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Definitions

• the present invention relates to a compound having a skeleton in which a triazine ring and a benzene ring are bonded, and to a light-emitting material and a delayed phosphor that use the compound.
• luminescent materials such as organic electroluminescent elements (organic EL elements)
• organic EL elements organic electroluminescent elements
• Fluorescent materials, phosphorescent materials, and fluorescent materials have long been known as luminescent materials, but fluorescent materials have the problem of low luminous efficiency, and phosphorescent materials contain rare metals, making them expensive and difficult to produce deep blue light.
• delayed fluorescent materials have been developed as luminescent materials that address these issues.
• Delayed fluorescent materials are materials that emit fluorescence when they undergo reverse intersystem crossing from an excited triplet state to an excited singlet state in an excited state, and then return from that excited singlet state to the ground state. Fluorescence from this route is observed later than fluorescence from an excited singlet state that occurs directly from the ground state (normal fluorescence), and is therefore called delayed fluorescence.
• delayed fluorescence when a luminescent compound is excited by injecting carriers, the probability of occurrence of an excited singlet state and an excited triplet state is statistically 25%:75%, so there is a limit to the improvement of luminous efficiency when only the fluorescence from the directly generated excited singlet state is used.
• delayed fluorescent materials can use not only the excited singlet state but also the excited triplet state for fluorescence emission via the above-mentioned route via reverse intersystem crossing, resulting in a higher luminous efficiency than normal fluorescent materials.
• the inventors have conducted extensive research with the aim of providing compounds that are more useful as delayed fluorescent materials for light-emitting devices. They have also conducted intensive research with the aim of deriving and generalizing a general formula for compounds that are more useful as delayed fluorescent materials.
• R 1 to R 5 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a donor group, or a group represented by the following general formula (2).
• R 2 or R 3 is a group represented by the following general formula (2), and two or more of R 1 to R 5 are donor groups.
• Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• X 1 to X 3 each independently represent N or C(R), but at least one of X 1 to X 3 is N.
• R represents a hydrogen atom, a deuterium atom, or a substituent.
• Ar 3 and Ar 4 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• L 1 represents a single bond or a divalent linking group.
• R 1 to R 5 is a donor group having a condensed ring structure of four or more rings
• at least one of Ar 1 to Ar 4 is a substituted or unsubstituted heteroaryl group (excluding a nitrogen-containing 6-membered ring group)
• R 1 to R 5 and Ar 1 to Ar 4 satisfy both of these conditions.
• R 1 to R 5 is a donor group represented by the following general formula (3):
• X represents O, S or N-R 14.
• R 11 to R 13 each independently represent a deuterium atom or a substituent.
• R 14 represents an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom and an aryl group.
• R 11 's, R 12 's and R 13 's may be bonded to each other to form a cyclic structure.
• n11 and n13 each independently represent an integer of 0 to 4, and n12 represents an integer of 0 to 2.
• Ar 1 to Ar 4 each independently represent a substituted or unsubstituted aryl group.
• [5] The compound according to any one of [1] to [3], wherein one or more of Ar 1 to Ar 4 is a substituted or unsubstituted heteroaryl group (excluding a nitrogen-containing 6-membered ring group).
• the compounds of the present invention are useful as materials for organic light-emitting devices.
• substituted means an atom or atomic group other than hydrogen atoms and deuterium atoms.
• substituted or unsubstituted means that hydrogen atoms may be substituted with deuterium atoms or substituents.
• R 1 to R 5 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a donor group, or a group represented by the following general formula (2).
• R 2 or R 3 is a group represented by the following general formula (2), and two or more of R 1 to R 5 are donor groups.
• Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• R 1 to R 5 are donor groups having a condensed ring structure of four or more rings
• one or more of Ar 1 to Ar 4 are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing six-membered ring groups), or R 1 to R 5 and Ar 1 to Ar 4 satisfy both of these conditions.
• Ar 3 and Ar 4 are groups present in general formula (2).
• the alkyl group that can be R 1 to R 5 may be linear, branched, or cyclic. In addition, two or more of the linear portion, the cyclic portion, and the branched portion may be mixed.
• the number of carbon atoms of the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. In addition, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
• alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
• the alkyl group as a substituent may be further substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom.
• the substituent of the alkyl group is one or more selected from the group consisting of an aryl group and a deuterium atom.
• the alkyl group is unsubstituted and may be selected from the group consisting of, for example, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group.
• the aryl group that can be R 1 to R 5 , Ar 1, and Ar 2 may be a single ring or a fused ring in which two or more rings are fused.
• the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4.
• Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring.
• the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, and is preferably a substituted or unsubstituted phenyl group.
• the substituent of the aryl group may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E.
• the substituent of the aryl group is one or more selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom.
• the aryl group is substituted with at least one deuterium atom.
• the aryl group is unsubstituted.
• R 1 to R 5 , Ar 1 , and Ar 2 Specific examples of substituted or unsubstituted aryl groups that can be used by R 1 to R 5 , Ar 1 , and Ar 2 are given below.
• the aryl groups that can be used in the present invention should not be construed as being limited to the following specific examples.
• * indicates a bonding position.
• methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.
• groups in which all hydrogen atoms present in Ar1 to Ar26 are replaced with deuterium atoms are exemplified here as Ar47 to Ar72, in that order.
• the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar1 to Ar72.
• the aryl group which R 1 to R 5 can take is Ar1 or Ar47.
• the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar2 to Ar11, Ar27 to Ar36, and Ar48 to 57.
