Composition, film, organic light-emitting element, method of providing a light-emitting composition, and program

Abstract

The durability of an organic light-emitting element using a light-emitting composition containing a first compound having a PBHT value of greater than 0.730 and a second compound having a ΔΕ S1 less than the first compound and a ΔΕ ST less than 0.20 eV. E S1 is the lowest excited singlet energy level, ΔΕ ST is the difference between the lowest excited singlet energy level and the lowest excited triplet energy level.

Description

Technical Field

[0001] This invention relates to a composition with excellent light-emitting properties, a film using the composition, and an organic light-emitting element. Furthermore, this invention relates to a method for providing a light-emitting composition and a procedure for performing the method. Background Technology

[0002] Research is actively underway to improve the luminous efficiency of light-emitting elements such as organic electroluminescent devices (organic EL devices). Particular attention has been paid to enhancing luminous efficiency by developing and combining new electron transport materials, hole transport materials, and luminescent materials that constitute organic electroluminescent devices. Research on organic electroluminescent devices utilizing delayed fluorescence materials has also been observed.

[0003] Delayed fluorescence materials are compounds that emit fluorescence upon returning to the ground state after a reverse intersystem crossing from an excited triplet state to an excited singlet state in the excited state. Because fluorescence generated via this pathway is observed later than fluorescence from an excited singlet state directly generated from the ground state (normal fluorescence), it is called delayed fluorescence. Here, for example, when a luminescent compound is excited via carrier injection, since the generation probabilities of the excited singlet state and the excited triplet state are statistically 25%:75%, there is a limit to the improvement in luminescence efficiency if only fluorescence from the directly generated excited singlet state is used. On the other hand, because delayed fluorescence materials can also emit fluorescence from the excited triplet state via the aforementioned reverse intersystem crossing pathway, in addition to the excited singlet state, they can achieve higher luminescence efficiency compared to conventional delayed fluorescence materials.

[0004] As such delayed fluorescence material, Patent Document 1 proposes a benzene derivative having a carbazoyl group or other heteroaryl group or a diphenylamino group and at least two cyano groups, and confirms that high luminous efficiency is obtained by using this benzene derivative in an organic EL element with a light-emitting layer.

[0005] Furthermore, Non-Patent Document 1 reports that a carbazole dibenzonitrile derivative (hereinafter referred to as "4CzIPN") represented by the following formula is a thermally active delayed fluorescence material, and reports that high internal EL quantum efficiency has been achieved using an organic electroluminescent element employing 4CzIPN. In addition, Non-Patent Document 2 reports that high luminous efficiency and high durability have been achieved by optimizing the structure of an organic electroluminescent element employing 4CzIPN.

[0006] [Chemical Formula 1]

[0007]

[0008] Previous technical documents

[0009] Patent documents

[0010] Patent Document 1: Japanese Patent Application Publication No. 2014-43541

[0011] Non-patent literature

[0012] Non-patent literature 1: H. Uoyama, et al., Nature 492, 234 (2012)

[0013] Non-patent literature 2: H. Nakanotani, et al., Scientific Reports, 3, 2127 (2013) Summary of the Invention

[0014] The technical problem to be solved by the invention

[0015] As explained above, current research has primarily focused on improving the properties of light-emitting elements by discovering compounds useful as delayed fluorescence materials or optimizing the structure of light-emitting elements using delayed fluorescence materials. Therefore, many compounds have been proposed as delayed fluorescence materials, and numerous structural improvements have been made for light-emitting elements. On the other hand, when fabricating light-emitting elements using delayed fluorescence materials, the delayed fluorescence material is combined with a host material to form a film; however, currently, the host material used in this combination is selected based on repeated experimentation.

[0016] In view of this current situation, the inventors have conducted in-depth research with the aim of providing useful indicators when selecting host materials to be combined with delayed fluorescence materials.

[0017] means for solving technical problems

[0018] As a result of in-depth research conducted to achieve the aforementioned objectives, the inventors discovered that by using the PBHT value, it is possible to provide organic light-emitting elements with high durability. The present invention is based on this insight and specifically has the following structure.

[0019] [1] A composition comprising a first compound satisfying formula (1a) and a second compound satisfying formula (2b) [wherein the first compound and the second compound satisfy formula (A)].

[0020] [Formula 1]

[0021] PBHT(1)>0.730 Formula (1a)

[0022] ΔE ST (2) < 0.20 eV Equation (2b)

[0023] E S1 (1) > E S1(2) Equation (A)

[0024] In the above formula, PBHT(1) is the PBHT value of the first compound. ΔE ST (2) is the lowest excited singlet state energy level E of the second compound. S1 (2) The lowest excited triplet energy level E of the second compound T1 (2) The difference. S1 (1) is the lowest excited singlet state energy level of the first compound.

[0025] [2] The composition according to [1], wherein the first compound further satisfies the following formula (1c).

[0026] [Formula 2]

[0027] BDE(1) > 4.20 eV Equation (1c)

[0028] [In the above formula, BDE(1) is the bond energy of the cation of the first compound.]

[0029] [3] According to the composition of [1], wherein the second compound also satisfies the following formula (2a).

[0030] [Formula 3]

[0031] 0.200 < PBHT(2) < 0.400 Equation (2a)

[0032] [In the above formula, PBHT(2) is the PBHT value of the second compound.]

[0033] [4] According to the composition of [1], wherein the first compound further satisfies the following formula (1c) and the second compound further satisfies the following formula (2a).

[0034] [Formula 4]

[0035] BDE(1) > 4.20 eV Equation (1c)

[0036] 0.200 < PBHT(2) < 0.400 Equation (2a)

[0037] [In the above formula, BDE(1) is the bond energy of the cation of the first compound. PBHT(2) is the PBHT value of the second compound.]

[0038] [5] The composition according to any one of [1] to [4], wherein the PBHT(1) is greater than 0.910.

[0039] [6] The composition according to any one of [1] to [5], wherein the second compound satisfies the following formula (2d).

[0040] [Formula 5]

[0041] τ DELAY <10μs Equation (2d)

[0042] In the above formula, τ DELAY [This refers to the delayed fluorescence lifetime of the second compound.]

[0043] [7] The composition according to any one of [1] to [6], wherein the first compound has one or more structures selected from the group consisting of a triazine structure, a carbazole structure, a fulvalene structure and a thiopentene structure.

[0044] [8] The composition according to any one of [1] to [7], wherein the first compound has at least one of a dibenzofuran structure or a dibenzothiophene structure.

[0045] [9] The composition according to [8], wherein the first compound has the structure represented by the following general formula (1).

[0046] [Chemical Formula 2]

[0047] General formula (1)

[0048]

[0049] In the above formula, multiple X's independently represent O or S. 1 ~Y 8 and Y 11 ~Y 18 Each can be represented independently as N or CR, where R represents a hydrogen atom, a substituent, or a direct bond with L. Y 21 ~Y 28 Each Y represents N or C-R' independently, where R' represents a hydrogen atom or substituent. L represents a (n+p+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. n represents an integer greater than or equal to 0. When n is 2 or greater, multiple Ys... 11 ~Y 18 They can be the same or different. p represents an integer greater than or equal to 0. When p is greater than or equal to 2, multiple Y's can be represented as Y's. 21 ~Y 28 They can be the same or different. n+p is 1 or more.

[0050]

[10] The composition according to [8], wherein the first compound has the structure represented by the following general formula (2).

[0051] [Chemical Formula 3]

[0052] General formula (2)

[0053]

[0054] In the above formula, multiple X's independently represent O or S. 1 ~Y 8 and Y 11 ~Y 18 Each Y represents N or CR independently, and R represents a hydrogen atom, a substituent, or a direct bond with L. L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. n represents an integer greater than or equal to 1. When n is 2 or greater, multiple Ys... 11 ~Y 18 They can be the same, or they can be different.

[0055]

[11] The composition according to [8], wherein the first compound has the structure represented by the following general formula (3).

[0056] [Chemical Formula 4]

[0057] General formula (3)

[0058]

[0059] In the above formula, multiple X's independently represent O or S. 1 Y 2 Y 4 ~Y 8 and Y 11 ~Y 18 Each of these can be represented independently as N or CR, where R represents a hydrogen atom, a substituent, or a direct bond with L. L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. n represents an integer greater than 2. Multiple Ys 11 ~Y 18 They can be the same, or they can be different.

[0060]

[12] The composition according to [8], wherein the first compound has the structure represented by the following general formula (4).

[0061] [Chemical Formula 5]

[0062] General formula (4)

[0063]

[0064] In the above formula, multiple X's independently represent O or S. 1 ~Y 8 and Y 12 ~Y 18Each of these can be represented independently as N or CR, where R represents a hydrogen atom, a substituent, or a direct bond with L. L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. n represents an integer greater than 2. Multiple Ys 11 ~Y 18 They can be the same, or they can be different.

[0065]

[13] The composition according to [8], wherein the first compound has the structure represented by the following general formula (5).

[0066] [Chemical Formula 6]

[0067] General formula (5)

[0068]

[0069] In the above formula, X represents O or S. 1 ~Y 8 Each can be represented independently as N or CR, where R represents a hydrogen atom, a substituent, or a direct bond with L. Y 21 ~Y 28 Each Y represents N or C-R' independently, where R' represents a hydrogen atom or substituent. L represents a (p+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. p represents an integer greater than 1. When p is 2 or greater, multiple Ys... 21 ~Y 28 They can be the same, or they can be different.

[0070]

[14] The composition according to any one of [9] to

[13] , wherein L has a structure formed by linking one or more rings selected from the group consisting of benzene rings and pyridine rings.

[0071]

[15] The composition according to any one of [9] to

[13] , wherein L comprises 1,3-phenylene or 2,6-pyridylene as a linking chain.

[0072]

[16] The composition according to any one of [9] to

[13] , wherein L comprises 1,4-phenylene or 2,6-pyridylene as a linking chain.

[0073]

[17] The composition according to any one of [9] to

[12] , wherein n is 2.

[0074]

[18] The composition according to any one of [9] to

[17] , wherein R is a hydrogen atom or a substituted or unsubstituted aryl group.

[0075]

[19] The composition according to any one of [1] to

[18] , wherein when the content of the first compound is set to 100 parts by weight, the content of the second compound is 0.01 to 70 parts by weight.

[0076]

[20] The composition according to any one of [1] to

[19] further comprises a third compound satisfying the following formula (B).

[0077] [Formula 6]

[0078] E S1 (1) > E S1 (2) > E S1 (3) Equation (B)

[0079] In the above formula, E S1 (3) is the lowest excited singlet state energy level of the third compound.

[0080]

[21] The composition according to

[20] , wherein the third compound also satisfies the following formula (3b).

[0081] [Formula 7]

[0082] ΔE ST (3) < 0.20 eV Equation (3b)

[0083] [ΔE ST (3) is the lowest excited singlet state energy level E of the third compound. S1 (3) The lowest excited triplet energy level E of the third compound T1 (3) difference. ]

[0084]

[22] A luminescent composition wherein the composition described in any one of [1] to

[21] is used as the luminescent composition.

[0085]

[23] A membrane comprising any one of the compositions described in [1] to

[21] .

[0086]

[24] A light-emitting film, wherein the film described in

[23] is used as a light-emitting film.

[0087]

[25] An organic light-emitting element comprising any one of the compositions described in [1] to

[21] .

[0088]

[26] The organic light-emitting element according to

[25] emits delayed fluorescence.

[0089]

[27] The organic light-emitting element according to

[25] or

[26] is an organic electroluminescent element.

[0090]

[28] An organic light-emitting element according to any one of

[25] to

[27] , wherein the amount of light emitted from the second compound is the largest among the materials contained in the light-emitting element.

[0091]

[29] An organic light-emitting element according to any one of

[26] to

[28] , wherein the composition is the composition of

[20] or

[21] , and the amount of light emitted from the third compound is the largest among the materials contained in the light-emitting element.

[0092]

[30] One method, whose design is related to ΔE ST (2) A first compound combined with a second compound of less than 0.20 eV to provide a luminescent composition comprising the first compound and the second compound, the method comprising designing the second compound to such that E S1 (1) Greater than E S1 (2) The step where PBHT(1) is greater than 0.730.

[0093]

[31] The method according to

[30] includes the step of designing the first compound to increase PBHT(1).

[0094]

[32] The method according to

[31] includes the step of selecting a compound with a larger PBHT(1) from a plurality of candidate compounds and using it as the first compound.

[0095]

[33] A program that performs any one of the methods described in

[30] to

[32] .

[0096] Invention Effects

[0097] By using the compositions of the present invention, organic light-emitting elements with excellent durability can be provided. Furthermore, according to the method of the present invention, compositions useful for manufacturing organic light-emitting elements with excellent durability can be easily designed. Attached Figure Description

[0098] Figure 1 This is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescent element.

[0099] Figure 2 This is a graph showing the relationship between the PBHT value of compound 1 and the measurement results of LT95.

[0100] Figure 3 This is a graph showing the relationship between the PBHT value of compound 1 and the measurement results of LT95. Detailed Implementation

[0101] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples of the invention, but the invention is not limited to such embodiments or specific examples. Furthermore, in this document, the numerical range indicated by “~” means a range including the values ​​described before and after “~” as a lower and upper limit value. Moreover, the types of isotopes of hydrogen atoms present within the molecules of the compounds used in the present invention are not particularly limited; for example, all hydrogen atoms within the molecule may be... 1 H can be partly or entirely. 2 H(deuterium)D).

[0102] (Compound 1)

[0103] Compound 1 is a compound with a PBHT value greater than 0.730. The PBHT value was proposed by Michael J. Peach, Peter Benfield, Trygve Helgaker, and David J. Tozer, and is named by combining the first letters of their surnames. The PBHT value is a numerical value representing the orbital properties of the excited state. Singlet and triplet PBHT values ​​exist, but the triplet PBHT value is used in this invention. A small PBHT value indicates that the excited state is charge-transfer (CT) and a large PBHT value indicates that the excited state is locally electronic (LE). The PBHT value is the value Λ calculated using the following formula.

[0104] [Formula 8]

[0105]

[0106] The terms in the above formula are defined as follows.

[0107] [Formula 9]

[0108]

[0109] Occupy the track

[0110] Valence orbit

[0111]

[0112] κ ia =X ia +Y ia

[0113] The method for calculating the PBHT value is described in detail in J. Chem. Phys. 128, 044118 (2008) "Excitation energies in density functional theory: An evaluation and a diagnostic test", the entire page of which is cited here as part of this paper.

[0114] The PBHT value of the first compound is preferably greater than 0.730, preferably greater than 0.750, preferably greater than 0.800, preferably greater than 0.830, preferably greater than 0.850, preferably greater than 0.900, preferably greater than 0.920, preferably greater than 0.950, preferably greater than 0.980, and preferably greater than 0.990.

[0115] The first compound is preferably a compound with a cation bond energy BDE(1) greater than 4.20 eV. The cation bond energy BDE(1) is preferably greater than 4.40 eV, preferably greater than 4.60 eV, preferably greater than 4.80 eV, preferably greater than 5.00 eV, preferably greater than 5.20 eV, preferably greater than 5.40 eV, preferably greater than 5.60 eV, preferably greater than 5.80 eV, preferably greater than 6.00 eV, and preferably greater than 6.10 eV.

