably less than 0.001% by mass, and even more preferably less than 0.0001% by mass. In some embodiments of the present invention, the organic electroluminescence device has a single light-emitting layer . In some embodiments of the present invention, the organic electroluminescence device has a single light-emitting layer

[0020] In some embodiments of the present invention, the organic electroluminescence device has a single light-emitting layer It may have only one layer, or it may have two or more light-emitting layers. 2 layers If the above conditions are met, at least one of the layers is composed of three or more compounds that make up the light-emitting layer. Our condition that "each of the two or more compounds contains a deuterium atom" is sufficient. Preferably, all light-emitting layers satisfy the conditions. Example of having two or more light-emitting layers. It has a light-emitting layer that emits blue light, a light-emitting layer that emits green light, and a light-emitting layer that emits red light. We can give some examples.

[0021] [Dopant] The structure of the dopant used in the light-emitting layer is not particularly limited. The dopant is intended to be made Select and use organic electroluminescent elements appropriately, taking into consideration their emission color and intended use. It can be used. The dopant used in the light-emitting layer may be a delayed fluorescence material, or it may emit light without emitting delayed fluorescence. It may also emit only fluorescence with a light lifetime of, for example, less than 10 nanoseconds. Examples of dopants include compounds having a donor and acceptor, or compounds exhibiting multiple resonance effects. Examples of polycyclic compounds that exhibit multiple resonance effects include those with a ring skeleton. Examples include those containing boron atoms as constituent atoms, and those containing both boron and nitrogen atoms. This is possible. Typical polycyclic compounds with multiple resonance effects include substituted or unsubstituted compounds. The structure obtained by replacing the carbon atoms at positions 9 and 10 of tracene with boron and nitrogen atoms, respectively. It contains, and more preferably, the boron and nitrogen atoms introduced at the 9th and 10th positions are substituted. k includes a structure in which an unsubstituted aryl group is bonded (the anthracene structure referred to here includes (Furthermore, the rings may be fused.) In polycyclic compounds with multiple resonance effects, there are six ring skeletons. The HOMO is localized to three carbon atoms on the benzene ring, which is composed of constituent carbon atoms, and the remaining three The LUMO can be localized to one carbon atom. The multiple resonance effect used in this invention Examples of polycyclic compounds include DABNA, ν-DANBA, ω-DABNA, and various others. such compounds, or at least one hydrogen atom of these compounds ( 1 By substituting H) with a deuterium atom Examples of such compounds can be given.

[0022] The light-emitting layer may use two or more types of dopants. Furthermore, all of the dopants may be compounds containing a deuterium atom, or some may contain heavy water It may be a compound that contains elementary atoms, with the remainder being a compound that does not contain deuterium atoms. Also, two or more compounds other than the dopant contained in the luminescent layer (for example, host and assist dopant) Pant (e.g., two or more hosts, e.g., two or more assist dopants) is a deuterium atom If such a compound is present, the dopants used in the light-emitting layer must all be compounds that do not contain a deuterium atom. That's fine.

[0023] In some embodiments of the present invention, the dopant having a deuterium atom is defined by the following general formula: Use the compound represented in 1). General formula (1) [ka]

[0024] In general formula (1), R 1 and R 2 Each of these independently consists of a hydrogen atom, a deuterium atom, or Represents a substituent. 3 ~R 26 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. , other R 3~R 26 They are bonded to each other to form a ring structure. 3 ~R 26 Among them, ring The possible combinations that form R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 1 5 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 20 and R 2 1 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 2 6 However, R 1 ~R 26 At least one of them contains a deuterium atom. That is, R 1 ~R 2 And R does not form a ring structure 3 ~R 26 And, R 3 ~R 26 annular structure formed by At least one element of the group consisting of a structure and others contains a deuterium atom.

[0025] R 3 ~R 26 The cyclic structure that can be formed may be an aromatic ring or an aliphatic ring, and 0]]it may contain heteroatoms, and furthermore, one or more other rings may be condensed, and it may be substituted with a substituent or a deuterium atom. The heteroatom mentioned here is preferably selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the formed cyclic structure include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an imidazoli ne ring, a furan ring, a thiophene ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentene ring, a cycl oheptatriene ring, a cycloheptadiene ring, a cycloheptene ring, and a ring in which one or more rings selected from the group consisting of these rings are further condensed. In some preferred embodiments of the present invention, the cyclic structure is a substituted or unsubstituted benzene ring (further one or more rings may be condensed), for example, a benzene ring that may be substituted with an alkyl group or an aryl group. In some preferred embodiments of the present invention, the cyclic structure is a substituted or unsubstituted heteroaromatic ring, preferably benzofuran (for example, one condensed with the benzene ring 3 to which R ~ 26 R is bonded), benzothiophene (for example, one condensed with the benzene ring 3 to which R 26 ~R 3 and R 4 、R4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 1 2 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 1 8 , R 18 and R 19 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 2 4 , R 24 and R 25 , R 25 and R 26 Among them, pairs that are connected to each other and form a ring structure The number of combinations can be 0, or it can be any number from 1 to 10, for example. It can be any of 1 to 6. Also, for example, it can be any of 1 to 4, and 1 You can select one, select two, or select three or four.

[0026] R that are not bonded to each other to form a ring structure 1 ~R 26 Each is an independent hydrogen atom, heavy It is a hydrogen atom or a substituent. The deuterium atom or substituent is, for example, from group A described below. You may choose from group B described below, or you may choose from group C described below. You may choose from group D described below, or you may choose from group E described below. Alternatively, multiple selections may be made from each of groups A to E. In one embodiment, R 1 ~R 26 The substituents it can take are substituted or unsubstituted alkyl groups. aryl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups (for example) It is a heteroaryl group bonded by a nitrogen atom. For example, R 1 ~R 26 Possible substituents R may be a substituted or unsubstituted aryl group. Also, for example, R 1 ~R 26 ga The substituent may be a substituted or unsubstituted alkyl group. Herein, The deuterium atoms and substituents that can be substituted for aryl groups and heteroaryl groups are also from groups A to E. These can be selected from, but preferably alkyl groups, aryl groups, and heteroaryl groups. One or more groups selected from the group consisting of groups, more preferably groups of group E, and unsubstituted. That's fine.

[0027] In some embodiments of the present invention, R 1 and R 2 Each is independently a hydrogen atom or heavy water It is an elementary atom. For example, R 1 and R 2 Both may be hydrogen atoms, or both may be It may also be a deuterium atom. Also, for example, R 1 is a hydrogen atom, and R 2 heavy water It may also be an elementary atom. Also, for example, R 1 is a deuterium atom, and R 2 is a hydrogen atom That's fine. In some preferred embodiments of the present invention, R 3 ~R 12 at least one of (for example, 2 (One or more, for example, four or more, for example, six or more) are substituents, preferably selected from group E. A selected deuterium atom or an alkyl or aryl group which may be substituted with a substituent (More preferably an alkyl group). For example, R 3 , R 7 , R 8 , R 12 at least One (e.g., two, e.g., four) substituent is preferably selected from group E. A hydrogen atom or an alkyl or aryl group which may be substituted with a substituent (preferably) It is an alkyl group. For example, R 3 , R 5 , R 7 , R 8 , R 10 , R 12 ga substituted It is a group, preferably substituted with a deuterium atom or substituent selected from group E. This is a good alkyl group or aryl group (more preferably an alkyl group). In some preferred embodiments of the present invention, R 13 ~R 26 at least one of (for example) Two or more (for example, four or more) are substituents, preferably deuterium selected from group E. Alkyl or aryl groups which may be substituted with atoms or substituents (more preferably (where is an alkyl group). For example, R 15 , R 18 , R 22 , R 25 at least one of (example) For example, two, or four, are substituents, preferably deuterium atoms selected from group E. or alkyl or aryl groups which may be substituted with substituents (more preferably) It is an alkyl group.

[0028] R in general formula (1) 1 ~R 26 At least one of them contains a deuterium atom. That is, R 1 ~ R 2 And R does not form a ring structure 3 ~R 26 And, R 3 ~R 26 Annular structure formed by At least one element of the group consisting of and contains a deuterium atom. 1 ~R 26 few Even if only one of them is a deuterium atom, R 1 ~R 26 At least one of them is a deuterium atom The substituent may include R 3 ~R 26 At least one of the other R 3 ~R 26 and mutual The cyclic structure formed by bonding may contain substituents or deuterium atoms. i. In some embodiments of the present invention, R 1 ~R 12 At least one of them contains a deuterium atom The substituent is a deuterium atom (for example, an alkyl group having a deuterium atom). Several embodiments of the present invention So, R 3 , R 7 , R 8 , R 12 At least one (e.g., two, e.g., four) of them is deuterium A substituent containing an atom (for example, an alkyl group having a deuterium atom), for example, R 3 , R 5 , R 7 , R 8 , R 10 , R 12 a substituent containing a deuterium atom (for example, a substituent having a deuterium atom) In some embodiments of the present invention, R 13 ~R 26 at least one (For example, 2, for example, 4) substituents containing a deuterium atom (for example, an atom having a deuterium atom) It is a kill group. In some embodiments of the present invention, R 15 , R 18 , R 22 , R 25 of At least one (e.g., two, e.g., four) substituents containing a deuterium atom (e.g., deuterium atom It is an alkyl group having a child. In some embodiments of the present invention, R 13 ~R 26 few At least one deuterium atom is present. In some embodiments of the present invention, R 13 ~R 19 of All are deuterium atoms. In some embodiments of the present invention, R 20 ~R 26 All of them overlap It is a hydrogen atom. In some embodiments of the present invention, R 20 ~R 26 Each independently of deuterium A substituent that may be substituted with an atom or a deuterium atom (e.g., an unsubstituted alkyl group, e.g.) For example, a hyperhydrogenated alkyl group. In some embodiments of the present invention, R 13 ~R 19 All of them are deuterium atoms, R 20 ~R 26 Each of them independently becomes a deuterium atom, or a deuterium atom Substituents may be substituted (e.g., unsubstituted alkyl groups, e.g., alkyl hyperdeuterated groups). It is the basis. In some embodiments of the present invention, R 13 , R 14 , R 16 , R 17 , R 1 9 This is a deuterium atom, and in this case R 15 , R18 This substituent may have a deuterium atom. In some embodiments of the present invention, R 20 , R 21 , R 23 , R 24 , R 26 but It is a deuterium atom, and in this case R 22 , R 25 is a substituent which may have a deuterium atom. In some embodiments of the present invention, R 3 ~R 26 At least one of them is another R 3 ~R 26 At least one cyclic structure formed by bonding with each other is a deuterium atom It holds.

