Organic electric field light-emitting element, its manufacturing method and main material composition

Abstract

This invention provides an organic electric field light-emitting element, its manufacturing method, and a composition of host materials. The organic EL element comprises one or more light-emitting layers between opposing anodes and cathodes. At least one light-emitting layer contains a host material comprising a first host material, a second host material, and a third host material, as well as a luminescent dopant material. The LUMO energy of the first host material is below -1.95 eV, and when the LUMO energies of the first host material, the second host material, and the third host material are set to LM1, LM2, and LM3, respectively, LM2 ≥ LM3 ≥ LM1 is satisfied. Suitable first host materials are indole-carbazole compounds represented by general formula (1); suitable second host materials are biscarbazole compounds represented by general formula (2); and suitable third host materials are indole-carbazole compounds represented by general formula (5).

Description

Technical Field

[0001] This invention relates to an organic electric field light-emitting element (referred to as an organic EL element), its manufacturing method, and a main material composition. Background Technology

[0002] By applying a voltage to an organic EL element, holes are injected into the emissive layer from the anode, and electrons are injected into the emissive layer from the cathode. In the emissive layer, the injected holes and electrons recombine to generate excitons. At this point, according to the statistical law of electron spin, singlet and triplet excitons are generated in a 1:3 ratio. Regarding fluorescent organic EL elements that utilize light emission generated by singlet excitons, the internal quantum efficiency is considered to be limited to 25%. On the other hand, it is known that phosphorescent organic EL elements using light emission generated by triplet excitons achieve an internal quantum efficiency of up to 100% when intersystem crossing from singlet excitons is efficiently performed.

[0003] Recently, high-efficiency organic EL devices utilizing delayed fluorescence have been developed. For example, an organic EL device utilizing the triplet-triplet fusion (TTF) mechanism, one of the mechanisms of delayed fluorescence, is known. The TTF mechanism utilizes the phenomenon of generating a singlet exciton through the collision of two triplet excitons, and it is theoretically believed to increase the internal quantum efficiency to 40%. However, compared with phosphorescent organic EL devices, the efficiency is low, thus requiring further improvement in efficiency.

[0004] Patent Document 1 discloses an organic EL device utilizing a thermally activated delayed fluorescence (TADF) mechanism. The TADF mechanism utilizes the phenomenon that, in materials with a small energy difference between singlet and triplet levels, an inverse intersystem crossing occurs from a triplet exciton to a singlet exciton, theoretically increasing the internal quantum efficiency to 100%. Currently, for practical devices utilizing fluorescent or phosphorescent materials, there is a demand for further improvements in efficiency, voltage characteristics, and drive lifetime. Furthermore, for devices utilizing the TADF mechanism, there is a requirement to achieve practical-level performance characteristics.

[0005] Existing technical documents

[0006] Patent documents

[0007] Patent Document 1: WO2011 / 070963

[0008] Patent Document 2: WO2013 / 062075

[0009] Patent Document 3: US Publication No. 2014 / 0374728

[0010] Patent Document 4: WO2011 / 136755

[0011] Patent Document 5: WO2016 / 194604

[0012] Patent Document 6: WO2018 / 0198844

[0013] Patent Document 7: US Publication No. 2017 / 098778

[0014] Patent Document 8: KR Publication No. 2020-017727

[0015] Non-patent literature

[0016] Non-patent literature 1: Advanced Materials (Adv. Mater) (2011, 23, 3590-3596)

[0017] Patent documents 2 and 3 disclose the use of biscarbazole compounds as mixed host materials.

[0018] Patent document 4 discloses the use of a host material, which is premixed with a variety of host materials containing an indolecarbazole compound.

[0019] Patent documents 5 and 6 disclose the use of a mixed host material comprising an indobenzocarbazole compound and a biscarbazole compound.

[0020] Patent document 7, patent document 8 and non-patent document 1 disclose the use of a mixed host material comprising three host materials.

[0021] However, none of these measures are sufficient, and further improvements are hoped for. Summary of the Invention

[0022] To apply organic EL elements to display elements such as flat panel displays or light sources, it is necessary to ensure stability during driving while improving the driving voltage and luminous efficiency of the element. The purpose of this invention is to provide an organic EL element with low driving voltage, high efficiency, and long driving lifetime characteristics, as well as suitable materials for such organic EL elements.

[0023] To improve the lifetime characteristics of organic EL devices, it is effective to increase the stability of the active state compared to the substrate state (charged state or excited state) of the material used, and to reduce the frequency of each molecule becoming active, i.e., to disperse the active state among a large number of molecules. In particular, to disperse the excited state, it is important to appropriately adjust the injection and transport of electrons and holes into the light-emitting layer, i.e., to adjust the charge balance. Furthermore, by adjusting the charge balance, leakage of electrons, holes, and excitons into the peripheral layer can be suppressed, which is also related to improved lifetime and thus improved efficiency.

[0024] To achieve the aforementioned point, the following method is currently employed: Two host materials, comprising a combination of an electron injection transport host and a hole injection transport host, are mixed around the phosphorescent emitting layer, and the mixing ratio is adjusted to optimize charge balance. However, while mixing the two host materials improves lifetime characteristics, it deteriorates charge injection transport, leading to an increase in driving voltage.

[0025] Through diligent research, the inventors discovered that by using specific first, second, and third host materials, an organic EL element exhibiting excellent properties was achieved, thus completing this invention.

[0026] This invention relates to an organic electric field light-emitting element, which includes one or more light-emitting layers between opposing anodes and cathodes. The organic electric field light-emitting element is characterized in that: at least one light-emitting layer contains a host material comprising a first host material, a second host material, and a third host material, as well as a light-emitting dopant material. The lowest unoccupied molecular orbital (LUMO) energy of the first host material is below -1.95 eV. When the LUMO energies of the first host material, the second host material, and the third host material are set to LM1, LM2, and LM3, respectively, LM2 ≥ LM3 ≥ LM1 is satisfied.

[0027] The preferred configuration is that the LUMO energy of the second host material is -1.54 eV or higher, the LUMO energy of the third host material is -1.94 eV to -1.77 eV, or the triplet excitation (T1) energy of the first host material, the second host material, and the third host material is 2.55 eV or higher.

[0028] The preferred configuration is that at least three of the materials, namely the first main material, the second main material, the third main material, and the luminescent dopant material, are deposited by a single vapor deposition source, or the first main material, the second main material, and the third main material are deposited by a single vapor deposition source.

[0029] Examples of luminescent dopant materials include fluorescent or phosphorescent materials, including those containing thermally activated delayed fluorescence.

[0030] The first host material may be a compound represented by the following general formula (1).

[0031] [Chemistry 1]

[0032]

[0033] Here, ring A is the heterocyclic ring represented by equation (1a), and ring A and its adjacent rings are condensed at any position.

[0034] R 1 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together.

[0035] a, c, and d each independently represent integers from 0 to 4, and b represents integers from 0 to 2.

[0036] L 1 and L 11 It is independently an aromatic hydrocarbon group having 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group having 3 to 17 carbon atoms, with at least one of the aromatic heterocyclic groups being said aromatic heterocyclic groups.

[0037] Ar 1 and Ar 11 Each of these can be independently represented as an aromatic hydrocarbon group having 6 to 30 carbon atoms, an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group having 2 to 7 of these aromatic rings.

[0038] Here, L is preferred. 1 and L 11 At least one of them is a substituted or unsubstituted nitrogen-containing six-membered ring group, or a substituted or unsubstituted condensed aromatic heterocyclic group containing a nitrogen-containing six-membered ring.

[0039] As compounds represented by general formula (1), there are compounds represented by formula (11), formula (12) or formula (13).

[0040] [Chemistry 2]

[0041]

[0042] [Chemistry 3]

[0043]

[0044] Here, R 1 , Ring A, Ar 1 a and b have the same meaning as in general formula (1).

[0045] Y represents O, S, NAr 14 , or CAr 15 Ar 16 ,

[0046] Ar 13 Ar 14 Ar 15 and Ar 16 Each of these groups independently represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted formed by the linkage of 2 to 5 of these aromatic rings.

[0047] m represents an integer from 0 to 4, n represents an integer from 0 to 3, and l represents an integer from 0 to 4.

[0048] L 12 This refers to aromatic hydrocarbon groups with 6 to 30 carbon atoms, whether substituted or unsubstituted.

[0049] L 13 Indicates a nitrogen-containing six-membered cyclic group.

[0050] Ar 12 Independently refers to an aromatic hydrocarbon group having 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 5 of these aromatic rings.

[0051] The second main material may be a compound represented by the following general formula (2), general formula (3), or general formula (4).