[0116] The bond dissociation energy of a cation can be calculated using b3lyp / 6-31gs.

[0117] As the first compound, a compound with a PBHT value greater than 0.80 and a cation bond energy greater than 4.30 eV is preferred. Alternatively, a compound with a PBHT value greater than 0.82 and a cation bond energy greater than 4.35 eV is also preferred. Another option is a compound with a PBHT value greater than 0.85 and a cation bond energy greater than 4.30 eV.

[0118] Furthermore, as the first compound, a compound with a PBHT value greater than 0.91 and a cation bond energy greater than 4.30 eV is preferably selected. Alternatively, a compound with a PBHT value greater than 0.91 and a cation bond energy greater than 4.35 eV is also preferred. A compound with a PBHT value greater than 0.95 and a cation bond energy greater than 4.30 eV is also preferred.

[0119] The structure of the first compound is not particularly limited as long as it satisfies formula (1a). Preferably, the first compound has one or more structures selected from the group consisting of a triazine structure, a carbazole structure, a fulvalene structure, and a thiopentene structure. These structures can be two or more, and when two or more are present, they can be identical or different. More preferably, the first compound has at least one of a dibenzofuran structure or a dibenzothiophene structure. It can have two or more dibenzofuran structures, two or more dibenzothiophene structures, or both dibenzofuran and dibenzothiophene structures simultaneously.

[0120] The preferred first compound may include a compound having the structure represented by the following general formula (1).

[0121] [Chemical Formula 7]

[0122] General formula (1)

[0123] In general formula (1), each of the multiple X's independently represents O or S. The X's present in the compound can all be O, all be S, or a mixture of O and S. Preferred compounds may include compounds in which n X's constituting the 3-ring structure on the right side of general formula (1) are all O. Furthermore, preferred compounds may include compounds in which n X's constituting the 3-ring structure on the right side of general formula (1) are all S.

[0124] In general formula (1), n ​​represents an integer greater than or equal to 0, and p represents an integer greater than or equal to 0. n+p is greater than or equal to 1. When n is greater than or equal to 2, multiple Y 11 ~Y 18 They can be the same or different. When p is 2 or higher, multiple Ys... 21 ~Y 28 They can be the same as each other, or they can be different.

[0125] Preferred compounds may include compounds in which n is 2 or more, and more preferred compounds may include compounds in which n is 2. In this case, p is preferably any integer from 0 to 2, for example, p can be 0 or p is 1. Preferred compounds are those in which, when n is 2 or more, n Y 11 All are the same, n Y 12 All are the same, n Y 13 All are the same, n Y 14 All are the same, n Y 15 All are the same, n Y 16 All are the same, n Y 17 All are the same, n Y 18 All are the same. In one aspect of the invention, a compound with n = 3 may be included. In another aspect of the invention, a compound with n = 1 may also be included.

[0126] Furthermore, other preferred compounds may also include compounds with p=1. In this case, p is preferably any integer from 1 to 3, more preferably 1 or 2. n is preferably 0 or 1, but can also be set to 0.

[0127] The compound represented by general formula (1) is preferably a compound with a PBHT value of 0.91 or higher, more preferably a compound with a PBHT value of 0.91 or higher and n of 2 or higher, and even more preferably a compound with a PBHT value of 0.91 or higher and n of 2. Furthermore, it is also preferred to have a compound with a PBHT value of 0.91 or higher, p of 1 and n of 0, or p of 1 and n of 1.

[0128] In general formula (1), Y 1 ~Y 8 and Y 11 ~Y 18 Each can be represented independently as N or CR, and R represents a hydrogen atom, a substituent, or a direct bond with L. For compounds where R represents a direct bond with L, Y... 1 ~Y 4 There is only one in the middle, and Y 11 ~Y 14 There is only one. In one aspect of the invention, it may include Y. 1 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 2 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 3 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 4 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 11 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 12 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 13 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 14 Compounds that are CR and where R represents a direct bond with L.

[0129] When n is 2 or more, in n dibenzofuran rings or dibenzothiophene rings, R represents the Y bond with the direct bond of L. 11 ~Y 14 They can be the same or different. The preference is for them to be the same.

[0130] Y in general formula (1) 1 ~Y 8 and Y 11 ~Y18 Both can be CR. Furthermore, Y 1 ~Y 8 and Y 11 ~Y 18 In compounds where N is represented, there can be one or more, two or more, three or more, four or more, six or more, or nine or more N atoms in the molecule. 1 ~Y 8 and Y 11 ~Y 18 The number of compounds representing N in the molecule can be 15 or less, 10 or less, 7 or less, or 5 or less. In one aspect of the invention, Y may be included. 1 Compounds of N. In one aspect of the invention, Y may be included. 2 Compounds of N. In one aspect of the invention, Y may be included. 3 Compounds of N. In one aspect of the invention, Y may be included. 4 Compounds of N. In one aspect of the invention, Y may be included. 5 Compounds of N. In one aspect of the invention, Y may be included. 6 Compounds of N. In one aspect of the invention, Y may be included. 7 Compounds of N. In one aspect of the invention, Y may be included. 8 Compounds of N. In one aspect of the invention, Y may be included. 11 Compounds of N. In one aspect of the invention, Y may be included. 12 Compounds of N. In one aspect of the invention, Y may be included. 13 Compounds of N. In one aspect of the invention, Y may be included. 14 Compounds of N. In one aspect of the invention, Y may be included. 15 Compounds of N. In one aspect of the invention, Y may be included. 16 Compounds of N. In one aspect of the invention, Y may be included. 17 Compounds of N. In one aspect of the invention, Y may be included. 18 Compounds containing nitrogen (N).

[0131] In general formula (1), Y 21 ~Y 28 Each can be represented independently as N or C-R'. R' represents a hydrogen atom or a substituent. Y 21 ~Y 28 The number of compounds representing N is preferably 0 to 3, more preferably 0 to 2, and may also be 1. Furthermore, Y... 21 ~Y 28Both can be C-R'.

[0132] In general formula (1), Y 1 ~Y 8 and Y 11 ~Y 18 In formula (1), two adjacent Rs represent CRs, which can form a ring structure by bonding with each other. Furthermore, in general formula (1), Y... 21 ~Y 28 Both adjacent rings in the diagram represent C-R', and these R's can bond with each other to form a ring structure. The ring structure is preferably a 5- to 8-membered ring, more preferably a 5- to 7-membered ring, and even more preferably a 5- or 6-membered ring. The formed ring structure can be a monocyclic ring or a polycyclic ring formed by ring fusion. Furthermore, the formed ring structure can be an aromatic ring or an aliphatic ring, and can be a hydrocarbon ring or a heterocyclic ring.

[0133] Substituents represented by R and R' may include, for example, hydroxyl groups, halogen atoms, alkyl groups with 1 to 20 carbon atoms, alkoxy groups with 1 to 20 carbon atoms, alkylthio groups with 1 to 20 carbon atoms, aryl groups with 6 to 40 carbon atoms, aryloxy groups with 6 to 40 carbon atoms, arylthio groups with 6 to 40 carbon atoms, heteroaryl groups with 3 to 40 carbon atoms, heteroaryloxy groups with 3 to 40 carbon atoms, heteroarylthio groups with 3 to 40 carbon atoms, alkenyl groups with 2 to 10 carbon atoms, alkynyl groups with 2 to 10 carbon atoms, trialkylsilyl groups with 3 to 20 carbon atoms, cyano groups, diarylamino groups (where the two aryl groups are not bonded to each other), and diarylamino groups (where the two aryl groups are bonded to each other to form a cyclic structure). In these specific examples, groups that can be further substituted by substituents may be substituted or unsubstituted. Further substituents for further substitution may include the substituents exemplified above. More preferred substituents are alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, alkoxy groups with 1 to 20 substituted carbon atoms, aryl groups with 6 to 40 substituted or unsubstituted carbon atoms, and heteroaryl groups with 3 to 40 substituted or unsubstituted carbon atoms. Further preferred substituents are alkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, alkoxy groups with 1 to 10 substituted or unsubstituted carbon atoms, aryl groups with 6 to 15 substituted or unsubstituted carbon atoms, and heteroaryl groups with 3 to 12 substituted or unsubstituted carbon atoms. For example, substituted or unsubstituted aryl groups may also be used.

[0134] Apart from the direct bond with L, all R atoms present in general formula (1) can be hydrogen atoms. Among the R atoms present in general formula (1), there can be only one, two, three, four or more, six or more, or nine or more substituents. Furthermore, among the R atoms present in general formula (1), there can be 15 or fewer, 10 or fewer, 7 or fewer, or 5 or fewer substituents.

[0135] In general formula (1), all R's can be hydrogen atoms. In general formula (1), there can be only one, two, three, or more than four substituents among the R's. Furthermore, in general formula (1), there can be eight or fewer, six or fewer, four or fewer, or five or fewer substituents among the R's.

[0136] In general formula (1), L represents a (n+p+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. The conjugated linking group here means a structure conjugated with the three-ring structure on the left side of general formula (1), the n three-ring structures on the right side, and the p three-ring structures on the upper side. The structure connecting these three-ring structures can consist only of aromatic or heteroaromatic rings, or it can consist of a combination of an aromatic or heteroaromatic ring and one or more structures selected from the group consisting of aromatic rings, heteroaromatic rings, alkenyl groups, and alkyne groups. When combining two or more structures, structures of the same kind (e.g., aromatic rings and aromatic rings) or structures of different kinds (e.g., aromatic rings and alkenyl groups) can be combined. Examples of combinations include aromatic rings and aromatic rings, aromatic rings and heteroaromatic rings, aromatic rings and alkenyl groups, heteroaromatic rings and heteroaromatic rings, and heteroaromatic rings and alkenyl groups. The aromatic rings, heteroaromatic rings, and alkenyl groups described herein can be substituted with substituents. Examples of substituents described herein may include the substituents illustrated in the description of R in general formula (1). Examples of alkenyl groups may include ethylene, phenyl ethylene, diphenyl ethylene, naphthyl ethylene, and dinaphthyl ethylene.

[0137] Specific examples of L can include benzene rings with (n+p+1) valence, naphthalene rings with (n+p+1) valence, anthracene rings with (n+p+1) valence, phenanthrene rings with (n+p+1) valence, triphenylene rings with (n+p+1) valence, pyrene rings with (n+p+1) valence, and so on. The ring is a (n+p+1) valent pyridine ring. Specific examples of L may also include (n+p+1) valent benzene structures, (n+p+1) valent biphenyl structures, (n+p+1) valent o-triphenyl structures, (n+p+1) valent meta-triphenyl structures, and (n+p+1) valent para-triphenyl structures. Preferred examples of L may include (n+p+1) valent benzene structures and (n+p+1) valent biphenyl structures, more preferably (n+p+1) valent benzene structures.

[0138] When L is a biphenyl structure, in a preferred embodiment, at least 3 positions in the biphenyl structure are replaced by a 3-ring structure. In a preferred embodiment, at least positions 3 and 5 are replaced by a 3-ring structure. In a preferred embodiment, at least positions 3, 5, and 3' are replaced by a 3-ring structure. In a preferred embodiment, at least positions 3, 5, and 4' are replaced by a 3-ring structure. In a preferred embodiment, at least positions 3, 5, and 2' are replaced by a 3-ring structure. Furthermore, in another preferred embodiment, at least position 4' is replaced by a 3-ring structure. In a preferred embodiment, at least positions 3 and 4' are replaced by a 3-ring structure. Furthermore, in another preferred embodiment, at least position 2' is replaced by a 3-ring structure. In a preferred embodiment, at least positions 3 and 2' are replaced by a 3-ring structure.

[0139] When L is a benzene structure, in preferred embodiments, two of the three ring structures bonded to the benzene structure are preferably substituted at the meta or para position, particularly preferably at the meta position. When L contains a phenylene group, the phenylene group can be any one of 1,2-phenylene, 1,3-phenylene, and 1,4-phenylene, preferably 1,3-phenylene or 1,4-phenylene, particularly preferably 1,3-phenylene.

[0140] Furthermore, when L contains a pyridinyl group, it can be any one of 2,3-pyridinyl, 2,4-pyridinyl, 2,5-pyridinyl, 2,6-pyridinyl, 3,4-pyridinyl, and 3,5-pyridinyl, preferably 2,6-pyridinyl.

[0141] The preferred first compound may also include compounds having the structure represented by the following general formula (2).

[0142] [Chemical Formula 8]

[0143] General formula (2)

[0144]

[0145] In general formula (2), multiple X's independently represent O or S. 1 ~Y 8 and Y 11 ~Y 18Each of these can be independently represented by N or CR, where R represents a hydrogen atom, a substituent, or a direct bond with L. L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. n represents an integer greater than 1. Multiple Ys 11 ~Y 18 They can be the same as each other, or they can be different.

[0146] Regarding X and Y 1 ~Y 8 Y 11 ~Y 18 For the description and preferred range of L and n, please refer to the corresponding description in general formula (1).

[0147] In a preferred aspect of the invention, compounds of general formula (2) in which n is an integer greater than or equal to 2 may be included. For example, compounds of general formula (2) in which n is 2 may be exemplified. In another preferred aspect of the invention, compounds of general formula (2) in which n is 1 and L is a heteroarylene may be included. For example, compounds of pyridine ring in which n1 is 1 and L is divalent may be exemplified. In another preferred aspect of the invention, compounds of general formula (2) in which Y... 12 Compounds of CR (where R is a single bond to L). In another preferred aspect of the invention, it may include Y of general formula (2). 2 For CR (R is a single bond with L) and Y 12 Compounds of CR (where R is a single bond to L). In a further preferred aspect of the invention, it may include Y of general formula (2). 2 For CR (R is a single bond with L), Y 12 Compounds that are CR (R being a single bond with L) and L being a divalent heteroarylene such as pyridylene.

[0148] The preferred first compound may also include compounds having the structure represented by the following general formula (3).

[0149] [Chemical Formula 9]

[0150] General formula (3)

[0151]

[0152] In general formula (3), multiple X's independently represent O or S. 1 Y 2 Y 4 ~Y 8 and Y 11 ~Y 18Each of these can be represented independently as N or CR, where R represents a hydrogen atom, a substituent, or a direct bond with L. L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. n represents an integer greater than 2. Multiple Ys 11 ~Y 18 They can be the same as each other, or they can be different.

[0153] Regarding X and Y 1 Y 2 Y 4 ~Y 8 Y 11 ~Y 18 For the description and preferred range of L and n, please refer to the corresponding description in general formula (1). Additionally, Y 3 CR represents a direct bond with L.

[0154] In a preferred aspect of the invention, Y may include general formula (3). 11 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 12 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 13 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 14 Compounds that are CR and where R represents a direct bond with L.

[0155] The preferred first compound may also include compounds having the structure represented by the following general formula (4).

[0156] [Chemical Formula 10]

[0157] General formula (4)

[0158]

[0159] In general formula (4), multiple X's independently represent O or S. 1 ~Y 8 and Y 12 ~Y 18 Each of these can be represented independently as N or CR, where R represents a hydrogen atom, a substituent, or a direct bond with L. L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. n represents an integer greater than 2. Multiple Ys 11 ~Y 18 They can be the same as each other, or they can be different.

