WO2023140374A1 - Composé, matériau électroluminescent et élément électroluminescent - Google Patents

Composé, matériau électroluminescent et élément électroluminescent Download PDF

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WO2023140374A1
WO2023140374A1 PCT/JP2023/001844 JP2023001844W WO2023140374A1 WO 2023140374 A1 WO2023140374 A1 WO 2023140374A1 JP 2023001844 W JP2023001844 W JP 2023001844W WO 2023140374 A1 WO2023140374 A1 WO 2023140374A1
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group
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substituted
light
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香織 藤澤
哲 大野
琢哉 比嘉
ヨン ジュ ジョ
善丈 鈴木
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株式会社Kyulux
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]

Definitions

  • the present invention relates to a compound useful as a light-emitting material and a light-emitting device using the same.
  • organic electroluminescence elements organic electroluminescence elements
  • various attempts have been made to improve the luminous efficiency by newly developing and combining electron transporting materials, hole transporting materials, light emitting materials, and the like, which constitute organic electroluminescence elements.
  • research on organic electroluminescence elements using delayed fluorescence materials can also be seen.
  • a delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after reverse intersystem crossing from the excited triplet state to the excited singlet state occurs in the excited state. Fluorescence by such a pathway is called delayed fluorescence because it is observed later than the fluorescence from the excited singlet state directly generated from the ground state (ordinary fluorescence).
  • the probability of occurrence of the excited singlet state and the excited triplet state is statistically 25%:75%.
  • the delayed fluorescence material not only the excited singlet state but also the excited triplet state can be used for fluorescence emission through the above-described reverse intersystem crossing pathway, so that higher luminous efficiency can be obtained than in ordinary fluorescent materials.
  • the present inventors conducted extensive research with the aim of providing compounds that are more useful as light-emitting materials for light-emitting devices. Then, intensive studies were carried out with the aim of deriving and generalizing the general formulas of compounds that are more useful as light-emitting materials.
  • a compound represented by the following general formula (1) A represents a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group, and hydrogen atoms of these groups may be substituted with deuterium atoms.
  • One of R2 and R3 represents an acceptor group.
  • At least one of R 1 , R 4 and R 5 other than R 2 and R 3 each independently represents a substituted or unsubstituted benzofuro-fused carbazol-9-yl group or a substituted or unsubstituted benzothieno-fused carbazol-9-yl group.
  • the remaining R 1 to R 5 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a donor group (however, the donor group does not include an alkyl group, a substituted or unsubstituted benzofuro-fused carbazol-9-yl group, and a substituted or unsubstituted benzothieno-fused carbazol-9-yl group).
  • [2] The compound according to [1], which has a maximum emission wavelength in the range of 420 nm to 575 nm.
  • R 2 is an acceptor group.
  • [10] The compound according to any one of [1] to [9], which has a symmetrical structure.
  • a luminescent material comprising the compound according to any one of [1] to [10].
  • a delayed phosphor comprising the compound according to any one of [1] to [10].
  • An organic semiconductor device comprising the compound according to any one of [1] to [10].
  • An organic light emitting device comprising the compound according to any one of [1] to [10].
  • the layer containing the compound also contains a delayed fluorescence material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescence material is lower than the host material and higher than the compound, [16].
  • the organic light-emitting device according to [16] wherein the device has a layer containing the compound, and the layer also contains a light-emitting material having a structure different from that of the compound.
  • the compound represented by general formula (1) has excellent luminescence properties.
  • General formula (1) includes luminescent materials that emit deep blue light.
  • general formula (1) includes a luminescent material with a short lifetime of delayed fluorescence.
  • An excellent organic light-emitting device can be provided by using the compound represented by the general formula (1).
  • A represents a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group.
  • the hydrogen atoms of the 2-cyanophenyl group and 4-cyanophenyl group referred to herein may be substituted with deuterium atoms, but are not substituted with other atoms or groups.
  • A is a 2-cyanophenyl group.
  • A is a 4-cyanophenyl group.
  • the bonding position of the cyano group of the cyanopyridyl group that A can take may be any of the 2nd to 4th positions of the pyridine ring.
  • the 2-position of the pyridine ring is a cyano group.
  • the 3-position of the pyridine ring is a cyano group.
  • the 4-position of the pyridine ring is a cyano group.
  • the bond of the cyanopyridyl group may be at any of the 2-6 positions of the pyridine ring.
  • Each hydrogen atom of the cyanopyridyl group represented by A may be independently substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, a phenyl group and a naphthyl group. Some or all of the phenyl groups referred to herein may be substituted with deuterium atoms. Some or all of the naphthyl groups referred to here may also be substituted with deuterium atoms. In one aspect of the invention, the cyanopyridyl group is substituted with at least one phenyl group. In one aspect of the invention, the cyanopyridyl group is substituted with at least one naphthyl group.