• the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar12 to Ar20, Ar37 to Ar45, and Ar58 to Ar66. In one embodiment of the present invention, the aryl group which R 1 to R 5 can take is selected from the group consisting of Ar22 to Ar26, and Ar68 to Ar72. In a preferred embodiment of the present invention, the aryl group which can be represented by R 1 to R 5 is selected from the group consisting of Ar1, Ar12 to Ar15, Ar24, Ar37 to Ar40, Ar47, Ar58 to Ar61, and Ar70. In one embodiment of the present invention, the aryl group that Ar 1 or Ar 2 can take is selected from the group consisting of Ar 1 to Ar 72.
• the aryl group that Ar 1 or Ar 2 can take is Ar 1 or Ar 47. In one embodiment of the present invention, the aryl group that Ar 1 or Ar 2 can take is selected from the group consisting of Ar 2 to Ar 11, Ar 27 to Ar 36, and Ar 48 to 57. In one embodiment of the present invention, the aryl group that Ar 1 or Ar 2 can take is selected from the group consisting of Ar 12 to Ar 20, Ar 37 to Ar 45, and Ar 58 to Ar 66. In a preferred embodiment of the present invention, the aryl group that R 1 to R 5 can take is selected from the group consisting of Ar 1, Ar 12 to Ar 14, Ar 37 to Ar 40, Ar 47, and Ar 58 to Ar 61.
• R 1 to R 5 in the general formula (1) are donor groups.
• the donor groups which can be R 1 to R 5 do not include substituted or unsubstituted aryl groups.
• the "donor group” can be selected from groups with a negative Hammett ⁇ p value.
• the "acceptor group” can be selected from groups with a positive Hammett ⁇ p value.
• the Hammett ⁇ p value was proposed by L. P. Hammett, and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative.
• k 0 is the rate constant of a benzene derivative having no substituent
• K 0 is the equilibrium constant of a benzene derivative having no substituent
• K is the equilibrium constant of a benzene derivative substituted with a substituent
• ⁇ is a reaction constant determined by the type and conditions of the reaction.
• the donor group which can be R 1 to R 5 has a ⁇ p of preferably ⁇ 0.3 or less, more preferably ⁇ 0.5 or less, and further preferably ⁇ 0.7 or less, and may be selected from the range of ⁇ 0.9 or less, or ⁇ 1.1 or less, for example.
• the donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group, or an aryl group to which a substituted amino group is bonded, particularly a phenyl group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is a substituted amino group.
• the substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
• the substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group.
• the two aryl groups constituting the diarylamino group here may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.
• the donor group which can be represented by R 1 to R 5 is preferably a group represented by the following general formula (a).
• Z 1 represents C-R 14 or N
• Z 2 represents C-R 15 or N
• Z 3 represents C-R 16 or N
• Z 4 represents C-R 17 or N
• Z 5 represents C or N
• Ar 5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring.
• R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be bonded to each other to form a cyclic structure.
• the number of N is preferably 0 to 3, and more preferably 0 to 2. In one aspect of the present invention, among Z 1 to Z 4 , the number of N is 1. In one aspect of the present invention, among Z 1 to Z 4 , the number of N is 0.
• R 14 to R 17 each independently represent a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. When two or more of R 14 to R 17 represent substituents, those two or more substituents may be the same or different.
• R 14 to R 17 are substituents, and for example, one may be a substituent or none may be a substituent (R 14 to R 17 are hydrogen atoms or deuterium atoms).
• R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be bonded to each other to form a cyclic structure.
• the cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a ring condensed with these.
• An aromatic ring or a heteroaromatic ring is preferable.
• An example of the aromatic ring is a substituted or unsubstituted benzene ring.
• the benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring.
• the heteroaromatic ring means a ring exhibiting aromaticity containing a heteroatom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted.
• a furan ring, a thiophene ring, or a pyrrole ring may be adopted as the heteroaromatic ring.
• the cyclic structure is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole.
• the benzofuran, benzothiophene, and indole mentioned here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E.
• a substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of the indole, and examples of the substituent include a substituent selected from any of the groups A to E.
• the cyclic structure may be a substituted or unsubstituted cyclopentadiene ring.
• a pair of R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 are bonded to each other to form a cyclic structure.
• R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 are not bonded to each other to form a cyclic structure.
• Z5 represents C or N
• Ar5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring.
• Z5 is C
• Ar5 is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring.
• Z5 is N
• Ar5 is a substituted or unsubstituted heteroaromatic ring.
• An example of the aromatic ring that Ar 5 can take is a benzene ring.
• the benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring.
• the heteroaromatic ring that Ar 5 can take is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted.
• a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring may be adopted as the heteroaromatic ring.
• Z 5 is C
• the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline.
• Z5 is N
• the heteroaromatic ring is a pyrrole ring of substituted or unsubstituted indole, or an imidazole ring of substituted or unsubstituted benzimidazole.
• the benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole mentioned here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E.
• Z 5 in formula (a) is C, it is preferably a group represented by the following formula (b).
• Z 1 represents C-R 14 or N
• Z 2 represents C-R 15 or N
• Z 3 represents C-R 16 or N
• Z 4 represents C-R 17 or N
• Z 6 represents C-R 18 or N
• Z 7 represents C-R 19 or N
• Z 8 represents C-R 20 or N
• Z 9 represents C-R 21 or N.
• R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19, R 19 and R 20 , and R 20 and R 21 may be bonded to each other to form a cyclic structure.
• the corresponding explanations for general formula (a) can be referred to.
• Z 6 to Z 9 and R 18 to R 21 in general formula (b) correspond to Z 1 to Z 4 and R 14 to R 17 in general formula (a) in that order, and for the contents thereof, the explanations for Z 1 to Z 4 and R 14 to R 17 in general formula (a) can be referred to.
• the number of N groups among Z 1 to Z 4 and Z 6 to Z 9 is preferably 0 to 2, and is preferably 0 or 1.