[0052] [Chemistry 4]

[0053]

[0054] Here, Ar 21 and Ar 22 Independently representing hydrogen, deuterium, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by two linked aromatic rings of these. L 21 and L 22 Independently represents direct bonding or phenylene.

[0055] [Chemistry 5]

[0056]

[0057] Here, ring B is the heterocyclic ring represented by equation (3a), and ring B and its adjacent rings are condensed at any position.

[0058] R 3 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together.

[0059] L 31 Independently, it is an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, either substituted or unsubstituted.

[0060] L 32 Independently, it is an aromatic hydrocarbon group with 6 to 10 carbon atoms, either substituted or unsubstituted.

[0061] Ar 31 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted linked aromatic group formed by the linkage of 2 to 5 of these aromatic rings.

[0062] Ar 32 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic group with 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 5 of these aromatic rings.

[0063] i represents an integer from 0 to 4, and j represents an integer from 0 to 2.

[0064] f is the repeating number, representing integers from 1 to 3; g is the repeating number, independently representing integers from 0 to 3; and h is the substitution number, representing integers from 0 to 7.

[0065] [Chemistry 6]

[0066]

[0067] Here, Ar 41 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, substituted or unsubstituted, an aromatic heterocyclic group with 3 to 17 carbon atoms, substituted or unsubstituted, or a linked aromatic group consisting of 2 to 5 of these aromatic rings. In Ar 41 In the case of hydrogen atoms, the hydrogen atoms may also be substituted with deuterium.

[0068] R 41 Each of the following is independently a deuterium group, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), wherein the group is not a carbazolyl group.

[0069] x is a repetition number, independently representing an integer from 1 to 4, with at least one x being an integer from 2 to 4. y is a substitution number, representing an integer from 1 to 4. When x and y are 2 or higher, the multiple carbazo groups in the formula can be the same or different. z is an integer from 0 to 3.

[0070] The third main material can be a compound represented by the following general formula (5).

[0071] [Chemistry 7]

[0072]

[0073] Here, ring D is the heterocyclic ring represented by equation (5a), and ring D and its adjacent rings are condensed at any position.

[0074] R 5 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together.

[0075] p, r, and s independently represent integers from 0 to 4, and q represents integers from 0 to 2.

[0076] L 5 and L 51 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, at least one of which is the aromatic heterocyclic group.

[0077] Ar 5 and Ar 51 Each of these can be independently represented as an aromatic hydrocarbon group having 6 to 30 carbon atoms, an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group having 2 to 7 of these aromatic rings.

[0078] The preferred form is: L 5 and L 51 At least one of them is a substituted or unsubstituted nitrogen-containing six-membered ring, or a condensed aromatic heterocyclic group containing a nitrogen-containing six-membered ring.

[0079] The third main material may be a compound represented by the following formula (51).

[0080] [Chemistry 8]

[0081]

[0082] Here, R 5 D, Ar 5 p, and q have the same meaning as general formula (5).

[0083] Compared to the total of the first main material, the second main material, and the third main material, the proportion of the first main material may exceed 1.0 wt% and be less than 30 wt%, and the proportion of the third main material may exceed 5.0 wt% and be less than 80 wt%.

[0084] Furthermore, this invention provides a method for manufacturing an organic electric field light-emitting element (OLED), characterized in that: when manufacturing an OLED containing one or more light-emitting layers between opposing anodes and cathodes, and at least one light-emitting layer comprising a host material and a luminescent dopant material, a host material composition and a luminescent dopant material are vapor-deposited to form the light-emitting layer. The host material composition comprises a first host material, a second host material, and a third host material, and the LUMO energy of the first host material is -1.95 eV or less. Furthermore, this invention provides a host material composition used in the method for manufacturing the OLED.

[0085] Currently, in the practical application of a hybrid approach using two main materials centered around phosphorescent light-emitting elements, while lifetime characteristics are improved, charge injection and transport properties deteriorate, leading to an increase in driving voltage. In other words, lifetime characteristics and driving voltage are often trade-offs.

[0086] In contrast, in this invention, by using a mixture of three host materials containing host materials with low LUMO energy, good efficiency and lifetime characteristics can be maintained, while the drive voltage can be improved.

[0087] In existing methods that combine electron-carrying and hole-carrying materials to optimize charge balance for improved lifetime characteristics, the transport speeds of electrons and holes are reduced, resulting in an increase in driving voltage. However, it is believed that by appropriately mixing in a material with low LUMO energy, good efficiency and lifetime characteristics can be maintained under optimized charge balance, while improving electron injection and reducing driving voltage. Attached Figure Description

[0088] Figure 1 This is a schematic cross-sectional view showing an example of an organic EL element. Detailed Implementation

[0089] The organic EL element of the present invention has an organic layer comprising multiple layers between opposing anodes and cathodes, at least one of which is a light-emitting layer, and multiple light-emitting layers may exist. Furthermore, at least one light-emitting layer contains a first host material, a second host material, a third host material, and a light-emitting dopant material. The light-emitting layer may include a vapor-deposited layer.

[0090] In this specification, the materials comprising the first host material, the second host material, and the third host material are collectively referred to as host materials. Furthermore, the materials comprising the first host material, the second host material, and the third host material used to form the light-emitting layer using a vapor deposition method are referred to as host material compositions.

[0091] When the LUMO energies of the first, second, and third host materials are set to LM1, LM2, and LM3 respectively, LM2 ≥ LM3 ≥ LM1 is satisfied. Preferably, LM2 > LM3 > LM1 is satisfied.

[0092] The LUMO energy LM1 of the first host material is -1.95 eV or less. Preferably, it is -1.97 eV or less, and even more preferably -2.00 eV or less.

[0093] The LUMO energy LM2 of the second host material can be -1.54 eV or higher, preferably -1.30 eV or higher, and even more preferably -1.07 eV or higher.

[0094] The LUMO energy LM3 of the third host material can be -1.94eV to -1.77eV, preferably -1.94eV to -1.83eV, and even more preferably -1.94eV to -1.87eV.

[0095] The triplet excitation (T1) energies of the first, second, and third host materials are preferably 2.55 eV or higher, more preferably 2.60 eV or higher, and even more preferably 2.65 eV or higher.

[0096] As the first, second, and third main materials, any compound that satisfies the aforementioned characteristics is acceptable, and preferably is one as shown below.

[0097] The compounds suitable as the first host material are those represented by the general formula (1).

[0098] In general formula (1),

[0099] Ar 1 and Ar 11Each of these groups independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 7 of these aromatic rings. Preferably, it refers to a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 7 of these aromatic rings.

[0100] As Ar 1 and Ar 11Specific examples of unsubstituted aromatic hydrocarbon groups, unsubstituted aromatic heterocyclic groups, or unsubstituted linked aromatic groups include: benzene, cyclopentadiene, indene, naphthalene, azulene, cycloheptadiene, cyclooctadiene, benzodiindene, acenaphthene, phenanthracene, anthracene, trindene, fluoranthene, phenanthrene, phenanthrene, phenanthrene, phenanthrene, phenanthrene, phenanthrene, pyrene, 1,2-benzophenanthrene, tetraphene, pleiadene, styrene, perylene, pentanphenene, pentaphenyl, tetraphenylene, cholanthracene, hexane, hexane, rubicene, hexabenzophenyl, and naphthalene. Heptanyl, anthracene, furan, benzofuran, isobenzofuran, xanthene, oxanthrene, dibenzofuran, peri-xanthenoxanthene, thioxanthene, thianthrene, phenoxathiin, thionaphthene, isothianaphthene, thiophthene, naphthothi Phenophenanthrene, dibenzothiophene, pyrrole, pyrazole, tellurazole, selenazole, thiazole, isothiazole, oxazole, furazolidone, indolizine, indole, isoindole, indazole, purine, quinazine, isoquinoline, imidazole, naphthidine, phthalazine, carbazole, benzodiazepines, quinoxaline, cinnoline, quinoline, pteridine, phenanthridine, acridine, perimidine The group is formed by removing one hydrogen atom from a compound consisting of phenanthroline, phenazine, carboline, phenotellurazine, phenoselenazine, phenothiazine, phenoxazine, 1,8,9-anthyridine, benzothiazole, benzimidazole, benzoxazole, benziisoxazole, benziisothiazole, or compounds consisting of 2 to 7 of these. Preferably, the group is formed from a compound consisting of pyridine, pyrimidine, triazine, dibenzofuran, dibenzothiophene, carbazole, benzene, naphthalene, or compounds consisting of 2 to 7 of these.

[0101] R 1Independently, it is a deuterium group, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having 2 to 5 of these aromatic rings linked together. Preferably, it is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 12 carbon atoms (substituted or unsubstituted).

[0102] In R 1 When the group is an aliphatic hydrocarbon group, it can be linear, branched, or cyclic, preferably an aliphatic hydrocarbon group with 1 to 8 carbons, and more preferably an alkyl group with 1 to 6 carbons.