[0029] The compound represented by general formula (1) may be either a symmetric or asymmetric compound. stomach. The following are specific examples of compounds represented by general formula (1). However, the compounds used in this invention are... The dopants capable of doing this should not be interpreted restrictively by the following specific examples. [ka]

[0030] Compounds represented by general formula (1) can be synthesized by combining known reactions. This can be done. For example, by utilizing ring-closing reactions or substitution reactions, synthesis can be achieved. This is possible. For specific synthesis procedures, please refer to the synthesis examples described later. .

[0031] The compound represented by general formula (1) is used in the light-emitting layer of an organic electroluminescent element. This improves durability. Also, other components used in the light-emitting layer include deuterium atoms. When this is present, by using a combination of compounds represented by general formula (1), a synergistic effect can be achieved. This effect can improve the durability of organic electroluminescent elements. In particular, the light-emitting layer When all other components used contain a deuterium atom, the compound is represented by general formula (1). By combining and using different materials, a synergistic effect occurs, resulting in organic electroluminescent elements. This can dramatically improve the durability of the child. For this reason, the compound represented by general formula (1) is an organic compound. It can be used as a durability enhancer for lectroluminescent elements. It may consist only of compounds represented by general formula (1), or other compounds used in the light-emitting layer. A mixture of the components (host, assist dopant, or a mixture of two or more thereof) It is also acceptable to do so. Furthermore, durability can be determined by measuring LT95 as described in the examples below. It can be evaluated.

[0032] The light-emitting layer uses a dopant containing deuterium atoms other than the compound represented by general formula (1). It is also possible that there are at least DABNA, ν-DANBA, and ω-DABNA. One hydrogen atom ( 1 Compounds in which H) is replaced with a deuterium atom can be used.

[0033] When using a dopant that does not contain deuterium atoms in the light-emitting layer, the type of dopant is also particularly important. It is not limited. Even with delayed fluorescence materials, if the luminescence lifetime is, for example, 10 minutes without emitting delayed fluorescence, It is also acceptable to use only fluorescence that lasts for less than 10 seconds. Specific examples include DABNA and ν-D ANBA, ω-DABNA (both of which do not contain a deuterium atom), and general formula (1) Ite R 1 ~R 26 These are all compounds that do not contain a deuterium atom.

[0034] [Assist Dopant] The structure of the assist dopant used in the light-emitting layer is not particularly limited. dopants and host cells to be used in the organic electroluminescent device that we are trying to fabricate. They can be selected and adopted as appropriate, taking into consideration their relationship with the other factors. The assist dopant used in the light-emitting layer is preferably a delayed fluorescence material. The photomaterial emits delayed fluorescence along with fluorescence with an emission lifetime of less than 10 nanoseconds. Used in the light-emitting layer. The assist dopant provides the lowest singlet excited state and the lowest triplet excited state at 77K. Energy difference (ΔE ST ) but for example, less than 0.5eV, less than 0.4eV, 0.3eV It is less than 0.2 eV or less than 0.1 eV. ΔE ST The value is less than 0.09 eV. Less than 0.08 eV, less than 0.07 eV, less than 0.06 eV, less than 0.05 eV, 0.04 It may be less than eV, less than 0.03 eV, less than 0.02 eV, or less than 0.01 eV. .

[0035] As an assist dopant used in the luminescent layer, a molecule having both a donor and an acceptor is used. Compounds can be given. For example, when the core ring (e.g., a benzene ring, a pyridine ring) Examples of compounds having a structure in which a donor and an acceptor are bound together include the donor and acceptor. It is a group that is child-donating, for example, a group with a negative Hammett σp value (for example, a group with σp of -0.3 or less). The groups below are, for example, groups where σp is -0.6 or less, and groups where σp is -0.9 or less. Examples of converted amino groups (such as diarylamino groups and carbazole-9-yl groups) can be cited. Acceptors are electron-withdrawing groups, for example, groups with a positive Hammett σp value. For example, groups with σp of 0.3 or higher, groups with σp of 0.6 or higher, groups with σp of 0.9 or higher) Yes, there are. For example, cyano groups and aromatic ring groups (triazinyl) that contain a nitrogen atom as a constituent atom of the ring skeleton. Examples include a benzene ring with one cyano group and two pyrimidinyl groups. One or more substitutions or no substitutions (e.g., 2, 3, 4, 5) A compound to which a ruvacole-9-yl group is attached, with two cyano groups and two or more (example) attached to a benzene ring. Substituted or unsubstituted carbazole-9-yl groups (for example, 2, 3, or 4) A compound in which a benzene ring is bonded, with one cyano group and one substituted or unsubstituted triazine. A yl group with two or more (e.g., two, three, four) substituted or unsubstituted carboxyl groups Compounds to which a bazole-9-yl group is attached, with two substituted or unsubstituted triglycerides on the benzene ring. A azinyl group and two or more (e.g., two, three, four) substituted or unsubstituted groups Examples include compounds to which a carbazole-9-yl group is attached. Here, triadi The deuterium atoms and substituents that can substitute for the nyl group or carbazole-9-yl group are among the group A described below. You may choose from group B described below, or you may choose from group C described below. You may choose from group D described below, or you may choose from group E described below. Alternatively, you may select from each of the groups A through E. Ano group, substituted or unsubstituted carbazole-9-yl group, substituted or unsubstituted tria group The ring skeleton constituent atoms of a benzene ring that is not bonded to a dinyl group include hydrogen atoms, deuterium atoms, and substituted or unsubstituted aryl groups (for example, those selected from group E described below) It is preferable that a phenyl group (which may be present) is bonded to it.

[0036] Two or more assist dopants may be used in the light-emitting layer. When using a pant, all of its assist dopants are compounds containing a deuterium atom. Alternatively, it may be a compound in which part contains deuterium atoms and the rest does not contain deuterium atoms. It may also be a compound. In addition, two or more chemicals other than the assist dopant contained in the luminescent layer. Compounds (e.g., two or more compounds selected from the group consisting of a host and a dopant) If hydrogen atoms are present, then all assist dopants used in the light-emitting layer must contain deuterium atoms. It may also be a compound that does not contain [unclear] compounds.

[0037] In some aspects of the present invention, the assist dopant used in the light-emitting layer is at least one Contains a deuterium atom. For example, the donor constituting the assist dopant contains at least one It has a deuterium atom. In some embodiments of the present invention, substituted or unsubstituted carbazo A deuterium atom is bonded to the ring skeleton constituent atoms of the yl-9-yl group, for example, carbazole- The 9-yl group has substituents and a deuterium atom bonded to it, but no hydrogen atom bonded to it. In some embodiments, the carbazole-9-yl group is substituted with a deuterium atom ( For example, it is substituted with a deuterated alkyl group (for example, a hyperdeuterated alkyl group). The assist dopant used in the light-emitting layer is composed of acceptors that make up the assist dopant. It may have at least one deuterium atom. Some embodiments of the present invention So, when a deuterium atom is bonded to a carbon atom in the ring skeleton of a substituted or unsubstituted triazinyl group... In some embodiments of the present invention, the two substituents of the disubstituted triazinyl group are At least one of the groups has a deuterium atom. For example, at least one of the diaryltriadinyl groups The aryl group has a deuterium atom, or one aryl group and one heteroaryl group Triazinyl groups substituted with (e.g., substituted or unsubstituted carbazole-9-yl groups) In the above, at least one of the aryl group or the heteroaryl group has a deuterium atom. I can list things.

[0038] WO20 is a delayed fluorescence material that can be used as an assist dopant in the light-emitting layer. Paragraphs 0008-0048 and 0095-0133 of Publication No. 13 / 154064, WO2 Paragraphs 0007-0047 and 0073-0085 of the Bulletin No. 013 / 011954, WO Paragraphs 0007-0033 and 0059-0066 of the 2013 / 011955 publication, W Paragraphs 0008-0071 and 0118-0133 of the Public Notice No. O2013 / 081088, Paragraphs 0009-0046 and 0093-0134 of Japanese Patent Publication No. 2013-256490 , paragraphs 0008-0020 and 0038-004 of Japanese Patent Publication No. 2013-116975 0, paragraphs 0007-0032 and 0079-00 of Publication No. WO2013 / 133359 84, paragraphs 0008-0054 and 0101-00 of Publication No. WO2013 / 161437 121, paragraphs 0007-0041 and 0060-00 of Japanese Patent Publication No. 2014-9352 69. Paragraphs 0008-0048 and 0067-007 of Japanese Patent Publication No. 2014-9224 6. Paragraphs 0013-0025 of Japanese Patent Publication No. 2017-119663, Japanese Patent Publication No. 2017-11 Paragraphs 0013-0026 of Japanese Patent Publication No. 9664, Paragraph 00 of Japanese Patent Publication No. 2017-222623 Paragraphs 012-0025, paragraphs 0010-0050 of Japanese Patent Publication No. 2017-226838, Japanese Patent Publication No. Paragraphs 0012-0043 of Bulletin No. 2018-100411, WO2018 / 047853 Compounds included in the general formulas described in paragraphs 0016-0044 of the publication, especially exemplary compounds This includes materials that can emit delayed fluorescence. Also, here, Japanese Patent Publication No. 2013-2 53121 publication, WO2013 / 133359 publication, WO2014 / 034535 publication Publications, WO2014 / 115743, WO2014 / 122895, WO2 014 / 126200 publication, WO2014 / 136758 publication, WO2014 / 13 3121 publication, WO2014 / 136860 publication, WO2014 / 196585 publication WO2014 / 189122, WO2014 / 168101, WO20 15 / 008580 publication, WO2014 / 203840 publication, WO2015 / 002 213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication , WO2015 / 072470, WO2015 / 108049, WO201 5 / 080182 publication, WO2015 / 072537 publication, WO2015 / 0801 Japanese Patent Publication No. 83, Japanese Patent Publication No. 2015-129240, Japanese Patent Publication No. WO2015 / 129714, WO2015 / 129715, WO2015 / 133501, WO2015 / 136880 publication, WO2015 / 137244 publication, WO2015 / 13720 2 Publication, WO2015 / 137136 Publication, WO2015 / 146541 Publication, W The following are examples of luminescent materials capable of emitting delayed fluorescence as described in Publication No. O2015 / 159541. This can be done. Among these, a compound having a deuterium atom, or at least one of the light-emitting materials Compounds in which hydrogen atoms are replaced with deuterium atoms can be preferably used. The above publications described in the document are incorporated herein by reference as part of this specification.

