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Definitions

• the present invention relates to a compound useful as a light-emitting material and a light-emitting device using the compound.
• organic electroluminescence elements organic electroluminescence elements
• various efforts have been made to improve luminous efficiency by developing and combining newly developed electron transport materials, hole transport materials, and luminescent materials that make up organic electroluminescence elements.
• organic electroluminescence elements that use delayed fluorescent materials.
• 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 cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group.
• at least one of R 1 to R 5 is a cyano group, and at least two of R 1 to R 5 are donor groups.
• 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 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, with at least one of Ar 1 and Ar 2 being a group that has a donor group bonded to a nitrogen atom but is bonded to a benzene ring that does not have an acceptor group.
• L 1 represents a single bond or a divalent linking group.
• each R independently represents a deuterium atom or a donor group.
• Each of Ar 6 and Ar 7 independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• Ar 6 and Ar 7 may be bonded to each other to form a cyclic structure, Ar 6 and R may be bonded to each other to form a cyclic structure, or Ar 7 and R may be bonded to each other to form a cyclic structure.
• n an integer of 0 to 4. * indicates a bonding position.
• Ar 1 is a group having a structure represented by the following general formula (d): [In general formula (d), each R independently represents a deuterium atom or a donor group. Z 1 represents C-R 14 or N, Z 2 represents C-R 15 or N, Z 3 represents C-R 16 or N, and Z 4 represents C-R 17 or N. Z 5 represents C or N, and 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.
• n represents an integer of 0 to 4. * indicates a bonding position.
• Ar 1 is a group having a structure represented by the following general formula (f): [In general formula (f), each R independently represents a deuterium atom or a donor group. Z 6 represents C-R 18 or N, Z 7 represents C-R 19 or N, Z 8 represents C-R 20 or N, and R 18 and R 19 , and R 19 and R 20 may be bonded to each other to form a cyclic structure.
• X is absent or represents a single bond, or represents a linking group having a linking chain of 1 or 2 atoms.
• Ar 7 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• m represents an integer of 0 to 3. * indicates a bonding position.] [7] The compound according to any one of [1] to [6], wherein Ar 2 is a substituted or unsubstituted aryl group having no donor group. [8] The compound according to any one of [1] to [6], wherein Ar 2 is a donor group bonded via a nitrogen atom.
• the organic light-emitting device according to [20], wherein the device has a layer containing the compound, the layer also containing a host material.
• the layer containing the compound contains a delayed fluorescent material in addition to the compound and the host material, and the minimum excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.
• the compounds of the present invention exhibit excellent luminescence properties. They 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 cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. At least one of R 1 to R 5 is a cyano group, and at least two of R 1 to R 5 are donor groups.
• 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 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, with at least one of Ar 1 and Ar 2 being a group that has a donor group bonded to a nitrogen atom but is bonded to a benzene ring that does not have an acceptor group.
• having a donor group bonded via a nitrogen atom means that the donor group is directly bonded to a benzene ring via a nitrogen atom constituting the donor group
• not having an acceptor group means that the acceptor group is not directly bonded to a benzene ring.
• 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.
• 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.
• the aryl group that R 1 to R 5 can take is selected from the group consisting of Ar1 to Ar88. In one embodiment of the present invention, the aryl group that R 1 to R 5 can take is Ar1 or Ar45. In one embodiment of the present invention, the aryl group that R 1 to R 5 can take is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, Ar46 to 55, and Ar70 to Ar79.
• the aryl group that R 1 to R 5 can take is selected from the group consisting of Ar12 to Ar19, Ar36 to Ar43, Ar56 to Ar63, and Ar80 to Ar87. In one embodiment of the present invention, the aryl group that R 1 to R 5 can take is selected from the group consisting of Ar21 to Ar26, and Ar65 to Ar70. 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 Ar14, Ar23, Ar36 to Ar38, Ar45, Ar56 to Ar58, Ar67, and Ar80 to Ar82.
• the aryl group which Ar 1 or Ar 2 may take is selected from the group consisting of Ar 1 to Ar 88. In one embodiment of the present invention, the aryl group which Ar 1 or Ar 2 may take is Ar 1 or Ar 45. In one embodiment of the present invention, the aryl group which Ar 1 or Ar 2 may take is selected from the group consisting of Ar 2 to Ar 11, Ar 26 to Ar 35, Ar 46 to 55, and Ar 70 to Ar 79. In one embodiment of the present invention, the aryl group which Ar 1 or Ar 2 may take is selected from the group consisting of Ar 12 to Ar 19, Ar 36 to Ar 43, Ar 56 to Ar 63, and Ar 80 to Ar 87. 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 Ar14, Ar36 to Ar38, Ar45, Ar56 to Ar58, and Ar80 to Ar82.
• 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. For example, it may be selected from the range of ⁇ 0.9 or less, or ⁇ 1.1 or less.
• 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 benzothieno[2,3-a]carbazol-9-yl group a benzothieno[3,2-a]carbazol-9-yl group, a benzothieno[2,3-b]carbazol-9-yl group, a benzothieno[3,2-b]carbazol-9-yl group, a benzothieno[2,3-c]carbazol-9-yl group, or a benzothieno[3,2-c]carbazol-9-yl group
• a benzothieno[2,3-a]carbazol-9-yl group a benzothieno[2,3-a]carbazol-9-yl group, a benzothieno[3,2-a]carbazol-9-yl group.
• an indolo[2,3-a]carbazole-9-yl group an indolo[3,2-a]carbazole-9-yl group, an indolo[2,3-b]carbazole-9-yl group, an indolo[3,2-b]carbazole-9-yl group, an indolo[2,3-c]carbazole-9-yl group, or an indolo[3,2-c]carbazole-9-yl group
• an indolo[2,3-a]carbazole-9-yl group an indolo[2,3-a]carbazole-9-yl group, an indolo[2,3-c]carbazole-9-yl group, or an indolo[3,2-c]carbazole-9-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 may be R 1 to R 5 in general formula (1) are shown below. However, the donor groups which may be employed in the present invention should not be construed as being limited by the following specific examples.
• Ph represents a phenyl group (C 6 H 5 ), and * represents the bonding 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.
• D727 to D1190 are disclosed as compounds obtained by substituting all hydrogen atoms present in the above D1 to D464 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 D1190. 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 D16, D465 to D476.
• the donor group which can be taken by R 1 to R 5 is selected from the group consisting of D17 to D76, D88 to D123, D190 to D303, D364 to D458, D477 to D524, D531 to D658, and D709 to D715.
• the donor groups which can be represented by R 1 to R 5 are selected from the group consisting of D77 to D82, D124 to D189, D304 to D363, D460 to D464, D525 to D530, D659 to D708, and D717 to D726.
• the donor group which R 1 to R 5 can take is selected from the group consisting of D1 to D189, D458 to D654, and D717 to D726. In a preferred embodiment of the present invention, the donor group which R 1 to R 5 can take is selected from the group consisting of D1 to D22, D35 to D38, D46 to D53, D74 to D89, D117 to D187, D458, D459, D465 to D478, D526 to D533, and D717 to D721.