[0103] Specific examples of aliphatic hydrocarbon groups include: methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, or decyl. Methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, or octyl are preferred, and methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, and cyclohexyl are even more preferred.

[0104] As R 1 Specific examples include unsubstituted aromatic hydrocarbon groups with 6 to 30 carbon atoms, unsubstituted aromatic heterocyclic groups with 3 to 17 carbon atoms, or unsubstituted linked aromatic groups, except for cases where the aromatic ring linked to the aromatic group has 2 to 5 linkages, and Ar 1 and Ar 11 The situation is the same.

[0105] a, b, c, and d represent substitution numbers, where a, c, and d each independently represent an integer from 0 to 4, preferably an integer from 0 to 3, and even more preferably 0 to 1. b represents an integer from 0 to 2, preferably 0 to 1.

[0106] In this specification, linked aromatic groups refer to aromatic groups in which the carbon atoms of the aromatic ring are linked together by single bonds. An aromatic group is formed by the linkage of two or more aromatic groups; these can be linear or branched. The aromatic group can be an aromatic hydrocarbon group or an aromatic heterocyclic group; multiple aromatic groups can be identical or different.

[0107] In this specification, the unsubstituted aromatic hydrocarbon group, aromatic heterocyclic group, nitrogen-containing six-membered ring group, condensed aromatic heterocyclic group, carbazole group, or linked aromatic group may each have substituents. When substituents are present, the substituents are aliphatic hydrocarbon groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 5 carbon atoms, alkenyl groups having 2 to 5 carbon atoms, diarylamino groups having 12 to 44 carbon atoms, deuterium, halogen, or cyano.

[0108] Furthermore, the number of substituents can be 0 to 5, preferably 0 to 3. When calculating the carbon number of aromatic hydrocarbon groups and aromatic heterocyclic groups having substituents, the carbon number of the substituents is not included. However, it is preferable that the total carbon number, including the carbon number of the substituents, satisfies the aforementioned range.

[0109] Specific examples of the substituents include: cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, diphenylamino, naphthylphenylamino, dinaphthylamino, dianthrylamino, diphenoxyamino, dipyreneamino, etc. Preferably, the substituents include: cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, diphenylamino, naphthylphenylamino, or dinaphthylamino.

[0110] In this specification, hydrogen can be understood to be deuterium. Therefore, in general formulas (1) to (5), the skeleton such as indolocarbazole ring or carbazole ring, R 1 L 11 Ar 11 When the radical has hydrogen, some or all of it can be deuterium.

[0111] L 1 and L 11 Independently, it is an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, either substituted or unsubstituted, with at least one being an aromatic heterocyclic group. Preferably, it is L. 1 and L 11 At least one of them is a substituted or unsubstituted nitrogen-containing six-membered ring, or a substituted or unsubstituted condensed aromatic heterocyclic group containing a nitrogen-containing six-membered ring.

[0112] As L 1 and L 11 Specific examples of unsubstituted aromatic groups or unsubstituted aromatic heterocyclic groups, except for those with a c+1 or d+1 valence, are related to Ar. 1 and Ar 11 The same applies. Preferably, it is a group formed from pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, naphthidine, phenazine, dibenzofuran, dibenzothiophene, carbazole, benzene, or naphthalene.

[0113] Specific examples of unsubstituted nitrogen-containing six-membered cyclic groups, or unsubstituted condensed aromatic heterocyclic groups containing nitrogen-containing six-membered rings, include pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, naphthidine, or phenazine.

[0114] As a preferred form of the general formula (1), there is formula (11), and as a preferred form of formula (11), there are formula (12) or formula (13).

[0115] Here, in equations (11) to (13), the symbols common to general equation (1) have the same meaning.

[0116] That is, R 1 , Ring A, Ar 1 a, b and general formula (1) have the same meaning.

[0117] In equation (12), Y represents O, S, and NAr. 14 CAr 15 Ar 16 Preferably O, S, or NAr 14 Therefore, O or S is preferred.

[0118] Ar 13 Ar 14 Ar 15 and Ar 16 Each of these groups independently represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having 2 to 5 of these aromatic rings. Preferably, it represents an aromatic hydrocarbon group having 6 to 24 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having 2 to 5 of these aromatic rings. More preferably, it represents an aromatic hydrocarbon group having 6 to 18 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 12 carbon atoms (substituted or unsubstituted), or a linked aromatic group having 2 to 5 of these aromatic rings.

[0119] As Ar 13 Ar 14 Ar 15 and Ar 16 Specific examples when it is an unsubstituted aromatic hydrocarbon group, an unsubstituted aromatic heterocyclic group, or an unsubstituted linked aromatic group, and Ar 1 and Ar 11 The situation is the same. Specifically, when an aromatic group is linked, 2 to 5 aromatic rings are linked. As a specific example when the group is an aliphatic hydrocarbon, it is similar to R... 1 The same applies to aliphatic hydrocarbon groups.

[0120] m represents an integer from 0 to 4, and n represents an integer from 0 to 3. m and n are preferably 0 to 2, and even more preferably 0 to 1.

[0121] In equation (13), L 12The term represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, whether substituted or unsubstituted, preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, and more preferably a phenylene group represented by either formula (1b) or formula (1c).

[0122] [Chemistry 9]

[0123]

[0124] L 13 It represents a nitrogen-containing six-membered ring group, preferably pyridyl or triazine, and more preferably triazine.

[0125] Ar 12 Independently refers to an aromatic hydrocarbon group having 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 5 of these aromatic rings. Preferably, it refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 5 of these aromatic rings.

[0126] As Ar 12 Specific examples of unsubstituted aromatic hydrocarbon groups, unsubstituted aromatic heterocyclic groups, or unsubstituted linked aromatic groups, except for cases where the aromatic ring linked to the aromatic group has 2 to 5 linkages, and Ar 1 and Ar 11 The situation is the same.

[0127] l represents an integer from 0 to 4, preferably from 0 to 2.

[0128] The following are specific examples of compounds represented by general formula (1), but are not limited to these exemplified compounds.

[0129] [Chemistry 10]

[0130]

[0131] [Chemistry 11]

[0132]

[0133] [Chemistry 12]

[0134]

[0135] [Chemistry 13]

[0136]

[0137] [Chemistry 14]

[0138]

[0139] [Chemistry 15]

[0140]

[0141] [Chemistry 16]

[0142]

[0143] [Chemistry 17]

[0144]

[0145] [Chemistry 18]

[0146]

[0147] [Chemistry 19]

[0148]

[0149] [Chemistry 20]

[0150]

[0151] [Chemistry 21]

[0152]

[0153] [Chemistry 22]

[0154]

[0155] [Chemistry 23]

[0156]

[0157] [Chemistry 24]

[0158]

[0159] [Chemistry 25]

[0160]

[0161] [Chemistry 26]

[0162]

[0163] [Chemistry 27]

[0164]

[0165] [Chemistry 28]

[0166]

[0167] [Chemistry 29]

[0168]

[0169] [Chemistry 30]

[0170]

[0171] [Chemistry 31]

[0172]

[0173] [Chemistry 32]

[0174]

[0175] [Chemistry 33]

[0176]

[0177] [Chemistry 34]

[0178]

[0179] [Chemistry 35]

[0180]

[0181] As the second main material, it is preferably a compound represented by general formula (2), general formula (3) or general formula (4).

[0182] In general formula (2), Ar 21 and Ar 22 Independently, it refers to hydrogen, deuterium, an aromatic hydrocarbon group having 6 to 14 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted two of these aromatic rings. Preferably, it is hydrogen, an aromatic hydrocarbon group having 6 to 12 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted two of these aromatic rings; more preferably, it is hydrogen, an aromatic hydrocarbon group having 6 to 10 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted two of these.

[0183] Ar 21 and Ar 22Specific examples of unsubstituted aromatic hydrocarbon groups, unsubstituted aromatic heterocyclic groups, or unsubstituted linked aromatic groups include linked aromatic groups formed by removing one H atom from compounds consisting of benzene, naphthalene, anthracene, phenanthrene, fluorene, dibenzofuran, dibenzothiophene, carbazole, pyridine, or two linked aromatic rings of these. Preferably, examples include aromatic groups formed from benzene, naphthalene, pyridine, dibenzofuran, dibenzothiophene, carbazole, or two linked aromatic rings of these; more preferably, aromatic groups formed from benzene or naphthalene. 21 、or Ar 22 It can be hydrogen, and in the case mentioned above, the other can be the aromatic group (referring to an aromatic hydrocarbon group or an aromatic heterocyclic group) or a linked aromatic group.