[0039] The following are specific examples of assist dopants used in the light-emitting layer. However, the ones used in this invention are not specified. The assist dopant that can do this should not be interpreted restrictively by the following specific examples. stomach. [ka] [ka]

[0040] The light-emitting layer can contain two or more delayed fluorescence materials as assist dopants. In some embodiments of the present invention, one type of primary delay fluorescent lamp is used as an assist dopant. The photomaterial and its main delayed fluorescence material have lower lowest excitation singlet energy levels (that is, (And the emission wavelength is long wavelength), and moreover, the concentration in the emission layer is higher than that of the main delayed fluorescence material. A delayed fluorescence material with a low degree of fluorescence is employed. In this invention, a delayed fluorescence material that satisfies these conditions is used. This is specifically called "ESM". For example, when the light-emitting layer consists of four types of compounds, the light-emitting layer is the host , the main delayed fluorescence material (referred to as "TADF" in this specification) is an assist dopant. It consists of an assist dopant called ESM and a dopant that is the main light source. This is possible. When the light-emitting layer consists of five or more compounds, the host, TADF, and ESM are used. It is possible to use two or more types of at least one dopant. In the embodiment, the concentration of ESM in the light-emitting layer is 10% by mass or less (for example, 5% by mass or less, e.g. For example, it can be 3% by mass or less, for example, 1% by mass or less. Several embodiments of the present invention Morphologically, the concentration of ESM in the emissive layer is less than half (for example, less than 1 / 4) the concentration of TADF. For example, it can be 1 / 10 or less, for example, 1 / 30 or less. In this embodiment, the concentration of ESM in the light-emitting layer is 5% by mass or more higher than the concentration of TADF (for example) The present invention reduces the amount by 10% by mass or more, for example, 20% by mass or more, for example, 25% by mass or more. In some embodiments, each ESM in the light-emitting layer has the lowest excitation singlet energy of the TADF. More than 0.10 eV above the Lugia level (for example, more than 0.15 eV, or more than 0.25 eV) ) to reduce. In some embodiments of the present invention, each ESM in the light-emitting layer is dopant Greater than the concentration of (in mass percent, for example, more than twice as great, for example, more than three times as great) .

[0041] When two or more ESMs are used in the light-emitting layer, all of the ESMs have deuterium atoms. It may be a compound, or a compound in which part has a deuterium atom and the rest has a deuterium atom It may also be a compound that does not contain ESM. (For example, two or more compounds selected from the group consisting of host, TADF, and dopant) If ) has deuterium atoms, then none of the ESMs used in the light-emitting layer have deuterium atoms. It may also be a compound.

[0042] [host] The structure of the host used in the light-emitting layer is not particularly limited. The host is the one that you are trying to fabricate. Assist dopants used in electroluminescent elements (TADF and ESM mentioned above) The present invention can be appropriately selected and adopted, taking into consideration its relationship with (including) and dopants. In some preferred embodiments, the lowest excited singlet energy and the lowest excited triplet energy Lugia selects a compound with a higher rating than the assist dopant or dopant as a host. As a result, singlet and triplet excitons generated in the light-emitting layer act as assist dopants. It can be confined within the dopant molecule, improving the efficiency of light emission.

[0043] Two or more types of hosts may be used in the light-emitting layer. When two or more hosts are used, All of the host compounds may contain deuterium atoms, or some may contain deuterium atoms. The compound may be one in which the remainder does not contain deuterium atoms. Two or more compounds other than the host compound (for example, an assist dopant and a dopant) If two or more compounds selected from the group have a deuterium atom, they are used in the light-emitting layer. The host compounds may not contain any deuterium atoms.

[0044] In some embodiments of the present invention, the host comprises a carbazole structure, for example, its carbazole structure. The basol structure contains at least one (e.g., six, seven, eight) deuterium atoms They are bound. In some embodiments of the present invention, the host comprises a dibenzofuran structure. For example, the dibenzofuran structure has at least one (for example, five, six, or seven) A deuterium atom is bonded to it. In some embodiments of the present invention, the host is benzofloxacin. It contains a carbazole structure, for example, at least one (e.g., in its benzoflocarbazole structure) For example, 6, 7, 8, 9, or 10 deuterium atoms bond together. In some embodiments of the present invention, the host is an arylene group (for example, a phenylene group). ) containing, for example, at least one (e.g., two, e.g., four) deuterium in the arylene Atoms are bonded together.

[0045] In some embodiments of the present invention, the host is a benzene ring that is substituted or unsubstituted. It has a structure to which a bazole-9-yl group is attached, for example, its carbazole-9-yl The base has a deuterium atom bonded to it, or a substituent substituted with a deuterium atom is bonded to it. In some embodiments of the present invention, the host is a benzene ring-fused carboxyl group with substitution or unsubstituted properties. It has a structure to which a bazole-9-yl group is bonded, for example, its ring-condensed carbazole-9 - The yl group is bonded to a deuterium atom, or a substituent substituted with a deuterium atom is bonded to it. In some embodiments of the present invention, the host is a benzene ring with substituted or unsubstituted gibel It has a structure to which a dibenzofuran-2-yl group is attached, for example, its dibenzofuran-2- The yl group is bonded to either a deuterium atom or a substituent substituted with a deuterium atom. In some embodiments of the present invention, the host is a benzene ring that is substituted or unsubstituted. A carbazole-9-yl group is bonded to a substituted or unsubstituted dibenzofuran-2-yl group. It has a structure such that, for example, a deuterium atom is bonded to its ring-condensed carbazole-9-yl group. Either it is, or a deuterium atom is bonded to the dibenzofuran-2-yl group. Deuterium sources that can be substituted for the carbazole-9-yl group and dibenzofuran-2-yl group mentioned here The children and substituents may be selected from group A described below, or from group B described below. You may choose from group C described later, or you may choose from group D described later. Alternatively, you may choose from group E described below, or from multiple groups A through E. The following may be selected: the carbazole-9-yl group and the dibenzofuran-2-yl group. The groups are a hyperhydrogenated carbazole-9-yl group and a hyperhydrogenated dibenzofuran-2- It may also be an yl group. Also, as a ring-condensed carbazole-9-yl group, benzoflocarb Examples of zole-9-yl groups include, for example, hyperhydrogenated benzoflocarbazole- It may also be a 9-yl group.

[0046] In some embodiments of the present invention, host substitution or unsubstituted carbazole-9- A deuterium atom is bonded to the ring skeleton of the yl group. For example, carbazole-9-yl The base has substituents and deuterium atoms bonded to it, but no hydrogen atoms bonded to it. Some of the present inventions In this embodiment, the carbazole-9-yl group is substituted with a deuterium atom (e.g., heavy Substituted with a hydride alkyl group (e.g., a hyperhydride alkyl group). Some of the present inventions In this embodiment, the ring skeleton of the host substituted or unsubstituted dibenzofuran-2-yl group A deuterium atom is bonded to the main atom. For example, the dibenzofuran-2-yl group has substituents and Deuterium atoms are bonded, but hydrogen atoms are not. In some embodiments of the present invention, , a substituent in which the dibenzofuran-2-yl group is substituted with a deuterium atom (e.g., deuterated alkyl It is substituted with a group (e.g., a hyperhydrogenated alkyl group). In some embodiments of the present invention The ring skeleton constituent of the host, whether substituted or unsubstituted, is the benzoflocarbazole-9-yl group. A deuterium atom is bonded to the child. For example, the benzoflocarbazole-9-yl group is substituted. The group is bonded to a deuterium atom, but not to a hydrogen atom. Several embodiments of the present invention So, the benzoflocarbazole-9-yl group is a substituent substituted with a deuterium atom (for example, heavy It is substituted with a hydride alkyl group (e.g., a hyperhydrogenated alkyl group).

[0047] In some embodiments of the present invention, the host is represented by the following general formula (2) or general formula (3). The compound used is the one described. [ka]

[0048] In general formulas (2) and (3), R 31 ~R 41 and R 51 ~R 61 teeth, Each independently consists of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or R represents an unsubstituted alkyl group. 42 ~R 49 Each is independently a hydrogen atom, a deuterium atom, and Represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group, or other R 42 ~R 49 They are bonded to each other to form a ring structure. 42 ~R 49 Among the ring structures The possible combinations that can form the structure are R 42 and R 43 , R 43 and R 44 , R 44 and R 45 , R 4 6 and R 47 , R 47 and R 48 , R 48 and R 49 That is. R 62 ~R 69 Each of them independently Elementary atoms, deuterium atoms, substituted or unsubstituted aryl groups, or substituted or unsubstituted aryl groups Represents a lukyl group, or other R groups 62 ~R 69They are bonded to each other to form a ring structure. 6 2 ~R 69 Among these, the combinations that can form a ring structure are R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 66 and R 67 , R 67 and R 68 , R 68 and R 69 However, R 31 ~R 49 At least one of them contains a deuterium atom. That is, R 31 ~R 41 And, ring R that does not form a symmetrical structure 42 ~R 49 And, R 42 ~R 49 The annular structure formed by and At least one element of the group contains a deuterium atom. Also, R 51 ~R 69 few It contains at least one deuterium atom. That is, R 51 ~R 61 And it does not form a ring structure. R 62 ~R 69 And, R 62 ~R 69 A ring structure formed by and a small group of the members At the very least, one element contains a deuterium atom.

[0049] R 42 ~R 49 A ring structure formed by R 62 ~R 69 Annular structure formed by This may be an aromatic ring or an fatty ring, and may also contain a heteroatom. Furthermore, one or more other rings may be fused. For details of the cyclic structure, see R above.3 ~R 26 But other R 3 ~R 26 See the description of the annular structure formed by their mutual bonding. It is possible. 42 ~R 49 and R 62 ~R 69 Among the others, 42 ~R 49 or R 62 ~R 69 Even if the number of combinations that are bonded to each other and form a ring structure is 0 That's fine, or any of 1 through 4 would be fine. For example, you could choose 1 or 2. You can choose 3 or 4, for example. 44 and R 45 Ya R 64 and R 65 When R combines with others to form a benzofloxic structure, 44 and R 45 Ya R 64 and R 65 but When R is bound to form a benzothieno structure, 43 and R 44 Ya R 63 and R 64 each other When it binds to form a benzofloxacin structure, R 43 and R 44 Ya R 63 and R 64 they are connected to each other When combined to form a benzothieno structure, R 42 and R 43 Ya R 62 and R 63 they are joined together When forming a benzofloxic structure, R 42 and R 43 Ya R 62 and R 63 they combine with each other One example is the formation of a benzothieno structure.

[0050] R that are not bonded to each other to form a ring structure 31 ~R 49 and R 51 ~R 69 Each is independent A hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. It is a substitute alkyl group. Here, the aryl group and the deuterium atom that can be substituted for the alkyl group are The substituent may be selected, for example, from group A described below, or from group B described below. You may choose from group C described below, or you may choose from group D described below. You may choose from group E described below, or you may choose multiple from groups A to E. They may be selected from among the following. In some embodiments of the present invention, they are joined together to form a ring structure R that does not form 31 ~R 49 and R 51 ~R 69 These are, independently, hydrogen atoms and deuterium atoms. , an aryl group which may be substituted with a deuterium atom. In some embodiments of the present invention R is not bonded to each other to form a ring structure. 31 ~R 49 and R 51 ~R 69 Each This alkyl group is independently substituted with a hydrogen atom, a deuterium atom, or a deuterium atom. In some embodiments of the invention, R that are not bonded to each other to form a ring structure 31 ~R 4 9 and R 51 ~R 69 Each of these is either a hydrogen atom or a deuterium atom, independently of the others.