  • the cyanopyridyl group is not substituted by either a phenyl group or a naphthyl group.
  • A has at least one deuterium atom.
  • in the 2-cyanophenyl group, 4-cyanophenyl group, and cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group represented by A all hydrogen atoms present in these groups are replaced with deuterium atoms.
  • A1(D) to A95(D) are disclosed as those in which all the hydrogen atoms present in A1 to A95 are replaced with deuterium atoms.
  • a in general formula (1) is selected from the group consisting of A1 to A95.
  • A is selected from the group consisting of A78-A95, A1(D)-A95(D).
  • A is selected from the group consisting of A3-A95.
  • A is selected from the group consisting of A3-A14.
  • A is selected from the group consisting of A15-A95.
  • A is selected from the group consisting of A3-A6, A15-A32, A78-A82. In one aspect of the invention, A is selected from the group consisting of A7-A10, A33-A59, A83-A91. In one aspect of the invention, A is selected from the group consisting of A11-A14, A60-77, A92-95.
  • R 2 and R 3 represents an acceptor group.
  • R2 is an acceptor group.
  • R 3 is an acceptor group.
  • the acceptor group that R 2 and R 3 can take may be a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group (the hydrogen atoms of these groups may be substituted with deuterium atoms).
  • the description of A above can be referred to for descriptions and preferred ranges of these groups.
  • the acceptor group is the same group as A.
  • a and R2 are the same group, or A and R3 are the same group.
  • one of R 2 and R 3 is a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group (the hydrogen atoms of these groups may be substituted with deuterium atoms), but is a different group from A.
  • one of R 2 and R 3 is an acceptor group, but is not a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group (the hydrogen atoms of these groups may be substituted with deuterium atoms).
  • Such an acceptor group can be selected from among groups having a positive Hammett's ⁇ p value. Hammett's ⁇ p values are given by L. P. Proposed by Hammett, it quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives.
  • k0 is the rate constant of the benzene derivative without a substituent
  • k is the rate constant of the benzene derivative substituted with a substituent
  • K0 is the equilibrium constant of the benzene derivative without the substituent
  • K is the equilibrium constant of the benzene derivative substituted with the substituent
  • ⁇ is the reaction constant determined by the type and conditions of the reaction.
  • the acceptor group that one of R 2 and R 3 can take preferably has ⁇ p of 0.3 or more, more preferably 0.5 or more, and even more preferably 0.7 or more. For example, it may be selected from a range of 0.9 or more, or selected from a range of 1.1 or more.
  • acceptor groups other than a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group include, for example, a cyano group.
  • Other typical acceptor groups include heteroaryl groups containing two or more nitrogen atoms as ring skeleton atoms. Examples include a triazinyl group and a pyrimidinyl group. Hydrogen atoms in these heteroaryl groups may be substituted with deuterium atoms or substituents.
  • the substituent may be selected, for example, from Substituent Group E, such as an unsubstituted aryl group, preferably an unsubstituted phenyl group.
  • acceptor group of formula (1) examples include the above A1 to A95 and A1(D) to A95(D). Other typical examples of acceptor groups are listed below. However, the acceptor group that can be employed in the present invention is not limitedly interpreted by the following specific examples. In the following specific examples, * indicates a bonding position, and C 6 D 5 represents a phenyl group in which all hydrogen atoms are deuterated.
  • the other of R 2 and R 3 (that is, the one that is not an acceptor group) and at least one of R 1 , R 4 and R 5 each independently represents a substituted or unsubstituted benzofuro-fused ring carbazol-9-yl group or a substituted or unsubstituted benzothieno-fused ring carbazol-9-yl group (hereinafter collectively referred to as a “fused ring carbazol-9-yl group”).
  • the number of fused-ring carbazol-9-yl groups is 1 to 4, for example 1 to 3, for example 1 or 2.
  • the number of condensed carbazol-9-yl groups may be 2 to 4, and may be 2 or 3.
  • R 3 is an acceptor group and at least one of R 1 , R 2 , R 4 , R 5 is each independently a fused carbazol-9-yl group.
  • R 2 is a fused carbazol-9-yl group.
  • only R 2 is a fused carbazol-9-yl group.
  • R 2 and R 5 are fused-ring carbazol-9-yl groups.
  • only R 2 and R 5 are fused-ring carbazol-9-yl groups.
  • R 2 , R 4 and R 5 are fused-ring carbazol-9-yl groups.
  • R 1 -R 4 are fused carbazol-9-yl groups.
  • R 2 is an acceptor group and at least one of R 1 , R 3 , R 4 , R 5 each independently represents a fused-ring carbazol-9-yl group.