[0160] Regarding X and Y 1 ~Y 8 Y 12 ~Y 18For the description and preferred range of L and n, please refer to the corresponding description in general formula (1). Additionally, Y 11 CR represents a direct bond with L.

[0161] In one aspect of the invention, Y may include general formula (4). 1 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 2 The compound is CR, where R represents a direct bond with L. In a preferred aspect of the invention, Y may be included. 3 Compounds are CR, where R represents a direct bond with L. In one aspect of the invention, Y may be included. 4 Compounds that are CR and where R represents a direct bond with L.

[0162] The preferred first compound may also include compounds having the structure represented by the following general formula (5).

[0163] [Chemical Formula 11]

[0164] General formula (5)

[0165]

[0166] In general formula (5), X represents O or S. Y 1 ~Y 8 Each can be represented independently as N or CR, where R represents a hydrogen atom, a substituent, or a direct bond with L. Y 21 ~Y 28 Each Y represents N or C-R' independently. R' represents a hydrogen atom or substituent. L represents a (p+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring. p represents an integer greater than 1. When p is 2 or greater, multiple Y 21 ~Y 28 They can be the same as each other, or they can be different.

[0167] Regarding X and Y 1 ~Y 8 Y 21 ~Y 28 The description and preferred scope of L and p can be referred to the corresponding description in general formula (1). In another preferred aspect of the invention, Y of general formula (5) may be included. 2 Compounds having a CR (R being a single bond with L) are included. In another preferred aspect of the invention, compounds in which L is phenylene, more preferably 1,3-phenylene, may be included. In another preferred aspect of the invention, compounds with a p=1 may be included.

[0168] The dibenzofuran and dibenzothiophene structures included in the formulas (1) to (5) can be any one of the following: a structure bonded to L at the 1-position, a structure bonded to L at the 2-position, a structure bonded to L at the 3-position, or a structure bonded to L at the 4-position. When L is a benzene ring (preferably a benzene ring bonded at the meta-position, such as a meta-phenylene ring), the dibenzofuran and dibenzothiophene structures are preferably compounds in which L is substituted at the 1-position or 2-position, more preferably compounds in which L is substituted at the 2-position. When L is a biphenyl structure, the dibenzofuran and dibenzothiophene structures are preferably compounds in which L is substituted at the 2-position or 4-position, more preferably compounds in which L is substituted at the 4-position.

[0169] [Chemical Formula 12]

[0170]

[0171] The following are specific examples of the first compound. However, the first compound that can be used in this invention should not be interpreted as limiting by these specific examples.

[0172] [Chemical Formula 13-1]

[0173]

[0174] [Chemical Formula 13-2]

[0175]

[0176] [Chemical Formula 14]

[0177]

[0178] The PBHT values ​​and bond energies of the cations of compounds 1–21 are shown in the table below.

[0179] [Table 1]

[0180] PBHT value Bond energy (eV) Compound 1 0.996 6.041 Compound 2 0.930 6.057 Compound 3 0.911 6.020 Compound 4 0.891 6.177 Compound 5 0.883 6.030 Compound 6 0.881 6.029 Compound 7 0.858 6.029 Compound 8 0.824 5.955 Compound 9 0.823 6.019 Compound 10 0.811 6.076 Compound 11 0.811 6.065 Compound 12 0.862 6.141 Compound 13 0.763 6.093 Compound 14 0.860 4.875 Compound 15 0.963 4.843 Compound 16 0.732 5.041 Compound 17 0.897 4.936 Compound 18 0.737 5.012 Compound 19 0.806 5.066 Compound 20 0.959 4.894 Compound 21 0.760 4.329 Compound 22 0.734 4.388 Compound 23 0.813 4.392 Compound 24 0.790 4.611 Compound 25 0.792 4.988 Compound 26 0.874 4.741

[0181] (Compound 2)

[0182] The second compound has a lowest excited singlet state energy level lower than that of the first compound, and ΔE ST (2) Compounds with an energy level less than 0.20 eV. Compound 2 exhibits the following tendency: due to the lowest excited singlet state energy level E S1 (2) with the lowest excited triplet energy level E T1 (2) They are close together, so they are prone to reverse intersystem crossing from the excited triplet state to the excited singlet state. As for the case that the second compound is the compound that causes reverse intersystem crossing, it can be confirmed by observing the delayed fluorescence emitted when the excited singlet state generated by reverse intersystem crossing is radiatively deactivated to the ground singlet state.

[0183] In this paper, "delayed fluorescence" refers to fluorescence with a fluorescence lifetime (τ) of 200 ns (nanoseconds) or more. Furthermore, the "fluorescence lifetime (τ)" in this paper refers to the time determined by measuring the decay of fluorescence after photoexcitation of a solution or vapor-deposited film sample under conditions such as nitrogen atmosphere or vacuum in the absence of oxygen. If two or more fluorescent components with different fluorescence lifetimes are observed, the fluorescence lifetime of the component with the longest lifetime is defined as the "fluorescence lifetime (τ)". In this paper, fluorescence lifetimes of 200 ns or more are specifically referred to as delayed fluorescence lifetime (τ). DELAY The delayed fluorescence lifetime (τ) of compound 2 DELAY Preferably less than 10 μs (microseconds).

[0184] The second compound is preferably a material that induces a reverse intersystem crossing from the excited triplet state to the excited singlet state, and more preferably a material that emits delayed fluorescence. By making the second compound a compound that induces a reverse intersystem crossing, the excited triplet state is converted into an excited singlet state, thereby enabling the energy of the excited singlet state to be effectively used in the luminescence of the second compound or the luminescent material (the third compound).

[0185] Furthermore, the ΔE of compound 2 ST (2) Preferably even lower, specifically, preferably less than 0.15 eV, more preferably less than 0.10 eV, even more preferably less than 0.05 eV, and still more preferably less than 0.01 eV, ideally 0 eV. The second compound exhibits ΔE ST (2) The smaller the value, the easier it is to induce the tendency of reverse intersystem crossing, and it can effectively manifest the role of converting the excited triplet state into the excited singlet state.

[0186] The second compound is preferably a compound with a PBHT value greater than 0.10, more preferably a compound with a PBHT value greater than 0.15, and even more preferably a compound with a PBHT value greater than 0.20. Furthermore, the second compound is preferably a compound with a PBHT value less than 0.50, more preferably a compound with a PBHT value less than 0.45, and even more preferably a compound with a PBHT value less than 0.40. The second compound is particularly preferred to be a compound with a PBHT value greater than 0.20 and less than 0.40.

[0187] The second compound can be a material composed of a single compound satisfying formula (2b), or it can be composed of two or more compounds forming an excimer complex, wherein the lowest excited singlet energy level E of the excimer complex is... S1 With the lowest excited triplet energy level E T1The difference is less than 0.20 eV. Furthermore, because the second compound readily undergoes radiative deactivation from the excited triplet state to the ground singlet state at room temperature (300 K), it is preferable to be a non-typical phosphorescent material, such as a metal complex with a heavy metal element like Ir or Pt as the central metal. In other words, the second compound is preferably a compound that does not contain any metal element, preferably a compound that does not contain any heavy metal element, preferably a compound composed only of atoms selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, sulfur, and silicon atoms, preferably a compound composed only of atoms selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, and sulfur atoms, preferably a compound composed only of atoms selected from the group consisting of carbon, hydrogen, nitrogen, and oxygen atoms, preferably a compound composed only of atoms selected from the group consisting of carbon, hydrogen, and nitrogen atoms.

[0188] The second compound may include, for example, compounds represented by the following general formula (2A).

[0189] General formula (2A)

[0190] DLA

[0191] In general formula (2A), D represents a substituent having a substituted amino group, L represents a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene, and A represents a cyano or a substituted or unsubstituted heteroarylene containing at least one nitrogen atom as a constituent atom of the ring skeleton.

[0192] The arylene or heteroarylene group represented by L can be a monocyclic ring or a fused ring formed by the fusion of two or more rings. When L is a fused ring, the number of fused rings is preferably 2 to 6, for example, selected from 2 to 4. Specific examples of the ring constituting L may include a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, or a naphthalene ring. Specific examples of arylene or heteroarylene groups represented by L may include 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 1,8-naphthylene, 2,7-naphthylene, 2,6-naphthylene, 1,4-naphthylene, 1,3-naphthylene, 9,10-anthraylene, 1,8-anthraylene, 2,7-anthraylene, 2,6-anthraylene, 1,4-anthraylene, 1,3-anthraylene, groups in which one nitrogen atom of the ring skeleton constituent atoms of these groups is substituted, groups in which two nitrogen atom substituted, and groups in which three nitrogen atom substituted. The arylene or heteroarylene group represented by L may have substituents or may not be substituted. When having two or more substituents, the substituents may be the same or different from each other. Substituents include, for example, hydroxyl groups, halogen atoms, alkyl groups with 1 to 20 carbon atoms, alkoxy groups with 1 to 20 carbon atoms, alkylthio groups with 1 to 20 carbon atoms, aryl groups with 6 to 40 carbon atoms, heteroaryl groups with 3 to 40 carbon atoms, alkenyl groups with 2 to 10 carbon atoms, alkynyl groups with 2 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 20 carbon atoms, trimethylsilylalkyl groups with 4 to 20 carbon atoms, trimethylsilylalkenyl groups with 5 to 20 carbon atoms, trimethylsilylalkynyl groups with 5 to 20 carbon atoms, substituents having a substituted amino group, cyano groups, etc. In these specific examples, groups that can be further substituted by substituents may be substituted. More preferably, the substituents are alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, alkoxy groups with 1 to 20 substituted carbon atoms, aryl groups with 6 to 40 substituted or unsubstituted carbon atoms, and heteroaryl groups with 3 to 40 substituted or unsubstituted carbon atoms. Even more preferably, the substituents are alkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, alkoxy groups with 1 to 10 substituted or unsubstituted carbon atoms, aryl groups with 6 to 15 substituted or unsubstituted carbon atoms, and heteroaryl groups with 3 to 12 substituted or unsubstituted carbon atoms.

[0193] In the heteroaryl group A, which contains at least one nitrogen atom as a ring backbone atom, the number of nitrogen atoms as ring backbone atom constituents is preferably 1 to 3. Regarding the preferred range and specific examples of the heteroaryl group, the preferred range and specific examples of the heteroarylene group represented by L above can be referred to by replacing them with a monovalent group. The heteroaryl group in A is preferably a group composed of a 6-membered ring containing 1 to 3 nitrogen elements as ring backbone constituents, more preferably pyridyl, pyrimidinyl, or triazineyl, and even more preferably triazineyl. The heteroaryl group can be substituted with substituents. Regarding the preferred range and specific examples of substituents, the preferred range and specific examples of substituents that can be substituted by the arylene group or heteroarylene group represented by L above can be referred to.

[0194] A can also be any of these substituted or unsubstituted heteroaryl groups, but cyano is preferred. In particular, a cyano group of A is more preferred than a triazine group of A.

[0195] Compounds represented by general formula (2A) may include compounds comprising the benzonitrile skeleton represented by general formula (2B) or compounds comprising the triazine skeleton represented by general formula (2C).

[0196] [Chemical Formula 15]

[0197] General formula (2B)

[0198]

[0199] In general formula (2B), R 1 ~R 5 The 0 to 4 groups represent cyano groups, R 1 ~R 5 At least one of them represents a substituent having a substituted amino group, and the remaining R 1 ~R 5 It represents a hydrogen atom or a substituent having a substituted amino group and substituents other than a cyano group.

[0200] [Chemical Formula 16]

[0201] General formula (2C)

[0202]

[0203] In general formula (2C), R 6 ~R 8 At least one of them represents a substituent, and the remaining R 6 ~R 8 It represents a hydrogen atom or a substituent having a substituted amino group and substituents other than a cyano group.

[0204] In general formulas (2A) to (2C), the substituent having the substituted amino group is preferably a substituent having a diarylamino group, wherein the two aryl groups constituting the diarylamino group can be linked together to form, for example, a carbazole group. Furthermore, in general formula (2B), the substituent having the substituted amino group can be R... 1 ~R 5 Any of them, but R can be preferably exemplified, for example. 2 R 3 R 4 R 1 and R 3 R 1 and R 4 R 1 and R 5 R 2 and R 3 R 1 and R 3 and R 5 R 1 and R 2 and R 3 R 1 and R 3 and R 4 R 2 and R 3 and R 4 R 1 and R 2 and R 3 and R 4 R 1 and R 2 and R 3 and R 4 and R 5 And so on. Furthermore, the substituents of the substituted amino group in general formula (2C) can be R. 6 ~R 8 Any of them, but for example, R can be exemplified. 6 R 6 and R 7 R 6 and R 7 and R 8 .

[0205] The substituents having the substituted amino group described in general formulas (2A) to (2C) are preferably substituents represented by the following general formula (W1). There may be two or more substituents represented by general formula (W1) in the molecule, and there may be three or more substituents. When the compound is represented by general formula (2A) or general formula (2B), there may be four or more substituents represented by general formula (W1) in the molecule. There are no particular limitations on the substitution positions of the substituents represented by general formula (W1).

[0206] [Chemical Formula 17]

[0207] General formula (W1)

[0208]

[0209] In the general formula (W1), Ar 1 and Ar 2 Each of the following independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. L represents a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. * indicates the bonding position with the carbon atom (C) in the general formulas (2A) to (2C).

[0210] Ar in general formula (W1) 1 and Ar 2 They can bond with each other to form a ring structure together with nitrogen atoms of the general formula (W1).

[0211] Ar 1 and Ar 2 The arylene or heteroarylene group represented can be a monocyclic ring or a fused ring composed of two or more rings. When it is a fused ring, the number of fused rings is preferably 2 to 6, for example, selected from 2 to 4. Ar 1 and Ar 2 Specific examples of rings can include benzene rings, pyridine rings, pyrimidine rings, triazine rings, and naphthalene rings. Ar 1 and Ar 2 Specific examples of the arylene or heteroarylene groups represented may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, 2-pyridyl, 3-pyridyl, and 4-pyridyl. 1 and Ar 2The arylene or heteroarylene groups represented may or may not have substituents. When there are two or more substituents, the substituents may be the same or different from each other. Substituents include hydroxyl groups, halogen atoms, alkyl groups with 1 to 20 carbon atoms, alkoxy groups with 1 to 20 carbon atoms, alkylthio groups with 1 to 20 carbon atoms, amino groups with 1 to 20 carbon atoms substituted with alkyl groups, amino groups with 1 to 20 carbon atoms substituted with aryl groups, aryl groups with 6 to 40 carbon atoms, heteroaryl groups with 3 to 40 carbon atoms, alkenyl groups with 2 to 10 carbon atoms, alkynyl groups with 2 to 10 carbon atoms, alkamido groups with 2 to 20 carbon atoms, aramido groups with 7 to 21 carbon atoms, and trialkylsilyl groups with 3 to 20 carbon atoms, etc. In these specific examples, groups that can be further substituted by substituents may be replaced. More preferably, the substituents are alkyl groups with 1 to 20 carbon atoms, alkoxy groups with 1 to 20 carbon atoms, alkylthio groups with 1 to 20 carbon atoms, amino groups with 1 to 20 carbon atoms substituted with alkyl groups, amino groups with 1 to 20 carbon atoms substituted with aryl groups, aryl groups with 6 to 40 carbon atoms, and heteroaryl groups with 3 to 40 carbon atoms.