[0051] R in general formula (2) 31 ~R 49 At least one of them contains a deuterium atom, and the general formula (3) R 51 ~R69 At least one of them contains a deuterium atom. That is, R 31 ~R 49 few At least one, R 51 ~R 69 At least one of them may be a deuterium atom, or heavy water It may be a group containing elementary atoms, or R 42 ~R 49 Ya R 62 ~R 69 But other R 42 ~R 4 9 Ya R 62 ~R 69 The cyclic structure formed by the bonding of these atoms contains at least one deuterium atom It may have. In some embodiments of the present invention, R 31 ~R 34 at least one (For example, 2, for example, 4) or R 51 ~R 54 at least one of (for example, two, for example, four) Each of these atoms is either a deuterium atom or a substituent containing a deuterium atom (e.g., a hyperdeuterated atom). In some embodiments of the present invention, R 35 ~R 41 at least one (For example, 5, for example, 6, for example, 7) or R 55 ~R 61 at least one of (for example, 5 Each of the particles (for example, 6 or 7) is independently a deuterium atom or contains a deuterium atom. These are substitution groups (e.g., perdeuterated phenyl groups, perdeuterated alkyl groups). Some of the present inventions In this embodiment, R 42 ~R 49 at least one of (for example, 6, 7, 8) (individual) or R 62 ~R 69 At least one of each (for example, 6, 7, or 8) Independently, a deuterium atom or a substituent containing a deuterium atom (e.g., a perdeuterated phenyl group) R is a hyperhydrogenated alkyl group. In some embodiments of the present invention, 42 ~R 49 But other R 42 ~R 49 They bond with each other to form a cyclic structure having at least one deuterium atom. And, R 62 ~R 69 But other R 62 ~R 69 and bond with each other to at least one deuterium atom It forms a ring-shaped structure having the following characteristics.

[0052] The following are specific examples of compounds represented by general formula (2). However, the compounds used in this invention are... The definition of a host capable of doing this is not limited by the following specific examples. [ka]

[0053] When using a host that does not contain deuterium atoms in the light-emitting layer, the type of host is not particularly limited. No. For example, in general formulas (2) and (3), R 31 ~R 41 and R 51 ~R 61 Compounds that do not contain a deuterium atom may also be used. For example, the following: You can list the hosts. [ka]

[0054] [Combination of compounds in the luminescent layer] The following describes the combinations of compounds that make up the light-emitting layer. Among the target dopant groups 1-10, assist dopant groups a-h, and host groups A-H The contents are as follows: Dopant group 1: Compounds that are delayed fluorescence materials Dopant group 2: Polycyclic compounds exhibiting multiple resonance effects Dopant group 3: Compounds containing both a donor and an acceptor. Dopant group 4: Compounds containing a boron atom Dopant group 5: Compounds containing five or more deuterium atoms Dopant group 6: Compounds represented by general formula (1) Dopant group 7: Compounds represented by general formula (1) that contain 10 or more deuterium atoms. Dopant group 8: Represented by general formula (1), R 13 ~R 19 A compound in which the atom is a deuterium atom. Dopant group 9: Represented by general formula (1), R 20 ~R 26 Each of them is an independent deuterium atom, A compound in which the substituent may be substituted with a deuterium atom. Dopant group 10: Represented by general formula (1), R 3 , R 7 , R 8 , R 12 Each is placed independently A compound that is a commutative group.

[0055] Assist dopant group a: Compounds that emit delayed fluorescence Assist dopant group b: ΔE ST Compounds with a value of less than 0.3 eV Assist dopant group c: Compounds containing 10 or more deuterium atoms Assist dopant group d: Compounds in which a donor and acceptor are bound to a core ring. Assist dopant group e: A benzene ring with one cyano group and two or more substitutions or absences. Compounds to which a carbazole-9-yl group is attached. Assist dopant group f: Two cyano groups and two or more substitutions or absences on the benzene ring. Compounds to which a carbazole-9-yl group is attached. Assist dopant group g: A benzene ring with one cyano group and one substituted or unsubstituted group A triazinyl group bonded to two or more substituted or unsubstituted carbazole-9-yl groups compound Assist dopant group h: Two substituted or unsubstituted triazinyl groups on a benzene ring Compounds to which two or more substituted or unsubstituted carbazole-9-yl groups are attached.

[0056] Host group A: Compounds having a deuterated carbazole-9-yl group Host group B: Compounds having a deuterated dibenzofuran-2-yl group Host group C: Compounds having a deuterated benzoflocarbazole-9-yl group Host group D: Compounds containing five or more deuterium atoms Host group E: Compounds represented by general formula (2) or general formula (3) Host group F: Represented by general formula (2) or general formula (3), R 31 ~R 34 and R 51 ~R 54 A compound in which each atom is either an independent deuterium atom or a substituent containing a deuterium atom. Host group G: Represented by general formula (2) or general formula (3), R 35 ~R 41 and R 55 ~R 61 A compound in which each atom is either an independent deuterium atom or a substituent containing a deuterium atom. Host group H: Represented by general formula (2) or general formula (3), R 42 ~R 49 and R 62 ~R 69 A compound in which each atom is either an independent deuterium atom or a substituent containing a deuterium atom.

[0057] Table 1 below lists the dopant-host combinations 1A to 10G. [Table 1]

[0058] For each of the dopant-host combinations 1A to 10H, further assistance is provided. A combination of any of the dopant groups a-h, and a combination of the dopant group and the host group. The combinations are displayed by adding one of a to h to the end of each combination 1A to 10H. The combination of dopant group and host group 1A is further combined with assist dopant group a. The combination of the dopant group and host group is designated as 1Aa, and the combination of the dopant group and host group 1A is further modified. The dopant is created by combining cystodopant group b to form combination 1Ab. This displays the combinations of the group, host group, and assist dopant group. 1Aa~h, 1Ba~h, 1Ca~h, 1Da~h, 1Ea~h, 1Fa~h, 1Ga ~h, 1Ha~h, 2Aa~h, 2Ba~h, 2Ca~h, 2Da~h, 2Ea~h, 2 Fa~h, 2Ga~h, 2Ha~h, 3Aa~h, 3Ba~h, 3Ca~h, 3Da~h , 3Ea~h, 3Fa~h, 3Ga~h, 3Ha~h, 4Aa~h, 4Ba~h, 4Ca ~h, 4Da~h, 4Ea~h, 4Fa~h, 4Ga~h, 4Ha~h, 5Aa~h, 5 Ba~h, 5Ca~h, 5Da~h, 5Ea~h, 5Fa~h, 5Ga~h, 5Ha~h , 6Aa~h, 6Ba~h, 6Ca~h, 6Da~h, 6Ea~h, 6Fa~h, 6Ga ~h, 6Ha~h, 7Aa~h, 7Ba~h, 7Ca~h, 7Da~h, 7Ea~h, 7 Fa~h, 7Ga~h, 7Ha~h, 8Aa~h, 8Ba~h, 8Ca~h, 8Da~h , 8Ea~h, 8Fa~h, 8Ga~h, 8Ha~h, 9Aa~h, 9Ba~h, 9Ca ~h, 9Da~h, 9Ea~h, 9Fa~h, 9Ga~h, 9Ha~h, 10Aa~h, 10Ba~h, 10Ca~h, 10Da~h, 10Ea~h, 10Fa~h, 10Ga~ h, 10Ha~h can be specified individually in this specification. It shall be disclosed to [the relevant authority].

[0059] [Definition] In this application, "alkyl group" may be linear, branched, or cyclic. A mixture of two or more of the linear, cyclic, and branched parts may be present. The number of carbon atoms can be, for example, 1 or more, 2 or more, or 4 or more. Also, the number of carbon atoms can be 30 or less. It can be 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group , 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooc Tyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl Examples include the cyclohexyl group, cycloheptyl group, and cycloheptyl group. In this application, the "aryl group" may be a monocyclic ring or a condensed ring formed by the fusion of two or more rings. It may also be a ring. If it is a fused ring, it is preferable that the number of fused rings be between 2 and 6. For example, you can choose from 2 to 4. Specific examples of rings include benzene rings and naphthium rings. Examples include talene rings, anthracene rings, phenanthrene rings, and pyrene rings. Examples of the phenyl group include the phenyl group, 1-naphthyl group, 2-naphthyl group, and 1-anthracenic group. Examples include aryl groups, 2-anthracenyl groups, and 9-anthracenyl groups. The number of constituent atoms in the ring skeleton is preferably 6 to 40, and more preferably 6 to 20. You may also choose a number within the range of 6 to 14, or within the range of 6 to 10. In this application, the "heteroaryl group" may be a monocyclic ring or a group formed by the fusion of two or more rings. It may also be a fused ring. If it is a fused ring, the number of fused rings is 2 to 6. Preferably, one can be selected from, for example, 2 to 4. Heteroaryl group ring skeleton structure At least one atom is a heteroatom. Examples of heteroatoms include nitrogen, oxygen, and sulfur. Yellow atoms can be cited. As a specific example of a ring constituting a heteroaryl group, pyridine is an example. Examples include rings, pyrimidine rings, triazine rings, and pyrrole rings, and these rings also include Another ring may be fused to it. Specific examples of heteroaryl groups include the 2-pyridyl group, 3 -Pyridyl group, 4-pyridyl group, carbazole-9-yl group, carbazole-1-yl group , carbazole-2-yl group, carbazole-3-yl group, carbazole-4-yl group It can be listed that the number of constituent atoms in the ring skeleton of a heteroaryl group is preferably 4 to 40. Furthermore, it is more preferable that the range is 5 to 20, and that it be selected within the range of 5 to 16, or 5 to 12. You can also select within the specified range.