[0184] L 21 and L 22 The phenylene oxide can be directly bonded or be phenylene, and can be any of ortho-phenylene, meta-phenylene, and para-phenylene. Para-phenylene or meta-phenylene is preferred. Additionally, in L... 21 and L 22 When direct bonding is used, Ar is preferred. 21 and Ar 22 It is neither hydrogen nor deuterium.

[0185] The following are specific examples of compounds represented by general formula (2), but are not limited to these exemplified compounds.

[0186] [Chemistry 36]

[0187]

[0188] [Chemistry 37]

[0189]

[0190] [Chemistry 38]

[0191]

[0192] In the general formula (3), ring B is the heterocyclic ring represented by formula (3a), and ring B and the adjacent ring are condensed at any position.

[0193] R 3Independently, it is a deuterium group, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having 2 to 5 of these aromatic rings linked together. Preferably, it is an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 12 carbon atoms (substituted or unsubstituted). More preferably, it is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, a phenyl group having substituted or unsubstituted, or an aromatic heterocyclic group having 3 to 6 carbon atoms (substituted or unsubstituted).

[0194] As R 3 Specific examples of aliphatic hydrocarbon groups, aromatic hydrocarbon groups, aromatic heterocyclic groups, or groups linked to aromatic groups, and the R group described above. 1 The situation is the same.

[0195] L 31 It is independently an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, either substituted or unsubstituted. Preferably, it is an aromatic hydrocarbon group with 6 to 10 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 12 carbon atoms, either substituted or unsubstituted.

[0196] L 32 It is independently an aromatic hydrocarbon group with 6 to 10 carbon atoms, either substituted or unsubstituted, preferably a group derived from benzene.

[0197] Ar 31 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted linked aromatic group formed by the linkage of 2 to 5 of these aromatic rings. Here, the aromatic ring is selected from aromatic hydrocarbon rings and carbazole rings.

[0198] Preferably, it is a substituted or unsubstituted aromatic hydrocarbon group with 6 to 10 carbon atoms, a carbazole group, or a substituted or unsubstituted linked aromatic group formed by linking 2 to 3 of these aromatic rings.

[0199] Specific examples of unsubstituted aromatic hydrocarbon groups include phenyl or naphthyl.

[0200] Ar 32It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic group with 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by linking 2 to 5 of these aromatic rings. Preferably, it is an aromatic hydrocarbon group with 6 to 10 carbon atoms, substituted or unsubstituted aromatic heterocyclic group with 3 to 12 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by linking 2 to 5 of these aromatic rings.

[0201] As R 3 L 31 and Ar 32 Specific examples of unsubstituted aromatic hydrocarbon groups or aromatic heterocyclic groups, except for L 31 Except for the case where the base is divalent or h+1 valent, with Ar 1 and Ar 11 The situation is the same. Additionally, as Ar... 32 and R 3 For specific examples of unsubstituted linked aromatic groups, except for cases where 2 to 5 aromatic rings are linked, and Ar 1 and Ar 11 The situation is the same.

[0202] f is the repetition number, representing an integer from 1 to 3; g is the repetition number, representing an integer from 0 to 3; and h is the substitution number, each independently representing an integer from 0 to 7. Preferably, f is 1, g is 0 to 1, and h is 0 to 2. i represents an integer from 0 to 4, and j represents an integer from 0 to 2, preferably i is 0 or 1, and j is 0 or 1.

[0203] As compounds represented by general formula (3), compounds represented by formula (31) or formula (32) are preferably listed below.

[0204] [Chemistry 39]

[0205]

[0206] In equation (31) or equation (32), rings B and R 3 L 32 Ar 31 The meanings of , g, h, i and j are the same as those in general formula (3).

[0207] The following are specific examples of compounds represented by general formula (3), but are not limited to these exemplified compounds.

[0208] [Chemistry 40]

[0209]

[0210] [Chemistry 41]

[0211]

[0212] [Chemistry 42]

[0213]

[0214] [Chemistry 43]

[0215]

[0216] [Chemistry 44]

[0217]

[0218] [Chemistry 45]

[0219]

[0220] Next, the general formula (4) will be explained.

[0221] In general formula (4), Ar 41 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, substituted or unsubstituted, an aromatic heterocyclic group with 3 to 17 carbon atoms, or a linked aromatic group consisting of 2 to 5 of these aromatic rings. Preferably, it is an aromatic hydrocarbon group with 6 to 10 carbon atoms, substituted or unsubstituted, an aromatic heterocyclic group with 3 to 12 carbon atoms, or a linked aromatic group consisting of 2 to 5 of these aromatic rings.

[0222] As Ar 41 Specific examples of unsubstituted aromatic hydrocarbon groups, unsubstituted aromatic heterocyclic groups, or unsubstituted linked aromatic groups, except for the case of y-valent groups and the case of 2 to 5 aromatic rings linked together when linked aromatic groups are involved, are related to Ar. 1 and Ar 11 Same. Preferably, it is a group formed by a compound consisting of pyridine, pyrimidine, triazine, dibenzofuran, dibenzothiophene, benzene, naphthalene, or 2 to 5 of these linked together.

[0223] R 41 Each group is independently composed of deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), wherein it is not a carbazole group. Advantageously, the group does not contain a carbazole ring. Preferably, it is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted).

[0224] R 41Specific examples of R when it is an aliphatic hydrocarbon group 1 The situation is the same.

[0225] Regarding R 41 Specific examples of aromatic hydrocarbon groups or aromatic heterocyclic groups, except for the absence of carbazole, are related to Ar. 1 and Ar 11 The situation is the same.

[0226] y is a substitution number, representing an integer from 1 to 4. It is preferably 1 or 2, and more preferably 1.

[0227] x is a repeating number, each independently representing an integer from 1 to 4. Preferably, it is 1 to 3. However, at least one x is an integer from 2 to 4. z is an integer from 0 to 3, preferably 0 or 1.

[0228] The sum of x (the total number of carbazole groups) can be an integer from 2 to 12, preferably from 2 to 9, and more preferably from 2 to 6.

[0229] In general formula (4), it is preferable that the formula has at least one bonding structure represented by formula (4a) or formula (4b) below. More preferably, all bonding structures between carbazole groups are bonding structures represented by formula (4a) or formula (4b).

[0230] [Chemistry 46]

[0231]

[0232] (Here, R) 41 (And z has the same meaning as general formula (4))

[0233] The following are specific examples of compounds represented by general formula (4), but are not limited to these exemplified compounds.

[0234] [Chemistry 47]

[0235]

[0236] [Chemistry 48]

[0237]

[0238] [Chemistry 49]

[0239]

[0240] [Transformation 50]

[0241]

[0242] [Chemistry 52]

[0243]

[0244] [Chemistry 53]

[0245]

[0246] Regarding the second main material, it is preferably a compound represented by general formula (2) or general formula (3).

[0247] As a third main material, the compound represented by the general formula (5) is suitable. Preferably, the compound represented by the formula (51) is preferred.

[0248] In general formula (5) and formula (51), the common symbols have the same meaning.

[0249] Ring D is a heterocyclic ring represented by equation (5a), and ring D and its adjacent rings are condensed at any position.

[0250] R 5 Independently, it is a deuterium group, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted). Preferably, it is hydrogen, an aliphatic hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 10 carbon atoms (substituted or unsubstituted).

[0251] As R 5 Specific examples when it is an aliphatic hydrocarbon group, and R 1 same.

[0252] As R 5 Specific examples of substituted or unsubstituted linked aromatic groups consisting of unsubstituted aromatic hydrocarbon groups having 6 to 30 carbon atoms, aromatic heterocyclic groups having 3 to 17 carbon atoms, or 2 to 5 of these aromatic rings linked together, except for the cases where 2 to 5 aromatic rings are linked together, are related to Ar. 1 and Ar 11 The situation is the same.

[0253] p, r, and s represent substitution numbers, each independently representing an integer from 0 to 4. Preferably, they are integers from 0 to 3, and more preferably from 0 to 2. q represents an integer from 0 to 2, and more preferably an integer from 0 to 1.

[0254] Ar 5 Ar 51Independently refers to an aromatic hydrocarbon group having 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 7 of these aromatic rings. Preferably, it refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 7 of these aromatic rings.

[0255] As Ar 5 and Ar 51 Specific examples of unsubstituted aromatic hydrocarbon groups, unsubstituted linked aromatic groups, and unsubstituted linked aromatic groups, and Ar 1 and Ar 11 The same applies. Preferably, it is a group formed by a compound consisting of pyridine, pyrimidine, triazine, dibenzofuran, dibenzothiophene, carbazole, benzene, naphthalene, or 2 to 7 of these linked together.