• the donor group which R 1 to R 5 can adopt is selected from the group consisting of D1 to D13, D17 to D22, D37, D47 to D52, D77 to D82, D124 to D136, D139, D142, D145, D151, D154, D157, D160, D163, D166, D169, D172, D175, D178, D181, D184, D187, D459, D466 to D471, D521 to D525, and D712 to D716.
• the donor group which R 1 to R 5 can adopt is selected from the group consisting of D1 to D13 and D466 to D471.
• the donor group which R 1 to R 5 can adopt is selected from the group consisting of D17 to D22, D37, and D47 to D52.
• the donor group which R 1 to R 5 can adopt is selected from the group consisting of D77 to D82, and D526 to D530.
• the donor group which R 1 to R 5 can adopt is selected from the group consisting of D124 to D136, D139, D142, D145, D151, D154, D157, D160, D163, D166, D169, D172, D175, D178, D181, D184, D187, and D712 to D716.
• At least one of R 1 to R 5 in general formula (1) is a cyano group. In one embodiment of the present invention, one or two of R 1 to R 5 are cyano groups. In a preferred embodiment of the present invention, at least R 2 is a cyano group. In one embodiment of the present invention, at least R 1 is a cyano group. In one embodiment of the present invention, at least R 3 is a cyano group. In a preferred embodiment of the present invention, only R 2 is a cyano group. In one embodiment of the present invention, only R 1 is a cyano group. In one embodiment of the present invention, only R 3 is a cyano group. In one embodiment of the present invention, only R 2 and R 4 are cyano groups. In one embodiment of the present invention, only R 2 and R 5 are cyano groups. In one embodiment of the present invention, only R 1 and R 3 are cyano groups.
• 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.
• one of R 1 to R 5 is a cyano group
• two are donor groups, one is a substituted or unsubstituted aryl group, and one is a hydrogen atom or a deuterium atom.
• the two donor groups are the same.
• the two donor groups are different from each other.
• R 1 is a hydrogen atom or a deuterium atom
• R 2 or R 3 is a cyano group.
• R 1 is a hydrogen atom or a deuterium atom
• R 2 is a cyano group
• R 3 and R 5 are donor groups
• R 4 is a substituted or unsubstituted aryl group.
• R 1 is a hydrogen atom or a deuterium atom
• R 2 is a cyano group
• R 4 and R 5 are donor groups
• R 3 is a substituted or unsubstituted aryl group.
• R 1 is a hydrogen atom or a deuterium atom
• R 2 is a cyano group
• R 3 and R 4 are donor groups
• R 5 is a substituted or unsubstituted aryl group.
• one of R 1 to R 5 is a cyano group
• three are donor groups
• one is a hydrogen atom or a deuterium atom.
• the three donor groups are the same.
• two of the three donor groups are the same and one is different.
• R 1 is a hydrogen atom or a deuterium atom
• R 2 is a cyano group
• R 3 to R 5 are donor groups.
• R 1 is a hydrogen atom or a deuterium atom
• R 3 is a cyano group
• R 2 , R 4 , and R 5 are donor groups.
• one of R 1 to R 5 is a cyano group
• two are donor groups
• two are hydrogen atoms or deuterium atoms.
• R 1 and R 4 are hydrogen atoms or deuterium atoms
• R 2 is a cyano group
• R 3 and R 5 are donor groups.
• R 1 and R 5 are hydrogen atoms or deuterium atoms
• R 2 is a cyano group
• R 3 and R 4 are donor groups.
• R 1 and R 3 are hydrogen atoms or deuterium atoms
• R 2 is a cyano group
• R 4 and R 5 are donor groups.
• R 1 and R 4 are hydrogen atoms or deuterium atoms
• R 3 is a cyano group
• R 2 and R 5 are donor groups.
• 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.
• At least one of Ar 1 and Ar 2 in general formula (1) has a donor group bonded through a nitrogen atom, but is a group bonded through a benzene ring that is not substituted with an acceptor group (hereinafter referred to as a "donor group bonded through a carbon atom"). That is, at least one of Ar 1 and Ar 2 is a group bonded through a carbon atom constituting the ring skeleton of a benzene ring, and the benzene ring is bonded to a donor group bonded through a nitrogen atom, but is not bonded to an acceptor group.
• the benzene ring may further be bonded to a hydrogen atom, a deuterium atom, and a donor group not bonded through a nitrogen atom.
• the donor group bonded via a carbon atom preferably has a structure represented by the following general formula (c).
• Ar 6 and Ar 7 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• the heteroaryl group is preferably one containing a nitrogen atom as a ring skeleton constituent atom, for example, a heteroaryl group containing a pyridine ring.
• Ar 6 and Ar 7 are preferably substituted or unsubstituted aryl groups, for example, substituted or unsubstituted phenyl groups.
• Each R independently represents a deuterium atom or a donor group.
• the donor group that R can take may be a donor group bonded by a nitrogen atom, or may be a donor group bonded by an atom other than a nitrogen atom (for example, a carbon atom).
• the donor group bonded by a nitrogen atom may be the same as or different from N(Ar 6 )(Ar 7 ).
• Ar 6 and Ar 7 may be bonded together to form a cyclic structure, Ar 6 and R may be bonded together to form a cyclic structure, or Ar 7 and R may be bonded together to form a cyclic structure. In a preferred embodiment of the present invention, Ar 6 and Ar 7 are bonded together to form a cyclic structure.
• Ar 6 and R are bonded together to form a cyclic structure.
• they are bonded via a single bond or a linking group.
• they are bonded via a single bond or a nitrogen atom (the nitrogen atom is preferably bonded to an alkyl group or an aryl group), and more preferably, they are bonded via a single bond.
• n represents any integer from 0 to 4. * indicates a bond position.
• the donor group bonded via a carbon atom has a structure represented by the following general formula (d), and more preferably has a structure represented by the following general formula (e).
• each of R in general formula (d) and general formula (e) independently represents a deuterium atom or a donor group.
• the donor group that R can take may be a donor group bonded via a nitrogen atom, or may be a donor group bonded via an atom other than a nitrogen atom (for example, a carbon atom).
• n represents any integer from 0 to 4. * indicates a bonding position.
• n is 0 or n is 4 and all four R are deuterium atoms.
• Z 1 to Z 4 and Z 6 to Z 9 preferably 0 to 2, preferably 0 to 1, and more preferably 0 are nitrogen atoms.
• phenyl groups in which the above D1 to D1190 are bonded to the 3-position i.e., groups in which a metaphenylene group is further bonded to the * of D1 to D1190
• Phenyl groups in which the above D1 to D1190 are bonded to the 4-position i.e., groups in which a paraphenylene group is further bonded to the * of D1 to D1190
• Perdeuterated phenyl groups in which the above D1 to D1190 are bonded to the 3-position i.e., groups in which a metaphenylene group in which all hydrogen atoms are deuterated is further bonded to the * of D1 to D1190
• Perdeuterated phenyl groups in which the above D1 to D1190 are bonded to the 4-position are disclosed as D4761 to D5950.