[0212] The substituent represented by the general formula (W1) is preferably the substituent represented by the following general formula (W2).

[0213] [Chemical Formula 18]

[0214] General formula (W2)

[0215]

[0216] In the general formula (W2), R 11～ R 20 Each can independently represent a hydrogen atom or a substituent. L represents a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 11 and R 12 R 12 and R 13 R 13 and R 14 R 14 and R 15 R 15 and R 16 R 16 and R 17 R 17 and R 18 R 18 and R 19 R 19 and R 20 They can bond together to form linking groups necessary for forming a cyclic structure. Furthermore, R 15 and R 16They can bond with each other to form single bonds or linking groups. * indicates the bonding position with carbon atoms (C) in general formulas (2A) to (2C).

[0217] Regarding R 11 ~R 20 For specific examples and preferred ranges of substituents that can be used, please refer to Ar in general formula (2A). 1 and Ar 2 The description corresponding to the substituents of the represented arylene or heteroarylene.

[0218] R 11 and R 12 R 12 and R 13 R 13 and R 14 R 14 and R 15 R 15 and R 16 R 16 and R 17 R 17 and R 18 R 18 and R 19 R 19 and R 20 The cyclic structure formed by the bonding of elements can be an aromatic ring, an aliphatic ring, or a structure containing heteroatoms, and the cyclic structure can be a fused ring with two or more rings. The heteroatoms mentioned herein are preferably atoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms. Examples of the formed cyclic structures can include benzene rings, naphthalene rings, pyridine rings, pyridazine rings, pyrimidine rings, pyrazine rings, pyrrole rings, imidazole rings, pyrazole rings, imidazoline rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, cyclohexadiene rings, cyclohexene rings, cyclopentene rings, cycloheptanetriene rings, cycloheptadiene rings, cycloheptene rings, etc.

[0219] In general formulas (W1) and (W2), L represents a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L is preferably a single bond or a substituted or unsubstituted aryl group.

[0220] The aromatic ring constituting the arylene group represented by L can be a monocyclic ring, a fused ring formed by two or more aromatic rings, or a linking ring formed by two or more aromatic rings. If two or more aromatic rings are linked, they can be connected in a straight chain or a branched chain. The number of carbon atoms in the aromatic ring constituting the arylene group represented by L is preferably 6 to 22, more preferably 6 to 18, further preferably 6 to 14, and even more preferably 6 to 10. Specific examples of arylene groups may include phenylene, naphthyl, and biphenylene.

[0221] Furthermore, the heterocycle constituting the heteroarylene group represented by L can be a monocyclic ring, a fused ring formed by the fusion of one or more heterocycles and aromatic rings, or a linking ring formed by the connection of one or more heterocycles and aromatic rings. The heterocycle preferably has 5 to 22 carbon atoms, more preferably 5 to 18, even more preferably 5 to 14, and still more preferably 5 to 10. The heteroatom constituting the heterocycle is preferably a nitrogen atom. Specific examples of heterocycles may include pyridine rings, pyridazine rings, pyrimidine rings, triazole rings, and benzotriazole rings.

[0222] The more preferred group represented by L is phenylene. When L is phenylene, the phenylene can be any one of 1,2-phenylene, 1,3-phenylene, and 1,4-phenylene, but is preferably 1,4-phenylene. Furthermore, L can be substituted with substituents. There are no particular limitations on the number or position of substituents in L. For a description and preferred range of substituents that can be introduced into L, please refer to the above-mentioned R. 11 ~R 20 Description and preferred range of substituents that can be used.

[0223] The substituent represented by general formula (W2) is preferably a substituent represented by any one of the following general formulas (W3) to (W7).

[0224] [Chemical Formula 19-1]

[0225] General formula (W3)

[0226]

[0227] General formula (W4)

[0228]

[0229] General formula (W5)

[0230]

[0231] [Chemical Formula 19-2]

[0232] General formula (W6)

[0233] General formula (W7)

[0234]

[0235] In general formulas (W3) to (W7), R 21 ~R 24 R 27 ~R 38 R 41 ~R 48 R 51~R 58 R 61 ~R 65 R 81 ~R 90 Each can be represented independently as a hydrogen atom or a substituent. For a description and preferred range of substituents described herein, please refer to the above-mentioned R. 11 ~R 20 Description and preferred range of substituents. R 21 ~R 24 R 27 ~R 38 R 41 ~R 48 R 51 ~R 58 R 61 ~R 65 R 71 ~R 79 R 81 ~R 90 Preferably, each group is independently represented by any one of the general formulas (W3) to (W7) mentioned above. Furthermore, R in general formula (W3) 21 R 23 R 28 R 30 At least two of them are preferably substituted or unsubstituted alkyl groups, more preferably R 21 R 23 R 28 R 30 All are substituted or unsubstituted alkyl groups, or R 21 and R 30 For substituted or unsubstituted alkyl groups, or R 23 and R 28 The alkyl group may be substituted or unsubstituted, and more preferably, it is an alkyl group having 1 to 6 carbon atoms. R in general formula (W7) 89 and R 90 Preferably, the alkyl group is substituted or unsubstituted, more preferably, it is an alkyl group with 1 to 6 carbon atoms that is substituted or unsubstituted. The number of substituents in general formulas (W3) to (W7) is not particularly limited. It is also preferred that all substituents are unsubstituted (i.e., hydrogen atoms). Furthermore, when two or more substituents are present in each of the general formulas (W3) to (W7), these substituents may be the same or different. When a substituent is present in general formulas (W3) to (W7), if it is in general formula (W3), then the substituent is preferably R. 22 ~R 24 R 27 ~R 29 Any one of them, more preferably R 23 and R 28At least one of them, if in general formula (W4), then the substituent is preferably R. 32 ~R 37 If any of the substituents is in the general formula (W5), then the substituent is preferably R. 42 ~R 47 If any of the substituents is in the general formula (W6), then the substituent is preferably R. 52 R 53 R 56 R 57 R 62 ~R 64 If any of the substituents is in the general formula (W7), then the substituent is preferably R. 82 ~R 87 R 89 R 90 Any one of them.

[0236] In general formulas (W3) to (W7), R 21 and R 22 R 22 and R 23 R 23 and R 24 R 27 and R 28 R 28 and R 29 R 29 and R 30 R 31 and R 32 R 32 and R 33 R 33 and R 34 R 35 and R 36 R 36 and R 37 R 37 and R 38 R 41 and R 42 R 42 and R 43 R 43 and R 44 R 45 and R 46 R 46 and R 47 R 47 and R 48 R 51 and R 52 R 52 and R 53 R 53 and R 54 R 55 and R56 R 56 and R 57 R 57 and R 58 R 61 and R 62 R 62 and R 63 R 63 and R 64 R 64 and R 65 R 54 and R 61 R 55 and R 65 R 81 and R 82 R 82 and R 83 R 83 and R 84 R 85 and R 86 R 86 and R 87 R 87 and R 88 R 89 and R 90 They can bond together to form a ring structure. For an explanation and preferred examples of the ring structure, please refer to R in the above general formula (W2). 11 and R 12 Explanation and preferred examples of ring structures formed by mutual bonding.

[0237] In general formulas (W3) to (W7), L 1 ~L 5 * Indicates a single bond, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. * Indicates the bonding position with the carbon atom (C) in general formulas (2A) to (2C). Regarding L... 1 ~L 5 The description and preferred range of the arylene or heteroarylene groups represented by L, and the substituents that can be introduced into these groups, can be found with reference to the description and preferred range of the arylene or heteroarylene groups represented by L, and the substituents that can be introduced into these groups. 1 ~L 5 Preferably, it is a single bond, a substituted or unsubstituted aryl group.

[0238] The second type of compound is mostly a compound known as a compound that emits delayed fluorescence. Preferred compounds of this type include those in segments 0008–0048 and 0095–0133 of WO2013 / 154064, segments 0007–0047 and 0073–0085 of WO2013 / 011954, segments 0007–0033 and 0059–0066 of WO2013 / 011955, segments 0008–0071 and 0118–0133 of WO2013 / 081088, segments 0009–0046 and 0093–0134 of Japanese Patent Application Publication No. 2013-256490, and Japanese Patent Application Publication No. 2013-256490. The compounds, especially exemplified compounds, contained in the general formulas described in Japanese Patent Application Publication No. 13-116975 (paragraphs 0008-0020 and 0038-0040), Japanese Patent Application Publication No. WO2013 / 133359 (paragraphs 0007-0032 and 0079-0084), Japanese Patent Application Publication No. WO2013 / 161437 (paragraphs 0008-0054 and 0101-0121), Japanese Patent Application Publication No. 2014-9352 (paragraphs 0007-0041 and 0060-0069), and Japanese Patent Application Publication No. 2014-9224 (paragraphs 0008-0048 and 0067-0076) are incorporated herein by reference.

[0239] Furthermore, compounds emitting delayed fluorescence (delayed phosphors) may preferably include Japanese Patent Application Publication No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, and WO Published in WO2014 / 133121, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, and WO2015 / 016200 Japan Patent Application Publication No. WO2015 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, Japan Patent Application Publication No. 2015-129240, WO2015 / 129714, WO2015 / 12 Compounds, especially exemplified compounds, contained in the general formulas described in Publications No. 9715, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541 are included in this document.

[0240] The emission wavelength of the second compound is not particularly limited and can be appropriately selected according to the intended use of the composition according to the invention. For example, if the composition of the invention is used in the light-emitting layer of an organic light-emitting element for image display or color display, then the second compound preferably has a maximum emission wavelength in the red region (620-750 nm), the green region (495-570 nm), or the blue region (450-495 nm).

[0241] The following are specific examples of the second compound. However, the second compound that can be used in this invention should not be interpreted as limiting by these specific examples.

[0242] [Chemical Formula 20-1]

[0243]

[0244] [Chemical Formula 20-2]

[0245]

[0246] [Chemical Formula 20-3]

[0247]

[0248] [Chemical Formula 20-4]

[0249]

[0250] [Chemical Formula 20-5]

[0251]

[0252] [Chemical Formula 20-6]

[0253]

[0254] [Chemical Formula 20-7]

[0255]

[0256] (A composition comprising compound 1 and compound 2)

[0257] The compositions of the present invention comprise a first compound and a second compound. The compositions of the present invention may consist only of the first compound and the second compound, or may contain other compounds.

[0258] Compound 1 and compound 2 satisfy the relationship of equation (A) above. Therefore, the lowest excited singlet state energy level E of compound 1 is... S1 (1) The lowest excited singlet state energy level E of the second compound is higher than that of the second compound. S1 (2). Therefore, it is easy to transfer the excited singlet energy from compound 1 to compound 2. E S1 (1) with E S1 (2) The difference [E] S1 (1)-E S1 (2) For example, it can be set to above 0.1eV, above 0.2eV, above 0.3eV, above 0.5eV, or below 1.2eV, below 1.0eV, below 0.8eV, or below 0.6eV.

[0259] The lowest excited triplet energy level E of compound 1 T1 (1) Preferably, the lowest excited triplet energy level E of the second compound is higher. T1 (2). Thus, the energy of the excited triplet state is confined within the molecule of the second compound, which increases the probability of reverse intersystem crossing from its excited triplet state to the excited singlet state. As a result, a composition with high luminescence efficiency can be obtained.

[0260] Regarding the lowest excited singlet state energy level E S1 and the lowest excited triplet energy level E T1 The concentration of the target compound can be determined using the following measurement method. During measurement, a sample is prepared as a solution of the target compound dissolved in toluene, or a sample is prepared by co-deposition with the host material to achieve a concentration of the target compound of 6% by weight. The host material is selected from materials whose lowest excited singlet state energy level is higher than the E0 level of the target compound. S1 Furthermore, the lowest excited triplet energy level is higher than the E of the measured compound. T1 In the material. Additionally, the E in this article S1 and E T1 The values ​​were obtained by measuring a 100 nm thick film of a sample co-deposited with mCP on a Si substrate to achieve a concentration of 6% by weight of the target compound.

[0261] (1) The lowest excited singlet state energy level E S1

[0262] The fluorescence spectrum of the sample was measured at room temperature (300 K). The fluorescence spectrum was obtained by accumulating the emission from the initial incident excitation light to 100 nanoseconds after incident, with the vertical axis representing the emission intensity and the horizontal axis representing the wavelength. In the fluorescence spectrum, the vertical axis represents emission intensity and the horizontal axis represents wavelength. A tangent was drawn relative to the rising short-wavelength side of the emission spectrum, and the wavelength value λedge [nm] at the intersection of this tangent and the horizontal axis was determined. This wavelength value was converted into an energy value using the following conversion formula, which is taken as E. S1 .

[0263] Conversion formula: E S1 [eV] = 1239.85 / λedge

[0264] For measuring the emission spectrum, a nitrogen laser (LTB Lasertechnik Berlin GmbH, MNL200) can be used as the excitation source and a streak camera (Hamamatsu Photonics K.K., C4334) can be used as the detector.

[0265] (2) The lowest excited triplet energy level E T1

[0266] This will be related to the lowest excited singlet state energy level E S1The same sample was cooled to 77 K, and excitation light (337 nm) was irradiated onto the phosphorescence measurement sample. The phosphorescence intensity was measured using a streak camera. By accumulating the emission from 1 ms to 10 ms after the excitation light incident, a phosphorescence spectrum was obtained with the vertical axis set to luminescence intensity and the horizontal axis set to wavelength. A tangent was drawn relative to the rising short-wavelength side of this phosphorescence spectrum, and the wavelength value λedge [nm] at the intersection of this tangent and the horizontal axis was determined. This wavelength value was converted into an energy value using the following conversion formula, which is taken as E. T1 .

[0267] Conversion formula: E T1 [eV] = 1239.85 / λedge

[0268] The rising tangent on the short-wavelength side of the phosphorescence spectrum is drawn as follows. Consider the tangent at each point on the curve towards the long-wavelength side as the spectral curve moves from the short-wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side of the spectrum. As the curve rises (i.e., as the vertical axis increases), the slope of this tangent increases. The tangent drawn at the point where this slope reaches its maximum value is taken as the rising tangent on the short-wavelength side of the phosphorescence spectrum. Furthermore, points with peak intensities less than 10% of the maximum peak intensity of the spectrum are not included in the aforementioned maximum value on the shortest wavelength side; the tangent drawn at the point closest to the maximum value on the shortest wavelength side and where the slope reaches its maximum value is taken as the rising tangent on the short-wavelength side of the phosphorescence spectrum.

[0269] The composition of the present invention needs to be a composition in which the first compound satisfies formula (1a), the second compound satisfies formula (2b), and the first and second compounds satisfy the relationship of formula (A).