• the number of N groups among Z 1 to Z 4 and Z 6 to Z 9 is 1.
• the number of N groups among Z 1 to Z 4 and Z 6 to Z 9 is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.
• the donor group which can be taken by R 1 to R 5 is preferably a substituted or unsubstituted carbazol-9-yl group.
• the carbazol-9-yl group referred to here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E.
• one or more rings may be further condensed to the two benzene rings constituting the carbazol-9-yl group.
• the donor group which can be taken by R 1 to R 5 is a carbazol-9-yl group which may be substituted with a group selected from the substituent group E, or may be condensed with one or more rings.
• the substitution position is not particularly limited, but is preferably at least one of the 2- to 7-positions, more preferably at least one of the 3- or 6-positions, and even more preferably the 3- and 6-positions.
• the donor group which can be taken by R 1 to R 5 is a carbazol-9-yl group to which one or more rings are fused, and hereinafter this is referred to as a "ring-fused carbazol-9-yl group".
• the ring-fused carbazol-9-yl group which can be taken by R 1 to R 5 may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E.
• the ring-fused carbazol-9-yl group is unsubstituted or substituted with a substituent selected from the substituent group E.
• the ring-fused carbazol-9-yl group is unsubstituted.
• the ring-fused carbazol-9-yl group is substituted with an aryl group which may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group in combination of two or more atoms selected from the group consisting of an alkyl group and an aryl group.
• the total number of fused rings in the ring-fused carbazole-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7.
• the number of rings constituting the fused ring is 5. Note that the number of rings here includes the number of fused carbazole rings (i.e., 3).
• the ring-fused carbazole-9-yl group is a group bonded through a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole.
• the fused ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, and may also be a ring in which these are further fused.
• An aromatic hydrocarbon ring or an aromatic heterocycle is preferable.
• An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring.
• the benzene ring may be further fused with another benzene ring, or may be fused with a heterocycle such as a pyridine ring.
• the aromatic heterocycle means a ring that exhibits aromaticity and contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted.
• a furan ring, a thiophene ring, or a pyrrole ring may be adopted as the aromatic heterocycle.
• the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole.
• the nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from the substituent group E (excluding the case where only a deuterium atom is present), and more preferably bonded to an aryl group which may be substituted with an alkyl group or an aryl group.
• a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms is fused.
• a carbazol-9-yl group in which a benzofuro structure is fused a carbazol-9-yl group in which a benzothieno structure is fused, or a carbazol-9-yl group in which an indolo structure is fused can be preferably employed.
• the compound has at least one carbazol-9-yl group in which a benzofuro structure is fused, for example, two or more carbazol-9-yl groups. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group condensed with a benzothieno structure, for example, two or more.
• a substituted or unsubstituted benzothieno[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazol-5-yl group can also be used.
• the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or may be, for example, 2.
• either the 3-position or the 6-position of the ring-fused carbazol-9-yl group is substituted.
• the ring-fused carbazol-9-yl group has at least one substituent at the para position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.
• the ring-fused carbazol-9-yl group has at least one substituent only at the para position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has a substituent at all of the substitutable para positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.
• donor groups which can be R 1 to R 5 in general formula (1) are shown below. However, the donor groups which can be employed in the present invention should not be construed as being limited to the following specific examples.
• Ph represents a phenyl group (C 6 H 5 ), and * represents the bond position.
• Methyl groups are not shown, so for example, D2 has one methyl group. However, a deuterated methyl group is represented as CD 3.
• C 6 D 5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.
• the compounds D55 to D85 are those in which all hydrogen atoms present in the above D1 to D31 have been replaced with deuterium atoms.
• the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D1 to D1210. In one embodiment of the present invention, the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D1 to D85. In one embodiment of the present invention, the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D86 to D1210.
• the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D86 to D695, D704 to D1133, and D1142 to D1210. In one embodiment of the present invention, the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D696 to D703, and D1134 to D1141.
• R 1 to R 5 in general formula (1) are donor groups.
• two or three of R 1 to R 5 are donor groups.
• two of R 1 to R 5 are donor groups.
• three of R 1 to R 5 are donor groups.
• at least R 3 is a donor group.
• at least R 4 is a donor group.
• at least R 5 is a donor group.
• only R 3 is a donor group.
• only R 4 is a donor group.
• only R 5 is a donor group.
• R 3 and R 5 are donor groups. In one embodiment of the present invention, only R 2 and R 5 are donor groups. In one embodiment of the present invention, only R 2 and R 4 are donor groups. In one embodiment of the invention, only R3 , R4 and R5 are donor groups. In one embodiment of the invention, only R2 , R4 and R5 are donor groups. When two or more of R1 to R5 are donor groups, they may be the same or different.
• the number of hydrogen atoms or deuterium atoms among R 1 to R 5 is 0 to 2, preferably 0 or 1, for example 1, for example 0.
• R 1 is a hydrogen atom or a deuterium atom.
• the compound exhibits better luminescence properties than a compound in which the number of hydrogen atoms or deuterium atoms among R 1 to R 5 is 3.
• the number of substituted or unsubstituted aryl groups among R 1 to R 5 is 0 or 1, preferably 1. It may be 0.
• the number of substituted or unsubstituted alkyl groups among R 1 to R 5 is 0 to 3, preferably 0 to 2, and may be 1 or 0.
• R 1 to R 5 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a donor group, and a group represented by general formula (2).
• R 1 to R 5 are each independently selected from a hydrogen atom, a deuterium atom, a donor group, and a group represented by general formula (2). In one embodiment of the present invention, R 1 to R 5 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted carbazol-9-yl group which may be fused, and a group represented by general formula (2).
• the heteroaryl group that can be Ar 1 and Ar 2 in the general formula (1) may be a single ring or a fused ring in which two or more rings are fused.