• the donor group bonded via a carbon atom has a structure represented by the following general formula (f).
• X is absent and represents a single bond, or represents a linking group having a linking chain of 1 or 2 atoms.
• An example of a linking group having a linking chain of 2 atoms is a substituted or unsubstituted ethylene group.
• An example of a linking group having a linking chain of 1 atom is an oxygen atom, a sulfur atom, or a nitrogen atom to which an aryl group or an alkyl group is bonded.
• the linking group is preferably a nitrogen atom to which an aryl group or an alkyl group is bonded. It is more preferable that X is absent and represents a single bond.
• R represents a deuterium atom or a donor group.
• the donor group that R can take may be a donor group bonded via a nitrogen atom, or may be a donor group bonded via an atom other than a nitrogen atom (for example, a carbon atom).
• m represents any integer from 0 to 3. * indicates a bonding position. It is preferable that m is 0 or m is 3, and all three R are deuterium atoms.
• Z 6 to Z 8 preferably 0 to 1, and more preferably 0, are nitrogen atoms.
• X is a single bond, and 0 of Z 6 to Z 8 are nitrogen atoms.
• it is a substituted or unsubstituted N-arylcarbazol-1-yl group.
• it is a substituted or unsubstituted N-arylcarbazol-2-yl group.
• it is a substituted or unsubstituted N-arylcarbazol-3-yl group.
• it is a substituted or unsubstituted N-arylcarbazol-4-yl group.
• the donor group represented by general formula (f) is not limited to the following specific examples.
• Ph represents a phenyl group (C 6 H 5 ), and * represents a bonding position. Since methyl groups are not shown, for example, Z2 has one methyl group. However, a deuterated methyl group is represented as CD 3. Also, C 6 D 5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.
• Z157 to Z312 are disclosed as compounds in which all hydrogen atoms present in the above Z1 to Z156 have been replaced with deuterium atoms.
• Z313 to Z468 are disclosed as compounds in which the hydrogen atoms bonded to the phenyl groups and alkyl groups (methyl groups and tert-butyl groups) present in the above Z1 to Z156 have been replaced with deuterium atoms.
• the donor group bonded at a carbon atom which Ar 1 and Ar 2 in general formula (1) can take is selected from the group consisting of Z1 to Z468.
• the donor group bonded at a carbon atom is selected from the group consisting of Z1 to Z8, Z89 to Z96, Z157 to Z164, Z245 to Z252, Z313 to Z320, and Z401 to Z408.
• the donor group bonded at a carbon atom is selected from the group consisting of Z9 to Z88, Z97 to Z156, Z165 to Z244, Z253 to Z312, Z321 to Z400, and Z409 to Z468.
• the donor group bonded at a carbon atom is selected from the group consisting of Z1 to 88, Z157 to Z244, and Z313 to Z400. In one embodiment of the present invention, the donor group attached at a carbon atom is selected from the group consisting of Z89 to Z156, Z245 to Z312, and Z401 to Z468.
• the donor group bonded at a carbon atom which Ar 1 and Ar 2 in general formula (1) can take is selected from the group consisting of D1191 to D5950. In one embodiment of the present invention, the donor group bonded at a carbon atom which Ar 1 and Ar 2 can take is selected from the group consisting of D1191 to D2380 and D3571 to D4760. In one embodiment of the present invention, the donor group bonded at a carbon atom which Ar 1 and Ar 2 can take is selected from the group consisting of D2381 to D3570 and D4761 to D5950.
• the donor group bonded at a carbon atom is selected from the group consisting of D1191 to D1206, D1655 to D1666, D3571 to D3586, and D4035 to D4046. In one embodiment of the present invention, the donor group bonded at a carbon atom is selected from the group consisting of D2381 to D2396, D2845 to D2856, D4761 to D4776, and D5225 to D5236.
• the donor group bonded at a carbon atom is selected from the group consisting of D1207 to D1266, D1278 to D1313, D1380 to D1493, D1554 to D1648, D1667 to D1714, D1721 to D1848, D1899 to D1905, D3587 to D3646, D3658 to D3693, D3760 to D3873, D3934 to D4028, D4047 to D4094, D4101 to D4228, and D4279 to D4285.
• the donor group bonded at a carbon atom is selected from the group consisting of D2397 to D2456, D2468 to D2503, D2570 to D2683, D2744 to D2838, D2857 to D2904, D2911 to D3038, D3089 to D3095, D4777 to D4836, D4848 to D4883, D4950 to D5063, D5124 to D5218, D5237 to D5284, D5291 to D5418, and D5469 to D5475.
• the donor group bonded at a carbon atom is selected from the group consisting of D1267 to D1272, D1314 to D1379, D1494 to D1553, D1650 to D1654, D1715 to D1720, D1849 to D1989, D1907 to D1916, D3647 to D3652, D3694 to D3759, D3874 to D3933, D4030 to D4034, D4095 to D4100, D4229 to D4278, and D4287 to D4296.
• the donor group bonded at a carbon atom is selected from the group consisting of D2457 to D2462, D2504 to D2569, D2684 to D2743, D2840 to D2844, D2905 to D2910, D3039 to D3088, D3097 to D3106, D4837 to D4842, D4884 to D4949, D5064 to D5123, D5220 to D5224, D5285 to D5290, D5419 to D5468, and D5477 to D5486.
• the donor group bonded at a carbon atom is selected from the group consisting of D1191 to D1379, D1648 to D1844, D1907 to D1916, D3571 to D3759, D4028 to D4224, and D4287 to D4296. In one embodiment of the present invention, the donor group bonded at a carbon atom is selected from the group consisting of D2381 to D2659, D2838 to D3034, D3097 to D3106, D4761 to D4949, D5218 to D5414, and D5477 to D5486.
• Ar 1 and Ar 2 in general formula (1) among Ar 1 and Ar 2 in general formula (1), only Ar 1 is a donor group bonded at a carbon atom. In one embodiment of the present invention, both Ar 1 and Ar 2 in general formula (1) are the same donor group bonded at a carbon atom. In one embodiment of the present invention, Ar 1 and Ar 2 in general formula (1) are the same donor group bonded at a carbon atom, but have different structures.
• Ar 1 in general formula (1) is a donor group bonded at a carbon atom
• Ar 2 is a substituted or unsubstituted aryl group (e.g., any of Ar1 to Ar88) or a donor group bonded at a nitrogen atom (e.g., any of D1 to D1190).
• the substituted or unsubstituted aryl group and the preferred range thereof the corresponding description of the substituted or unsubstituted aryl group that can be taken by R 1 to R 5 , Ar 1 , and Ar 2 in general formula (1) can be referred to.
• the donor group reference can be made to the corresponding descriptions of the donor groups which can be R 1 to R 5 in formula (1).
• 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.
• X 1 to X 3 are N, L 1 is a single bond, Ar 1 is a group represented by general formula (d), Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, R 2 is a cyano group, two of R 1 and R 3 to R 5 are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), one is a substituted or unsubstituted aryl group, and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.