[0270] In a preferred aspect, the composition of the present invention is a composition in which the first compound satisfies formulas (1a) and (1c), the second compound satisfies formula (2b), and the first and second compounds satisfy the relationship of formula (A).

[0271] In a preferred aspect, the composition of the present invention is a composition in which the first compound satisfies formula (1a), the second compound satisfies formulas (2a) and (2b), and the first compound and the second compound satisfy the relationship of formula (A).

[0272] In a preferred aspect, the composition of the present invention is a composition in which the first compound satisfies formulas (1a) and (1c), the second compound satisfies formulas (2a) and (2b), and the first and second compounds satisfy the relationship of formula (A).

[0273] When the content of the first compound in the composition of the present invention is set to 100 parts by weight, the content of the second compound is preferably 0.01 parts by weight or more, and can be selected from, for example, the range of 0.1 parts by weight or more, 1 part by weight or more, 3 parts by weight or more, 5 parts by weight or more, and 9 parts by weight or more. Furthermore, when the content of the first compound is set to 100 parts by weight, the content of the second compound can be selected from, for example, the range of less than 50 parts by weight, 30 parts by weight or less, 20 parts by weight or less, 15 parts by weight or less, 10 parts by weight or less, 6 parts by weight or less, 2 parts by weight or less, and 0.5 parts by weight or less. And, for example, it can be selected from the range of 30 to 70 parts by weight or from the range of 40 to 55 parts by weight.

[0274] The content of the first compound in the composition of the present invention is preferably 30% by weight or more, more preferably 50% by weight or more. For example, it can be set in the range of 70% by weight or more, 80% by weight or more, 90% by weight or more, 95% by weight or more, or 99% by weight or more. The content of the first compound in the composition of the present invention is preferably 99.99% by weight or less, for example, it can be set in the range of 99.9% by weight or less, 99% by weight or less, 95% by weight or less, 85% by weight or less, 75% by weight or less, 55% by weight or less, or 35% by weight or less. Furthermore, it can be selected, for example, from the range of 50 to 90% by weight or from the range of 60 to 80% by weight.

[0275] The compositions of the present invention preferably do not contain any metal elements, and more preferably do not contain any heavy metal elements. The compositions of the present invention are preferably composed only of atoms selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, sulfur, and silicon atoms, and are even more preferably composed only of atoms selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, and sulfur atoms.

[0276] The composition of the present invention can be adjusted to maximize the amount of light emitted from the second compound in the light emitted from the composition of the present invention. In this case, the amount of light emitted from the second compound is preferably 50% or more of the total amount of light emitted from the composition, and can also be adjusted to 70% or more, 90% or more, 95% or more, 99% or more, 99.9% or more, or 100%.

[0277] Additionally, when referring to the amount of light emitted from the composition, it means the amount of light emitted when the composition is formed into a thin film and inserted between a pair of electrodes is excited by an electric current.

[0278] (Compound 3)

[0279] In addition to the first and second compounds, the compositions of the present invention may also contain a third compound satisfying the following formula (B).

[0280] [Formula 10]

[0281] E S1 (1) > E S1 (2) > E S1 (3) Equation (B)

[0282] In equation (B), E S1 (1) represents the lowest excited singlet state energy level of the first compound, E S1 (2) represents the lowest excited singlet state energy level of the second compound, E S1 (3) represents the lowest excited singlet energy level of the third compound.

[0283] E S1 (2) with E S1 (3) The difference [E] S1 (2)-E S1 (3) For example, it can be set to 0.1 eV or higher, 0.2 eV or higher, 0.3 eV or higher, 0.5 eV or higher, or 1.2 eV or lower, 1.0 eV or lower, 0.8 eV or lower, 0.6 eV or lower. By using the third compound that satisfies formula (B), the excited singlet state energy of the second compound can be easily transferred to the third compound, thereby enabling the energy of the excited singlet state generated by the reverse intersystem crossing of the second compound to be efficiently used in the luminescence of the third compound.

[0284] The third compound is preferably a fluorescent material. In this invention, "fluorescent material" means an organic material that emits fluorescence when irradiated with excitation light onto a solution sample or vapor-deposited film sample, such as toluene or dichloromethane, at 20°C. Here, "fluorescence" refers to light emitted during deactivation from the excited singlet state to the ground singlet state, and capable of passing through the lowest excited singlet state energy level S. 1,q and the lowest excited triplet energy level T 1,q The lowest excited singlet state energy level S of fluorescent materials 1,f and the lowest excited triplet energy level T 1,f for

[0285] S 1,q >S 1,f

[0286] T 1,q <T 1,f

[0287] Phosphorescence is distinguished by the fact that the triplet-state deactivated material or the introduction of oxygen does not extinguish the fluorescence. The fluorescent material in this invention can be a material that emits phosphorescence along with fluorescence, but in this case, the fluorescence intensity is preferably more than 9 times the phosphorescence intensity.

[0288] The third compound can be a compound with a fluorescence lifetime (τ) of less than 200 ns (nanoseconds), or a delayed fluorescence material with a fluorescence lifetime (τ) of more than 200 ns (nanoseconds). For an explanation of the fluorescence lifetime (τ), please refer to the explanation of the fluorescence lifetime (τ) of the second compound.

[0289] The third compound preferably also satisfies the following formula (3b).

[0290] [Formula 11]

[0291] ΔE ST (3) <0.20 eV (3b)

[0292] In equation (3b), ΔE ST (3) is the lowest excited singlet state energy level E of the third compound. S1 (3) The lowest excited triplet energy level E of the third compound T1 (3) difference.

[0293] ΔE of compound 3 ST (3) For example, it can be set in the range of less than 0.15 eV, less than 0.10 eV, less than 0.05 eV, and less than 0.01 eV. Compound 3 has ΔE ST (3) The smaller the value, the easier it is to induce the tendency of reverse intersystem crossing, and it can effectively manifest the role of converting the excited triplet state into the excited singlet state.

[0294] The third compound can be a material composed of a single compound satisfying formula (B), or it can be composed of two or more compounds forming an excimer complex, wherein the lowest excited singlet energy level E of the excimer complex is... S1 Compounds satisfying formula (B). Furthermore, when an excitocomplex is formed, the lowest excited singlet state energy level E of the excitocomplex... S1 With the lowest excited triplet energy level E T1The difference is preferably less than 0.20 eV. The third compound is preferably a compound that does not contain any metal elements, preferably a compound that does not contain any heavy metal elements, preferably a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms and silicon atoms, preferably a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms and sulfur atoms, preferably a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms, preferably a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms and nitrogen atoms.

[0295] When the composition of the present invention contains a third compound, the content of the third compound is preferably less than the content of the first compound. Furthermore, the content of the third compound is preferably less than the content of the second compound. When the total amount of the first and second compounds is set to 100 parts by weight, the content of the third compound is preferably 0.01 parts by weight or more, for example, selected from the range of 0.1 parts by weight or more, 1 part by weight or more, 3 parts by weight or more, 5 parts by weight or more, and 9 parts by weight or more. Furthermore, when the total amount of the first and second compounds is set to 100 parts by weight, the content of the third compound can be selected from the range of 30 parts by weight or less, 20 parts by weight or less, 15 parts by weight or less, 10 parts by weight or less, 6 parts by weight or less, 2 parts by weight or less, and 0.5 parts by weight or less. Furthermore, it can be selected from the range of 0.01 to 5 parts by weight or from the range of 0.1 to 3% by weight.

[0296] When the composition of the present invention contains the third compound, it can be adjusted so that the amount of light emitted from the third compound is the largest among the light emitted from the composition of the present invention. In this case, the amount of light emitted from the third compound is preferably 50% or more of the total amount of light emitted from the composition, and can also be adjusted to 70% or more, 90% or more, 95% or more, 99% or more, 99.9% or more, or 100%.

[0297] Even when the composition of the present invention contains a third compound, it is possible to adjust the amount of light emitted from the second compound to be the maximum among the light emitted from the composition of the present invention. In this case, the amount of light emitted from the second compound can be adjusted to be 50% or more, 70% or more, 90% or more, 95% or more, 99% or more, or 99.99% or more of the total amount of light emitted from the composition, and the amount of light emitted from the third compound can be adjusted to be in the range of 0.01 to 50%, 0.01 to 30%, 0.01 to 10%, 0.01 to 5%, or 0.01 to 1%.

[0298] The luminescence levels of compounds 2 and 3 can be controlled by adjusting their types and amounts.

[0299] The emission wavelength of the third compound is not particularly limited and can be appropriately selected according to the intended use of the composition according to the invention. For example, if the composition of the invention is used in the light-emitting layer of an organic light-emitting element for image display or color display, then the third compound preferably has a maximum emission wavelength in the red region (620-750 nm), the green region (495-570 nm), or the blue region (450-495 nm).

[0300] The third compound can be derived from anthracene derivatives, tetraphenylene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, etc. Compounds with boron-containing polycyclic aromatic skeletons, such as derivatives of rubrene, coumarin, pyran, stilbene, fluorene, anthracene, pyrrolemethylene, terphenyl, terphenylene, fluoranthene, amines, quinacridones, oxadiazoles, malononitriles, pyrans, carbazoles, juulolidines, thiazoles, and diazaboron (naphthoanthracene), exhibit multiple resonance effects. These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons can be combined with each other.

[0301] Specific examples of the third compound may include compounds included as specific examples of the second compound. The third compound is selected such that it satisfies the relationship of formula (B) relative to the second compound. The compound used as the third compound preferably exhibits a PL emission quantum yield of 60% or more, more preferably 80% or more. Furthermore, the compound used as the third compound preferably exhibits an instantaneous fluorescence lifetime of 50 ns or less, more preferably 20 ns or less. Here, the instantaneous fluorescence lifetime refers to the emission lifetime of the earliest decaying component among multiple exponentially decaying components observed when the emission lifetime of a compound exhibiting thermally active delayed fluorescence is measured. Furthermore, the compound used as the third compound preferably has a fluorescence emission rate from S1 to the ground state greater than the intersystem crossing rate from S1 to T1. For methods of calculating the rate constant of the compound, refer to known literature mentioning thermally active delayed fluorescence materials (H. Uoyama, et al., Nature 492, 234 (2012) or K. Masui, et al., Org. Electron. 14, 2721, (2013), etc.).

[0302] Furthermore, specific examples of other compounds that can be used in the third compound can also be illustrated by the compounds described below. In the structures of the illustrated compounds, t-butyl and t-Bu both represent tert-butyl. However, the compounds that can be used in the third compound in this invention should not be interpreted as limiting by these specific examples.

[0303] [Chemical Formula 21-1]

[0304]

[0305] [Chemical Formula 21-2]

[0306]

[0307] [Chemical Formula 21-3]

[0308]

[0309] [Chemical Formula 22-1]

[0310]

[0311] [Chemical Formula 22-2]

[0312]

[0313] [Chemical Formula 22-3]

[0314]

[0315] [Chemical Formula 22-4]

[0316]

[0317] [Chemical Formula 22-5]

[0318]

[0319] [Chemical Formula 22-6]

[0320]

[0321] [Chemical Formula 22-7]

[0322]

[0323] [Chemical Formula 22-8]

[0324]

[0325] [Chemical Formula 22-9]

[0326]

[0327] [Chemical Formula 22-10]

[0328]

[0329] [Chemical Formula 22-11]

[0330]

[0331] (Luminescent Composition)

[0332] The composition of the present invention comprising the first compound and the second compound is useful as a luminescent composition.

[0333] The luminescent composition can be in a solution state or a solid state. When in a solution state, the solvent used can be appropriately selected from solvents capable of dissolving the composition. For example, it can include organic solvents such as toluene. When in a solid state, it is preferably formed into a film (film-like, thin film-like). When formed into a thin film state, it can, for example, be formed as a single layer of a luminescent element having a multilayered structure.

[0334] In one embodiment, a film comprising the composition of the present invention can be formed in a wet process. In the wet process, a solution obtained by dissolving the composition of the present invention is coated onto a surface, and after removing the solvent, a film is formed. The wet process may include, but is not limited to, spin coating, slot coating, inkjet printing, gravure printing, offset printing, and flexographic printing. In the wet process, a suitable organic solvent capable of dissolving the composition of the present invention is selected and used. In one embodiment, a substituent (e.g., an alkyl group) that improves solubility relative to the organic solvent can be introduced into the compound comprising the composition.

[0335] In one embodiment, a film comprising the composition of the present invention can be formed in a dry process. In one embodiment, vacuum deposition can be used as the dry process, but it is not limited thereto. When using vacuum deposition, the compounds constituting the film can be co-deposited from a single deposition source, or from a single deposition source containing a mixture of compounds. When using a single deposition source, a mixed powder formed by mixing powders of compounds can be used, a compression molded body formed by compressing the mixed powder can be used, or a mixture of compounds heated, melted, and cooled can be used. In one embodiment, by co-depositing under conditions where the vapor deposition rates (weight loss rates) of the multiple compounds contained in a single deposition source are consistent or substantially consistent, a film with a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source can be formed. If multiple compounds are mixed with the same composition ratio as the composition ratio of the formed film and used as a deposition source, a film with the desired composition ratio can be easily formed. In one embodiment, the temperature at which the co-deposited compounds achieve the same weight loss rate can be determined, and this temperature is used as the temperature for co-deposition.

[0336] (Method for providing a luminescent composition)

[0337] The present invention also relates to a method for providing a luminescent composition comprising a first compound and a second compound.

[0338] The method for providing the luminescent composition of the present invention is as follows: designing and ΔE ST (2) A method of combining a first compound with a second compound having a voltage less than 0.20 eV to provide a luminescent composition comprising the first compound and the second compound. The method is characterized by designing the second compound to achieve an Eluminescent... S1 (1) Greater than E S1 (2) The step where PBHT(1) is greater than 0.730. When designing, it is preferable to perform the following steps at least once: determine the PBHT value and E for the specific molecular structure. S1 For a molecular structure that has undergone a change in a specific part of its molecular structure, determine the PBHT value and E. S1 Confirm E S1 With E S1(1) Equal, and select the structure with the larger PBHT value. This step is preferably repeated multiple times until the PBHT value is not expected to increase due to the change in molecular structure. A change in part of the molecular structure can be made by replacing a hydrogen atom in the molecular structure with a substituent or by replacing a substituent in the molecular structure with another substituent. Examples of substituents mentioned here include those represented by R in the first compound. Furthermore, it is also possible to change the ring skeleton constituent atom from a carbon atom to a nitrogen atom or from a nitrogen atom to a carbon atom. Additionally, it is possible to change the ring skeleton constituent atom from an oxygen atom to a sulfur atom or from a sulfur atom to an oxygen atom. Alternatively, the substitution position of the substituent or the bonding position can be changed. These changes can be performed while confirming E. S1 With E S1 (1) Equal, and choose the structure with the larger PBHT value.