• the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4.
• Specific examples of the ring include a pyridine ring, a pyrimidine ring, and a pyrrole ring, and these rings may be further fused with another ring.
• heteroaryl group examples include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazol-9-yl group, a carbazol-1-yl group, a carbazol-2-yl group, a carbazol-3-yl group, and a carbazol-4-yl group.
• the number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and may be selected within the range of 5 to 16 or 5 to 12.
• Ar 1 and Ar 2 are substituted or unsubstituted aryl groups.
• R2 or R3 is a group represented by the following general formula (2):
• R1 , R4 , and R5 can also be a group represented by the following general formula (2).
• X 1 to X 3 each independently represent N or C(R), with at least one of X 1 to X 3 being N.
• R represents a hydrogen atom, a deuterium atom, or a substituent.
• Ar 3 and Ar 4 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• L 1 represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
• * represents a bonding position.
• L 1 represents a single bond or a divalent linking group.
• the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group.
• L 1 is a single bond.
• L 1 is a substituted or unsubstituted arylene group.
• L 1 is a substituted or unsubstituted heteroarylene group.
• the description of the aryl group and the preferred range thereof in the above description of R 1 to R 5 can be referred to.
• heteroarylene group examples include a linking group in which at least one of the ring skeleton carbon atoms constituting the arylene group is replaced with a nitrogen atom.
• L1 Specific examples of L1 are given below. However, L1 that can be employed in the present invention should not be construed as being limited by these specific examples. Note that in the specific examples below, methyl groups are omitted. For example, L3 to L5 are substituted with methyl groups. * indicates the bond position. L1 is a single bond.
• L1 is selected from the group consisting of L1 to L25. In one aspect of the present invention, L1 is selected from the group consisting of L1 to L7, and L14 to L19. In one aspect of the present invention, L1 is selected from the group consisting of L1, L8 to L13, and L20 to L25. In one aspect of the present invention, L1 is selected from the group consisting of L2 to L25.
• X 1 to X 3 each independently represent N or C(R). However, at least one of X 1 to X 3 is N.
• R represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E.
• X 1 to X 3 are N.
• X 1 and X 3 are N
• X 2 is C(R).
• X 1 and X 2 are N
• X 3 is C(R).
• X 1 is N, and X 2 and X 3 are C(R). In one embodiment of the present invention, X 2 is N, and X 1 and X 3 are C (R). In one embodiment of the present invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R is an alkyl group optionally substituted with a deuterium atom. In one embodiment of the present invention, R is an aryl group optionally substituted with a deuterium atom, an alkyl group, or an aryl group.
• Ar 1 and Ar 3 are the same.
• Ar 1 and Ar 3 are the same, and Ar 2 and Ar 4 are the same.
• Ar 1 to Ar 4 are the same.
• X 1 to X 3 are N and L 1 is a single bond.
• X 1 to X 3 are N and L 1 is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, more preferably an unsubstituted phenylene group (e.g., L2, e.g., L6).
• X 1 to X 3 are N, L 1 is a single bond, and Ar 3 and Ar 4 are the same.
• X 1 to X 3 are N, L 1 is a single bond, and Ar 3 and Ar 4 are each independently a substituted or unsubstituted aryl group.
• X 1 to X 3 are N, L 1 is a single bond, and Ar 3 and Ar 4 are each independently a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups), preferably a donor heteroaryl group bonded via a nitrogen atom, and more preferably a substituted or unsubstituted carbazol-9-yl group.
• X 1 to X 3 are N, L 1 is a single bond, Ar 3 is a substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups), preferably a donor heteroaryl group bonded via a nitrogen atom, more preferably a substituted or unsubstituted carbazol-9-yl group, and Ar 4 is a substituted or unsubstituted aryl group.
• only R2 is a group represented by formula (2).
• only R3 is a group represented by formula (2).
• one of R1 , R3 , R4 , and R5 and only R2 are each independently a group represented by formula (2).
• one of R1 , R2 , R4 , and R5 and only R3 are each independently a group represented by formula (2).
• R 1 to R 5 is a donor group having a fused ring structure with four or more rings
• one or more of Ar 1 to Ar 4 is a substituted or unsubstituted heteroaryl group (excluding a nitrogen-containing 6-membered ring group)
• R 1 to R 5 and Ar 1 to Ar 4 satisfy both of these conditions.
• the "donor group having a condensed ring structure of four or more rings” as used herein refers to a donor group having a condensed ring structure of four or more rings and bonded via one of the atoms constituting the ring skeleton of the condensed ring structure.
• the one atom is preferably a carbon atom or a nitrogen atom, and more preferably a nitrogen atom.
• the donor group as used herein refers to a group having a negative Hammett ⁇ p value.
• the donor group having a fused ring structure of 4 or more rings preferably has a fused ring structure of 5 or more rings, and more preferably has a fused ring structure of 5 to 7 rings, for example, a fused ring structure of 5 rings or a fused ring structure of 7 rings.
• the donor group having a fused ring structure of 4 or more rings is preferably a ring-fused carbazol-9-yl group. Specific examples include D86 to D1210. In particular, a group having a structure represented by the following general formula (3) is preferred.
• X represents O, S or N-R 14.
• R 11 to R 13 each independently represent a deuterium atom or a substituent.
• R 14 represents an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom and an aryl group.
• R 11 's, R 12 's and R 13 's may be bonded to each other to form a cyclic structure.
• n11 and n13 each independently represent an integer of 0 to 4, and n12 represents an integer of 0 to 2.
• X represents O, S or N-R 14.
• R 14 represents an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group and an aryl group, or an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom and an aryl group.