• Ar 1 is a group represented by general formula (d)
• Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula
• X 1 to X 3 are N, L 1 is a single bond, Ar 1 is a group represented by general formula (e), Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, R 2 is a cyano group, two of R 1 and R 3 to R 5 are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), one is a substituted or unsubstituted aryl group, and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.
• Ar 1 is a group represented by general formula (e)
• Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula
• X 1 to X 3 are N, L 1 is a single bond, Ar 1 is a group represented by general formula (d), Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, R 2 is a cyano group, three of R 1 and R 3 to R 5 are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.
• Ar 1 is a group represented by general formula (d)
• Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom
• X 1 to X 3 are N, L 1 is a single bond, Ar 1 is a group represented by general formula (e), Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, R 2 is a cyano group, three of R 1 and R 3 to R 5 are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.
• Ar 1 is a group represented by general formula (e)
• Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom
• X 1 to X 3 are N, L 1 is a single bond, Ar 1 is a group represented by general formula (d), Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, R 3 is a cyano group, 2 to 3 of R 1 , R 2 , R 4 , and R 5 are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), 1 to 2 (preferably at least R 1 ) are hydrogen atoms or deuterium atoms, and 0 to 1 is a substituted or unsubstituted aryl group.
• Ar 1 is a group represented by general formula (d)
• Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having
• X 1 to X 3 are N, L 1 is a single bond, Ar 1 is a group represented by general formula (e), Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having no donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, R 3 is a cyano group, 2 to 3 of R 1 , R 2 , R 4 , and R 5 are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), 1 to 2 (preferably at least R 1 ) are hydrogen atoms or deuterium atoms, and 0 to 1 is a substituted or unsubstituted aryl group.
• Ar 1 is a group represented by general formula (e)
• Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group having
• Ar 2 is, for example, a substituted or unsubstituted aryl group having no donor group.
• Ar 2 is, for example, a donor group bonded via a nitrogen atom.
• Ar 2 is, for example, a group represented by general formula (e).
• Ar 2 is, for example, a group represented by general formula (f).
• 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).
• 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).
• 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.
• Ar 1 is a 4-(perdeuterated carbazol-9-yl)phenyl group (D3107)
• Ar 2 is a perdeuterated phenyl group (Ar45)
• X 1 to X 3 are nitrogen atoms (N)
• L 1 is a single bond (L1)
• R 1 is a hydrogen atom
• R 2 is a cyano group
• R 3 to R 5 are groups specified in Table 1 are shown individually as structures of compounds 1 to 240.
• the structures of compounds 1 to 1594600 are shown by collectively displaying R 3 to R 5 of a plurality of compounds in each row.
• R 3 to R 5 compounds in which R 3 to R 5 are the same and D1 to D240 are listed as compounds 1 to 240, in that order. That is, the row of compounds 1 to 240 in Table 2 collectively displays compounds 1 to 240 specified in Table 1 in one row.
• compounds 241 to 5950 in Table 2 compounds in which R 3 to R 5 are the same and D241 to D5950 are listed as compounds 241 to 5950, in that order.
• compound 2(1) shows a compound having a structure in which Ar 1 in compound 2 is replaced with D1191.
• Compound 3189200(1) shows a compound having a structure in which Ar 1 of compound 3189200 is replaced with D1191.
• Compounds 1(2) to 3189200(2) in the third row of Table 4 and the compounds in the subsequent rows are specified in the same manner.
• X 1 to X 3 of the compounds specified in Table 4 are all nitrogen atoms (N), L 1 is a single bond (L1), and R 1 is a hydrogen atom.
• Compounds 1 to 3189200 in which Ar 1 and Ar 2 are both D1191 are designated compounds 1(1191) to 3189200(1191), in that order.
• Compounds 1 to 3189200 in which Ar 1 and Ar 2 are both D1192 are designated compounds 1(1192) to 3189200(1192), in that order.
• compounds 1 to 3189200 in which Ar 1 and Ar 2 are both Dx are designated compounds 1(x) to 3189200(x).
• compounds 1 to 3189200 in which Ar 1 and Ar 2 are both D5950 are designated compounds 1(5950) to 3189200(5950), in that order.
• Compounds 1 to 3189200 in which Ar 1 and Ar 2 are both Z1 are designated compounds 1(Z1) to 3189200(Z1), in that order.
• Compounds 1 to 3189200 in which Ar 1 and Ar 2 are both Z2 are designated compounds 1(Z2) to 3189200(Z2), in that order.
• compounds 1 to 3189200 in which Ar 1 and Ar 2 are both Z468 are designated compounds 1(Z468) to 3189200(Z468), in that order. All compounds identified by the above numbers are considered to be individually disclosed.
• the compound is selected from the group consisting of compounds 1 to 3189200 and compounds 1(n) to 3189200(n) [wherein n is 1 to 255, 1191 to 5950, Z1 to Z468].
• 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.
• 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 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 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 containing the compound as a light-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.
• the organic light-emitting device includes an emitting layer.
• the emitting layer includes a compound represented by general formula (1) as a light-emitting material.
• the organic light-emitting device is an organic photoluminescence device (organic PL device).
• the organic light-emitting device is an organic electroluminescence device (organic EL device).
• the compound represented by general formula (1) assists the light emission of other light-emitting materials included in the emitting layer (as a so-called assist dopant).
• the compound represented by general formula (1) included in the emitting layer is at its lowest excited singlet energy level, and is included between the lowest excited singlet energy level of the host material included in the emitting layer and the lowest excited singlet energy level of the other light-emitting materials included in the emitting layer.
• the organic photoluminescent device includes at least one light-emitting layer.
• the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode.
• the organic layer includes at least a light-emitting layer. In some embodiments, the organic layer includes only a light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.
• the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi some embodiments, the layer emits light. In some embodiments, only the light-emitting material is used as the light-emitting layer. In some embodiments, the light-emitting layer includes a light-emitting material and a host material. In some embodiments, the light-emitting material is one or more compounds represented by general formula (1).
• a host material is used in the light-emitting layer in addition to the light-emitting material.
• the host material is an organic compound.
• the organic compound has an excited singlet energy and an excited triplet energy, at least one of which is higher than those of the light-emitting material of the present invention.
• the singlet excitons and triplet excitons generated in the light-emitting material of the present invention are trapped in the molecules of the light-emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently trapped to improve the light emission efficiency. In some embodiments, the singlet and triplet excitons are not sufficiently trapped, although a high light emission efficiency is still obtained, i.e., a host material that can achieve a high light emission efficiency can be used in the present invention without any particular limitation. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence.
• the emitted light includes the emitted light from the host material. In some embodiments, the emitted light consists of the emitted light from the host material. In some embodiments, the emitted light includes the emitted light from the compound represented by formula (1) and the emitted light from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.
• various compounds can be adopted as a light-emitting material (preferably a fluorescent material).
• a light-emitting material preferably a fluorescent material.
• exemplary skeletons may or may not have a substituent. These exemplary skeletons may also be combined with each other. Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by general formula (1) are given below.
• Further preferred light-emitting materials include compounds represented by the following general formula (2).