[0339] For example, for compounds having a specific structure represented by the above general formula (1), determine the PBHT value and E. S1 For compounds whose structure has been modified, determine the PBHT value and E. S1 And by comparing, the method of the present invention can be implemented. When changing, X in general formula (1) can be changed, and Y can be changed. 1 ~Y 8 and Y 11 ~Y 18 At least one of them is changed from CR to N or from N to CR, or Y is changed. 1 ~Y 8 and Y 11 ~Y 18 At least one CR of R, change n, change the substituent of L, change the skeleton of L, change the Y bonded to L 1 ~Y 4 Or change the Y bonded to L. 11 ~Y 14 Being able to make these changes appropriately and confirm E S1 With E S1 (1) Equal, and choose the structure with the larger PBHT value.

[0340] In the method of this invention, regarding the PBHT value and E S1 The result can be calculated. Furthermore, a program can be created to execute the method of this invention, and the method can be implemented using this program. The program can be operated using a computer such as a personal computer.

[0341] (Organic light-emitting diode)

[0342] The compositions of the present invention are useful as light-emitting compositions. Therefore, by using the compositions of the present invention, excellent organic light-emitting elements such as organic photoluminescent elements (organic PL elements) or organic electroluminescent elements (organic EL elements) can be provided. The organic photoluminescent element has a structure in which at least a light-emitting layer is formed on a substrate. Furthermore, the organic electroluminescent element has a structure in which at least an anode, a cathode, and an organic layer is formed between the anode and the cathode. The organic layer includes at least a light-emitting layer, and may be formed solely of the light-emitting layer, or may have one or more organic layers in addition to the light-emitting layer. Such other organic layers may include hole transport layers, hole injection layers, electron blocking layers, hole blocking layers, electron injection layers, electron transport layers, exciton blocking layers, etc. The hole transport layer may be a hole injection and transport layer with hole injection function, and the electron transport layer may be an electron injection and transport layer with electron injection function. A specific structure of an organic electroluminescent element is shown below. Figure 1 In. Figure 1 In the diagram, 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 composition of the present invention can be used in the light-emitting layer.

[0343] The following describes the components and layers of an organic photoluminescent device. Additionally, the descriptions of the substrate and light-emitting layer also correspond to the substrate and light-emitting layer of the organic photoluminescent device.

[0344] Substrate:

[0345] In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, wherein the substrate is not particularly limited and may be any of those substrates commonly used in organic electroluminescent elements, such as those formed of glass, transparent plastic, quartz and silicon.

[0346] anode:

[0347] In some embodiments, the anode of the organic electroluminescent device is made of a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a large work function (above 4 eV). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is fabricated by vapor deposition or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, when high precision (e.g., above about 100 μm) may not be required for the pattern, the pattern can be formed by vapor deposition or sputtering of the electrode material using a mask with the desired shape. In some embodiments, when a coating material (such as an organic conductive compound) can be coated, wet film formation methods, such as printing and coating, are used. In some embodiments, when emitted light passes through the anode, the transmittance of the anode is greater than 10%, and the sheet resistance of the anode is less than several hundred ohms per square meter. In some embodiments, the thickness of the anode is 10–1,000 nm. In some embodiments, the thickness of the anode is 10–200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0348] cathode:

[0349] In some embodiments, the cathode is made of a metal (below 4 eV) (referred to as an electron-injecting metal), alloy, conductive compound, or combination thereof, with an electrode material having a low work function. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al2O3) mixtures, indium, lithium-aluminum mixtures, and rare earth metals. In some embodiments, a mixture of the electron-injecting metal and a second metal is used, wherein the second metal is a stable metal with a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al2O3) mixtures, lithium-aluminum mixtures, and aluminum. In some embodiments, the mixture increases electron injection characteristics and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film using vapor deposition or sputtering. In some embodiments, the film resistivity of the cathode is below several hundred ohms per square meter. In some embodiments, the thickness of the cathode is in the range of 10 nm to 5 μm. In some embodiments, the thickness of the cathode is in the range of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent element is transparent or translucent in order to transmit the emitted light. In some embodiments, transparent or translucent electroluminescent elements enhance the luminous brightness.

[0350] In some embodiments, the cathode is formed using a conductive transparent material as described for the anode to form a transparent or translucent cathode. In some embodiments, the element comprises a uniformly transparent or translucent anode and cathode.

[0351] Emissive layer:

[0352] In some embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, are rebonded to form excitons. In some embodiments, the layer emits light.

[0353] The compositions of the present invention are used in the light-emitting layer. In some embodiments, the emitted light comprises both fluorescence and delayed fluorescence. In some embodiments, the emitted light comprises phosphorescence. In some embodiments, the emitted light comprises light emitted from a second compound. In some embodiments, the emitted light comprises light emitted from a second compound and light emitted from a first compound. Furthermore, in embodiments using a third compound, the emitted light comprises light emitted from a third compound. In other embodiments using a third compound, the emitted light comprises light emitted from a third compound and light emitted from a second compound. In other embodiments using a third compound, the emitted light comprises light emitted from a third compound, light emitted from a second compound, and light emitted from a first compound. In some embodiments using a third compound, the second compound is an auxiliary dopant.

[0354] Injection layer:

[0355] The injection layer is a layer located between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the luminous intensity. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer may be disposed between the anode and the luminescent layer or hole transport layer, and between the cathode and the luminescent layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present.

[0356] Examples of preferred compounds that can be used as hole injection materials.

[0357] [Chemical Formula 23]

[0358] MoO3,

[0359]

[0360] Next, preferred examples of compounds that can be used as electron injection materials are included.

[0361] [Chemical Formula 24]

[0362] LiF, CsF,

[0363] Barrier layer:

[0364] A blocking layer is a layer capable of suppressing the diffusion of charges (electrons or holes) and / or excitons in the light-emitting layer to the outside of the light-emitting layer. In some embodiments, an electron blocking layer is located between the light-emitting layer and the hole transport layer, and suppresses electrons from passing through the light-emitting layer toward the hole transport layer. In some embodiments, a hole blocking layer is located between the light-emitting layer and the electron transport layer, and suppresses holes from passing through the light-emitting layer toward the electron transport layer. In some embodiments, the blocking layer suppresses exciton diffusion to the outside of the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that function as both electron blocking layers and exciton blocking layers.

[0365] Cavity blocking layer:

[0366] The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer suppresses holes from reaching the electron transport layer while transporting electrons. In some embodiments, the hole blocking layer enhances the probability of rebonding between electrons and holes in the light-emitting layer. The material used for the hole blocking layer can be the same material described for the electron transport layer.

[0367] Next, preferred examples of compounds that can be used in hole-blocking layers are included.

[0368] [Chemical Formula 25]

[0369]

[0370] Electron blocking layer:

[0371] Holes are transported by an electron blocking layer. In some embodiments, the electron blocking layer suppresses electrons from reaching the hole transport layer while transporting holes. In some embodiments, the electron blocking layer enhances the probability of rebonding between electrons and holes in the light-emitting layer. The material used for the electron blocking layer can be the same material described for the hole transport layer.

[0372] The following are specific examples of preferred compounds that can be used as electron blocking materials.

[0373] [Chemical Formula 26]

[0374]

[0375] Exciton blocking layer:

[0376] An exciton blocking layer suppresses the diffusion of excitons generated via the rebonding of holes and electrons in the light-emitting layer into the electron transport layer. In some embodiments, the exciton blocking layer enables the effective confinement of excitons within the light-emitting layer. In some embodiments, it enhances the luminous efficiency of the device. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is on the anode side, the layer may be located between and adjacent to the hole transport layer and the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, the layer may be located between and adjacent to the light-emitting layer and the cathode. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is located between the anode and the exciton blocking layer, with the exciton blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is located between the cathode and the exciton blocking layer, with the exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer includes an excitation singlet energy and an excitation triplet energy, at least one of which is higher than the excitation singlet energy and excitation triplet energy of the luminescent material, respectively.

[0377] Hole transport layer:

[0378] The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers.

[0379] In some embodiments, the hole transport material has one of hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in this invention include (but are not limited to) triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkyl derivatives, pyrazoline derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, aromatic amine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene-anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers) or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amines, and styrene amine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound.

[0380] The following are specific examples of preferred compounds that can be used as hole transport materials.

[0381] [Chemical Formula 27]

[0382]

[0383] Electron transport layer:

[0384] The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers.

[0385] In some embodiments, the electron transport material only needs to have the function of transporting electrons injected from the cathode into the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples that can be used in the electron transport layer of the present invention include (but are not limited to) nitro-substituted fluorene derivatives, dibenzoquinone derivatives, thiopiperanoxide derivatives, carbodiimide, fluorenemethane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, aziridine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material.

[0386] The following are specific examples of preferred compounds that can be used as electron transport materials.

[0387] [Chemical Formula 28]

[0388]

[0389] Preferred materials for use in organic electroluminescent devices are specifically exemplified, but the materials that can be used in this invention are not limited to the compounds exemplified above. Furthermore, even compounds exemplified as materials with specific functions can be used as materials with other functions.

[0390] Device:

[0391] In some embodiments, compounds represented by general formula (1) are incorporated into the device. For example, the device includes, but is not limited to, OLED bulbs, OLED lights, television screens, computer monitors, mobile phones, and tablet computers.

[0392] In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host material and a light-emitting material.

[0393] In some embodiments, the OLED's emissive layer further comprises a fluorescent material that converts a triplet state into a singlet state.

[0394] In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or photovoltaic devices. In some embodiments, the compositions can be suitable for facilitating charge transfer or energy transfer within the device and / or for use as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic photodetectors, organic photosensors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0395] Light bulb or lamp:

[0396] In some embodiments, the electronic device includes an OLED, the OLED including an anode, a cathode and at least one organic layer including a light-emitting layer between the anode and the cathode, wherein the light-emitting layer includes a host material, a light-emitting material and an OLED driving circuit.

[0397] In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array comprising combinations of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors.

[0398] In some embodiments, the device is an OLED light, the OLED light comprising:

[0399] The circuit board has a first surface having a mounting surface and a second surface opposite thereto, and at least one opening is defined thereon;

[0400] At least one OLED is disposed on the mounting surface and has a structure in which the at least one OLED includes an anode, a cathode and at least one organic layer containing a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host material and a light-emitting material and emits light.

[0401] Housing, used for circuit board; and

[0402] At least one connector is disposed at an end of the housing, and the housing and the connector define an encapsulation suitable for mounting to a lighting device.

[0403] In some embodiments, the OLED lamp includes a plurality of OLEDs mounted on a circuit board to emit light in multiple directions. In some embodiments, a portion of the light emitted in a first direction is deflected to be emitted in a second direction. In some embodiments, a reflector is used to deflect the light emitted in the first direction.

[0404] Monitor or screen:

[0405] In some embodiments, the compound of formula (1) can be used in a screen or display. In some embodiments, the compound of formula (1) is deposited onto a substrate using methods including (but not limited to) vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photographic plate structure suitable for double-sided etching, providing pixels with a unique aspect ratio. The screen (which may also be referred to as a mask) is used in methods for manufacturing OLED displays. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction and promotes large swept-bevel openings in the horizontal direction. This allows for tight patterning of pixels required for high-definition displays while optimizing chemical vapor deposition onto the TFT substrate.

[0406] Internal patterning of pixels allows for the construction of 3D pixel openings with varying aspect ratios in both the horizontal and vertical directions. Furthermore, imaging "strips" or halftone circles within the pixel region suppress etching in specific areas until these specific patterns are undercut and leave the substrate. At this point, all pixel regions are processed at the same etching rate, but the depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows etching to be suppressed at different rates within the pixel, enabling locally deeper etching to create steep vertical bevels.

[0407] The preferred material for deposition masks is invar steel. Invar steel is a metal alloy that is cold-rolled into long thin sheets in a steel mill. Invar steel cannot be used as a nickel mask for electrodeposition onto a spin mandrel. A suitable and low-cost method for forming opening regions within a vapor deposition mask is a wet chemical etching method.

[0408] In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In other embodiments, the screen or display pattern is fabricated using plasma etching.

[0409] Method for manufacturing the device:

[0410] OLED displays are typically manufactured by forming a large motherboard and then cutting the motherboard into unit cells. Generally, each unit cell on the motherboard is formed by: forming a thin-film transistor (TFT) including an active layer and source / drain electrodes on a substrate, coating a planarization film onto the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then cutting it from the motherboard.

[0411] OLED displays are typically manufactured by forming a large motherboard and then cutting the motherboard into unit cells. Generally, each unit cell on the motherboard is formed by: forming a thin-film transistor (TFT) including an active layer and source / drain electrodes on a substrate, coating a planarization film onto the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then cutting it from the motherboard.

[0412] In another aspect of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method comprising:

[0413] The process of forming a barrier layer on the substrate of the motherboard;

[0414] The process of forming multiple display units from unit board units on the barrier layer;

[0415] The process of forming an encapsulation layer on each of the display units of the unit board; and

[0416] The process of coating an organic film on the interface portion between the unit plates.

[0417] In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edge portions of the barrier layer are covered with an organic film formed of polyimide or acryloyl groups. In some embodiments, the organic film facilitates the gentle cutting of the motherboard into unit panels.

[0418] In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and a source / drain electrode. Each of the plurality of display units may include a thin-film transistor (TFT), a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, wherein an organic film coated on the interface portion is formed of the same material as the planarization film and is formed at the same time as the planarization film is formed. In some embodiments, the light-emitting unit is connected to the TFT layer, wherein a passivation layer, a planarization film, and an encapsulation layer are provided therebetween, and the encapsulation layer covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film does not contact either the display unit or the encapsulation layer.

[0419] Each of the organic film and the planarization film may comprise either polyimide or acryloyl groups. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the substrate may be formed of polyimide. The method may further include mounting a carrier substrate formed of a glass material onto another surface of the substrate before forming the barrier layer on one surface of the substrate formed of polyimide, and separating the carrier substrate from the substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display.

[0420] In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylamide, as in the case of an organic film formed on an edge portion of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously when manufacturing an OLED display. In some embodiments, the organic film may be formed on an edge portion of the barrier layer such that a portion of the organic film directly contacts the substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0421] In some embodiments, the light-emitting layer has a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to the source / drain electrode of the TFT layer.

[0422] In some embodiments, when a voltage is applied to the pixel electrode via the TFT layer, an appropriate voltage is formed between the pixel electrode and the opposite electrode, thereby causing the organic light-emitting layer to emit light and thus forming an image. Hereinafter, the image forming unit having a TFT layer and light-emitting units will be referred to as a display unit.

[0423] In some embodiments, the encapsulation layer covering the display units and preventing external moisture penetration can be formed as a thin-film encapsulation structure having organic and inorganic films alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure having multiple thin films stacked. In some embodiments, the organic film coated on the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0424] In one embodiment, the OLED display is flexible and uses a soft substrate formed of polyimide. In some embodiments, the substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.

[0425] In some embodiments, a barrier layer is formed on the surface of the substrate opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit plate. For example, while forming the substrate over the entire surface of the motherboard, the barrier layer is formed according to the size of each unit plate, thereby forming a groove at the interface portion between the unit plate barrier layers. Each unit plate can be cut along the groove.