• the aryl group as a substituent of the aryl group and the alkyl group can be selected, for example, from an aryl group having 6 to 22 carbon atoms
• the alkyl group as a substituent of the alkyl group and the aryl group can be selected, for example, from an alkyl group having 1 to 20 carbon atoms.
• X is O.
• X is N-R 14.
• R 14 of N-R 14 is an aryl group (e.g., having 6 to 22 carbon atoms).
• the aryl group may be substituted or unsubstituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms) and an aryl group (e.g., having 6 to 22 carbon atoms).
• X may be an oxygen atom or a sulfur atom.
• the two bonds on one benzene ring of the carbazole ring are bonded to adjacent positions on the benzene ring to form a fused ring structure between the carbazole ring and a hetero fused ring containing X.
• a benzofurocarbazole ring is formed as a fused ring structure
• a benzothienocarbazole ring is formed as a fused ring structure
• an indolocarbazole ring is formed as a fused ring structure.
• the positions to which the two bonds are bonded may be the 1st and 2nd positions, the 2nd and 3rd positions, or the 3rd and 4th positions of the carbazole ring.
• the position to which the bond of X is bonded may be the 1st or 2nd position
• the position to which the bond of X is bonded may be the 2nd or 3rd position
• the position to which the bond of X is bonded may be the 3rd or 4th position.
• * represents a bonding position.
• R 11 to R 13 each independently represent a deuterium atom or a substituent.
• R 11 , R 12 , and R 13 may be bonded to each other to form a cyclic structure, but R 11 does not bond to any of R 12 to R 14 to form a cyclic structure, R 12 does not bond to any of R 13 and R 14 to form a cyclic structure, and R 13 does not bond to R 14 to form a cyclic structure.
• the substituent may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E.
• the substituent means one group selected from the group consisting of an alkyl group (e.g., 1 to 20 carbon atoms) and an aryl group (e.g., 6 to 22 carbon atoms) or a group consisting of a combination of two or more groups.
• n11 and n13 each independently represent an integer of 0 to 4, and n12 represents an integer of 0 to 2.
• n11 is 2 or more, two or more R 11 may be the same or different.
• n13 is 2 or more, two or more R 13 may be the same or different.
• two R 12 may be the same or different.
• n11 and n13 may be any number of 0, 1, 2, 3, or 4, and n12 may be any number of 0, 1, or 2.
• R 11 may be a deuterium atom or a substituent.
• n11 is 2 or more, two or more R 11 may all be deuterium atoms or all be substituents, or a part of them may be deuterium atoms and the rest may be substituents.
• n13 is 1, R 13 may be a deuterium atom or a substituent.
• all of the two or more R 13 may be deuterium atoms or all of them may be substituents, or some of them may be deuterium atoms and the rest may be substituents.
• R 12 may be a deuterium atom or a substituent.
• both of the two R 12 may be deuterium atoms or both of them may be substituents, or one of the two may be a deuterium atom and the other may be a substituent.
• the donor group has a fused ring structure of four or more rings
• two or more of R 1 to R 5 are donor groups having a fused ring structure of four or more rings, for example, two, for example, three.
• they may be the same or different, but are preferably the same.
• at least R 3 is a donor group having a fused ring structure of four or more rings.
• at least R 4 is a donor group having a fused ring structure of four or more rings.
• At least R 5 is a donor group having a fused ring structure of four or more rings.
• R 3 and R 5 are donor groups having a fused ring structure of four or more rings.
• R 3 , R 4, and R 5 are donor groups having a fused ring structure of four or more rings.
• one or more of Ar 1 to Ar 4 are substituted or unsubstituted heteroaryl groups (excluding nitrogen-containing 6-membered ring groups).
• the substituted or unsubstituted heteroaryl groups may be only one, two, three, or all of Ar 1 to Ar 4. When there are two or more, they may be the same or different, but are preferably the same.
• the substituted or unsubstituted heteroaryl group (excluding nitrogen-containing 6-membered ring groups) is preferably a heteroaryl group bonded at a nitrogen atom that is one of the ring skeleton constituent atoms, is preferably a heteroaryl group having a 5-membered ring bonded at a nitrogen atom (a group bonded at the nitrogen atom of a pyrrole ring, the pyrrole ring may be substituted, and is preferably a condensed ring), and is more preferably a substituted or unsubstituted carbazol-9-yl group.
• the carbazol-9-yl group may be substituted with an alkyl group or an aryl group which may be substituted with a group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or may be substituted with a deuterium atom.
• a group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group or may be substituted with a deuterium atom.
• R 1 to R 5 may take, the descriptions of the ring-fused carbazol-9-yl groups, and specific examples D1 to D1210.
• Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group.
• Ar 1 to Ar 4 may all be the same, and may be, for example, an unsubstituted phenyl group or a perdeuterated phenyl group.
• R 1 to R 5 are donor groups having a condensed ring structure of four or more rings.
• the number of donor groups having a condensed ring structure of four or more rings may be two or more, for example, two, for example, three.
• donor groups having a condensed ring structure of four or more rings specific examples D86 to D1210 can be referred to.
• donor groups having a condensed ring structure of five or more rings for example, five rings, for example, seven rings
• Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group
• one or more of R 1 to R 5 have a deuterium atom.
• it may have a donor group having a deuterated three-ring condensed ring structure (e.g., a perdeuterated carbazol-9-yl group), or it may have a deuterated aryl group (e.g., a perdeuterated phenyl group).
• a donor group having a deuterated three-ring condensed ring structure e.g., a perdeuterated carbazol-9-yl group
• a deuterated aryl group e.g., a perdeuterated phenyl group
• the compound represented by the general formula (1) preferably does not contain metal atoms, and may be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
• the compound represented by the general formula (1) is composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms.
• the compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms.