• R 1 , R 3 to R 16 each independently represent a hydrogen atom, a deuterium atom or a substituent.
• R 2 represents an acceptor group, or R 1 and R 2 are bonded together to form an acceptor group, or R 2 and R 3 are bonded together to form an acceptor group.
• R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , and R 15 and R 16 may be bonded together to form a cyclic structure.
• X 1 represents O or NR
• R represents a substituent.
• at least one of X 3 and X 4 is O or NR, and the remaining may be O or NR or may not be linked.
• both ends independently represent a hydrogen atom, a deuterium atom or a substituent.
• C-R 1 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 12 , C-R 13 , C-R 14 , C-R 15 and C-R 16 may be substituted with N.
• R7 is an acceptor group
• R6 and R7 are bonded to each other to form an acceptor group
• R7 and R8 are bonded to each other to form an acceptor group
• X3 is O or NR
• R10 is an acceptor group
• R9 and R10 are bonded to each other to form an acceptor group
• R10 and R11 are bonded to each other to form an acceptor group
• R15 is an acceptor group
• R14 and R15 are bonded to each other to form an acceptor group
• R15 and R16 are bonded to each other to form an acceptor group.
• R when X2 is NR, R is a substituted or unsubstituted phenyl group and forms a carbazole ring by directly bonding to the carbon atom to which R8 is bonded, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group.
• R when X3 is NR, R is a substituted or unsubstituted phenyl group and forms a carbazole ring by directly bonding to the carbon atom to which R9 is bonded, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group.
• R when X4 is NR, R is a substituted or unsubstituted phenyl group and forms a carbazole ring by directly bonding to the carbon atom to which R16 is bonded, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group.
• X1 when X1 is NR, R is a substituted or unsubstituted phenyl group and is directly bonded to the carbon atom to which R1 is bonded to form a carbazole ring, the 3-position of the carbazole ring is substituted with an acceptor group (wherein the 3-position is on the phenyl group).
• the compound is represented by the following general formula (2a).
• R 1 , R 3 , R 6 to R 11 , and R to R 16 each independently represent a hydrogen atom, a deuterium atom , or a substituent.
• R 2 represents an acceptor group, or R 1 and R 2 are bonded to each other to form an acceptor group, or R 2 and R 3 are bonded to each other to form an acceptor group.
• R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 14 and R 15 , and R 15 and R 16 may be bonded to each other to form a cyclic structure.
• X 1 represents O or NR, and R represents a substituent.
• X 3 and X 4 are O or NR, and the remaining may be O or NR or may not be linked.
• both ends each independently represent a hydrogen atom, a deuterium atom, or a substituent.
• Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• C-R 1 , C-R 3 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 14 , C-R 15 and C-R 16 may be substituted with N.
• Further preferred light-emitting materials include compounds represented by the following general formula (3).
• R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
• R 3 to R 16 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
• R 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 2 , R 2 and R 10 , R 10 and R 11 , 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 , and R 16 and R 1 may be bonded to each other to form a cyclic structure.
• C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 12 , C-R 13 , C-R 14 , C-R 15 and C-R 16 may be substituted with N.
• R1 and R2 are each independently a substituted or unsubstituted phenyl group which may be condensed with another ring.
• R3 and R10 are each independently a substituted amino group.
• at least one combination of R1 and R3 , and R2 and R10 are bonded to each other to form a cyclic structure.
• the cyclic structure includes a benzoazaborine ring.
• Further preferred light-emitting materials include compounds represented by the following general formula (4).
• Z1 and Z2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
• R1 to R9 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
• R1 and R2 , R2 and R3 , R3 and R4 , R4 and R5 , R5 and R6 , R7 and R8 , and R8 and R9 may be bonded to each other to form a cyclic structure.
• At least one of Z 1 , Z 2 , the ring formed by bonding R 1 and R 2 together, the ring formed by bonding R 2 and R 3 together, the ring formed by bonding R 4 and R 5 together, and the ring formed by bonding R 5 and R 6 together 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, and at least one of R 1 to R 9 is a substituted or unsubstituted aryl group or an acceptor group, or at least one of Z 1 and Z 2 is a ring having an aryl group or an acceptor group as a substituent.
• a substitutable carbon atom may be substituted with a nitrogen atom.
• C-R 1 , C-R 2 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 and C-R 9 may be substituted with N.
• Z 1 and Z 2 are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring.
• R 1 to R 9 are each independently a substituted or unsubstituted aryl group or an acceptor group, or one or more rings selected from the group consisting of a ring formed by R 1 and R 2 bonding together, a ring formed by R 2 and R 3 bonding together, a ring formed by R 4 and R 5 bonding together, and a ring formed by R 5 and R 6 bonding together are a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring.
• R 8 is a substituted or unsubstituted aryl group or an acceptor group.
• the compound contains two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.
• Further preferred light-emitting materials include compounds having a fused ring structure A (wherein a hydrogen atom in the structure may be substituted with a deuterium atom or a substituent) in which a carbon-carbon bond a in the following structure ⁇ is fused with a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring,
• X1 and X2 each independently represent a substituted or unsubstituted aryl group, a nitrogen atom to which a substituted or unsubstituted aryl group is bonded, or an oxygen atom;
• Z represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring;
• R1 represents a hydrogen atom, a deuterium atom, or a substituent; and Z and X2 may be bonded to each other to form a cyclic structure.
• the fused to b and X 1 , the structure fused to b and Z, and Z and X 2 may be bonded to each other to form a cyclic structure.
• Further preferred light-emitting materials include compounds represented by the following general formula (5).
• Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• Z 2 and Z 3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
• R 1 represents a hydrogen atom, a deuterium atom, or a substituent
• R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
• Z 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 are bonded to each other to form a cyclic structure.
• Further preferred light-emitting materials include compounds represented by the following general formula (6).
• X3 represents an oxygen atom or a sulfur atom
• Z2 and Z3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
• R1 and R4 to R7 each independently represent a hydrogen atom, a deuterium atom or a substituent
• R2 and R3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
• R2 and Z2 , Z2 and Z3 , Z3 and R3 , R4 and R5 , R5 and R6 , and R6 and R7 may be bonded to each other to form a cyclic structure. However, at least one pair of R2 and Z2 , Z2 and Z3 , and Z3 and R3 are bonded to each other to form a cyclic structure.
• Further preferred light-emitting materials include compounds represented by the following general formula (7).
• X4 represents an oxygen atom or a sulfur atom
• Z2 and Z3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
• R1 and R4a to R7a each independently represent a hydrogen atom, a deuterium atom or a substituent
• R2 and R3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
• R2 and Z2 , Z2 and Z3 , Z3 and R3 , R4a and R5a , R5a and R6a , R6a and R7a , and R7a and R1 may be bonded to each other to form a cyclic structure.
• at least one pair of R2 and Z2 , Z2 and Z3 , and Z3 and R3 are bonded to each other to form a cyclic structure.
• Further preferred light-emitting materials include compounds represented by the following general formula (8).
• Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
• R 1 and R 8 to R 14 each independently represent a hydrogen atom, a deuterium atom, or a substituent
• R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• Z 1 and R 1 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure.