  • R 1 is a fused carbazol-9-yl group.
  • R 3 is a fused carbazol-9-yl group.
  • R 4 is a fused carbazol-9-yl group.
  • R 5 is a fused carbazol-9-yl group. In one aspect of the invention, only R 3 is a fused carbazol-9-yl group.
  • R 4 is a fused carbazol-9-yl group.
  • R 5 is a fused carbazol-9-yl group.
  • R 3 and R 5 are fused-ring carbazol-9-yl groups.
  • R 3 and R 4 are fused carbazol-9-yl groups.
  • R 4 and R 5 are fused carbazol-9-yl groups.
  • only R 3 and R 5 are fused-ring carbazol-9-yl groups.
  • R 3 to R 5 are fused-ring carbazol-9-yl groups.
  • R 1 , R 3 , R 4 , R 5 are fused ring carbazol-9-yl groups.
  • those fused-ring carbazol-9-yl groups are identical.
  • those fused carbazol-9-yl groups are different from each other.
  • the fused-ring carbazol-9-yl group is a benzofuro-fused carbazol-9-yl group.
  • the fused carbazol-9-yl group is a benzenofused carbazol-9-yl group.
  • a benzofuro[2,3-a]carbazol-9-yl group can be employed as the benzofuro-fused carbazol-9-yl group.
  • a benzofuro[3,2-a]carbazol-9-yl group can also be employed.
  • a benzofuro[2,3-b]carbazol-9-yl group can also be employed.
  • a benzofuro[3,2-b]carbazol-9-yl group can also be employed.
  • a benzofuro[2,3-c]carbazol-9-yl group can also be employed.
  • a benzofuro[3,2-c]carbazol-9-yl group can also be employed.
  • a preferred benzofuro-fused carbazol-9-yl group is a carbazol-9-yl group in which only one benzofuran ring is fused at the 2,3 positions and the other rings are not fused. Specifically, it is a group having any one of the following structures, and at least one hydrogen atom in the following structure may be substituted.
  • a benzothieno[2,3-a]carbazol-9-yl group can be employed as the benzothieno-fused carbazol-9-yl group.
  • a benzothieno[3,2-a]carbazol-9-yl group can also be employed.
  • a benzothieno[2,3-b]carbazol-9-yl group can also be employed.
  • a benzothieno[3,2-b]carbazol-9-yl group can also be employed.
  • a benzothieno[2,3-c]carbazol-9-yl group can also be employed.
  • a benzothieno[3,2-c]carbazol-9-yl group can also be employed.
  • a preferred benzoeno-fused carbazol-9-yl group is a carbazol-9-yl group in which only one benzothiophene ring is fused at the 2,3 positions and the other rings are not fused. Specifically, it is a group having any one of the following structures, and at least one hydrogen atom in the following structure may be substituted.
  • the substituent of the condensed carbazol-9-yl group may be selected from substituent group A, may be selected from substituent group B, may be selected from substituent group C, may be selected from substituent group D, or may be selected from substituent group E.
  • the fused-ring carbazol-9-yl group is unsubstituted.
  • the substituent of the condensed carbazol-9-yl group is substituted with an unsubstituted aryl group.
  • substituents of the fused-ring carbazol-9-yl group are substituted with unsubstituted alkyl groups.
  • An "aryl group” may be a monocyclic ring or a condensed ring in which two or more rings are condensed.
  • the number of condensed rings is preferably 2 to 6, and can be selected from 2 to 4, for example.
  • Specific examples of rings include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, and 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, preferably a substituted or unsubstituted phenyl group.
  • the substituent of the aryl group may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.
  • the substituents of the aryl group are one or more selected from the group consisting of alkyl groups, aryl groups and deuterium atoms.
  • the aryl group is unsubstituted.
  • the "alkyl group” may be linear, branched or cyclic. Moreover, two or more of the linear portion, the cyclic portion and the branched portion may be mixed.
  • the number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decanyl, isodecanyl, and cyclopentyl groups. , cyclohexyl group and 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 substituents of the alkyl group are one or more selected from the group consisting of aryl groups and deuterium atoms.
  • the alkyl group is unsubstituted.
  • the number of substituents on the condensed carbazol-9-yl group is preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 4. For example, it may be 1, or it may be 2.
  • either the 3- or 6-position of the fused carbazol-9-yl group is substituted.
  • the benzene ring has at least one substituent at the para-position relative to the heteroatom present in the fused-ring carbazol-9-yl group.
  • the 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.
  • all substitutable para-positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group have substituents.