• the compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen ... and nitrogen atoms. Furthermore, the compound represented by the general formula (1) may not contain hydrogen atoms, but may contain deuterium atoms.
• substituted group A refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), It means
• substituted group B means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms).
• an alkyl group e.g., having 1 to 40 carbon atoms
• an alkoxy group e.g., having 1 to 40 carbon atoms
• an aryl group e.g., having 6 to 30 carbon
• substituted group C means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms).
• an alkyl group e.g., having 1 to 20 carbon atoms
• an aryl group e.g., having 6 to 22 carbon atoms
• a heteroaryl group e.g., having 5 to 20 ring skeleton atoms
• diarylamino group e.g., having 12 to 20 carbon atoms
• substituted group D means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms).
• substituted group E means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms) and an aryl group (e.g., having 6 to 22 carbon atoms).
• the substituent when it is described as “substituted or unsubstituted” or “optionally substituted", the substituent may be selected, for example, from Substituent Group A, or may be selected from Substituent Group B, or may be selected from Substituent Group C, or may be selected from Substituent Group D, or may be selected from Substituent Group E.
• R 2 is a group represented by general formula (2)
• Ar 1 and Ar 3 are perdeuterated carbazol-9-yl groups (D55)
• Ar 2 and Ar 4 are perdeuterated phenyl groups (Ar47)
• X 1 to X 3 are nitrogen atoms (N)
• L 1 is a single bond (L1)
• R 1 is a hydrogen atom
• R 3 to R 5 are groups specified in Table 1 are shown individually as structures of compounds 1 to 170.
• R 3 to R 5 of a plurality of compounds are displayed together in each row to show the structures of compounds 1 to 442987.
• R 4 is fixed to D1 (carbazol-9-yl group), R 3 and R 5 are the same, and D1 to D85 are compounds 1 to 85, in that order.
• D1 to D85 are compounds 1 to 85, in that order.
• R 4 is fixed to D2 (3-methylcarbazol-9-yl group), R 3 and R 5 are the same, and D1 to D85 are compounds 86 to 170, in that order. That is, the row of compounds 1 to 85 and the row of compounds 86 to 170 in Table 2 are compounds 1 to 170 specified in Table 1 displayed together in two rows.
• R 4 is fixed to D3 (3,6-dimethylcarbazol-9-yl group)
• R 3 and R 5 are the same
• D1 to D85 are identified in that order as compounds 171 to 255.
• Compounds 256 to 442987 in Table 2 are also identified in the same manner.
• compounds 1 to 636657 are displayed in the first row, and compounds 636658 to 1257639 are displayed in the second row.
• compounds 1 to 636657 in which Ar 1 and Ar 3 are both D1 are sequentially designated as compounds 1(1) to 636657(1).
• compound 1(1) indicates a compound having a structure in which Ar 1 and Ar 3 of compound 1 are replaced with D1.
• compound 2(1) indicates a compound having a structure in which Ar 1 and Ar 3 of compound 2 are replaced with D1.
• Compound 636657(1) shows a compound having a structure in which Ar 1 and Ar 3 of compound 636657 are replaced with D1.
• compounds 1 to 636657 in which Ar 1 and Ar 3 are both D7 are designated as compounds 1(2) to 636657(2) in order.
• compounds 1 to 636657 in which Ar 1 and Ar 3 , and Ar 2 and Ar 4 are those listed in Table 8 are specified in order.
• X 1 to X 3 are all nitrogen atoms (N)
• L 1 is a single bond (L1)
• R 1 is a hydrogen atom.
• Ar 1 and Ar 3 are the same, and Ar 2 and Ar 4 are the same.
• Compounds 1 to 636657 (371) in Table 8 are compounds in which R 1 in general formula (1) is a hydrogen atom. Compounds having structures in which R 1 in these compounds is replaced with a deuterium atom are referred to as Compounds 1d to 636657 (371) d, respectively. Compounds having structures in which R 1 in these compounds is replaced with a perdeuterated phenyl group (Ar47) are referred to as Compounds 1D to 636657 (371) D, respectively.
• the compounds identified by numbers in Tables 1 to 8, Compound 1d to Compound 636657(371)d, and Compound 1D to Compound 636657(371)D are all considered to be individually disclosed.
• the compound is selected from the group of compounds identified in Table 8.
• the molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less.
• the lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1).
• the compound represented by the general formula (1) may be formed into a film by a coating method regardless of the molecular weight. By using the coating method, it is possible to form a film even with a compound having a relatively large molecular weight.
• the compound represented by the general formula (1) has the advantage that it is easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) is easy to apply the coating method and is easy to purify to increase the purity.
• a polymerizable group may be present in the structure represented by the general formula (1) in advance, and the polymerizable group may be polymerized to obtain a polymer, which may be used as a light-emitting material.
• a monomer containing a polymerizable functional group at any site of the general formula (1) may be prepared, and the monomer may be polymerized alone or copolymerized with another monomer to obtain a polymer having a repeating unit, which may be used as a light-emitting material.
• compounds having a structure represented by the general formula (1) may be coupled together to obtain a dimer or trimer, which may be used as a light-emitting material.
• Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas.
• Q represents a group containing a structure represented by general formula (1)
• L 1 and L 2 represent a linking group.
• the number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10.
• the linking group preferably has a structure represented by -X 11 -L 11 -.
• X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
• L 11 represents a linking group, and is preferably a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenylene group.
• R 101 , R 102 , R 103 and R 104 each independently represent a substituent, preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and still more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms.
• the linking groups represented by L1 and L2 can be bonded to any site of the general formula (1) constituting Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.
• repeating unit examples include structures represented by the following formulas.
• a polymer having repeating units containing these formulas can be synthesized by introducing a hydroxyl group into any site of general formula (1), reacting the hydroxyl group as a linker with the compound below to introduce a polymerizable group, and polymerizing the polymerizable group.