[0060] In this specification, "Group A" refers to deuterium atoms, hydroxyl groups, halogen atoms (for example) Fluorine atoms, chlorine atoms, bromine atoms, iodine atoms), alkyl groups (e.g., 1 to 40 carbon atoms) , alkoxy group (e.g., 1-40 carbon atoms), alkylthio group (e.g., 1-40 carbon atoms), Aryl group (e.g., 6-30 carbon atoms), aryloxy group (e.g., 6-30 carbon atoms), A Rielthio groups (e.g., 6-30 carbon atoms), heteroaryl groups (e.g., 5 atoms in the ring skeleton) ~30), heteroaryloxy group (e.g., 5-30 atoms in the ring skeleton), heteroaryl Luthio group (e.g., 5-30 atoms in the ring skeleton), acyl group (e.g., 1-40 carbon atoms), A Lukenyl group (e.g., 1-40 carbon atoms), alkynyl group (e.g., 1-40 carbon atoms), alkynyl group Xycarbonyl group (e.g., 1-40 carbon atoms), aryloxycarbonyl group (e.g., carbon (1-40 carbon atoms), heteroaryloxycarbonyl group (e.g., 1-40 carbon atoms), silyl group This group consists of (for example, trialkylsilyl groups with 1 to 40 carbon atoms) and nitro groups. Here, alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, Arylthio group, heteroaryl group, heteroaryloxy group, heteroarylthio group, Acyl group, alkenyl group, alkynyl group, alkoxycarbonyl group, aryloxycal Bonyl groups, heteroaryloxycarbonyl groups, silyl groups, and nitro groups constitute group A. A structure in which a deuterium atom and one or more of the above substituents are bonded together. It may be substituted with a substituent having the following properties: In this specification, "Group B" refers to deuterium atoms, alkyl groups (e.g., C1-C40), Alkoxy groups (e.g., 1-40 carbon atoms), aryl groups (e.g., 6-30 carbon atoms), aryl groups Luoxy group (e.g., 6-30 carbon atoms), heteroaryl group (e.g., 5-30 carbon atoms in the ring skeleton) 30), heteroaryloxy groups (e.g., ring skeleton constituent atoms number 5-30), diarylamine aryl groups (for example, groups with 12-20 carbon atoms; where two aryl groups are single-bonded or linked to each other) This group consists of alkyl groups (which may be linked together to form a cyclic structure). Alkyl group, aryl group, aryloxy group, heteroaryl group, heteroaryloxy The cy group and diarylamino group are among the deuterium atoms and substituents that make up group B. It may be substituted with substituents having a structure in which one or more of them are bonded. In this specification, "Group C" refers to a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), Aryl groups (e.g., 6-22 carbon atoms), heteroaryl groups (e.g., 5-22 carbon atoms in the ring skeleton) 20) diarylamino group (for example, 12-20 carbon atoms; here the two aryl groups are mutual This group consists of elements that may be linked by single bonds or linking groups to form a cyclic structure. Here, alkyl groups, aryl groups, heteroaryl groups, and diarylamino groups refer to group C. It has a structure in which one or more of the constituent deuterium atoms and the substituents mentioned above are bonded together. It may be substituted with a substituent. In this specification, "Group D" refers to deuterium atoms, alkyl groups (e.g., C1-C20), Aryl groups (e.g., 6-22 carbon atoms) and heteroaryl groups (e.g., number of atoms in the ring skeleton) This group consists of 5-20). Here, alkyl groups, aryl groups, and heteroaryl groups are referred to as alkyl groups, aryl groups, and heteroaryl groups. The group consists of one or more of the deuterium atoms and substituents that make up group D. The above may be substituted with a substituent having a bonded structure. In this specification, "Group E" refers to deuterium atoms, alkyl groups (e.g., C1-C20) This group consists of alkyl groups (for example, groups with 6 to 22 carbon atoms). The aryl group consists of a deuterium atom constituting group E and one of the substituents mentioned above. Alternatively, it may be substituted with substituents having a structure in which two or more are bonded together. In this specification, the terms "substituted or unsubstituted" or "may be substituted" are used. The deuterium atom or substituent to be substituted in this case may be selected from, for example, group A. Okay, you may choose from group B, or from group C, or from group D. You may choose from these, or you may choose from group E.

[0061] [Configuration of an organic electroluminescent element] The organic electroluminescent element of the present invention comprises an anode, a cathode, and the anode and the cathode. There is at least one organic layer between the poles. At least one of these organic layers is a light-emitting layer. In some embodiments of the present invention, the organic layer is one or more organic layers in addition to the light-emitting layer. Includes. Examples of organic layers include hole transport layers, hole injection layers, electron barrier layers, hole barrier layers, electron Examples include an injection layer, an electron transport layer, and an exciton barrier layer. In some embodiments of the present invention, The organic layer includes at least an electron barrier layer in addition to the light-emitting layer. In some embodiments of the present invention, The hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer is The present invention may also be an electron injection transport layer having an electron injection function. An example of a sense element configuration is a substrate, anode, hole injection layer, hole transport layer, electron barrier layer, and light-emitting layer. Examples include those having a hole barrier layer, an electron transport layer, an electron injection layer, and a cathode in that order.

[0062] In the following, each component of the organic electroluminescent element and each layer other than the light-emitting layer I will explain about this.

[0063] Base material: In some embodiments, the organic electroluminescent element of the present invention is maintained by a substrate. The substrate is not particularly limited and is commonly used in organic electroluminescent elements. For example, they can be made from glass, clear plastic, quartz, and silicon. Any of the materials will suffice.

[0064] anode: In some embodiments, the anode of an organic electroluminescent apparatus is made of a metal, alloy, It is manufactured from conductive compounds or combinations thereof. In some embodiments, the The metals, alloys, or conductive compounds have a high work function (4 eV or more). In the embodiment, the metal is Au. In some embodiments, the anode is CuI, Conductive transparent materials selected from indium tin oxide (ITO), SnO2, and ZnO. The material used is IDIXO(In2O3-Zn). In some embodiments, the anode is IDIXO(In2O3-Zn Amorphous materials that can form transparent conductive films, such as O), are used. In one embodiment, the anode is a thin film. In some embodiments, the thin film is deposited or It is manufactured by sputtering. In some embodiments, the conductive film is The pattern is created by photolithography. In some embodiments, the pattern is If high precision is not required (for example, approximately 100 μm or more), the pattern will be applied to the electrode material. It may be formed using a mask with a shape suitable for deposition or sputtering. In the embodiment, when a coating material such as an organic conductive compound can be applied, the printing method Wet film formation methods such as coating methods are used. In some embodiments, When synchrotron radiation passes through the anode, the anode has a transmittance of more than 10%, and the anode has a transmittance of more than 10% per unit area. It has a sheet resistance of several hundred ohms or less. In some embodiments, the anode thickness is 10 It is ~1,000 nm. In some embodiments, the anode thickness is 10~200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0065] cathode: In some embodiments, the cathode is a metal having a low work function (4 eV or less) (electrical power). Electrode materials such as (referred to as implanted metals), alloys, conductive compounds, or combinations thereof are used. It is manufactured. In some embodiments, the electrode material is sodium, sodium-potassium Alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, Magnesium-aluminum mixture, magnesium-indium mixture, aluminum- Aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture and rare earth elements are selected. In some embodiments, electron-injected metals and electron-injected gold A mixture of a second metal, which is a stable metal with a higher work function than the first metal, is used. In one embodiment, the mixture is a magnesium-silver mixture, a magnesium-aluminum mixture, and Indium mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al Selected from 2O3 mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and resistance to oxidation. In some embodiments, the cathode is made by depositing or sputtering an electrode material into a thin film. It is manufactured by forming it as follows. In some embodiments, the cathode is a unit area It has a sheet resistance of several hundred ohms or less per unit. In some embodiments, the thickness of the cathode is It is 10 nm to 5 μm. In some embodiments, the thickness of the cathode is 50 to 200 nm. Yes. In some embodiments, organic electroluminescent light is used to transmit synchrotron radiation. Either the anode or cathode of the element is transparent or translucent. Several embodiments Therefore, transparent or translucent electroluminescent elements enhance light radiance. In some embodiments, the cathode is made of the conductive transparent material described above with respect to the anode. By forming in this manner, a transparent or translucent cathode is formed. In some embodiments, The element includes an anode and a cathode, both of which are transparent or semi-transparent.

[0066] Injection layer: The injection layer is the layer between the electrode and the organic layer. In some embodiments, the injection layer is driven The dynamic voltage is reduced and the light radiance is increased. In some embodiments, the injection layer is positive It includes a pore injection layer and an electron injection layer. The injection layer is between the anode and the light-emitting layer or hole transport layer. It can also be placed between the cathode and the light-emitting layer or electron transport layer. Several implementations In this configuration, an injection layer is present. In some embodiments, an injection layer is absent. The following are examples of preferred compounds that can be used as hole injection materials.

[0067] [ka]

[0068] Next, we will list some examples of preferred compounds that can be used as electron injection materials. [ka]

[0069] Barrier layer: The barrier layer allows charge (electrons or holes) and / or excitons present in the light-emitting layer to reach the light-emitting layer. It is a layer that can prevent diffusion to the outside. In some embodiments, the electron barrier layer is It exists between the light-emitting layer and the hole transport layer, and prevents electrons from passing through the light-emitting layer to reach the hole transport layer. To stop. In some embodiments, the hole barrier layer is located between the light-emitting layer and the electron transport layer. This prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, The wall layer prevents excitons from diffusing to the outside of the light-emitting layer. In some embodiments, The electron barrier layer and hole barrier layer constitute the exciton barrier layer. The term "electron barrier" as used herein refers to the electron barrier. The "layer" or "exciton barrier layer" has both the function of an electron barrier layer and an exciton barrier layer. This includes the layer that does so.

[0070] Hole barrier layer: The hole barrier layer functions as an electron transport layer. In some embodiments, during electron transport... The hole barrier layer prevents holes from reaching the electron transport layer. In some embodiments, The barrier layer increases the probability of electron-hole recombination in the light-emitting layer. The material may be the same material described above for the electron transport layer. The following are examples of preferred compounds that can be used in the hole barrier layer.

[0071] [ka]

[0072] Electron barrier layer: The electron barrier layer transports holes. In some embodiments, during hole transport, the electron barrier The layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron barrier layer is The probability of electron-hole recombination in the light-emitting layer is increased. The material used for the electron barrier layer is hole The transport layer may be made of the same material as described above. The following are specific examples of preferred compounds that can be used as electron barrier materials.

[0073] [ka] JPEG2026060872000019.jpg45170

[0074] Exciton barrier layer: The exciton barrier layer is a charge transport layer that receives excitons generated through the recombination of holes and electrons in the light-emitting layer. It prevents diffusion to the transmission layer. In some embodiments, the exciton barrier layer is located in the light-emitting layer. This enables effective confinement of excitons. In some embodiments, This improves the light emission efficiency of the device. In some embodiments, the exciton barrier layer is on the anode side and On either side of the cathode, and adjacent to the light-emitting layers on both sides thereof. In some embodiments, When the exciton barrier layer is located on the anode side, this layer is located between the hole transport layer and the light-emitting layer. The light-emitting layer may be adjacent to the exciton barrier layer. In some embodiments, the exciton barrier layer is located on the cathode side. In this case, the layer is located between the light-emitting layer and the cathode, and may be adjacent to the light-emitting layer. In that embodiment, the hole injection layer, electron barrier layer, or similar layer is the anode and the anode-side light-emitting layer It exists between the hole injection layer and the adjacent exciton barrier layer. In some embodiments, the hole injection layer, electron The barrier layer, hole barrier layer, or similar layer is located between the cathode and the exciton barrier layer adjacent to the cathode-side light-emitting layer. It exists between. In some embodiments, the exciton barrier layer is between the excitation singlet energy and The excitation triplet energy is included, and at least one of them is the excitation singlet energy of the luminescent material. Its energy is higher than the excitation triplet energy.