  • substituted or unsubstituted benzofuro-fused-ring carbazol-9-yl group or the substituted or unsubstituted benzothieno-fused-ring carbazol-9-yl group that is, the fused-ring carbazol-9-yl group
  • the condensed carbazol-9-yl group that can be employed in the present invention is not limited to the following specific examples.
  • * indicates a bonding position
  • Ph represents a phenyl group
  • C 6 D 5 represents a phenyl group in which all hydrogen atoms are deuterated.
  • the display of the methyl group is omitted.
  • D7 to D18 for example, have a methyl group.
  • D1(D) to D459(D) are disclosed as those in which all the hydrogen atoms present in D1 to D459 are replaced with deuterium atoms.
  • the condensed carbazol-9-yl group that R 1 to R 5 in general formula (1) can take is selected from the group consisting of D1 to D459.
  • the condensed carbazol-9-yl group that can be taken by R 1 to R 5 in general formula (1) is selected from the group consisting of D1 to D30.
  • the condensed carbazol-9-yl group that can be taken by R 1 to R 5 in general formula (1) is selected from the group consisting of D31 to D60.
  • the condensed carbazol-9-yl group that can be taken by R 1 to R 5 in general formula (1) is selected from the group consisting of D61 to D84. In one aspect of the present invention, the condensed carbazol-9-yl group that can be taken by R 1 to R 5 in general formula (1) is selected from the group consisting of D88 to D91, D95 to D198, D287 to D293, D306 to D317 and D330 to D459. In one aspect of the present invention, the condensed carbazol-9-yl group that can be taken by R 1 to R 5 in general formula (1) is selected from the group consisting of D92, D93 and D199 to D286. In one aspect of the present invention, the condensed carbazol-9-yl group that R 1 to R 5 in general formula (1) can take is selected from the group consisting of D294 to D459.
  • the remaining R 1 to R 5 in general formula (1) each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a donor group (however, the donor group herein does not include an alkyl group, a substituted or unsubstituted benzofuro-fused-ring carbazol-9-yl group, and a substituted or unsubstituted benzothieno-fused-ring carbazol-9-yl group).
  • the “remaining R 1 to R 5 ” as used herein means a group that is neither an acceptor group, a substituted or unsubstituted benzofuro-fused carbazol-9-yl group, nor a substituted or unsubstituted benzothieno-fused carbazol-9-yl group.
  • the remaining number of R 1 to R 5 is 0 to 3.
  • the remaining R 1 -R 5 are hydrogen atoms or deuterium atoms.
  • the remaining R 1 -R 5 comprise substituted or unsubstituted aryl groups.
  • the remaining R 1 -R 5 contain donor groups.
  • all remaining R 1 -R 5 are donor groups. In one aspect of the invention, the remaining R 1 -R 5 are hydrogen atoms, deuterium atoms or donor groups. In one aspect of the invention, the remaining R 1 -R 5 are hydrogen atoms, deuterium atoms or substituted or unsubstituted aryl groups. In one aspect of the invention, the remaining R 1 -R 5 contain deuterium atoms.
  • the description and preferred range of the substituted or unsubstituted aryl group that the remaining R 1 to R 5 can take the description and preferred range of the aryl group as a substituent of the condensed carbazol-9-yl group can be referred to.
  • the substituted or unsubstituted aryl group that the remaining R 1 to R 5 can take is an unsubstituted aryl group, preferably an unsubstituted phenyl group.
  • the remaining aryl groups that can be taken by R 1 to R 5 are not substituted with cyano groups.
  • the remaining donor groups that can be taken by R 1 to R 5 can be selected from groups having a negative Hammett's ⁇ p value.
  • the ⁇ p of the remaining donor groups that can be taken by R 1 to R 5 is preferably ⁇ 0.3 or less, more preferably ⁇ 0.5 or less, and even more preferably ⁇ 0.7 or less. For example, it may be selected from the range of -0.9 or less, or from the range of -1.1 or less.
  • the number of donor groups taken by the remaining R 1 to R 5 is 2 or more, all of those donor groups are preferably the same. In one aspect of the invention, each of the two or more donor groups is different from each other.
  • the remaining donor groups that can be taken by R 1 to R 5 are preferably groups containing substituted amino groups.
  • 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.
  • Two aryl groups constituting the diarylamino group herein may be bonded to each other, and two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.
  • the description and preferred range of the aryl group and alkyl group referred to herein the description and preferred range of the aryl group and alkyl group as substituents of the condensed carbazol-9-yl group can be referred to.
  • heteroaryl group as used herein may be a monocyclic ring or a condensed ring in which two or more rings are condensed.
  • the number of condensed rings is preferably 2 to 6, and can be selected from 2 to 4, for example.
  • Specific examples of the ring include a pyridine ring and a pyrimidine ring, and these rings may be condensed with another ring.