• a polymer containing a structure represented by general formula (1) in the molecule may be a polymer consisting of only repeating units having a structure represented by general formula (1), or may be a polymer containing repeating units having other structures.
• the repeating units having a structure represented by general formula (1) contained in the polymer may be of a single type, or of two or more types.
• Examples of repeating units not having a structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.
• the compound represented by formula (1) is a light-emitting material.
• the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence.
• the compounds represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, red region of the visible spectrum (e.g., from about 420 nm to about 500 nm, from about 500 nm to about 600 nm, or from about 600 nm to about 700 nm), or the near infrared region when excited by thermal or electronic means.
• the compounds represented by general formula (1) can emit light in the red or orange region of the visible spectrum (e.g., from about 620 nm to about 780 nm, about 650 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) when excited by thermal or electronic means.
• the compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the blue region of the visible spectrum (e.g., from about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet region of the spectrum (eg, 280-400 nm) when excited by thermal or electronic means.
• compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 ⁇ m) when excited by thermal or electronic means.
• an organic semiconductor element can be prepared using a compound represented by general formula (1).
• the organic semiconductor element may be an organic optical element in which light is mediated, or an organic element in which light is not mediated.
• the organic optical element may be an organic light-emitting element that emits light, an organic light-receiving element that receives light, or an element in which energy transfer occurs by light within the element.
• an organic optical element such as an organic electroluminescence element or a solid-state imaging element (e.g., a CMOS image sensor) can be prepared using a compound represented by general formula (1).
• a CMOS complementary metal oxide semiconductor
• a compound represented by general formula (1) can be prepared using a compound represented by general formula (1).
• the electronic properties of small molecule chemical libraries can be calculated using known ab initio quantum chemical calculations, for example, the Hartree-Fock equations (TD-DFT/B3LYP/6-31G*) can be solved using time-dependent density functional theory with 6-31G* as a basis and a family of functions known as the Becke three-parameter, Lee-Yang-Parr hybrid functional, to screen for molecular fragments (moieties) with HOMOs above a particular threshold and LUMOs below a particular threshold.
• TD-DFT/B3LYP/6-31G* time-dependent density functional theory with 6-31G* as a basis and a family of functions known as the Becke three-parameter, Lee-Yang-Parr hybrid functional, to screen for molecular fragments (moieties) with HOMOs above a particular threshold and LUMOs below a particular threshold.
• the donor moiety (“D") can be selected, for example, for its HOMO energy (e.g., ionization potential) of -6.5 eV or greater
• the acceptor moiety (“A") can be selected, for example, for its LUMO energy (e.g., electron affinity) of -0.5 eV or less.
• the bridging moiety (“B") prevents overlap between the pi-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly restrict the acceptor and donor moieties to specific conformations.
• the compound library is screened using one or more of the following properties: 1. Emission near a particular wavelength2. Calculated triplet state above a particular energy level3.
• the difference between the lowest singlet excited state and the lowest triplet excited state ( ⁇ E ST ) at 77K is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV.
• the ⁇ E ST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV.
• the compounds represented by general formula (1) exhibit a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.
• the compounds represented by the general formula (1) include novel compounds.
• the compound represented by the general formula (1) can be synthesized by combining known reactions.
• at least two of R 1 to R 5 are donor groups, and for example, a compound of the general formula (1) in which a substituted or unsubstituted carbazole-9-yl group is a donor group can be synthesized by reacting a precursor in which the donor group site is a fluorine atom with a substituted or unsubstituted carbazole.
• the synthesis examples described later can be referred to.
• the compound of formula (1) is combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compound to form a solid film or layer.
• the compound of formula (1) can be combined with an electroactive material to form a film.
• the compound of formula (1) can be combined with a hole transport polymer.
• the compound of formula (1) can be combined with an electron transport polymer.
• the compound of formula (1) can be combined with a hole transport polymer and an electron transport polymer.
• the compound of formula (1) can be combined with a copolymer having both a hole transport moiety and an electron transport moiety.
• electrons and/or holes formed in the solid film or layer can interact with the compound of formula (1).
• the film containing the compound represented by general formula (1) can be formed by a wet process.
• a solution containing the composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent.
• the wet process include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing.
• a suitable organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used.
• a substituent e.g., an alkyl group
• a substituent that increases the solubility in organic solvents can be introduced into the compound contained in the composition.
• the film containing the compound of the present invention can be formed by a dry process.
• the dry process can be a vacuum deposition method, but is not limited thereto.
• the compounds constituting the film may be co-deposited from individual deposition sources, or may be co-deposited from a single deposition source in which the compounds are mixed.
• a single deposition source a mixed powder in which the powders of the compounds are mixed may be used, a compression molded body in which the mixed powder is compressed may be used, or a mixture in which each compound is heated, melted, and cooled may be used.
• a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source can be formed by performing co-deposition under conditions in which the deposition rates (weight reduction rates) of the multiple compounds contained in a single deposition source are the same or almost the same. If a multiple compound is mixed in the same composition ratio as the composition ratio of the film to be formed and used as a deposition source, a film having a desired composition ratio can be easily formed.
• a temperature at which each compound to be co-deposited has the same weight reduction rate can be specified, and the temperature can be used as the temperature during co-deposition.
• the compound represented by the general formula (1) is useful as a material for an organic light-emitting device, and is particularly preferably used for an organic light-emitting diode.
• Organic Light-Emitting Diode One aspect of the present invention relates to the use of a compound represented by the general formula (1) of the present invention as a light-emitting material of an organic light-emitting device.
• the compound represented by the general formula (1) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device.
• the compound represented by the general formula (1) includes a delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence.