[0426] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, wherein a groove is formed in the barrier layer, wherein at least a portion of an organic film is formed in the groove, and the groove does not penetrate into the substrate. In some embodiments, a TFT layer is formed for each unit panel, and a passivation layer (i.e., an inorganic film) and a planarization film (i.e., an organic film) are disposed on the TFT layer to cover the TFT layer. The groove at the interface portion is covered with an organic film, such as a polyimide or acrylamide, while a planarization film formed of, for example, polyimide or acrylamide is formed. This is to prevent cracking by allowing the organic film to absorb shocks generated when cutting each unit panel along the groove at the interface portion. That is, if the entire barrier layer is completely exposed without the organic film, the shock generated when cutting each unit panel along the groove at the interface portion is transferred to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, because the grooves at the interface portions between the barrier layers are covered with an organic film, and this organic film absorbs impacts that would otherwise be transferred to the barrier layers, each unit panel can be cut gently, and cracking in the barrier layers can be prevented. In one embodiment, the organic film covering the grooves at the interface portions is spaced apart from the planarization film. For example, if the organic film and the planarization film are connected to each other as a single layer, then because external moisture may penetrate into the display unit through the planarization film and a portion of the residual organic film, the organic film and the planarization film are spaced apart from each other so that the organic film is separated from the display unit.

[0427] In some embodiments, a display unit is formed by forming light-emitting units, and an encapsulation layer is disposed on the display unit to cover it. Thus, after the motherboard is fully manufactured, a carrier substrate supporting the substrate is separated from the substrate. In some embodiments, when a laser beam is emitted toward the carrier substrate, the carrier substrate separates from the substrate due to the difference in thermal expansion coefficients between the carrier substrate and the substrate.

[0428] In some embodiments, the motherboard is cut into unit panels. In some embodiments, the motherboard is cut along the interface portion between the unit panels using a cutting machine. In some embodiments, because the grooves at the interface portion along which the motherboard is cut are covered with an organic film, the organic film absorbs impact during cutting. In some embodiments, cracking can be prevented from occurring in the barrier layer during cutting.

[0429] In some embodiments, the method reduces the defect rate of the product and stabilizes its quality.

[0430] On the other hand, there is an OLED display having: a barrier layer formed on a substrate; a display unit formed on the barrier layer; an encapsulation layer formed on the display unit; and an organic film coated on the edge portion of the barrier layer.

[0431] <Definition>

[0432] Unless otherwise defined herein, the scientific and technical terms used in this application shall have the meanings commonly understood by one of ordinary skill in the art. Generally, the nomenclature and techniques used in conjunction with the chemical substances described herein are those well-known and commonly used in the art.

[0433] The term "alkoxy" refers to an alkyl group to which an oxygen atom is bonded. Representative alkoxy groups may include methoxy, trifluoromethoxy, ethoxy, propoxy, tert-butoxy, etc.

[0434] As used in this invention, the term "alkenyl" refers to an aliphatic group containing at least one double bond, and is defined to include both "unsubstituted alkenyl" and "substituted alkenyl," wherein the latter refers to an alkenyl moiety having a substituent replacing a hydrogen atom on one or more carbon atoms of the alkenyl group. Generally, unless otherwise defined, straight-chain or branched alkenyl groups have 1 to about 20 carbon atoms, preferably 1 to about 10 carbon atoms. Such substituents may appear on one or more carbon atoms, including or not included in one or more double bonds. Furthermore, as described later, such substituents include all those substituents covered by alkyl groups, except for those substituents that impair stability. For example, the covered alkenyl group is substituted by one or more alkyl, carbocyclic, aryl, heterocyclic, or heteroaryl groups.

[0435] "alkyl" refers to a fully saturated straight-chain or branched non-aromatic hydrocarbon. Generally, unless otherwise defined, straight-chain or branched alkyl groups have 1 to about 20 carbon atoms, preferably 1 to about 10 carbon atoms. In some embodiments, the alkyl group has 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms, or 1 to 3 carbon atoms. Examples of straight-chain and branched alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, pentyl, and octyl.

[0436] Furthermore, as used throughout the specification, examples, and claims, the term "alkyl" is intended to include both "unsubstituted alkyl" and "substituted alkyl," the latter referring to an alkyl moiety having a substituent substituted hydrocarbon skeleton with one or more hydrogen atoms that can replace carbon atoms. Unless otherwise specified, such substituents may include, for example, halogens (e.g., fluorine), hydroxyl groups, carbonyl groups (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), thiocarbonyl groups (e.g., thioesters, thioacetates, or thiocarbamates), alkoxy groups, phosphoryl groups, phosphate esters, phosphonates, phosphonites, amino groups, amide groups, amidines, imines, cyano groups, nitro groups, azides, thiohydrothio groups, alkylthio groups, sulfate esters, sulfonates, aminosulfonyl groups, sulfonamide groups, sulfonyl groups, heterocyclic groups, aralkyl groups, or aromatic or heteroaromatic moieties. In a preferred embodiment, the substituent on the substituted alkyl group is selected from C10. 1-6 Alkyl, C 3-6 Cycloalkyl, halogen, carbonyl, cyano, or hydroxyl groups. In a more preferred embodiment, the substituent on the substituted alkyl group is selected from fluorine, carbonyl, cyano, or hydroxyl. Those skilled in the art will understand that the portion substituted on the hydrocarbon chain can be replaced as needed. For example, the substituents of the substituted alkyl group may include substituted and unsubstituted amino, azide, imino, amide, phosphoryl (including phosphonates and phosphonites), sulfonyl (including sulfates, sulfonamides, aminosulfonyls, and sulfonates), and silyl, as well as ethers, alkyl thio groups, carboxyl (including ketones, aldehydes, carboxyl esters, and esters), -CF3, -CN, etc. Exemplary substituted alkyl groups are described below. Cycloalkyl groups may be further substituted with alkyl, alkenyl, alkoxy, alkyl thio, aminoalkyl, carbonyl-substituted alkyl, -CF3, -CN, etc.

[0437] When used in conjunction with a chemical moiety (e.g., acyl, acyloxy, alkyl, alkenyl, or alkoxy), the term "C" is used. x-y "This means including groups containing x to y carbon atoms in the chain. For example, the term "C" x-y "Alkyl" refers to a substituted or unsubstituted saturated hydrocarbon group (including straight-chain alkyl and branched-chain alkyl) containing x to y carbon atoms in the chain, and includes haloalkyl groups. Preferred haloalkyl groups include trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, and pentafluoroethyl. CO alkyl indicates a hydrogen atom when the group is terminal, and a bond when it is internal. The term "C"... 2-y "Alkenyl" and "C" 2-y "Alkyne" refers to an unsaturated aliphatic group that is similar in length and possible substitution to the alkyl groups mentioned above, but contains at least one double or triple bond, whether substituted or unsubstituted.

[0438] As used in this invention, the term "alkynyl" refers to an aliphatic group containing at least one triple bond, and is defined to include both "unsubstituted alkynyl" and "substituted alkynyl," wherein the latter refers to an alkynyl moiety having a substituent replacing a hydrogen atom on one or more carbon atoms of the alkynyl group. Generally, unless otherwise defined, straight-chain or branched alkynyl groups have 1 to about 20 carbon atoms, preferably 1 to about 10 carbon atoms. Such substituents may appear on one or more carbon atoms, including or not included in one or more triple bonds. Furthermore, as described later, such substituents include all those substituents covered by alkyl groups, except for substituents that impair stability. For example, covering an alkynyl group substituted with one or more alkyl, carbocyclic, aryl, heterocyclic, or heteroaryl groups.

[0439] The terms "amine" and "ammonia" are those well-known in the relevant field, referring to unsubstituted and substituted amines and their salts, such as the following components.

[0440] [Chemical Formula 29]

[0441]

[0442] Where R A Each can independently represent a hydrogen or hydrocarbon group, or two R groups. A It combines with the attached N atom to form a heterocycle with 4 to 8 atoms in the ring structure.

[0443] As used in this invention, the term "aryl" includes a monocyclic aromatic group in which each atom of the ring is a carbon atom, whether substituted or unsubstituted. Preferably, the ring is a 6-membered or 20-membered ring, more preferably a 6-membered ring. The term "aryl" also includes a polycyclic system having two or more rings, wherein the two or more carbon atoms are shared by two adjacent rings, wherein at least one ring is an aromatic ring, for example, the other rings may be cycloalkyl, cycloalkenyl, cycloynyl, aryl, heteroaryl, and / or heterocyclic groups. Aryl groups include benzene, naphthalene, phenanthrene, phenol, aniline, etc.

[0444] The terms “halogen” and “halogen” as used in this invention mean halogen atoms and include chlorine, fluorine, bromine and iodine.

[0445] The term "heteroaryl" includes substituted or unsubstituted aromatic monocyclic structures, preferably 5- to 20-membered rings, more preferably 5- to 6-membered rings, whose ring structure includes at least one heteroatom, preferably 1- to 4 heteroatoms, more preferably one or two heteroatoms. The term "heteroaryl" also includes polycyclic systems having two or more rings, wherein two or more carbon atoms are shared by two adjacent rings, wherein at least one ring is a heteroaromatic ring; for example, the other rings can be cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclic groups. Heteroaryl groups include, for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrazine, pyridazine, and pyrimidine.

[0446] The term "heteroatom" as used in this invention means an atom of any element other than carbon or hydrogen. Preferred heteroatoms are nitrogen, oxygen, and sulfur atoms.

[0447] The terms "heterocyclic group," "heterocyclic," and "heterocyclic" refer to a substituted or unsubstituted non-aromatic ring structure, preferably a 3- to 20-membered ring, more preferably a 3- to 7-membered ring, whose ring structure includes at least one heteroatom, preferably 1 to 4 heteroatoms, more preferably one or two heteroatoms. The terms "heterocyclic group" and "heterocyclic" also include polycyclic systems having two or more rings, wherein two or more carbon atoms are shared by two adjacent rings, and at least one ring is a heterocyclic ring; for example, the other rings can be cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclic groups. Heterocyclic groups include, for example, piperidine, piperazine, pyrrolidine, morpholine, lactone, lactam, etc.

[0448] The term "silyl" refers to a silicon moiety with three hydrocarbon groups bonded to it.

[0449] The term "substituted" refers to a partial substitution of a hydrogen atom on one or more carbon atoms in the main chain by a substituent. It should be understood that "substituted" or "substituted" includes the following implicit limitations: such substitution is consistent with the permissible valence states of the substituted atom and the substituent, and the substitution produces a stable compound, such as a compound that does not spontaneously transform (e.g., through rearrangement, cyclization, elimination, etc.). The substituted portion includes any suitable substituents described herein, such as acyl, amide, acyloxy, alkoxy, alkoxyalkyl, alkenyl, alkyl, alkylamino, alkylthio, arylthio, alkynyl, amide, amino, aminoalkyl, aralkyl, carbamate, carbocyclic, cycloalkyl, carbocyclic alkyl, carbonate, ester, ether, heteroarylalkyl, heterocyclic, heterocyclic alkyl, hydrocarbon, silyl, sulfone, or thioether. The intended use of the term "substituted" herein includes all permissible substituents in organic compounds. In a broad sense, permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and non-aromatic substituents of organic compounds. For suitable organic compounds, there may be more than one permissible substituent, and they may be the same or different. For the purposes of this invention, the heteroatom of nitrogen may have a hydrogen substituent and / or any permissible substituent of the organic compound described herein that satisfies the valence state of the heteroatom. Substituents may include any substituents described herein, such as halogens, hydroxyl groups, carbonyl groups (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), thiocarbonyl groups (e.g., thioesters, thioacetic acids, or thiocarbamates), alkoxy groups, phosphoryl groups, phosphate groups, phosphonates, phosphonites, amino groups, amide groups, amidines, imines, cyano groups, nitro groups, azides, thiohydrothio groups, alkylthio groups, sulfates, sulfonates, aminosulfonyl groups, sulfonamide groups, sulfonyl groups, heterocyclic groups, aralkyl groups, or aromatic or heteroaromatic moieties. In a preferred embodiment, the substituents on the substituted alkyl group are selected from C10. 1-6 Alkyl, C 3-6 Cycloalkyl, halogen, carbonyl, cyano, or hydroxyl groups. In a more preferred embodiment, the substituent on the substituted alkyl group is selected from fluorine, carbonyl, cyano, or hydroxyl groups. Those skilled in the art will understand that the substituent itself can be suitably substituted. Unless otherwise stated as “unsubstituted,” references to the chemical part herein should be understood to include substituted variants. For example, references to the “aryl” group or part thereof implicitly include both substituted and unsubstituted variants.

[0450] In the compounds of this invention, any atom not specifically designated as a particular isotope is intended to represent any stable isotope of said atom. Unless otherwise stated, when a position is specifically designated as “H” or “hydrogen”, said position is understood to have hydrogen in its natural abundance isotopic composition. And, unless otherwise stated, when a position is specifically designated as “D” or “deuterium”, said position is understood to have a deuterium abundance of at least 3340 times that of the natural deuterium abundance (i.e., 0.015%) (i.e., at least 50.1% deuterium inclusion).

[0451] The term "isotope enrichment factor" as used in this invention means the ratio between the isotopic abundance of a specified isotope and its natural abundance.

[0452] In various embodiments, the compounds of the present invention have an isotopic enrichment factor of at least 3500 (52.5% deuterium inclusion at each specified deuterium atom), at least 4000 (60% deuterium inclusion), at least 4500 (67.5% deuterium inclusion), at least 5000 (75% deuterium inclusion), at least 5500 (82.5% deuterium inclusion), at least 6000 (90% deuterium inclusion), at least 6333.3 (95% deuterium inclusion), at least 6466.7 (97% deuterium inclusion), at least 6600 (99% deuterium inclusion), or at least 6633.3 (99.5% deuterium inclusion) for each specified deuterium atom.

[0453] The term "isotope" refers to a species that differs from the specific compound of this invention only in its isotopic composition.

[0454] When referring to the compounds of the present invention, the term "compound" means a collection of molecules having the same chemical structure except that isotopic variations may exist among the constituent atoms of the molecules. Therefore, it will be apparent to those skilled in the art that a compound represented by a specific chemical structure containing a designated deuterium atom will also contain a small amount of isotopes having hydrogen atoms at one or more designated deuterium positions in said structure. The relative amount of such isotopes in the compounds of the present invention will depend on a variety of factors, including the isotopic purity of the deuterating agent used to prepare the compound and the deuterium incorporation efficiency in the various synthetic steps used to prepare the compound. However, as explained above, the relative amount of all such isotopes will be less than 49.9% of the compound. In other embodiments, the relative amount of all such isotopes will be less than 47.5%, less than 40%, less than 32.5%, less than 25%, less than 17.5%, less than 10%, less than 5%, less than 3%, less than 1%, or less than 0.5% of the compound.

[0455] The following includes examples and further detailed descriptions of the features of the present invention. The materials, processing contents, and processing steps shown below can be appropriately modified without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be limited by the specific examples shown below. Furthermore, the evaluation of luminescence characteristics was performed using a source meter (Keithley 2400 series), a semiconductor parameter analyzer (Agilent Technologies Japan, Ltd. E5273A), an optical power meter (Newport Corporation 1930C), a spectrometer (Ocean Optics USB2000), a spectroradiometer (TOPCON CORPORATION SR-3), and a streak camera (Hamamatsu Photonics KK C4334).