[0256] L 5 and L 51 Independently, it is an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, either substituted or unsubstituted, with at least one being an aromatic heterocyclic group. Preferably, it is L. 5 and L 51 At least one of them is a substituted or unsubstituted nitrogen-containing six-membered ring or a substituted or unsubstituted condensed aromatic heterocyclic group formed by the condensation of a nitrogen-containing six-membered ring.

[0257] Specific examples of unsubstituted nitrogen-containing six-membered rings, or unsubstituted condensed aromatic heterocyclic groups containing nitrogen-containing six-membered rings, include: pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, naphthidine, or phenazine.

[0258] As specific examples of unsubstituted aromatic hydrocarbon groups or aromatic heterocyclic groups, except for those with an r+1 or s+1 valence, they are related to Ar. 1 and Ar 11 The same applies to these cases. Preferably, the group is formed from pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, naphthidine, phenazine, dibenzofuran, dibenzothiophene, carbazole, benzene, or naphthalene.

[0259] The following are specific examples of compounds represented by general formula (5), but are not limited to these exemplified compounds.

[0260] [Chemistry 54]

[0261]

[0262] [Chemistry 55]

[0263]

[0264] [Chemistry 56]

[0265]

[0266] [Chemistry 57]

[0267]

[0268] [Chem.58]

[0269]

[0270] [Chemistry 59]

[0271]

[0272] [Transformation 60]

[0273]

[0274] [Chemistry 61]

[0275]

[0276] [Chemistry 62]

[0277]

[0278] [Chemistry 63]

[0279]

[0280] [Chemistry 64]

[0281]

[0282] [Chemistry 65]

[0283]

[0284] [Chemistry 66]

[0285]

[0286] [Chemistry 67]

[0287]

[0288] [Chemistry 68]

[0289]

[0290] [Chemistry 69]

[0291]

[0292] [Chemistry 70]

[0293]

[0294] [Chemistry 71]

[0295]

[0296] [Chemistry 72]

[0297]

[0298] [Chemistry 73]

[0299]

[0300] [Chemistry 74]

[0301]

[0302] The method for manufacturing the organic electric field light-emitting element of the present invention is a method for forming a light-emitting layer by vapor deposition of a host material composition comprising the first host material, the second host material, and the third host material, and a light-emitting dopant material.

[0303] The main material composition of the present invention is a main material composition used in the manufacturing method of the organic electric field light-emitting element. The main material composition only needs to include a first main material, a second main material, and a third main material, and may also include other materials such as dopant materials as needed.

[0304] The first, second, and third host materials, as well as the luminescent dopant material, can be deposited separately from different vapor deposition sources. Preferably, the host material composition (also called a premix) is pre-mixed before vapor deposition, and the premix is ​​simultaneously vapor-deposited from one vapor deposition source to form the luminescent layer. In this case, it is preferable to premix the host materials with each other. Alternatively, the luminescent dopant material can be mixed with the host material. If there is a large temperature difference to achieve the desired vapor pressure, vapor deposition can also be performed from other vapor deposition sources.

[0305] Ideally, premixing methods should aim to achieve the most uniform mixing possible. Examples include pulverization and mixing, heating and melting under reduced pressure or inert gas conditions such as nitrogen, or sublimation, but these methods are not the only options.

[0306] Here, regarding the first host material, its LUMO energy is below -1.95 eV, making it the host material with the lowest LUMO energy among the first, second, and third host materials. Regarding the third host material, its LUMO energy is between -1.94 eV and -1.77 eV, making it the material with the second lowest LUMO energy after the first host material. Regarding the second host material, its LUMO energy is above -1.54 eV, making it the host material with the highest LUMO energy among the first, second, and third host materials.

[0307] Furthermore, regarding the mixing ratio (by weight) of the first, second, and third main materials, relative to the total of the first, second, and third main materials, the proportion of the first main material exceeds 1.0 wt% and is less than 30 wt%, and the proportion of the third main material exceeds 5.0 wt% and is less than 80 wt%. Preferably, the proportion of the first main material is 2 wt% to 20 wt%, and the proportion of the third main material is 10 wt% to 70 wt%, more preferably, the proportion of the first main material is 5 wt% to 20 wt%, and the proportion of the third main material is 10 wt% to 60 wt%. The proportion of the second main material is a value obtained by subtracting the proportions of the first and third main materials from 100 wt%, preferably 19 wt% to 80 wt%.

[0308] In addition, the triplet excitation (T1) energies of the first host material, the second host material, and the third host material are preferably all above 2.55 eV.

[0309] The LUMO and T1 energies can be obtained through quantum chemical calculations. The LUMO energy specified in this specification is assumed to be the value calculated using the Gaussian 03 molecular orbital method and density functional theory (DFT) for B3LYP / 6-31G* level structural optimization calculations.

[0310] Next, while referring to the appendix Figure 1 The structure of the organic EL element of the present invention will be described, but the structure of the organic EL element of the present invention is not limited thereto.

[0311] Figure 1This is a cross-sectional view showing a typical organic EL element structure used in this invention. 1 represents the substrate, 2 represents the anode, 3 represents the hole injection layer, 4 represents the hole transport layer, 5 represents the light-emitting layer, 6 represents the electron transport layer, and 7 represents the cathode. The organic EL element of this invention may also have an exciton blocking layer adjacent to the light-emitting layer. Furthermore, an electron blocking layer may also be present between the light-emitting layer and the hole injection layer. The exciton blocking layer can be inserted into either the anode side or the cathode side of the light-emitting layer, or simultaneously into both sides. In the organic EL element of this invention, an anode, a light-emitting layer, and a cathode are essential layers. However, in addition to these essential layers, a hole injection transport layer and an electron injection transport layer may also be present, and a hole blocking layer may also be present between the light-emitting layer and the electron injection transport layer. Furthermore, the hole injection transport layer refers to either or both of the hole injection layer and the hole transport layer, and the electron injection transport layer refers to either or both of the electron injection layer and the electron transport layer.

[0312] It can also be used for Figure 1 In the opposite structure, where the cathode 7, electron transport layer 6, light-emitting layer 5, hole transport layer 4, and anode 2 are sequentially stacked on the substrate 1, layers can be added or omitted as needed.

[0313] -Substrate-

[0314] The organic EL element of the present invention is preferably supported on a substrate. The substrate is not particularly limited, as long as it is a substrate that has been used in organic EL elements before, such as a substrate containing glass, transparent plastic, quartz, etc.

[0315] -anode-

[0316] As the anode material in an organic electroluminescent (EL) element, materials containing metals, alloys, conductive compounds, or mixtures thereof with a high work function (4 eV or higher) are preferably used. Specific examples of such electrode materials include metals such as Au; conductive transparent materials such as CuI, indium tin oxide (ITO), SnO2, and ZnO. Alternatively, amorphous materials such as IDIXO (In2O3-ZnO) that can be formed into transparent conductive films can also be used. The anode can be formed into a thin film by methods such as evaporation or sputtering, and then patterned into the desired shape using photolithography. Alternatively, when pattern precision is not critical (around 100 μm or higher), a mask of the desired shape can be used during the evaporation or sputtering of the electrode material to form the pattern. Alternatively, when using a coatable substance such as an organic conductive compound, wet film formation methods such as printing or coating can be used. When light is extracted from the anode, it is ideal to have a transmittance greater than 10%, and the sheet resistance of the anode is preferably less than several hundred Ω / Y. The film thickness also depends on the material, and is typically selected in the range of 10 nm to 1000 nm, preferably 10 nm to 200 nm.

[0317] -cathode-

[0318] On the other hand, as cathode materials, materials comprising metals (electron-injecting metals), alloys, conductive compounds, or mixtures thereof with low work functions (below 4 eV) can be used. Specific examples of such electrode materials include: sodium, sodium-potassium alloys, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / alumina (Al₂O₃) mixtures, indium, lithium / aluminum mixtures, rare earth metals, etc. Among these, in terms of electron injection performance and durability against oxidation, mixtures of electron-injecting metals and a second metal that is stable and has a work function greater than that are suitable, such as magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / alumina mixtures, lithium / aluminum mixtures, aluminum, etc. The cathode can be fabricated by forming a thin film from these cathode materials through methods such as vapor deposition or sputtering. Furthermore, as a cathode, the sheet resistance is preferably several hundred Ω / Y or less, and the film thickness is typically selected in the range of 10 nm to 5 μm, preferably 50 nm to 200 nm. Furthermore, in order to allow the emitted light to pass through, if either the anode or cathode of the organic EL element is transparent or translucent, the luminous brightness will be increased, which is advantageous.

[0319] Furthermore, after forming the metal on the cathode with a film thickness of 1 nm to 20 nm, a conductive transparent material listed in the description of the anode is formed on it, thereby making a transparent or semi-transparent cathode. By applying the method described above, an element in which both the anode and cathode are permeable can be made.