  • Specific examples of heteroaryl groups include 2-pyridyl, 3-pyridyl and 4-pyridyl groups.
  • 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 14 or within the range of 5 to 10.
  • the remaining donor groups that R 1 to R 5 can take are preferably substituted or unsubstituted carbazol-9-yl groups (excluding substituted or unsubstituted benzofuro-fused carbazol-9-yl groups and substituted or unsubstituted benzothieno-fused carbazol-9-yl groups).
  • the two benzene rings constituting the carbazol-9-yl group may be further condensed with a benzene ring.
  • the two benzene rings constituting the carbazol-9-yl group may be further condensed with a pyridine ring.
  • At least one of the ring skeleton-constituting carbon atoms constituting the carbazol-9-yl group is substituted with a nitrogen atom.
  • substituent of the carbazol-9-yl group may be selected from substituent group A, may be selected from substituent group B, may be selected from substituent group C, may be selected from substituent group D, or may be selected from substituent group E.
  • the remaining carbazol-9-yl groups that can be taken by R 1 to R 5 may be condensed, but hydrogen atoms are not substituted.
  • the optionally condensed carbazol-9-yl group is substituted with an unsubstituted aryl group.
  • the optionally condensed carbazol-9-yl group is substituted with an unsubstituted alkyl group.
  • the donor groups that the remaining R 1 to R 5 can take are shown below.
  • the donor group that can be employed in the present invention is not limitedly interpreted by the following specific examples.
  • * indicates a binding position.
  • Methyl groups are omitted, so Z2, for example, has one methyl group.
  • Z1(D) to Z36(D) are disclosed as those in which all the hydrogen atoms present in Z1 to Z36 are replaced with deuterium atoms.
  • the donor groups that the remaining R 1 to R 5 in general formula (1) can take are selected from the group consisting of Z1 to Z36.
  • the donor group that the remaining R 1 to R 5 in general formula (1) can take is selected from the group consisting of Z1 to Z6.
  • the donor groups that the remaining R 1 to R 5 in general formula (1) can take are selected from the group consisting of Z7 to Z36.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 in general formula (1) do not combine with each other to form a cyclic structure.
  • the compound represented by general formula (1) has a symmetrical structure.
  • the compound represented by general formula (1) has an axisymmetric structure.
  • the compound represented by general formula (1) has a rotationally symmetric structure.
  • the compound represented by general formula (1) has an asymmetric structure.
  • the compound represented by general formula (1) contains at least one deuterium atom.
  • One aspect of the invention has deuterated alkyl groups (eg, deuterated methyl groups, deuterated ethyl groups, deuterated cyclohexyl groups).
  • One aspect of the invention has deuterated aryl groups (eg, deuterated phenyl groups). In one aspect of the invention, all hydrogen atoms are deuterated.
  • the compound represented by the general formula (1) preferably does not contain a metal atom, and may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms.
  • the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms.
  • the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and sulfur atoms.
  • the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms and nitrogen atoms.
  • the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms and nitrogen atoms.
  • the compound represented by general formula (1) may be a compound containing no hydrogen atom and containing a deuterium atom.
  • substituted group A refers to a hydroxyl group, a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), an alkyl group (e.g., 1 to 40 carbon atoms), an alkoxy group (e.g., 1 to 40 carbon atoms), an alkylthio group (e.g., 1 to 40 carbon atoms), an aryl group (e.g., 6 to 30 carbon atoms), an aryloxy group (e.g., 6 to 30 carbon atoms), an arylthio group (e.g., 6 to 30 carbon atoms), a heteroaryl group (e.g., ring skeleton atoms).
  • a halogen atom e.g., fluorine atom, chlorine atom, bromine atom, iodine atom
  • an alkyl group e.g., 1 to 40 carbon atoms
  • an alkoxy group
  • heteroaryloxy groups eg, 5 to 30 ring atoms
  • heteroarylthio groups eg, 5 to 30 ring atoms
  • acyl groups eg, 1 to 40 carbon atoms
  • alkenyl groups eg, 1 to 40 carbon atoms
  • alkynyl groups eg, 1 to 40 carbon atoms
  • alkoxycarbonyl groups eg, 1 to 40 carbon atoms
  • aryloxycarbonyl groups eg, 1 to 40 carbon atoms
  • heteroaryloxycarbonyl groups eg, 1 to 40 carbon atoms
  • substituted group B refers to an alkyl group (eg, 1 to 40 carbon atoms), an alkoxy group (eg, 1 to 40 carbon atoms), an aryl group (eg, 6 to 30 carbon atoms), an aryloxy group (eg, 6 to 30 carbon atoms), a heteroaryl group (eg, 5 to 30 ring atoms), a heteroaryloxy group (eg, 5 to 30 ring atoms), and a diarylaminoamino group (eg, 0 to 20 carbon atoms). It means a group in which the above are combined.