[0075] Hole transport layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, hole transport materials have hole injection or transport properties and electron obstruction It has one of the wall properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Known hole transport materials include, but are not limited to, triazole derivatives and oxadiazo Imidazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, Polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine amine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene Lyl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, Silazane derivatives, aniline copolymers and conductive polymer oligomers (especially thiophene) Examples include oligomers, or combinations thereof. In some embodiments, hole transport materials These are selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are given below.

[0076] [ka]

[0077] Electron transport layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material transports electrons injected from the cathode to the light-emitting layer. All that is needed is the function of transporting electrons. In some embodiments, the electron transport material is also a hole barrier material. It also functions. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro Substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbo Diimide, fluorenylidene methane derivatives, anthraquinodimethane, anthrone derivatives, Oxadiazole derivatives, azole derivatives, azine derivatives or combinations thereof, or the Polymers are examples. In some embodiments, the electron transport material is a thiadiazole derivative. or quinoxaline derivatives. In some embodiments, the electron transport material is a polymer material. It is a material. Below are specific examples of preferred compounds that can be used as electron transport materials. ru.

[0078] [ka]

[0079] Furthermore, examples of preferred compounds that can be added to each organic layer are given. For example, stabilization It could be added as an ingredient, among other things.

[0080] [ka]

[0081] Specific examples of preferred materials that can be used in organic electroluminescent elements However, the materials that can be used in the present invention are not limited by these exemplary compounds. It will not be interpreted as such. Also, the compounds exemplified as materials having a specific function Furthermore, it can be repurposed as a material with other functional properties.

[0082] [Applications of the Invention] device: In some embodiments, the components described in this specification are OLEDs or optoelectronic devices. It can be incorporated into various photosensitive or photoactivating devices, such as S. Therefore, the aforementioned components facilitate charge transfer or energy transfer within the device, and / or It can be useful as a hole transport material. Examples of such devices include organic light-emitting diodes. OLED (Organic Light-Emitting Diode), Organic Integrated Circuit (OIC), Organic Field-Effect Transistor (OFET), Organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells Battery (O-SC), organic optical detector, organic photoreceptor, organic magnetic field quench (field- quench) device (O-FQD), light-emitting fuel cell (LEC) or organic laser diode One example is the O-laser.

[0083] Bulb or lamp: In some embodiments, the electronic device includes an anode, a cathode, and between the anode and the cathode. OL includes at least one organic layer, and at least one of those organic layers is a light-emitting layer. Includes ED. In some embodiments, the device includes OLEDs of different colors. In this configuration, the device includes an array containing a combination of OLEDs. In some embodiments, O The aforementioned combination of LEDs is a combination of three colors (e.g., RGB). In some embodiments, The aforementioned combination of OLEDs is a color that is neither red, green, nor blue (for example, orange and This is a combination of yellow-green. In some embodiments, the above combination of OLEDs is 2 colors, 4 It is a single color or a combination of more than one color. In some embodiments, the device is It has a first surface with a mounting surface and a second surface opposite to it, and has at least one opening The circuit board to be defined, At least one OLED on the mounting surface, the at least one OLED D includes an anode, a cathode, and at least one organic layer between the anode and the cathode. At least one of the organic layers is a light-emitting layer, and has a light-emitting configuration One OLED and A housing for a circuit board, At least one connector located at the end of the housing, The ring and the connector define a package suitable for mounting to lighting equipment, It is an OLED light equipped with a single connector. In some embodiments, the OLED light is configured to emit light in multiple directions. It has multiple OLEDs mounted on a circuit board. In some embodiments, the first direction Some of the light emitted is polarized and radiated in a second direction. In some embodiments, The light emitted in the first direction is polarized using a ray emitter.

[0084] Display or screen: The organic electroluminescent elements of some embodiments of the present invention are screens or It can be used in displays. Compounds according to some embodiments of the present invention are limited to However, it is not possible to deposit it onto the substrate using processes such as vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). To stack. In some embodiments, the substrate provides pixels with a unique aspect ratio. This is a photoplate structure useful in two-sided etching. The screen (also known as (also called a squeegee) is used in the manufacturing process of OLED displays. The design of the work pattern results in very steep, narrow tie bars between pixels in the vertical direction. Furthermore, it allows for the placement of large, wide-ranging oblique-angled apertures in the horizontal direction. While optimizing chemical deposition on the backplane, the pin required for high-resolution displays This enables the creation of fine patterns in Xel. Internal pixel patterning allows for three different aspect ratios in the horizontal and vertical directions. It becomes possible to construct a dimensional pixel aperture. Furthermore, the image within the pixel region The use of "stripes" or halftone circles undercuts these particular patterns. Etching in a specific area is protected until it is removed from the substrate. At that time, all pins The stencil region is processed at a similar etching rate, but its depth is different from that of a halftone pattern. It changes more. By changing the size and spacing of the halftone pattern, the pixels Etching with varying protection rates within the groove becomes possible, which is necessary for forming steep vertical bevels. This enables localized, deep etching. A preferred material for vapor deposition masks is Invar. Invar is used in long, thin sheets in steel mills. It is a metal alloy that has been cold-rolled into a certain shape. Invar is a nickel mask on a spin mandrel. It cannot be electrodeposited. A suitable and low-cost method for forming an opening region within the deposition mask. The method used is a wet chemical etching method. In some embodiments, the screen or display pattern is a pixel on a substrate. It is a matrix. In some embodiments, it is a screen or display pattern. The technology involves lithography (e.g., photolithography and e-beam lithography). It is used and processed. In some embodiments, it is used to create a screen or display pattern. This is processed using wet chemical etching. In further embodiments, a screen or The display pattern is processed using plasma etching.

[0085] Device manufacturing method: OLED displays typically form a large motherboard panel, and then the motherboard It is manufactured by cutting the panel into cell panels. Typically, on the motherboard panel Each cell panel consists of a thin film transistor on a base substrate, having an active layer and source / drain electrodes. A zista (TFT) is formed, a planarization film is applied to the TFT, and pixel electrodes and light emission are formed. The layers, counter electrodes, and encapsulation layers are formed sequentially over time, and then cut from the mother panel. It is formed by this process.

[0086] In another aspect of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided. The method is provided, A process of forming a barrier layer on the base substrate of the mother panel, The process of forming multiple display units on the barrier layer in cell panel units, A process for forming an encapsulation layer on each of the display units of the cell panel. To what extent, The process includes the step of applying an organic film to the interface portion between the cell panels. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx. The edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film is soft and cut in cell panel units by the mother panel. To assist in doing so. In some embodiments, the thin-film transistor (TFT) layer includes an emissive layer and a gate electrode. It has source / drain electrodes and each of the multiple display units is a thin film tracer. A ray tube (TFT) layer, a planarization film formed on the TFT layer, and on the planarization film It may have a light-emitting unit formed thereon, and the interface portion may have an organic coating The film is formed from the same material as the planarization film, and the shape of the planarization film It is formed at the same time as the building process. In some embodiments, the light-emitting unit includes a passivation layer and Between the planarization film and the encapsulation layer that covers and protects the light-emitting unit, TF It is connected to the T layer. In some embodiments of the manufacturing method, the organic film is D It is not connected to either the spray unit or the encapsulation layer.

[0087] Each of the aforementioned organic film and planarization film is made of either polyimide or acrylic. It may include one. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. Furthermore, before forming a barrier layer on one surface of the polyimide base substrate, A step of attaching a carrier substrate made of glass material to another surface of the base substrate, Before cutting along the interface portion, the carrier substrate is separated from the base substrate. It may include the degree. In some embodiments, the OLED display is flexible It's a blue display. In some embodiments, the passivation layer is arranged on the TFT layer to cover the TFT layer. It is an organic film that has been placed on top. In some embodiments, the planarization film is passivated. It is an organic film formed on a chemical layer. In some embodiments, the planarized film These are formed from polyimide or acrylic, as well as from the organic film formed at the edges of the barrier layer. In some embodiments, the planarizing film is used during the manufacturing of an OLED display. And the organic film is formed simultaneously. In some embodiments, the organic film is It may also be formed at the edge of the barrier layer, thereby allowing a portion of the organic film to directly connect to the base The remaining portion of the organic film, in contact with the substrate, surrounds the edges of the barrier layer and is in contact with the barrier layer. To touch.

[0088] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and the pixel electrode It has an organic light-emitting layer disposed between the electrode and the counter electrode. In some embodiments, The aforementioned pixel electrodes are connected to the source / drain electrodes of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, An appropriate voltage is formed between the Xel electrode and the counter electrode, causing the organic light-emitting layer to emit light. , thereby forming an image. Below, an image forming unit having a TFT layer and a light-emitting unit is described. The set is referred to as a display unit. In some embodiments, the display unit is covered to prevent external moisture from penetrating. The encapsulation layer is a thin film-like encapsulation in which organic films and inorganic films are alternately stacked. It may be formed in a structure. In some embodiments, the encapsulation layer is made up of multiple thin films It has a stacked thin-film encapsulation structure. In some embodiments, the interface portion The applied organic film is positioned at intervals from each of the multiple display units. In some embodiments, the organic film is a part of the organic film that is directly connected to the base group. The material is in contact with the remaining portion of the organic film, which surrounds the edges of the barrier layer while also being in contact with the barrier layer. It is formed by [something].

[0089] In some embodiments, the OLED display is flexible and made of polyimide. A flexible base substrate is formed. In some embodiments, the base substrate is made of It is formed on a carrier substrate made of lath material, and then the carrier substrate is separated. In some embodiments, the barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In some embodiments, the barrier layer is patterned according to the size of each cell panel. For example, the base substrate is formed on all surfaces of the mother panel, while the barrier The layers are formed according to the size of each cell panel, thereby creating an indentation between the barrier layers of the cell panels. Grooves are formed in the tough surface. Each cell panel can be cut along these grooves.

[0090] In some embodiments, the manufacturing method further involves cutting along the interface portion. The process includes the formation of grooves in the barrier layer, and at least a portion of the organic film is formed in the grooves. The groove does not penetrate the base substrate. In some embodiments, the TF of each cell panel A T layer is formed, and the passivation layer, which is an inorganic film, and the planarization film, which is an organic film, are formed. It is placed on the TFT layer and covers the TFT layer. For example, a flat plate made of polyimide or acrylic. As the blunting film is formed, the grooves in the interface portion are made of, for example, polyimide or It is covered with an acrylic organic film. This is because each cell panel is at the interface section. When cut along a groove, the resulting impact is absorbed by the organic film, causing cracks. To prevent it from occurring; that is, all barrier layers are completely exposed without the organic film. In this case, when each cell panel is cut along the groove at the interface, the resulting impact acts as a barrier. It is transmitted to the layers, thereby increasing the risk of cracking. However, in some cases In the application method, the grooves in the interface between barrier layers are covered with an organic film, Without the barrier layer, each cell panel is softly cut to absorb the impact that could otherwise be transmitted to the barrier layer. In some embodiments, the interface may be prevented from cracking in the barrier layer. The organic film and the planarizing film covering the grooves are arranged at intervals from each other. For example, when the organic film and the planarization film are connected to each other as a single layer. The display unit is located through the parts where the planarization film and organic film remain. Because external moisture may penetrate, the organic film and the planar film are organic The films are spaced apart from each other so that they are positioned at a distance from the display unit. They are arranged in that manner.