[0320] -Emitting Layer-

[0321] The light-emitting layer is a layer that emits light after excitons are generated by the recombination of holes and electrons injected from the anode and cathode, respectively, and contains organic light-emitting dopant material and host material.

[0322] The main body material uses the first main body material, the second main body material, and the third main body material.

[0323] One or more compounds represented by general formula (1) may be used as the first main material. Similarly, one or more carbazole or indolocarbazole compounds represented by general formulas (2) to (4) may be used as the second main material. One or more compounds represented by general formula (5) may be used as the third main material.

[0324] Materials other than the first main material, the second main material, and the third main material may be added as needed.

[0325] In the case of using multiple host materials or host materials premixed with dopants, in order to fabricate organic EL devices with good reproducibility and properties, it is ideal to achieve a 50% weight reduction temperature (T0). 50 The difference is small. The 50% weight loss temperature refers to the temperature at which a 50% weight loss occurs when the temperature is increased from room temperature to 550°C at a rate of 10°C per minute in a thermogravimetric-differential thermal analysis (TG-DTA) under reduced pressure (1 Pa) nitrogen flow. It is believed that vaporization caused by evaporation or sublimation occurs most strongly near this temperature.

[0326] The materials used in the premix are preferably within 15°C, more preferably within 12°C, of ​​the 50% weight reduction temperature difference.

[0327] Ideally, premixing methods should aim to achieve the most uniform mixing possible. Examples include pulverization and mixing, heating and melting under reduced pressure or inert gas conditions such as nitrogen, or sublimation, but these methods are not the only options.

[0328] The main body and its premixed mixture can be in the form of powder, rod, or granules.

[0329] When using phosphorescent dopant as the luminescent dopant material, the phosphorescent dopant may contain an organometallic complex, said organometallic complex comprising at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold. Specifically, iridium complexes described in the Journal of the American Chemical Society (J. Am. Chem. Soc.) (2001, 123, 4304) or Japanese Patent Publication No. 2013-530515 may be used, but are not limited to these.

[0330] The phosphorescent dopant material may contain only one type or two or more types in the luminescent layer. The content of the phosphorescent dopant material relative to the host material is preferably 0.10 wt% to 30 wt%, more preferably 1.0 wt% to 20 wt%.

[0331] There are no particular limitations on phosphorescent dopant materials; examples such as those listed below can be cited.

[0332] [Chemistry 75]

[0333]

[0334] [Chemistry 76]

[0335]

[0336] When using fluorescent dopants as luminescent dopant materials, there are no particular limitations on what constitutes a fluorescent dopant. Examples include: benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, styrene-based benzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalene-dicarboximide derivatives, coumarin derivatives, condensed aromatic compounds, violet ketone derivatives, oxadiazole derivatives, oxazine derivatives, aldehyde azide derivatives, pyrrolidine derivatives, cyclopentadiene derivatives, bis(styrene)-anthracene derivatives, quinacrine derivatives, pyrrolopyridine derivatives, thiadiazopyridine derivatives, styrene-based amine derivatives, diketone-pyrrolopyrrole derivatives, aromatic secondary methyl compounds, metal complexes of 8-hydroxyquinoline derivatives or metal complexes of pyrrole methylene derivatives, rare earth complexes, various metal complexes represented by transition metal complexes, etc., polymer compounds such as polythiophene, polyphenylene, and polyphenylene oxide, organosilanes, etc. Preferably, the derivatives include condensed aromatic derivatives, styryl derivatives, diketopyrrolopyrrole derivatives, oxazine derivatives, pyrrole methylene metal complexes, transition metal complexes, or lanthanide complexes. More preferably, the derivatives include naphthalene, pyrene, 1,2-benzophenanthrene, triphenylene, benzo[c]phenanthrene, benzo[a]anthracene, pentaphenylene, perylene, fluoranthene, acenaphthofluoranthene, dibenzo[a,j]anthracene, dibenzo[a,h]anthracene, benzo[a]naphthalene, hexaphenylene, naphtho[2,1-f]isoquinoline, α-naphthophenidine, phenanthrooxazole, quinolino[6,5-f]quinoline, benzothiophanthrene, etc. These may also have alkyl, aryl, aromatic heterocyclic groups, or diarylamino groups as substituents.

[0337] The fluorescent dopant material may contain only one type or more types in the luminescent layer. The content of the fluorescent dopant material relative to the host material is preferably 0.1% to 20%, more preferably 1% to 10%.

[0338] When using thermally activated delayed fluorescence (TEF) dopants as luminescent dopant materials, there are no particular limitations on what constitutes a TEF dopant. Examples include metal complexes such as tin or copper complexes, indole-carbazole derivatives described in WO2011 / 070963, cyanobenzene derivatives and carbazole derivatives described in Nature (2012, 492, 234), and phenazine derivatives, oxadiazole derivatives, triazole derivatives, sulfone derivatives, phenoxazine derivatives, and acridine derivatives described in Nature Photonics (2014, 8, 326).

[0339] There are no particular limitations on thermally activated delayed fluorescence dopants; examples such as those listed below can be cited.

[0340] [Chemistry 77]

[0341]

[0342] The thermally activated delayed fluorescence (TEF) dopant material may contain only one type or two or more types in the luminescent layer. Furthermore, the TEF dopant may be used in combination with phosphorescent or fluorescent dopant. The content of the TEF dopant material relative to the host material is preferably 0.10% to 50%, more preferably 1.0% to 30%.

[0343] -Injection Layer-

[0344] An injection layer is a layer placed between the electrode and the organic layer to reduce the driving voltage or increase the luminous brightness. There are hole injection layers and electron injection layers, which can exist between the anode and the luminescent layer or hole transport layer, and between the cathode and the luminescent layer or electron transport layer. The injection layer can be added as needed.

[0345] -hole blocking layer-

[0346] In a broad sense, hole blocking layers function as electron transport layers. They include hole blocking materials that have the ability to transport electrons but have a significantly lower ability to transport holes. By transporting electrons and blocking holes, they can increase the recombination probability of electrons and holes in the light-emitting layer.

[0347] In the hole blocking layer, known hole blocking layer materials can also be used.

[0348] -Electron blocking layer-

[0349] In a broad sense, the electron blocking layer functions as a hole transport layer, increasing the probability of electrons and holes recombinating in the luminescent layer by transporting holes and blocking electrons.

[0350] As the material for the electron blocking layer, known electron blocking layer materials can be used. Alternatively, hole transport layer materials described later can be used, depending on the need. The thickness of the electron blocking layer is preferably 3 nm to 100 nm, more preferably 5 nm to 30 nm.

[0351] -Exciton blocking layer-

[0352] An exciton blocking layer is used to prevent excitons generated by the recombination of holes and electrons in the light-emitting layer from diffusing into the charge transport layer. By inserting this layer, excitons can be efficiently sealed into the light-emitting layer, thereby improving the luminous efficiency of the device. In devices with two or more adjacent light-emitting layers, the exciton blocking layer can be inserted between two adjacent light-emitting layers.

[0353] As the material for the exciton blocking layer, known exciton blocking layer materials can be used. Examples include 1,3-dicarbazolylbenzene (mCP) or bis(2-methyl-8-hydroxyquinoline)-4-phenylphenolaluminum(III) (BAlq).

[0354] -Hole transport layer-

[0355] The hole transport layer contains hole transport material with the function of transporting holes, and the hole transport layer can be a single layer or multiple layers.

[0356] The hole transport material is any material that possesses either hole injection or transport or electron barrier properties, and can be either organic or inorganic. In the hole transport layer, any compound can be selected from those already known. Examples of such hole transport materials include porphyrin derivatives, arylamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene-anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymeric oligomers, particularly thiophene oligomers. Porphyrin derivatives, arylamine derivatives, and styrene-anthracene derivatives are preferred, and arylamine derivatives are more preferred.

[0357] -Electron transport layer-

[0358] The electron transport layer contains materials that can transport electrons, and the electron transport layer can be a single layer or multiple layers.

[0359] As an electron transport material (and sometimes a hole blocking material), it simply needs to have the function of transporting electrons injected from the cathode to the light-emitting layer. The electron transport layer can be any compound selected from existing known compounds, such as polycyclic aromatic derivatives of naphthalene, anthracene, phenanthroline, tris(8-hydroxyquinoline)aluminum(III) derivatives, phosphine oxide derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiamethane dioxide derivatives, carbodiimide, fluorenemethane derivatives, anthraquinone dimethane and anthrone derivatives, bipyridine derivatives, quinoline derivatives, oxadiazole derivatives, benzimidazole derivatives, benzothiazole derivatives, indolecarbazole derivatives, etc. Furthermore, polymers incorporating these materials into polymer chains or using these materials as the backbone of polymers can also be used.