  • substituted group C means one group or a combination of two or more selected from the group consisting of an alkyl group (eg, 1 to 20 carbon atoms), an aryl group (eg, 6 to 22 carbon atoms), a heteroaryl group (eg, 5 to 20 ring atoms), and a diarylamino group (eg, 12 to 20 carbon atoms).
  • substituted group D means one group selected from the group consisting of an alkyl group (eg, 1 to 20 carbon atoms), an aryl group (eg, 6 to 22 carbon atoms) and a heteroaryl group (eg, 5 to 20 ring atoms), or a combination of two or more groups.
  • substituted group E means one group selected from the group consisting of an alkyl group (for example, 1 to 20 carbon atoms) and an aryl group (for example, 6 to 22 carbon atoms) or a combination of two or more groups.
  • substituent when described as “substituent” or “substituted or unsubstituted” may be selected, for example, from substituent group A, may be selected from substituent group B, may be selected from substituent group C, may be selected from substituent group D, or may be selected from substituent group E.
  • Tables 1 and 2 below list specific examples of the compound represented by the general formula (1). However, the compound represented by the general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. Tables 1 and 2 show the structures of compounds 1 to 24786 individually by specifying A and R 1 to R 5 in the following general formula (1) for each compound.
  • Ph represents a phenyl group.
  • Table 2 shows the structures of compounds 1 to 24786 by collectively displaying A and R 1 to R 5 of a plurality of compounds in each row. For example, in the row of compounds 1 to 459 in Table 2, compounds in which A and R 3 are fixed to A1, R 1 and R 4 are fixed to Z1, and R 2 and R 5 are the same and D1 to D459 are designated as compounds 1 to 459 in order. That is, the columns of compounds 1 to 459 in Table 2 collectively display the compounds 1 to 459 specified in Table 1.
  • Compounds 16525-20655 in Table 2 identify those where R 3 -R 5 are the same and D1-D459.
  • R 3 -R 5 are the same and D1-D459.
  • compounds in which A and R 2 are A1 R 1 is fixed to a hydrogen atom (H)
  • R 3 to R 5 are the same
  • D1 to D459 are designated as compounds 16525 to 16983 in order.
  • Compounds 20656-24786 in Table 2 identify those where R 3 and R 5 are the same and are D1-D459.
  • compounds are selected from compounds 1-24786. In one aspect of the invention, compounds are selected from compounds 1(D) to 24786(D). In one aspect of the invention, compounds are selected from compounds 1-1324. In one aspect of the invention, compounds are selected from compounds 1325-2648. In one aspect of the invention, compounds are selected from compounds 2649-3972. In one aspect of the invention, compounds are selected from compounds 3973-5296. In one aspect of the invention, compounds are selected from compounds 1-8262. In one aspect of the invention, compounds are selected from compounds 8263-16524. In one aspect of the invention, compounds are selected from compounds 16525-20655. In one aspect of the invention, compounds are selected from compounds 20656-24786.
  • compounds 1-918, 2755-3672, 5509-6426, 8263-9180, 11017-11934, 13771-14688, 16525-16983, 17902-18360, 19279-19737, 20656-21114, 22033-2 Select compounds from among 2491, 23410-23868.
  • compounds 919-2754, 3673-5508, 6427-8262, 9181-11016, 11935-13770, 14689-16524, 16984-17901, 18361-19278, 19738-20655, 21115-22032, 224 Select compounds from 92-23409, 23869-24786.
  • the compound represented by general formula (1) is selected from the group of compounds below.
  • the molecular weight of the compound represented by the general formula (1) is preferably 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and even more preferably 900 or less, when intending to use the organic layer containing the compound represented by the general formula (1) by vapor deposition.
  • the lower limit of molecular weight is the molecular weight of the smallest compound represented by general formula (1).
  • the compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. If a coating method is used, it is possible to form a film even with a compound having a relatively large molecular weight.
  • the compound represented by general formula (1) has the advantage of being easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) can be easily applied to the coating method, and can be easily purified to increase its purity.
  • a compound containing a plurality of structures represented by general formula (1) in its molecule as a light-emitting material.
  • a polymerizable group is previously present in the structure represented by the general formula (1), and a polymer obtained by polymerizing the polymerizable group is used as the light-emitting material.
  • a monomer containing a polymerizable functional group at any site of general formula (1) and polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and use the polymer as a light-emitting material.
  • it is conceivable to obtain a dimer or trimer by coupling compounds having a structure represented by general formula (1) and use them as a light-emitting material.