• the compound represented by the general formula (1) is applied to phosphorescence sensitized fluorescence.
• the present invention provides a delayed fluorescent material having a structure represented by the general formula (1).
• the present invention relates to the use of a compound represented by the general formula (1) as a delayed fluorescent material.
• the compound represented by the general formula (1) can be used as a host material and can be used together with one or more light-emitting materials, and the light-emitting material can be a fluorescent material, a phosphorescent material, or a TADF.
• the compound represented by the general formula (1) can also be used as a hole transport material.
• the compound represented by the general formula (1) can be used as an electron transport material.
• the present invention relates to a method for generating delayed fluorescence from a compound represented by the general formula (1).
• an organic light-emitting device including the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency.
• the light-emitting layer comprises a compound represented by formula (1), and the compound represented by formula (1) is aligned parallel to the substrate.
• the substrate is a film-forming surface.
• the orientation of the compound represented by formula (1) relative to the film-forming surface affects or dictates the propagation direction of light emitted by the aligned compound.
• aligning the propagation direction of light emitted by the compound represented by formula (1) improves the efficiency of light extraction from the light-emitting layer.
• the compound represented by formula (1) can be used in combination with a host material described in paragraphs [0123] to [0145] of WO2022/270602A1, which is incorporated herein by reference as a part of this specification, or in combination with a dopant described in paragraphs [0006] to [0129] of WO2022/270354A1, which is incorporated herein by reference as a part of this specification.
• the emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K. C4334 type).
• Phenyl-d5-boronic acid (6.2 g, 48.8 mmol), bis(triphenylphosphine)palladium(II) dichloride (1.4 g, 2.0 mmol), and potassium carbonate (29.0 g, 210 mmol) were added to a mixed solution of 1,5-dibromo-2,4-difluoro-3-iodobenzene (15.8 g, 39.9 mmol) in toluene (100 mL) and ion-exchanged water (30 mL), and the mixture was stirred at 100° C. for 23 hours under a nitrogen atmosphere.
• reaction mixture of compound j (2.1 g, 5.98 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.22 g, 0.30 mmol), potassium acetate (4.1 g, 42.0 mmol), bis(pinacolato)diboron (7.1 g, 27.9 mmol), and 1,4-dioxane (60 mL) was stirred at 110°C for 15 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through silica. The filtrate was concentrated, and the resulting reaction mixture was dissolved in methylene chloride and filtered through silica.
• Carbazole-1,2,3,4,5,6,7,8-d8 (1.28 g, 7.30 mmol) and potassium carbonate (1.37 g, 9.91 mmol) were added to a mixture of compound n (2.85 g, 3.30 mmol) and DMF (65 mL), and the mixture was stirred at 150° C. for 3 hours.
• the reaction solution was cooled to room temperature, and the solid was filtered and washed with ethyl acetate.
• the filtrate obtained was concentrated, and methanol was added to the resulting solid, which was then filtered and washed with methanol.
• reaction mixture of compound q (4.8 g, 9.40 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.36 g, 0.50 mmol), potassium acetate (6.5 g, 66.2 mmol), bis(pinacolato)diboron (12.1 g, 47.6 mmol), and 1,4-dioxane (100 mL) was stirred at 110°C for 15 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through silica. The filtrate was concentrated, and the resulting reaction mixture was dissolved in methylene chloride and filtered through silica.
• Carbazole-1,2,3,4,5,6,7,8-d8 (1.16 g, 6.61 mmol) and potassium carbonate (1.24 g, 8.97 mmol) were added to a mixture of compound s (3.06 g, 3.00 mmol) and DMF (60 mL), and the mixture was stirred at 150° C. for 3 hours.
• the reaction solution was cooled to room temperature, and the solid was filtered and washed with ethyl acetate.
• the filtrate obtained was concentrated, and methanol was added to the resulting solid, which was then filtered and washed with methanol.
• H1, compound C1, and dopant EM1 were co-deposited from different deposition sources to form a layer with a thickness of 40 nm to serve as an emission layer.
• the concentration of H1 in the emission layer was 44.2% by mass
• the concentration of compound C1 was 55.0% by mass
• the concentration of EM1 was 0.8% by mass.
• SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a layer with a thickness of 30 nm.
• the concentrations of Liq and SF3-TRZ in this layer were 30% by mass and 70% by mass, respectively.
• Liq was further formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, thereby forming an organic electroluminescence element.
• Al aluminum
• EQE external quantum efficiency
• Test Example 2 Preparation and Evaluation of Organic Electroluminescence Element
• H2, compound C1, and dopant EM1 were co-evaporated from different deposition sources to form a light-emitting layer having a thickness of 40 nm and a concentration of H2 of 64.2 mass%, a concentration of compound C1 of 35.0 mass%, and a concentration of EM1 of 0.8 mass%.
• an organic electroluminescence element was prepared according to the same procedure as Test Example 1.
• H2, compound C3, and dopant EM1 were co-evaporated from different deposition sources to form a 40 nm thick light-emitting layer with a concentration of H2 of 74.2 mass%, a concentration of compound C3 of 25.0 mass%, and a concentration of EM1 of 0.8 mass%.
• the organic electroluminescence element was otherwise produced according to the same procedure as Test Example 1.
• organic electroluminescence elements were produced in the same manner using compounds C4, C5, C12, C14, and comparative compound A instead of compound C3.
• Each of these elements was driven at 25.2 mA/ cm2 , and the time (LT95) from the start of driving until the luminous intensity reached 95% was measured.
• the measurement results are shown in Table 9 as relative values when the LT95 of the organic electroluminescence element using comparative compound A was set to 1.
• the results in Table 9 show that by using the compound represented by general formula (1), an organic light-emitting element having a long life can be provided.
• the present invention has a high industrial applicability.

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