[0360] Example

[0361] The present invention will be described in more detail below through embodiments, but the present invention is not limited to these embodiments and can be implemented in various forms as long as it does not depart from its spirit.

[0362] The percentages in the blending ratio and concentration are in wt%.

[0363] Example 1

[0364] For compounds used as the first, second, and third host materials, the molecular orbital method Gaussian 03 was used, and density functional theory (DFT) was employed to perform B3LYP / 6-31G* level structure optimization calculations to determine the LUMO energy and T1 energy. The results are shown in Table 1.

[0365] In addition, the LUMO energy and T1 energy of the compounds used in the comparative examples are shown in Table 1.

[0366] [Table 1]

[0367] compound LUMO(eV) T1(eV) 1-326 -2.01 2.68 1-327 -1.98 2.70 1-217 -2.00 2.66 1-6 -1.98 2.75 3-21 -0.94 2.97 3-33 -0.96 2.96 4-69 -1.32 3.16 2-3 -0.98 3.01 2-51 -1.26 2.65 2-2 -0.98 3.01 2-43 -0.99 3.00 5-2 -1.93 2.73 5-3 -1.88 2.81 5-38 -1.92 2.73 5-151 -1.93 2.73 5-152 -1.93 2.73 A -2.02 2.38 B -1.20 3.01 C -2.15 2.49

[0368] Example 2

[0369] On a glass substrate with an ITO-containing anode having a film thickness of 110 nm, a vacuum evaporation method was used to deposit the film at a vacuum degree of 4.0 × 10⁻⁶. -5 Pa is used to stack the thin films. First, HAT-CN is formed on ITO with a thickness of 25 nm as a hole injection layer, followed by NPD with a thickness of 30 nm as a hole transport layer. Next, HT-1 is formed with a thickness of 10 nm as an electron blocking layer. Then, compound 1-326 as the first host material, compound 3-21 as the second host material, compound 5-2 as the third host material, and Ir(ppy)3 as the luminescent dopant are co-deposited from different evaporation sources to form a luminescent layer with a thickness of 40 nm. At this time, co-deposition is performed under evaporation conditions where the concentration of Ir(ppy)3 is 10% and the concentration of the host material is 90% (the ratio of the first host material, the second host material, and the third host material is 5%:70%:25%). Next, ET-1 is formed with a thickness of 20 nm as an electron transport layer. Then, LiF is formed on the electron transport layer with a thickness of 1 nm as an electron injection layer. Finally, Al is formed on the electron injection layer to a thickness of 70 nm as a cathode, thereby fabricating an organic EL device.

[0370] Examples 3 to 17

[0371] Except that the ratios of the first main material, the second main material, and the third main material, as shown in Table 2, are set, the organic EL element is fabricated in the same manner as in Example 2.

[0372] Table 2 shows the brightness, driving voltage, luminous efficiency, and lifetime characteristics of the organic EL elements fabricated in Examples 2 to 17. In the table, brightness, driving voltage, and luminous efficiency are defined as a driving current of 20 mA / cm². 2 The value at that time represents the initial characteristics. LT70 is the value at an initial brightness of 9000 cd / m². 2 The time required for the brightness to decay to 70% of its initial brightness indicates the lifetime characteristic. The same applies to the following tables.

[0373] In the columns for the first, second, and third subjects, the numbers in parentheses represent the allocation ratios.

[0374] [Table 2]

[0375]

[0376] Example 18

[0377] The 50% weight reduction temperature (T50) of the compounds used as the first, second, and third host materials was determined. The results are recorded in Table 3.

[0378] [Table 3]

[0379] compound <![CDATA[T 50 [℃]]]> 1-6 312 2-3 315 5-151 312 2-2 279 5-38 278 2-43 316 5-152 311 1-327 273

[0380] Example 19

[0381] Take the first main material 1-6 (0.10g), the second main material 2-3 (0.70g), and the third main material 5-151 (0.20g), and mix them while crushing them in a mortar to prepare the premix H1.

[0382] On a glass substrate with an ITO-containing anode having a film thickness of 110 nm, a vacuum evaporation method was used to deposit the film at a vacuum degree of 4.0 × 10⁻⁶. -5Pa is used to stack various thin films. First, on ITO, HAT-CN is formed to a thickness of 25 nm as a hole injection layer, followed by NPD to a thickness of 30 nm as a hole transport layer. Next, HT-1 is formed to a thickness of 10 nm as an electron blocking layer. Then, a premix of H1 and Ir(ppy)3 as a light-emitting dopant are co-deposited from different evaporation sources to form a light-emitting layer to a thickness of 40 nm. At this time, co-deposition is performed under evaporation conditions where the concentration of Ir(ppy)3 is 10% and the concentration of the host material is 90%. Next, ET-1 is formed to a thickness of 20 nm as an electron transport layer. Then, on the electron transport layer, LiF is formed to a thickness of 1 nm as an electron injection layer. Finally, Al is formed to a thickness of 70 nm on the electron injection layer as a cathode, thereby fabricating an organic EL device.

[0383] Examples 20 to 23

[0384] Except for setting the types and proportions of the first, second, and third main materials as shown in Table 4, premixes H2 to H5 were prepared in the same manner as in Example 19.

[0385] Organic EL elements were fabricated in the same manner as in Example 19, except that premixes H2 to H5 were used.

[0386] [Table 4]

[0387]

[0388] The evaluation results of the organic EL elements prepared in Examples 19 to 23 are shown in Table 5.

[0389] [Table 5]

[0390]

[0391] Comparative Examples 1 to 5

[0392] Except for setting the types and mixing ratios of the first main material, the second main material, and the third main material as shown in Table 6, the organic EL element is fabricated in the same manner as in Example 2.

[0393] The evaluation results of the fabricated organic EL elements are shown in Table 6.

[0394] [Table 6]

[0395]

[0396] Comparative Examples 7 to 8

[0397] Except for setting the types and proportions of the main materials as shown in Table 7, premixes H6 to H7 were prepared in the same manner as in Example 19.

[0398] [Table 7]

[0399]

[0400] Organic EL elements were fabricated in the same manner as in Example 19, except that the premixes H6 to H7 were used.

[0401] The evaluation results of the fabricated organic EL elements are shown in Table 8.

[0402] [Table 8]

[0403]

[0404] As described above, the embodiments exhibit lifetime characteristics comparable to or better than the comparative examples, while also improving driving voltage and power efficiency. In other words, the present invention achieves an organic electric field light-emitting element that combines excellent lifetime characteristics, driving voltage, and power efficiency.

[0405] The following shows the compounds used in the examples and comparative examples.

[0406] [Chemistry 78]

[0407]

Claims

1. An organic electric field light-emitting element, comprising one or more light-emitting layers between opposing anodes and cathodes, characterized in that: at least one light-emitting layer contains a host material comprising a first host material, a second host material, and a third host material, and a light-emitting dopant material; the lowest unoccupied molecular orbital energy of the first host material is below -1.95 eV; the lowest unoccupied molecular orbital energy of the second host material is above -1.54 eV; when the lowest unoccupied molecular orbital energies of the first host material, the second host material, and the third host material are respectively set as LM1, LM2, and LM3, LM2 ≥ LM3 ≥ LM1 is satisfied; and the lowest unoccupied molecular orbital energy of the third host material is -1.94 eV to -1.77 eV. The first host material is a compound represented by the following general formula (1), the second host material is a compound represented by the following general formula (2), general formula (3), or general formula (4), and the third host material is a compound represented by the following general formula (5). Here, ring A is the heterocyclic ring represented by equation (1a), and ring A and its adjacent rings are condensed at any position. R 1 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together. a, c, and d each independently represent integers from 0 to 4, and b represents integers from 0 to 2. L 1 and L 11 It is independently an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, at least one of which is the aromatic heterocyclic group; Ar 1 and Ar 11 Each of these can be independently represented as an aromatic hydrocarbon group having 6 to 30 carbon atoms, an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group having 2 to 7 of these aromatic rings. Here, Ar 21 and Ar 22 Independently representing hydrogen, deuterium, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by two linked aromatic rings of these; L 21 and L 22 Independently representing direct bonding or phenylene; Here, ring B is the heterocyclic ring represented by equation (3a), and ring B and its adjacent rings are condensed at any position. R 3 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together. L 31 Independently, it is an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, either substituted or unsubstituted. L 32 Independently, it is an aromatic hydrocarbon group with 6 to 10 carbon atoms, either substituted or unsubstituted. Ar 31 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted linked aromatic group formed by the linkage of 2 to 5 of these aromatic rings. Ar 32 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic group with 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 5 of these aromatic rings. i represents an integer from 0 to 4, and j represents an integer from 0 to 2. f is the repetition number, representing integers from 1 to 3; g is the repetition number, independently representing integers from 0 to 3; and h is the substitution number, representing integers from 0 to 7. Here, Ar 41 It is an aromatic hydrocarbon group with 6 to 30 carbons that has been substituted or unsubstituted, an aromatic heterocyclic group with 3 to 17 carbons that has been substituted or unsubstituted, or a linked aromatic group consisting of 2 to 5 of these aromatic rings. R 41 Each is independently a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), wherein it is not a carbazolyl group. x is a repetition number, independently representing an integer from 1 to 4; y is a substitution number, representing an integer from 1 to 4; when y is 2 or more, at least one x is an integer from 2 to 4; when x and y are 2 or more, the multiple carbazo groups in the formula can be the same or different; z is an integer from 0 to 3. Here, ring D is the heterocyclic ring represented by equation (5a), and ring D and its adjacent rings are condensed at any position. R 5 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together. p, r, and s independently represent integers from 0 to 4, and q represents integers from 0 to 2. L 5 and L 51 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, at least one of which is the aromatic heterocyclic group; Ar 5 and Ar 51 Each of these can be independently represented as a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 7 of these aromatic rings. When the aromatic hydrocarbon group, the aromatic heterocyclic group, the carbazoyl group, or the linked aromatic group has a substituent, the substituent is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a deuterium, a halogen, or a cyano group.