  • polymers having repeating units containing the structure represented by general formula (1) include polymers containing structures 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 linking groups.
  • the number of carbon atoms in the linking group is preferably 0-20, more preferably 1-15, still more preferably 2-10.
  • the linking group preferably has a structure represented by -X 11 -L 11 -.
  • X 11 represents an oxygen atom or a sulfur atom, preferably an oxygen atom.
  • L 11 represents a linking group, preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, 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.
  • the linking groups represented by L 1 and L 2 can be bonded to any part of general formula (1) constituting Q. Two or more linking groups may be linked to one Q to form a crosslinked structure or network structure.
  • a polymer having a repeating unit containing these formulas can be synthesized by introducing a hydroxy group into any site of the general formula (1), reacting it with the following compound as a linker to introduce a polymerizable group, and polymerizing the polymerizable group.
  • a polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having a structure represented by general formula (1), or may be a polymer containing repeating units having other structures.
  • the repeating unit having the structure represented by the general formula (1) contained in the polymer may be of a single type, or may be of two or more types.
  • Examples of repeating units having no structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. Examples thereof include repeating units derived from monomers having ethylenically unsaturated bonds such as ethylene and styrene.
  • the compound represented by general formula (1) is a luminescent material. In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the UV region, the blue region (e.g., about 420 nm to about 500 nm, especially 420 nm to 480 nm) and the green region (e.g., about 490 nm to about 575 nm, about 510 nm) of the visible spectrum when excited by thermal or electronic means. In one aspect of the invention, the maximum emission wavelength is within the range of 530 nm to 575 nm.
  • the maximum emission wavelength is within the range of 480 nm to 530 nm. In one aspect of the invention, the maximum emission wavelength is within the range of 460 nm to 480 nm. In one aspect of the present invention, the maximum emission wavelength is within the range of 440 nm to 460 nm. In one aspect of the present invention, the maximum emission wavelength is within the range of 420 nm to 440 nm. In certain embodiments of the present disclosure, compounds of general formula (1) are capable of emitting light in the ultraviolet spectral region (eg, 280-400 nm) when excited by thermal or electronic means. In an embodiment of the present disclosure, an organic semiconductor device using the compound represented by general formula (1) can be produced.
  • the organic semiconductor element referred to here may be an organic optical element in which light is interposed, or an organic element in which light is not interposed.
  • 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 that causes energy transfer by light within the element.
  • the compound represented by formula (1) can be used to fabricate organic optical devices such as organic electroluminescence devices and solid-state imaging devices (for example, CMOS image sensors).
  • CMOS complementary metal oxide semiconductor
  • Electronic properties of small molecule chemical substance libraries can be calculated using known ab initio quantum chemical calculations.
  • the Hartree-Fock equation (TD-DFT/B3LYP/6-31G*) can be analyzed using time-dependent density functional theory with 6-31G* as a basis and a family of functions known as Becke's three-parameter, Lee-Yang-Parr hybrid functionals, to screen for molecular fragments (parts) with HOMOs above a certain threshold and LUMOs below a certain threshold.
  • HOMO energy eg ionization potential
  • acceptor moieties can be selected when there is a LUMO energy (eg, electron affinity) of ⁇ 0.5 eV or less.
  • the bridging moiety (“B”) prevents overlap between the ⁇ -conjugated systems of the donor and acceptor moieties, for example by being a strongly conjugated system that can tightly constrain the acceptor and donor moieties to specific conformations.
  • compound libraries are screened using one or more of the following properties. 1. Emission around a specific wavelength2. Calculated triplet states above a particular energy level;3. ⁇ EST values below a specified value;4. quantum yield above a specified value;5. HOMO level6.
  • the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K 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 ⁇ EST 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.
  • compounds represented by general formula (1) exhibit a quantum yield of greater than 25%, such as 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 general formula (1) include novel compounds.
  • the compound represented by general formula (1) can be synthesized by combining known reactions.
  • a compound of general formula (1) having a benzofuro-fused carbazol-9-yl group or a benzothieno-fused carbazol-9-yl group can be synthesized by reacting A 1 and benzene having an acceptor group with benzofuro-fused carbazole or benzothieno-fused carbazole.
  • a 1 and benzene having an acceptor group with benzofuro-fused carbazole or benzothieno-fused carbazole.
  • the compounds of general formula (1) are combined, dispersed, covalently bonded, coated, supported, or associated with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) to form a solid film or layer.
  • a compound represented by general formula (1) can be combined with an electroactive material to form a film.
  • compounds of general formula (1) may be combined with hole-transporting polymers.
  • a compound of general formula (1) may be combined with an electron transport polymer.
  • compounds of general formula (1) may be combined with hole-transporting and electron-transporting polymers.