• Z 1 and Z 4 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
• R 1 and R 15 to R 17 each independently represent a hydrogen atom, a deuterium atom, or a substituent
• R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• Z 1 and R 1 , Z 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and Z 3 , and Z 3 and R 3 may be
• Z 1 and Z 5 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• Z 3 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
• R 1 represents a hydrogen atom, a deuterium atom, or a substituent
• R 2 and R 3 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• Z 1 and R 1 , R 2 and Z 5 , Z 5 and Z 3 , and Z 3 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 3 , and Z 3 and R 3 are bonded to each other to form a cyclic structure.
• Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring;
• Z 2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring;
• R 1 and R 21 to R 27 each independently represent a hydrogen atom, a deuterium atom, or a substituent; and R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• R1 and Z1 , R2 and Z2 , Z2 and R21 , R21 and R22 , R22 and R23 , R23 and R24 , R24 and R25 , R25 and R26 , and R26 and R27 may be bonded to each other to form a cyclic structure.
• Further preferred light-emitting materials include compounds represented by the following general formula (12).
• Z 1 and Z 6 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• Z 2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
• R 1 and R 28 to R 30 each independently represent a hydrogen atom, a deuterium atom, or a substituent
• R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• R 1 and Z 1 , R 2 and Z 2 , Z 2 and R 28 , R 28 and R 29 , R 29 and R 30 , and R 30 and Z 6 may be
• Further preferred light-emitting materials include compounds represented by the following general formula (13).
• Z 1 and Z 7 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• Z 2 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring
• R 1 represents a hydrogen atom, a deuterium atom, or a substituent
• R 2 and R 3 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• R 1 and Z 1 , R 2 and Z 2 , Z 2 and Z 7 , and Z 7 and R 3 may be bonded to each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 7 , and Z 7 and R 3 are bonded to each other to form a cyclic structure.
• Further preferred light-emitting materials include compounds represented by the following general formula (14).
• Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and R 1 and R 31 to R 44 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• R 1 and Z 1 , R 31 and R 32 , R 32 and R 33 , R 33 and R 34 , R 34 and R 35 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , R 42 and R 43 , and R 43 and R 44 may be bonded to each other to form a cyclic structure.
• Z 1 and Z 8 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• R 1 and R 51 to R 60 each independently represent a hydrogen atom, a deuterium atom, or a substituent.
• R 1 and Z 1 , R 51 and R 52 , R 52 and R 53 , R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 56 and R 57 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 , and R 60 and Z 8 may be bonded to each other to form a cyclic structure.
• Z 1 , Z 8 and Z 9 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• R 1 and R 61 to R 66 each independently represent a hydrogen atom, a deuterium atom or a substituent.
• R 1 and Z 1 , Z 9 and R 61 , R 61 and R 62 , R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 65 and R 66 , and R 66 and Z 8 may be bonded to each other to form a cyclic structure.
• Z 1 , Z 9 and Z 10 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• R 1 and R 67 to R 69 each independently represent a hydrogen atom, a deuterium atom or a substituent
• R 70 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• R 1 and Z 1 , Z 9 and R 67 , R 67 and R 68 , R 68 and R 69 , R 69 and Z 10 , and Z 10 and R 70 may be bonded to each other to form a cyclic structure.
• Z 1 , Z 11 and Z 12 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• R 1 and R 72 to R 74 each independently represent a hydrogen atom, a deuterium atom or a substituent
• R 71 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• R 1 and Z 1 , R 71 and Z 11 , Z 11 and R 72 , R 72 and R 73 , R 73 and Z 74 , and R 74 and Z 12 may be bonded to each other to form a cyclic structure.
• Z 1 and Z 11 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring
• R 1 and R 76 to R 82 each independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
• R 75 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
• R 1 and Z 1 , R 75 and Z 11 , Z 11 and R 76 , R 76 and R 77 , R 77 and R 78 , R 78 and R 79 , R 79 and R 80 , R 80 and R 81 , and R 81 and R 82 may be bonded to each other to form a cyclic structure.
• Further preferred light-emitting materials include compounds represented by the following general formula (20).
• X5 represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded;
• R101 to R130 each independently represent a hydrogen atom, a deuterium atom, or a substituent;
• R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group
• Z 1 and Z 2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
• R 3 to R 9 each independently represent a hydrogen atom, a deuterium atom, or a substituent, provided that at least one of R 1 , R 2 , Z 1 , and Z 2 contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring.
• R1 and Z1 , Z1 and R3 , R3 and R4 , R4 and R5 , R5 and Z2 , Z2 and R2 , R2 and R6 , R6 and R7 , R7 and R8 , R8 and R9 , and R9 and R1 may be bonded to each other to form a ring structure.
• the substitutable carbon atoms may be substituted with a nitrogen atom.
• C- R3 , C- R4 , C- R5 , C- R6 , C- R7 , C- R8 , and C- R9 in the general formula (21) may be substituted with N.
• R 1 and R 2 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring.
• Z 1 and Z 2 are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring.
• R 1 and Z 1 are bonded to each other to form a cyclic structure.
• R 1 and Z 1 are bonded to each other to form a cyclic structure.
• one of X1 and X2 is a nitrogen atom and the other is a boron atom.
• R1 to R26 , A1 and A2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
• R1 and R2 , R2 and R3 , R3 and R4 , R4 and R5 , R5 and R6 , R6 and R7 , R7 and R8 , R8 and R9, R9 and R10 , R10 and R11 , R11 and R12 , R13 and R14 , R14 and R15 , R15 and R16 , R16 and R17 , R17 and R18 , R18 and R19 , R19 and R20 , R20 and R21 , R21 and R22 , R22 and R23 , R23 and R24 , R24 and R25 , R25 and R 26 may be bonded to each other to form a cyclic structure.
• R 1 to R 6 is a substituted or unsubstituted aryl group, or any of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , and R 5 and R 6 are bonded to each other to form an aromatic ring or a heteroaromatic ring.
• R3 and R6 is a substituent. In one embodiment of the present invention, R3 and R6 are both substituents. In one embodiment of the present invention, the substituents represented by R3 and R6 are one group selected from the group consisting of an alkyl group and an aryl group, or a group consisting of a combination of two or more groups. In one embodiment of the present invention, R8 and R12 are both substituents. In one embodiment of the present invention, the compound is represented by the following general formula (1a).
• a 1 and A 2 are each independently a group having a Hammett ⁇ p value of more than 0.2. In one embodiment of the present invention, A 1 and A 2 are both cyano groups. In one embodiment of the present invention, A 1 and A 2 are both halogen atoms. In one embodiment of the present invention, the compound has a rotationally symmetric structure.
• the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 20% by weight or less.
• the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 10% by weight or less.
• the host material of the light-emitting layer is an organic compound that has hole transport and electron transport functions.
• the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing.
• the host material of the light-emitting layer is an organic compound that has a high glass transition temperature.
• the host material is selected from the group consisting of:
• the light-emitting layer comprises two or more kinds of TADF molecules with different structures.