[0091] In some embodiments, the display unit is formed by the formation of a light-emitting unit. The encapsulation layer is placed on the display unit to cover the display unit. It is placed there. This allows the base substrate to be supported after the mother panel has been completely manufactured. The rear substrate is separated from the base substrate. In some embodiments, a laser beam is used to carry When radiated onto the base material, the carrier material exhibits a coefficient of thermal expansion between the carrier material and the base material. Due to the difference, it is separated from the base material. In some embodiments, the mother panel is cut into cell panel units. In this embodiment, the mother panel is cut along the interface portion between the cell panels using a cutter. And it is cut. In some embodiments, the interface along which the mother panel is cut. Because the grooves in the cutting section are covered with an organic film, the organic film absorbs the impact during cutting. It absorbs. In some embodiments, it can prevent cracking in the barrier layer during cutting. In some embodiments, the method reduces the defect rate of the product and stabilizes its quality. . Another embodiment includes a barrier layer formed on a base substrate and a display formed on the barrier layer. The unit, the encapsulation layer formed on the display unit, and the coating applied to the edges of the barrier layer. This is an OLED display having an organic film. [Examples]

[0092] The following describes specific embodiments of the present invention. The materials, processing details, and processing procedures shown below are The present invention may be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is This should not be interpreted restrictively by the specific examples shown below. Furthermore, regarding the evaluation of luminescence characteristics... This includes a source meter (Keithley 2400 series), and a semiconductor parameter analyzer. The (Agilent Technologies: E5273A), Optical Power Meter Measurement Device (New Port Corporation: 1930C), Optical Spectrometer (Ocean Optics: USB2000) ), spectroradiometer (Topcon SR-3) and streak camera (Hamamatsu Photonics) The procedure was performed using a C4334 model manufactured by [Company Name].

[0093] Compound synthesis The following shows examples of the synthesis of the deuterated compounds used in the examples. (Synthesis Example 1) Synthesis of Dorp(D)1 [ka]

[0094] Under a nitrogen atmosphere, 9H-carbazole-1,2,3,4,5,6,7,8-d8(40. (8g, 233 mmol), 3,6-di-tert-butyl-9H-carbazole-1,2,4 ,5,7,8-d6 (35.5g, 124mmol), 1,4-dibromo-2,5-diph Luolobenzene (42.1g, 155mmol), potassium phosphate (98.4g, 464mmol) A solution of dimethylformamide (DMF, 160 mL) containing 1 mmol of dimethylformamide was heated at 150°C. The mixture was stirred for 6 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered. The resulting filtrate was then mixed with Thanol was added, the mixture was stirred for 1 hour, and the precipitated crystals were filtered. The obtained crystals were dispersed in toluene. The filtrate was then filtered to remove insoluble matter. Finally, methanol was added to the resulting filtrate and stirred for 30 minutes. By filtration, a white solid intermediate a (17.3g, 24.9 mmol, yield 20%) was obtained. I got it. MS (ASAP): (M + ). Calcd for. C 38 H 20 D 14 Br2N2:692.7

[0095] [ka]

[0096] Under a nitrogen atmosphere, a toluene solution (612m) of intermediate a (21.2g, 30.6 mmol) was prepared. L) In an outdoor bath at 50°C, n-BuLi (1.6 mol / L hexane solution, 47.8 mL, 76 Add 0.5 mmol) and stir for 2 hours. Cool the reaction mixture to -80°C and add boron tribromide. (18.9g, 75.5 mmol) was added and the mixture was heated to room temperature and stirred for one hour. This reaction solution In addition, 2,4,6-triisopropylphenylmagnesium bromide (1.0 mol / L) Add 137 mL of tetrahydrofuran solution (137 mmol) and stir overnight at room temperature. Methanol was added to this mixture to quench it, and the precipitated crystals were filtered off. The resulting crystals The resulting solution was purified by silica gel column chromatography (dichloromethane:hexane) and yielded a yellow solution. Solid Dorp(D)1 (5.2 g, 5.43 mmol, yield 17.8%) was obtained. MS (ASAP): (M + ). Calcd for. C 68 H 66 D 12 B2N2: 956.8

[0097] (Synthesis Example 2) Synthesis of Dorp(D)2 [ka]

[0098] By carrying out the reaction in the same manner as in Synthesis Example 1 according to the above reaction equation, Dorp(D)2 can be produced. I got it.

[0099] Fabrication and evaluation of an organic electroluminescent device having a light-emitting layer composed of three types of compounds. (Compounds used in the light-emitting layer) The organic electroluminescent element having a light-emitting layer composed of three types of compounds, as described later In the examples and reference examples, the non-deuterated dopant Dorp(H) was used, following the procedure of the above synthesis example. The synthesized deuterated dopants Dorp(D)1-2 and non-deuterated host Host(H) ), deuterated host (D), non-deuterated assist dopant TADF (H), heavy The hydrogenation-assisted dopant TADF(D) was used in the light-emitting layer. Here, "non-deuterated" means This means that it does not contain any deuterium atoms at all, and "deuterated" means reducing the number of deuterium atoms. This means having one of each. [ka]

[0100] (Example 1) Both are organic electroluminescent layers made of three deuterated compounds. Fabrication of lorluminescence elements A glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm is formed. Each thin film is deposited onto the plate using a vacuum deposition method at a vacuum level of 5.0 × 10⁻⁶. -5 It was laminated with Pa. First, IT α-NPD and HAT-CN, described later, were co-deposited onto O from different deposition sources to form a 5 nm thick layer. A layer was formed. At this time, the concentration of HAT-CN was set to 5% by mass. On top of that, the α-NP described later was added. D was formed to a thickness of 60 nm, and then Host(H), described later, was formed on top of it to a thickness of 5 nm. Next, the above Host(D), the above TADF(D), and the above Dorp(D)1 are different. Co-deposition was performed from a deposition source to form a 35 nm thick layer, which served as the light-emitting layer. The concentration of ost(D) is 54.2% by mass, the concentration of TADF(D) is 45.0% by mass, Dor The concentration of p(D)1 was set to 0.8 mass%. Next, SF3-TRZ, described later, was applied to a thickness of 10 nm. After forming, Liq and SF3-TRZ, as described later, are co-deposited from different deposition sources to form a 30nm layer. A layer of a certain thickness was formed. The concentrations of Liq and SF3-TRZ in this layer were 30 mass each. It is % and 70 mass%. Furthermore, Liq, as described later, is formed to a thickness of 2 nm, and then aluminum By depositing aluminum (Al) to a thickness of 100 nm, a cathode is formed, and the organic element of Example 1 is used. It was designed as an octoluminescent element.

[0101] (Reference Examples 1-5) In a light-emitting layer consisting of three compounds, 0-1 of the compounds are deuterated. Fabrication of an organic electroluminescent device The host, assist dopant, and dopant used in the light-emitting layer were changed as shown in Table 2. Except for the above, the organic electroluminescent elements of Reference Examples 1 to 5 were constructed using the same procedure as in Example 1. I made it.

[0102] (Measurement and evaluation) Each organic electroluminescent element in Example 1 and Reference Examples 1-5 was subjected to a current of 12.6 mA / cm². 2 The device is powered on, and the time it takes for the light emission intensity to decrease to 95% of the initial level (LT95) is measured. Also, 25mA / cm² 2 LT95 when powered on, and 50mA / cm 2 The power was turned on. The LT95 was also measured in this case. The measurement results are for the organic electroluminescent element in Reference Example 1. The relative values ​​are shown in Table 2, with LT95 set to 1. [Table 2]

[0103] Reference Example 1 shows that the host, assist dopant, and dopant in the luminescent layer are all deuterium atoms. It is a compound that does not contain [a certain substance], and the luminescent layer does not contain deuterium atoms. In contrast, luminescence In Reference Example 2, where only the host of the layer was replaced with a deuterated compound, the reading was 12.6 mA / cm². 2 of LT95 is 1.25 times longer. Also, only the assist dopant in the luminescent layer is made of heavy water. In Reference Example 3, where the compound was replaced with a synthetic compound, LT95 was 1.65 times longer. In Reference Example 4, where only the dopant in the luminescent layer was replaced with a deuterated compound, LT95 was It has become 1.05 times longer. Based on the results of these reference examples 2-4, the host and assistant Magnification when all three components of the dopant are replaced with deuterated compounds. It is expected that this will be 2.16 times, obtained by multiplying by the magnifications of Reference Examples 2-4 (1.25 × 1.6 (5 × 1.05 = 2.16). Example 1 in which all three components were deuterated compounds. The measured value is 2.23 times higher, indicating that all components in the light-emitting layer have been deuterated. When combined into a compound, the synergistic effect results in a higher magnification than expected. The synergistic effect is 25mA / cm 2 Even with the LT95, it's 50mA / cm 2 This has also been confirmed with the LT95, and the current is large. The more the amount increases, the greater the synergistic effect tends to be (see Table 3). Therefore, the amount contained in the light-emitting layer By deuterizing the three components present, durability is significantly improved through a synergistic effect. This was confirmed. [Table 3]

[0104] (Example 2) An organic light-emitting layer consisting of three compounds, in which two of the compounds are deuterated. Fabrication of electroluminescent elements The host, assist dopant, and dopant used in the light-emitting layer are referred to as Host(D), respectively. The procedure was the same as in Example 1, except that TADF(D) and Dorp(H) were changed. An organic electroluminescent device was fabricated as shown in Example 2.