[0456] (Durability test 1 of blue light-emitting element)

[0457] Compound 20, PYD2Cz, Host2-4, 6, and 7 were selected as the first compound, and T58, a blue delayed fluorescence material, was selected as the second compound. The durability of the blue light-emitting element was then tested.

[0458] Regarding the content of compound 1 and compound 2 in the light-emitting layer, compound 1 was set to 70% by mass and compound 2 was set to 30% by mass, thereby producing a blue light-emitting element.

[0459] Vacuum deposition method was used to achieve a vacuum level of 5.0 × 10⁻⁶. -5 Pa stacked thin films on a glass substrate having an anode composed of indium tin oxide (ITO) with a film thickness of 50 nm. First, HAT-CN was formed on the ITO with a thickness of 10 nm, and NPD was formed on it with a thickness of 30 nm. Next, Tris-PCz was formed with a thickness of 10 nm, and PYD2Cz was formed on it with a thickness of 5 nm. Then, the first and second compounds were co-deposited from different deposition sources to form a layer with a thickness of 30 nm, which served as the light-emitting layer. Next, SF3-TRZ was formed with a thickness of 10 nm, and Liq and SF3-TRZ were co-deposited from different deposition sources to form a layer with a thickness of 30 nm. The contents of Liq and SF3-TRZ in this layer were set to 30% by mass and 70% by mass, respectively. Furthermore, a cathode was formed by forming Liq with a thickness of 2 nm, followed by vapor deposition of aluminum (Al) with a thickness of 100 nm, which served as the organic electroluminescent element (EL element).

[0460] Measurement at 1000 cd / m 2The time until the luminescence intensity of the blue luminescent element reaches 95% of its initial intensity is defined as LT95. A graph showing the relationship between the PBHT value of compound 1 and the measured LT95 is presented below. Figure 2 middle. Figure 2 The chart shows HOST3 with LT95 set to 1. (For example, from...) Figure 2 It has been observed that a higher PBHT value results in a longer LT95. In particular, the element using compound 20 of the present invention, which has the highest PBHT value, exhibited an LT95 7.63 times longer than the element using Host3, demonstrating excellent performance.

[0461] By changing the use of compounds 13-19 and compounds 21-26 as the first compound, each blue emitting element was manufactured according to the above steps, and the LT95 was measured. As a result, a longer LT95 was observed than that of the blue emitting element using PYD2Cz (PBHT value of 0.671) as the first compound.

[0462] (Durability test 2 for blue light-emitting elements)

[0463] Compound 20 was used as the first compound, T58 as the second compound, and T80 as the third compound. Regarding the content in the luminescent layer, the first compound was set to 69% by mass, the second compound to 30% by mass, and the third compound to 1% by mass. In addition, the durability test of the blue luminescent element was carried out according to the same steps as described above, and the results showed a good LT95 as described above.

[0464] (Durability Test 1 of Green Light-Emitting Components)

[0465] A green light-emitting element was fabricated using any one of Host 1-5 and compound 13 as the first compound, and compound T8 (4CzIPN) as the green delayed fluorescence material as the second compound. Measurements were taken at 12.5 mA / cm². 2 The time until the luminous intensity of the green light-emitting element becomes 95% of its initial intensity is defined as LT95.

[0466] Green light-emitting elements are manufactured as follows: by vacuum deposition at a vacuum level of 5.0 × 10⁻⁶. -5Pa stacked thin films on a glass substrate having an anode composed of indium tin oxide (ITO) with a film thickness of 50 nm. First, NPD (95% by mass) and HI1 (5% by mass) were formed on the ITO with a thickness of 5 nm, and then NPD was formed on it with a thickness of 60 nm. Next, PTCz was formed with a thickness of 10 nm. Then, compound 1 (65% by mass) and compound 2 (35% by mass) were co-deposited from different deposition sources to form a layer with a thickness of 40 nm, which served as the light-emitting layer. Next, SF3-TRZ was formed with a thickness of 10 nm, and then Liq (30% by mass) and SF3-TRZ (70% by mass) were co-deposited from different deposition sources to form a layer with a thickness of 30 nm. Furthermore, a cathode was formed by forming Liq with a thickness of 2 nm, followed by aluminum (Al) vapor deposition with a thickness of 100 nm, which served as the organic electroluminescent element (EL element).

[0467] A graph showing the relationship between the PBHT value and LT95 of compound 1 is presented in... Figure 3 middle. Figure 3 The chart shows HOST3 with LT95 set to 1. (For example, from...) Figure 3 It was found that a tendency exists where a higher PBHT value results in a longer LT95. Furthermore, it was confirmed that compounds with a PBHT value greater than 0.730 (used as Host1) exhibited particularly long LT95 values. Additionally, by changing the use of compounds 14–26 as the first compound, each green emitting element was manufactured according to the above steps, and its LT95 was measured. The results showed that the LT95 of the green emitting element using Host1 as the first compound was longer than that observed in other green emitting elements.

[0468] (Durability Test 2 of Green Light-Emitting Components)

[0469] The first compound was selected from any one of compounds 20, 21, and 23, and the second compound was T69. The content of the first compound in the luminescent layer was set to 65% by mass and the content of the second compound was set to 35% by mass. Otherwise, the same green element as described above was made, and as a result, good LT95 was observed as described above.

[0470] (Durability Test 3 for Green Light-Emitting Components)

[0471] Furthermore, any one of compounds 20, 21, and 23 was selected as the first compound, and T67 was used as the second compound. Regarding the content in the light-emitting layer, the first compound was set to 65% by mass, and the second compound was set to 35% by mass. In addition, the durability test of the green light-emitting element was carried out according to the same steps as described above, and the results showed that a good LT95 was observed as described above.

[0472] [Chemical Formula 30-1]

[0473]

[0474] [Chemical Formula 30-2]

[0475]

[0476] [Chemical Formula 30-3]

[0477]

[0478] Industrial availability

[0479] By using compositions that satisfy the conditions of this invention, organic light-emitting elements with excellent durability can be provided. Furthermore, by using the method of this invention, compositions useful for manufacturing organic light-emitting elements with excellent durability can be easily designed. Therefore, this invention has high industrial applicability.

[0480] Symbol Explanation

[0481] 1-Substrate, 2-Anode, 3-Hole injection layer, 4-Hole transport layer, 5-Light emission layer, 6-Electron transport layer, 7-Cathode.

Claims

1. A composition comprising a first compound satisfying formula (1a) and a second compound satisfying formula (2b), wherein, Compound 1 and compound 2 satisfy the following formula (A), where compound 1 is a compound represented by the following general formula (1) or (5). PBHT(1)>0.730 Formula (1a), ΔE ST (2) <0.20 eV Equation (2b), E S1 (1) > E S1 (2) Formula (A), In the above formula, PBHT(1) is the PBHT value of the first compound, ΔE ST (2) is the lowest excited singlet state energy level E of the second compound. S1 (2) The lowest excited triplet energy level E of the second compound T1 (2) The difference, E S1 (1) is the lowest excited singlet state energy level of the first compound. In the above formula, multiple X's independently represent O or S, and Y's... 1 ~Y 8 and Y 11 ~Y 18 Each can be used independently to represent N or CR, R represents a hydrogen atom, a substituent, or a direct bond with L, and Y represents... 21 ~Y 28 Each Y represents N or C-R' independently, where R' represents a hydrogen atom or substituent, L represents a (n+p+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring, and n represents an integer greater than or equal to 1. When n is greater than or equal to 2, multiple Ys represent... 11 ~Y 18 They can be the same or different. p represents an integer greater than 0. When p is greater than 2, multiple Ys can be represented. 21 ~Y 28 They can be the same as each other, or they can be different. In the above formula, X represents O or S, Y 1 ~Y 8 Each can be used independently to represent N or CR, R represents a hydrogen atom, a substituent, or a direct bond with L, and Y represents... 21 ~Y 28 Each of the following can be independently represented as N or C-R', where R' represents a hydrogen atom or substituent, L represents a (p+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring, and p represents an integer greater than or equal to 1. When p is greater than or equal to 2, multiple Y's can be represented as N or C-R'. 21 ~Y 28 They can be the same as each other, or they can be different.

2. The composition according to claim 1, wherein, The first compound also satisfies the following formula (1c). BDE(1) > 4.20 eV Equation (1c), In the above formula, BDE(1) is the bond energy of the cation of the first compound.

3. The composition according to claim 1, wherein, The second compound also satisfies the following formula (2a). 0.200 < PBHT (2) < 0.400 Equation (2a), In the above formula, PBHT(2) is the PBHT value of the second compound.

4. The composition according to claim 1, wherein, The first compound also satisfies the following formula (1c), and the second compound also satisfies the following formula (2a). BDE(1) > 4.20 eV Equation (1c), 0.200 < PBHT (2) < 0.400 Equation (2a), In the above formula, BDE(1) is the bond energy of the cation of the first compound, and PBHT(2) is the PBHT value of the second compound.

5. The composition according to claim 1, wherein, The PBHT(1) is greater than 0.

910.

6. The composition according to claim 1, wherein, The second compound satisfies the following formula (2d). τ DELAY <10 μs formula (2d), In the above formula, τ DELAY This represents the delayed fluorescence lifetime of the second compound.

7. The composition according to claim 1, wherein, The first compound has the structure represented by the general formula (1).

8. The composition according to claim 1, wherein, The first compound has the structure represented by the following general formula (2), In the above formula, multiple X's independently represent O or S, Y'. 1 ~Y 8 and Y 11 ~Y 18 Each of these can be independently represented by N or CR, R represents a hydrogen atom, a substituent, or a direct bond with L, L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring, and n represents an integer greater than or equal to 1. When n is greater than or equal to 2, multiple Ys can be represented. 11 ~Y 18 They can be the same as each other, or they can be different.

9. The composition according to claim 1, wherein, The first compound has the structure represented by the following general formula (3), In the above formula, multiple X's independently represent O or S, Y'. 1 Y 2 Y 4 ~Y 8 and Y 11 ~Y 18 Each of these can be independently represented by N or CR, R represents a hydrogen atom, a substituent, or a direct bond with L, L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring, n represents an integer greater than 2, and multiple Ys... 11 ~Y 18 They can be the same as each other, or they can be different.

10. The composition according to claim 1, wherein, The first compound has the structure represented by the following general formula (4), In the above formula, multiple X's independently represent O or S, Y'. 1 ~Y 8 and Y 12 ~Y 18 Each of these can be independently represented by N or CR, R represents a hydrogen atom, a substituent, or a direct bond with L, L represents a (n+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring, n represents an integer greater than 2, and multiple Ys... 11 ~Y 18 They can be the same as each other, or they can be different.

11. The composition according to claim 1, wherein, The first compound has the structure represented by the general formula (5).

12. The composition according to claim 1, wherein, The L of the general formula (1) has a structure formed by connecting one or more rings selected from the group consisting of benzene rings and pyridine rings.

13. The composition according to claim 1, wherein, The L in the general formula (1) contains 1,3-phenylene or 2,6-pyridylene as a linking chain.

14. The composition according to claim 1, wherein, The L in the general formula (1) contains 1,4-phenylene or 2,6-pyridylene as a linking chain.

15. The composition according to claim 1, wherein, The n in the general formula (1) is 2.

16. The composition according to claim 1, wherein, In the general formula (1), R is a hydrogen atom or an aryl group that is substituted or unsubstituted.

17. The composition according to claim 1, wherein, When the content of the first compound is set to 100 parts by weight, the content of the second compound is 0.01 to 70 parts by weight.

18. The composition according to claim 1, further comprising a third compound satisfying formula (B) below, E S1 (1) > E S1 (2) > E S1 (3) Formula (B), In the above formula, E S1 (3) is the lowest excited singlet energy level of the third compound.

19. The composition according to claim 18, wherein, The third compound also satisfies the following formula (3b). ΔE ST (3) <0.20eV Equation (3b), ΔE ST (3) is the lowest excited singlet state energy level E of the third compound. S1 (3) The lowest excited triplet energy level E of the third compound T1 (3) difference.

20. A luminescent composition, wherein, The composition according to any one of claims 1 to 19 may be used as a luminescent composition.

21. A membrane comprising the composition of any one of claims 1 to 19.

22. A light-emitting film, wherein, The membrane according to claim 21 is used as a light-emitting membrane.

23. An organic light-emitting element comprising the composition of any one of claims 1 to 19.

24. The organic light-emitting element according to claim 23, wherein it emits delayed fluorescence.

25. The organic light-emitting element according to claim 23, wherein it is an organic electroluminescent element.

26. The organic light-emitting element according to claim 23, wherein, The material contained in the light-emitting element emits the most light from the second compound.

27. The organic light-emitting element according to any one of claims 24 to 26, wherein, The composition is a composition further comprising a third compound satisfying formula (B) below, wherein the material contained in the light-emitting element emits the most light from the third compound. E S1 (1) > E S1 (2) > E S1 (3) Formula (B), In the above formula, E S1 (3) is the lowest excited singlet energy level of the third compound.

28. A method for designing luminescent compositions, the design of which is related to ΔE ST (2) A first compound in combination with a second compound having a concentration less than 0.20 eV to provide a luminescent composition comprising the first compound and the second compound, the method comprising designing the first compound to have a structure represented by the following general formula (1) or (5) and making E S1 (1) Greater than E S1 (2) Steps where PBHT(1) is greater than 0.730 in, PBHT(1) is the PBHT value of the first compound, ΔE ST (2) is the lowest excited singlet state energy level E of the second compound. S1 (2) The lowest excited triplet energy level E of the second compound T1 (2) The difference, E S1 (1) is the lowest excited singlet state energy level of the first compound. In the above formula, multiple X's independently represent O or S, and Y's... 1 ~Y 8 and Y 11 ~Y 18 Each can be used independently to represent N or CR, R represents a hydrogen atom, a substituent, or a direct bond with L, and Y represents... 21 ~Y 28 Each Y represents N or C-R' independently, where R' represents a hydrogen atom or substituent, L represents a (n+p+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring, and n represents an integer greater than or equal to 1. When n is greater than or equal to 2, multiple Ys represent... 11 ~Y 18 They can be the same or different. p represents an integer greater than 0. When p is greater than 2, multiple Ys can be represented. 21 ~Y 28 They can be the same as each other, or they can be different. In the above formula, X represents O or S, Y 1 ~Y 8 Each can be used independently to represent N or CR, R represents a hydrogen atom, a substituent, or a direct bond with L, and Y represents... 21 ~Y 28 Each of the following can be independently represented as N or C-R', where R' represents a hydrogen atom or substituent, L represents a (p+1) valence conjugated linking group containing at least one aromatic or heteroaromatic ring, and p represents an integer greater than or equal to 1. When p is greater than or equal to 2, multiple Y's can be represented as N or C-R'. 21 ~Y 28 They can be the same as each other, or they can be different.

29. The method of claim 28, further comprising the step of designing the first compound to increase PBHT(1).

30. The method of claim 29, comprising the step of selecting a compound with a larger PBHT(1) from a plurality of candidate compounds as the first compound.

31. A computer program product that performs the method of any one of claims 28 to 30.

Images