• the light-emitting layer may comprise three kinds of materials, the excited singlet energy level of which is higher in the order of the host material, the first TADF molecule, and the second TADF molecule.
• the difference ⁇ E ST between the lowest excited singlet energy level and the lowest excited triplet energy level at 77K of both the first TADF molecule and the second TADF molecule is preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and especially preferably 0.01 eV or less.
• the concentration of the first TADF comprises two or more kinds of TADF
• the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecule.
• the concentration of the first TADF molecule in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material.
• the composition in the light-emitting layer may be 10 to 70% by weight of the host material, 10 to 80% by weight of the first TADF molecule, and 0.1 to 30% by weight of the second TADF molecule.
• the composition in the light-emitting layer may be 20 to 45% by weight of the host material, 50 to 75% by weight of the first TADF molecule, and 5 to 20% by weight of the second TADF molecule.
• the light-emitting layer can contain three types of TADF molecules with different structures.
• the compound of the present invention may be any of the multiple TADF compounds contained in the light-emitting layer.
• the light-emitting layer can be made of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer does not contain a metal element. In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms.
• the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.
• the TADF material may be a known delayed fluorescent material.
• Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013/011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013/011955, and paragraph 0008 of WO2013/081088.
• JP 2013-256490 A paragraphs 0009 to 0046 and 0093 to 0134; JP 2013-116975 A, paragraphs 0008 to 0020 and 0038 to 0040; WO 2013/133359 A, paragraphs 0007 to 0032 and 0079 to 0084; WO 2013/161437 A, paragraph 0 No. 008 to 0054 and No.
• the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.
• the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof.
• the metal, alloy, or conductive compound has a high work function (4 eV or more).
• the metal is Au.
• the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2 , and ZnO.
• an amorphous material capable of forming a transparent conductive film such as IDIXO ( In2O3 - ZnO ), is used.
• the anode is a thin film.
• the thin film is made by evaporation or sputtering.
• the film is patterned by a photolithographic method.
• the pattern may be formed using a mask with a shape suitable for evaporation or sputtering on the electrode material.
• a wet film formation method such as a printing method or a coating method, is used.
• the anode has a transmittance of greater than 10% when emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.
• the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron injecting metal), an alloy, a conductive compound, or a combination thereof.
• the electrode material is selected from sodium, sodium-potassium alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-aluminum oxide (Al 2 O 3 ) mixtures, indium, lithium-aluminum mixtures, and rare earth elements.
• a mixture of an electron injecting metal and a second metal is used, the second metal being a stable metal with a higher work function than the electron injecting metal.
• the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-aluminum oxide (Al 2 O 3 ) mixtures, lithium-aluminum mixtures, and aluminum.
• the mixture improves electron injection properties and resistance to oxidation.
• the cathode is fabricated by forming the electrode material as a thin film by evaporation or sputtering.
• the cathode has a sheet resistance of a few hundred ohms or less per unit area. In some embodiments, the cathode has a thickness of 10 nm to 5 ⁇ m. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semi-transparent to allow the emitted light to pass through. In some embodiments, a transparent or semi-transparent electroluminescent device enhances light radiance.
• the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semi-transparent cathode, hi some embodiments, an element includes an anode and a cathode, both of which are transparent or semi-transparent.
• An injection layer is a layer between an electrode and an organic layer.
• the injection layer reduces the driving voltage and enhances the light radiance.
• the injection layer includes a hole injection layer and an electron injection layer.
• the injection layer can be disposed between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer.
• an injection layer is present. In some embodiments, an injection layer is not present. Preferred examples of compounds that can be used as the hole injection material are given below.
• a barrier layer is a layer that can prevent charges (electrons or holes) and/or excitons present in the light-emitting layer from diffusing outside the light-emitting layer.
• an electron barrier layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer.
• a hole barrier layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer.
• a barrier layer prevents excitons from diffusing outside the light-emitting layer.
• the electron barrier layer and the hole barrier layer constitute an exciton barrier layer.
• the term "electron barrier layer" or "exciton barrier layer” includes layers that have both the functions of an electron barrier layer and of an exciton barrier layer.
• Hole blocking layer functions as an electron transport layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transport layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer.
• the materials used for the hole blocking layer can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are given below.
• Electron Barrier Layer The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer blocks electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer.
• the materials used for the electron blocking layer can be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as the electron blocking material are given below.
• Exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the light-emitting layer. In some embodiments, the light emission efficiency of the device is improved. 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 present on the anode side, the layer may be present between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer.
• the layer when the exciton blocking layer is present on the cathode side, the layer may be present between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and 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 present between the cathode and the exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.
• the hole transport layer comprises a hole transport material.
• the hole transport layer is a single layer.
• the hole transport layer has multiple layers.
• the hole transport material has one of the following properties: hole injection or transport property and electron blocking property.
• the hole transport material is an organic material.
• the hole transport material is an inorganic material.
• Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof.
• the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are given below.
• the electron transport layer comprises an electron transport material.
• the electron transport layer is a single layer.
• the electron transport layer has multiple layers.
• the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer.
• the electron transport material also functions as a hole-blocking material.
• electron transport layers examples include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof.
• the electron transport material is a thiadiazole derivative or a quinoxaline derivative.
• the electron transport material is a polymeric material. Specific examples of preferred compounds that can be used as electron transport materials are given below.
• the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet.
• an electronic device includes an OLED having an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode.
• the compositions described herein may be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices.
• compositions may be useful in facilitating charge or energy transfer within devices and/or as hole transport materials, such as organic light emitting diodes (OLEDs), organic integrated circuits (OICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light emitting fuel cells (LECs), or organic laser diodes (O-lasers).
• OLEDs organic light emitting diodes
• OICs organic integrated circuits
• O-FETs organic field effect transistors
• OF-TFTs organic thin film transistors
• O-LETs organic light emitting transistors
• O-SCs organic solar cells
• organic optical detectors organic photoreceptors, organic field-quench devices (O-FQDs), light emitting fuel cells (LECs), or organic laser diodes (O-lasers
• the electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode.
• the device includes OLEDs of different colors.
• the device includes an array including a combination of OLEDs.
• the combination of OLEDs is a three-color combination (e.g., RGB).
• the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green).
• the combination of OLEDs is a two-color, four-color, or more-color combination.
• the device comprises: a circuit board having a first side having a mounting surface and an opposing second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture.
• the OLED light comprises a plurality of OLEDs mounted on a circuit board such that light is emitted in a plurality of directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.
• the light-emitting layer of the present invention can be used in a screen or display.
• the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD).
• the substrate is a photoplate structure useful in two-sided etching to provide pixels with unique aspect ratios.
• the screen also called a mask
• the corresponding artwork pattern design allows for the placement of very steep narrow tie bars between pixels in the vertical direction, as well as large wide angled openings in the horizontal direction.
• the internal patterning of the pixel allows for the construction of three-dimensional pixel openings of various aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged "stripes" or halftone circles in the pixel area protects etching in certain areas until those particular patterns are undercut and removed from the substrate. At that point, all pixel areas are treated with similar etch rates, but the depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with different protection rates within the pixel, allowing for the localized deep etching required to create steep vertical bevels.