[0105] (Measurement and evaluation) The organic electroluminescent element of Example 2 was set to 50 mA / cm². 2 The power is turned on, and the light intensity The time (LT95) until the voltage drops to 95% of its initial value was measured. In Example 2, The two components, the host and the assist dopant, are deuterated compounds. The ratio of hydrogenated compound in Reference Example 2, and the deuterated assist dopant only. By multiplying by the magnification of Reference Example 3, which was used as the compound, the expected value of the magnification of Example 2 can be calculated. This can be done (1.22 × 1.55 = 1.89). Compare this predicted value with the measured value in Example 2. The results are shown in Table 4. It can be seen that the measured values ​​are larger than the predicted values. Also, The difference between the predicted value and the measured value was greater for Example 1, which is a compound with three deuterated components. The component is larger than in Example 2, which is a deuterated compound. By using deuterated compounds for more components, better synergistic effects can be achieved. It was confirmed that the effect was obtained. [Table 4]

[0106] Fabrication and evaluation of an organic electroluminescent device having a light-emitting layer composed of four types of compounds. (Compounds used in the light-emitting layer) The organic electroluminescent element having a light-emitting layer composed of four types of compounds, as described later Examples and reference examples show a non-deuterated host. 4 (H), Deuterated Host 4 ( D) Non-deuterated assist dopant TADF 4 (H), deuterized dopant T ADF 4 (D), non-deuterated assist dopant ESM 4 (H), deuterization-assisted do Pant ESM4 (D), non-deuterated dopant Dorp 4 (H), deuterated dopant D orp 4 (D) was used as the light-emitting layer. [ka]

[0107] (Examples 3-7, Reference Examples 6-8) All of these luminescence samples consist of 2-4 deuterated compounds. Fabrication of layered organic electroluminescent devices The light-emitting layer contains the host, assist dopant (TADF and ESM), and dopant shown in Table 5. Examples 3-7 and Reference Examples 6-8 were carried out using the same procedure as Example 1, except for the use of [specific material]. We fabricated electroluminescent elements. In all of these elements, the light-emitting layer The host concentration was 68.7% by mass, and the assist dopant was TADF at a concentration of 30.0% by mass. The ESM concentration was set to 1.0 mass%, and the dopant concentration to 0.3 mass%.

[0108] (Measurement and evaluation) The organic electroluminescent elements in Examples 3-7 and Reference Examples 6-8 were energized to 100°C. The time it takes for the light intensity to decrease from 0 nits to 95% of the initial intensity (LT95). The measurement was taken. The measurement results were set to 1 for the LT95 of the organic electroluminescent element in Reference Example 6. The relative value at that time, and the LT95 of the organic electroluminescent element in Reference Example 8, set to 1. The relative values ​​at that time are shown in Table 5. [Table 5]

[0109] Reference Example 6 shows that the host, TADF, ESM, and dopant of the luminescent layer all contain deuterium atoms. It is a compound that does not contain deuterium atoms, and the luminescent layer does not contain deuterium atoms. In contrast, the luminescent layer In Reference Example 7, where only the host was replaced with a deuterated compound, the LT95 was 1.27 times longer. In addition, in Reference Example 8, where only the TADF in the light-emitting layer is replaced with a deuterated compound, LT95 has become 1.34 times longer. Based on these results, the host and TADF The magnification when both are replaced with deuterated compounds is obtained by multiplying the magnifications of Reference Example 7 and Reference Example 8. It is expected to be 1.70 times (1.27 × 1.34 = 1.70). The measured value in Example 5, in which TADF was used as a deuterated compound, was 1.80 times higher. Therefore, when the two components contained in the light-emitting layer are deuterated, a synergistic effect is achieved, resulting in a higher multiplier than expected. It was confirmed that this is a percentage. [Table 6]

[0110] Reference Example 8 is a compound in which only the TADF of the light-emitting layer contains deuterium atoms, while the host and ESM are different. The dopant is a compound that does not contain a deuterium atom. In contrast, the TADF of the light-emitting layer In addition, in Example 3, ESM was replaced with a deuterated compound, and in addition to the TADF of the light-emitting layer, In Example 4, the panto was also replaced with a deuterated compound, and in addition to the TADF in the light-emitting layer, the host was also deuterated. In Example 5, where the hydrogenated compound was substituted, the LT95 was increased by 1.25 times, 1.20 times, and 1. It has increased 34 times. Based on these results, the host, TADF, ESM, and dopant If any of these compounds contain a deuterium atom, then multiply all the magnifications from Examples 3-5 by 2. It is expected to be multiplied by 0.01 (1.25 × 1.20 × 1.34 = 2.01). In contrast, the host, TADF, ESM, and dopant are all compounds containing a deuterium atom. The measured value in Example 7 is 2.26 times. From this, the four components contained in the light-emitting layer If all of them are made into deuterated compounds, a synergistic effect will result in a higher magnification than expected. This was confirmed. Similarly, for Reference Example 8, where only TADF is a deuterated compound, a dopant was applied. In Example 4, LT95 was replaced with a deuterated compound, and in Reference Example 8, the host was also deuterated. Based on LT95 of Example 5, with the synthesized compound replaced, the host, TADF, and dopant were used. If the three components of the compound are deuterated, it is expected to be 1.61 times that of Reference Example 8. It is thought that (1.20 × 1.34 = 1.61). In contrast, host, TADF, dopamine In Example 6, where all three components of the compound were deuterated, the measured value was 1.72 times higher. This suggests that even if the three components contained in the light-emitting layer are deuterated compounds, It was confirmed that the synergistic effect resulted in a higher multiplier than expected. The results above are summarized in Table 6. The difference between the predicted and measured values ​​is due to the deuterated state of the three components. Example 7, in which all four components were deuterated, was larger than Example 6, which was a compound. This means that more of the components in the light-emitting layer are deuterated compounds. This indicates that doing so will result in a greater effect. [Table 7]

[0111] In Reference Example 8, only TADF is a deuterated compound, whereas ESM is also deuterated. In Example 3, the LT95 compound was increased by 1.25 times. On the other hand, the host and TADF In contrast to Example 6, where the three components of the dopant are deuterated compounds, ESM is also deuterated The LT95 of Example 7, which was converted into a compound, is 1.31 times (2.26 ÷ 1.7) 2 = 1.31). From this, it can be seen that more of the components contained in the luminescent layer are deuterated compounds. If the remaining components are also made into deuterated compounds when it is a substance, the effect will be even greater. It was confirmed that the problem would be resolved.

[0112] [ka] [Industrial applicability]

[0113] The organic electroluminescent element of the present invention has excellent durability. Ming has high potential for industrial use.

Claims

1. an organic electrode having an anode, a cathode, and at least one organic layer between the anode and the cathode. It is a lectroluminescent element, One of the organic layers consists of three or more compounds, and two or more of these compounds An organic electroluminescent element in which each light-emitting layer contains a deuterium atom.

2. Claim 1, each of the three or more compounds constituting the light-emitting layer has a deuterium atom. The organic electroluminescent element described above.

3. The organic electroluminescence according to claim 1, wherein the light-emitting layer is composed of three compounds. element.

4. The organic electroluminescence according to claim 1, wherein the light-emitting layer is composed of four types of compounds. element.

5. The claim states that none of the three or more compounds constituting the light-emitting layer contain heavy metal elements. The organic electroluminescent element described in 1.

6. The light-emitting layer includes at least one host and at least one assist dopant. The host and the assist dopant are The organic electroluminescent element according to claim 1, wherein each element has a deuterium atom.

7. The light-emitting layer contains at least one host, at least one assist dopant, and a small It contains at least one type of Dopant, The at least one host, the at least one assist dopant, and the The organic element according to claim 1, wherein each of at least one dopant has a deuterium atom. Ctroluminescent element.

8. The light-emitting layer comprises at least one dopant having a boron atom, as described in claim 1. Organic electroluminescent element.

9. The organic compound according to claim 8, wherein the dopant is a compound represented by the following general formula (1). Lectroluminescent element. General formula (1) 【Chemistry 1】 [In general formula (1), R １ and R ２ Each of these independently consists of a hydrogen atom, a deuterium atom, or Represents a substituent. R ３ ~R ２６ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. Or, other R ３ ~R ２６ They are bonded to each other to form a ring structure. ３ ~R ２６ Of these, Combinations that can form an annular structure are R ３ and R ４ 、R ４ and R ５ 、R ５ and R ６ 、R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １ ４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R ２ ０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２ ５ and R ２６ However, R １ ~R ２６ At least one of them contains a deuterium atom.

10. Claims that the light-emitting layer includes a host represented by the following general formula (2) or the following general formula (3). The organic electroluminescent element described in item 1. 【Chemistry 2】 [In general formulas (2) and (3), R ３１ ~R ４１ and R ５１ ~R ６１ teeth, Each independently consists of a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or R represents an unsubstituted alkyl group. ４２ ~R ４９ Each is independently a hydrogen atom, a deuterium atom, and Represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group, or other R ４２ ~R ４９ They are bonded to each other to form a ring structure. ４２ ~R ４９ Among the ring structures The possible combinations that form the structure are R ４２ and R ４３ , R ４３ and R ４４ , R ４４ and R ４５ , R ４ ６ and R ４７ , R ４７ and R ４８ , R ４８ and R ４９ That is. R ６２ ~R ６９ Each of them independently Elementary atoms, deuterium atoms, substituted or unsubstituted aryl groups, or substituted or unsubstituted aryl groups Represents a lukyl group, or other R groups ６２ ~R ６９ They are bonded to each other to form a ring structure. ６ ２ ~R ６９ Among these, the combinations that can form a ring structure are R ６２ and R ６３ , R ６３ and R ６４ , R ６４ and R ６５ , R ６６ and R ６７ , R ６７ and R ６８ , R ６８ and R ６９ That is. However, R ３１ to R ４９ at least one of which contains a deuterium atom, and at least one of R ５１ to R ６９ の少なくとも1個 at least one of which It contains a deuterium atom.

11. R ４２ and R ４３ , R ４３ and R ４４ , R ４４ and R ４５ , R ４６ and R ４７ , R ４７ and R ４８ , R ４８ and R ４９ At least one pair of these are joined together to form a ring structure, R ６２ and R ６３ , R ６３ and R ６４ , R ６４ and R ６５ , R ６６ and R ６７ , R ６７ and R ６８ , R ６８ and R ６９ The organic e according to claim 10, wherein at least one set of is bonded to each other to form a ring structure. Lectroluminescent element.

12. The organic according to claim 1, wherein the light-emitting layer includes an assist dopant which is a delayed fluorescence material. Electroluminescent element.

13. The assist dopant is substituted or unsubstituted, having at least one deuterium atom. A carbazolyl group and a substituted or unsubstituted tria having at least one deuterium atom The organic electroluminescent element according to claim 12, having a dinyl group or a cyano group. child.

14. The organic electroluminescent element according to claim 1, further comprising an electron barrier layer.

15. A compound represented by the following general formula (1). General formula (1) 【Transformation 3】 [In general formula (1), R １ and R ２ Each of these independently consists of a hydrogen atom, a deuterium atom, or Represents a substituent. R ３ ~R ２６ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. Or, other R ３ ~R ２６ They are bonded to each other to form a ring structure. ３ ~R ２６ Of these, The combinations that can form a ring structure are R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １ ４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R ２ ０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２ ５ and R ２６ However, R １ ~R ２６ At least one of them contains a deuterium atom.

16. The compound according to claim 15, having any of the following structures. 【Chemistry 4】

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