2. The organic electric field light-emitting element according to claim 1, characterized in that... The triplet excitation (T1) energies of the first host material, the second host material, and the third host material are above 2.55 eV.

3. The organic electric field light-emitting element according to claim 1, characterized in that... It contains one or more light-emitting layers between opposing anodes and cathodes. In the organic electric field light-emitting element, at least one light-emitting layer contains a first host material, a second host material, a third host material, and a light-emitting dopant material. The at least three materials contained in the light-emitting layer are deposited by a vapor deposition source.

4. The organic electric field light-emitting element according to claim 3, characterized in that... The first, second, and third main materials are deposited by a vapor deposition source.

5. The organic electric field light-emitting element according to claim 1, characterized in that... The luminescent dopant material is a fluorescent luminescent material containing thermally activated delayed fluorescence material.

6. The organic electric field light-emitting element according to claim 1, characterized in that... The luminescent dopant material is a phosphorescent material.

7. The organic electric field light-emitting element according to claim 1, wherein L 1 and L 11 At least one of them is a substituted or unsubstituted nitrogen-containing six-membered ring group, or a substituted or unsubstituted condensed aromatic heterocyclic group containing a nitrogen-containing six-membered ring. When the nitrogen-containing six-membered ring group or the condensed aromatic heterocyclic group has a substituent, the substituent is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a deuterium, a halogen, or a cyano group.

8. The organic electric field light-emitting element according to claim 1, characterized in that... General formula (1) is the following formula (11). Here, R 1 , Ring A, Ar 1 a, b and general formula (1) have the same meaning.

9. The organic electric field light-emitting element according to claim 8, characterized in that... Formula (11) is a compound represented by formula (12) or formula (13) below. Here, R 1 , Ring A, Ar 1 a and b have the same meaning as in general formula (1). Y represents O, S, NAr 14 , or CAr 15 Ar 16 , Ar 13 Ar 14 Ar 15 and Ar 16 Each of these groups independently represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted formed by the linkage of 2 to 5 of these aromatic rings. m represents an integer from 0 to 4, n represents an integer from 0 to 3, and l represents an integer from 0 to 4; L 12 This refers to aromatic hydrocarbon groups with 6 to 30 carbon atoms, whether substituted or unsubstituted. L 13 Indicates a nitrogen-containing six-membered cyclic group. Ar 12 Independently refers to an aromatic hydrocarbon group having 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 5 of these aromatic rings.

10. The organic electric field light-emitting element according to claim 1, wherein L 5 and L 51 At least one of them is a substituted or unsubstituted nitrogen-containing six-membered ring, or a condensed aromatic heterocyclic group containing a nitrogen-containing six-membered ring.

11. The organic electric field light-emitting element according to claim 1, characterized in that... The third main material is the compound represented by the following formula (51), Here, R 5 D, Ar 5 p, and q have the same meaning as general formula (5).

12. The organic electric field light-emitting element according to any one of claims 1 to 11, characterized in that... Compared with the total of the first main material, the second main material and the third main material, the proportion of the first main material is more than 1.0 wt% and less than 30 wt%, and the proportion of the third main material is more than 5.0 wt% and less than 80 wt%.

13. A method for manufacturing an organic electric field light-emitting element, characterized in that: In manufacturing an organic electric field light-emitting element comprising one or more light-emitting layers between opposing anodes and cathodes, and at least one light-emitting layer containing a host material comprising a first host material, a second host material, and a third host material, and a light-emitting dopant material, the light-emitting layer is formed by vapor deposition of the host material composition and the light-emitting dopant material. In the host material composition, the lowest unoccupied molecular orbital energy of the first host material is -1.95 eV or less, and the lowest unoccupied molecular orbital energy of the second host material is -1.54 eV or more. When the lowest unoccupied molecular orbital energies of the first host material, the second host material, and the third host material are set to LM1, LM2, and LM3, respectively, LM2 ≥ LM3 ≥ LM1 is satisfied, and the lowest unoccupied molecular orbital energy of the third host material is -1.94 eV to -1.77 eV. The first host material is a compound represented by the following general formula (1), the second host material is a compound represented by the following general formula (2), general formula (3), or general formula (4), and the third host material is a compound represented by the following general formula (5). Here, ring A is the heterocyclic ring represented by equation (1a), and ring A and its adjacent rings are condensed at any position. R 1 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together. a, c, and d each independently represent integers from 0 to 4, and b represents integers from 0 to 2. L 1 and L 11 It is independently an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, at least one of which is the aromatic heterocyclic group; Ar 1 and Ar 11 Each of these can be independently represented as an aromatic hydrocarbon group having 6 to 30 carbon atoms, an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group having 2 to 7 of these aromatic rings. Here, Ar 21 and Ar 22 Independently representing hydrogen, deuterium, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by two linked aromatic rings of these; L 21 and L 22 Independently representing direct bonding or phenylene; Here, ring B is the heterocyclic ring represented by equation (3a), and ring B and its adjacent rings are condensed at any position. R 3 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together. L 31 Independently, it is an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, either substituted or unsubstituted. L 32 Independently, it is an aromatic hydrocarbon group with 6 to 10 carbon atoms, either substituted or unsubstituted. Ar 31 It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted linked aromatic group formed by the linkage of 2 to 5 of these aromatic rings. Ar 32 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, substituted or unsubstituted aromatic heterocyclic group with 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 5 of these aromatic rings. i represents an integer from 0 to 4, and j represents an integer from 0 to 2. f is the repetition number, representing integers from 1 to 3; g is the repetition number, independently representing integers from 0 to 3; and h is the substitution number, representing integers from 0 to 7. Here, Ar 41 It is an aromatic hydrocarbon group with 6 to 30 carbons that has been substituted or unsubstituted, an aromatic heterocyclic group with 3 to 17 carbons that has been substituted or unsubstituted, or a linked aromatic group consisting of 2 to 5 of these aromatic rings. R 41 Each is independently a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), or an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), wherein it is not a carbazolyl group. x is a repetition number, independently representing an integer from 1 to 4; y is a substitution number, representing an integer from 1 to 4; when y is 2 or more, at least one x is an integer from 2 to 4; when x and y are 2 or more, the multiple carbazo groups in the formula can be the same or different; z is an integer from 0 to 3. Here, ring D is the heterocyclic ring represented by equation (5a), and ring D and its adjacent rings are condensed at any position. R 5 Independently, it is a deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms (substituted or unsubstituted), an aromatic heterocyclic group having 3 to 17 carbon atoms (substituted or unsubstituted), or a linked aromatic group having substituted or unsubstituted aromatic rings of these connected together. p, r, and s independently represent integers from 0 to 4, and q represents integers from 0 to 2. L 5 and L 51 It is an aromatic hydrocarbon group with 6 to 30 carbon atoms, either substituted or unsubstituted, or an aromatic heterocyclic group with 3 to 17 carbon atoms, at least one of which is the aromatic heterocyclic group; Ar 5 and Ar 51 Each of these can be independently represented as a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group consisting of 2 to 7 of these aromatic rings. When the aromatic hydrocarbon group, the aromatic heterocyclic group, the carbazoyl group, or the linked aromatic group has a substituent, the substituent is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a diarylamino group having 12 to 44 carbon atoms, a deuterium, a halogen, or a cyano group.

14. A host material composition used in the method of manufacturing an organic electric field light-emitting element as described in claim 13.

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