• the preferred material for the deposition mask is Invar.
• the screen or display pattern is a pixel matrix on a substrate.
• the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).
• the screen or display pattern is fabricated using wet chemical etching.
• the screen or display pattern is fabricated using plasma etching.
• OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
• each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, coating a planarizing film on the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel.
• TFT thin film transistor
• a method for manufacturing an organic light emitting diode (OLED) display comprising the steps of: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in the form of a cell panel; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels.
• the barrier layer is an inorganic film, for example made of SiNx, and the ends of the barrier layer are covered with an organic film made of polyimide or acrylic.
• the organic film helps the mother panel to be cut softly into cell panels.
• the thin film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source/drain electrodes.
• Each of the plurality of display units may have a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is formed of the same material as the planarization film and is formed at the same time as the planarization film.
• the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit.
• the organic film is not connected to the display unit or the encapsulation layer.
• each of the organic film and the planarization film may comprise one of polyimide and acrylic.
• the barrier layer may be an inorganic film.
• the base substrate may be formed of polyimide.
• the method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide prior to forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate prior to cutting along the interface.
• the OLED display is a flexible display.
• the passivation layer is an organic film disposed on the TFT layer for covering the TFT layer.
• the planarization film is an organic film formed on the passivation layer.
• the planarization film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.
• the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled to a source/drain electrode of a TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image.
• a display unit an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit.
• the encapsulation layer that covers the display units and prevents the penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated.
• the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated.
• the organic film applied to the interface portion is disposed at an interval with each of the plurality of display units.
• the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the end of the barrier layer.
• the OLED display is flexible and uses a flexible base substrate formed from polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed from a glass material, and the carrier substrate is then separated.
• a barrier layer is formed on a surface of the base substrate opposite the carrier substrate.
• the barrier layer is patterned according to the size of each cell panel. For example, the base substrate is formed on all surfaces of the mother panel, while the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.
• the manufacturing method further includes a step of cutting along the interface, where a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate.
• a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on the TFT layer to cover the TFT layer.
• the planarization film for example made of polyimide or acrylic
• the groove of the interface is covered with an organic film, for example made of polyimide or acrylic.
• the interface grooves between the barrier layers are covered with an organic film to absorb shocks that would otherwise be transmitted to the barrier layers, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layers.
• the organic film and the planarizing film covering the interface grooves are spaced apart from each other.
• the organic film and the planarizing film were connected to each other as one layer, there would be a risk of external moisture penetrating the display unit through the planarizing film and the remaining portion of the organic film, so the organic film and the planarizing film are spaced apart from each other such that the organic film is spaced apart from the display unit.
• the display unit is formed by forming a light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit.
• the carrier substrate carrying the base substrate is separated from the base substrate.
• the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate.
• the mother panel is cut into individual cell panels.
• the mother panel is cut along the interface between the cell panels using a cutter.
• the grooves of the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting.
• the barrier layer is prevented from cracking during cutting. In some embodiments, the methods reduce product defect rates and stabilize product quality.
• Another aspect is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to the edges of the barrier layer.
• the characteristics of the present invention will be described in more detail below with reference to synthesis examples and examples.
• the materials, processing contents, processing procedures, etc. shown below can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the specific examples shown below.
• the evaluation of the emission characteristics was performed 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 C4334).
• the energy of HOMO and LUMO was measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.).
• compounds within the scope of general formula (1) were synthesized.
• the obtained brown solution was cooled to room temperature and slowly added dropwise to a THF solution (120mL) of 2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine at 0°C. After the dropwise addition, the temperature was returned to room temperature and stirring was continued for 18 hours.
• the reaction vessel was cooled to 0°C, and saturated aqueous ammonium chloride solution (100 mL) was added to separate the organic phase and the aqueous phase. The organic phase was concentrated, and the resulting solid was washed with THF and hexane. The solid was dissolved in hot toluene, passed through a silica pad, and the filtrate was concentrated.
• the resulting reaction solution was extracted with toluene, and the organic layer was washed with saturated saline and then dried over anhydrous magnesium. The solvent was removed, and the resulting yellow liquid was dissolved in dehydrated toluene (100 mL), and bis(triphenylphosphine)palladium(II) dichloride (0.71 g, 1.0 mmol) and compound X4 (4.43 g, 10.0 mmol) were added, followed by stirring at 120° C. for 15 hours. The reaction vessel was returned to room temperature, and the resulting gray solid was washed with toluene and hexane.
• Example 1 Preparation and Evaluation of Thin Film Compound 727 was deposited on a quartz substrate by vacuum deposition under conditions of a degree of vacuum of less than 1 ⁇ 10 ⁇ 3 Pa to form a neat thin film of compound 727 with a thickness of 100 nm.
• compound 727 and H1 having the following structure were deposited from different deposition sources on a quartz substrate by vacuum deposition under conditions of a vacuum degree of less than 1 ⁇ 10 ⁇ 3 Pa to form a doped thin film having a concentration of compound 727 of 30% by weight with a thickness of 100 nm.
• Neat and doped thin films were formed in the same manner except that Compound 727(28) and Comparative Compound A were used instead of Compound 727.
• the photoluminescence of each doped thin film formed was analyzed when 300 nm excitation light was irradiated to measure the proportion of delayed fluorescent components and the lifetime ( ⁇ 2) of the delayed fluorescent components.
• the HOMO energy and LUMO energy were also measured using each neat thin film formed. The results are shown in the table below.
• Example 2 Preparation and evaluation of organic electroluminescence element On a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm was formed, each thin film was laminated by vacuum deposition at a vacuum degree of 5.0 ⁇ 10 ⁇ 5 Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 30 nm, TrisPCz was further formed thereon to a thickness of 10 nm, and H1 was formed thereon to a thickness of 5 nm.
• ITO indium tin oxide
• H1, compound 727, 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 34.2% by mass
• the concentration of compound 727 was 65% 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
• organic electroluminescence devices were prepared in the same manner. When the external quantum efficiency (EQE) of each organic electroluminescence device was measured, all of them showed high values exceeding 20%, confirming the usefulness of the compound represented by the general formula (1).
• Example 3 Evaluation of ⁇ E ST Quantum chemical calculations were performed using B3LYP-631G for each of compound 727 and compound 6677 synthesized in Synthesis Example 1, and comparative compound B and comparative compound C having the structures shown below.
• the energy difference ( ⁇ E ST ) between the lowest excited singlet state (S1) and the lowest excited triplet state (T1) was calculated using a value obtained by optimizing the structure in the lowest excited triplet state (T1). The results are shown in the table below.
• Example 4 Evaluation of ⁇ E ST Compound 727 (28), compound 6677 (28), and comparative compound D and comparative compound E having the following structures were each subjected to quantum chemical calculations in the same manner as in Example 3 to determine ⁇ E ST . The results are shown in the table below.
• the present invention has a high industrial applicability.

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