  • compounds of general formula (1) may be combined with copolymers having both hole-transporting and electron-transporting moieties.
  • electrons and/or holes formed in the solid film or layer can interact with the compound represented by general formula (1).
  • a film comprising a compound represented by general formula (1) can be formed in a wet process.
  • a solution of a composition containing a compound of the invention is applied to the surface and a film is formed after removal of the solvent.
  • wet processes include spin coating, slit coating, inkjet (spray), gravure printing, offset printing, and flexographic printing, but are not limited to these.
  • suitable organic solvents are selected and used that are capable of dissolving compositions containing the compounds of the present invention.
  • compounds included in the composition can be introduced with substituents (eg, alkyl groups) that increase their solubility in organic solvents.
  • films comprising compounds of the invention can be formed in a dry process.
  • the dry process can be vacuum deposition, but is not limited to this.
  • the compounds forming the film may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source in which the compounds are mixed.
  • a single vapor deposition source a mixed powder obtained by mixing compound powders may be used, a compression molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating and melting and cooling each compound may be used.
  • a film having a composition ratio corresponding to the composition ratio of a plurality of compounds contained in a vapor deposition source can be formed by performing co-evaporation under conditions in which the vapor deposition rates (weight loss rates) of a plurality of compounds contained in a single vapor deposition source match or substantially match.
  • a film having a desired composition ratio can be easily formed by mixing a plurality of compounds at the same composition ratio as that of the film to be formed and using this as a vapor deposition source.
  • the temperature at which each of the co-deposited compounds has the same weight loss rate can be identified and used as the temperature during co-deposition.
  • the compound represented by formula (1) is useful as a material for organic light-emitting devices. In particular, it is preferably used for organic light-emitting diodes and the like.
  • Organic Light Emitting Diode One aspect of the present invention relates to use of the compound represented by general formula (1) of the present invention as a light-emitting material for an organic light-emitting device.
  • the compound represented by 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 general formula (1) contains delayed fluorescence that emits delayed fluorescence (delayed phosphor).
  • the present invention provides a delayed phosphor having a structure represented by general formula (1).
  • the present invention relates to the use of compounds represented by general formula (1) as delayed phosphors.
  • the present invention provides that the compound represented by general formula (1) can be used as a host material and can be used with one or more light-emitting materials, which can be fluorescent materials, phosphorescent materials or TADF.
  • the compound represented by general formula (1) can also be used as a hole transport material.
  • the compound represented by general formula (1) can be used as an electron transport material.
  • the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1).
  • an organic light-emitting device containing a compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency.
  • the emissive layer comprises a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate.
  • the substrate is a film-forming surface.
  • the orientation of the compounds of general formula (1) with respect to the film-forming surface affects or dictates the direction of propagation of light emitted by the aligning compounds.
  • aligning the propagation direction of light emitted by compounds represented by general formula (1) improves light extraction efficiency from the emissive layer.
  • One aspect of the present invention relates to an organic light emitting device.
  • the organic light emitting device includes an emissive layer.
  • the light-emitting layer contains a compound represented by general formula (1) as a light-emitting material.
  • the organic light emitting device is an organic photoluminescent device (organic PL device).
  • the organic light-emitting device is an organic electroluminescent device (organic EL device).
  • the compound represented by general formula (1) assists (as a so-called assist dopant) the light emission of other light-emitting materials contained in the light-emitting layer.
  • the compound represented by general formula (1) contained in the light-emitting layer is at its lowest excited singlet energy level, and is contained between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting material contained in the light-emitting layer.
  • the organic photoluminescent device includes at least one emissive layer.
  • an organic electroluminescent device includes at least an anode, a cathode, and an organic layer between said anode and said cathode.
  • the organic layers include at least the emissive layer. In some embodiments, the organic layers include only the emissive layer.
  • the organic layers include one or more organic layers in addition to the emissive layer.
  • organic layers include hole transport layers, hole injection layers, electron blocking layers, hole blocking layers, electron injection layers, electron transport layers and exciton blocking layers.
  • the hole transport layer may be a hole injection transport layer with hole injection functionality
  • the electron transport layer may be an electron injection transport layer with electron injection functionality.
  • the emissive layer is the layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons.
  • the layer emits light.
  • only emissive materials are used as emissive layers.
  • the emissive layer includes an emissive material and a host material.
  • the luminescent material is one or more compounds represented by general formula (1).
  • singlet and triplet excitons generated in the light-emitting material are confined within the light-emitting material to improve the light emission efficiency of organic electroluminescent and organic photoluminescent devices.
  • a host material is used in addition to the emissive material in the emissive layer.
  • the host material is an organic compound.
  • the organic compound has excited singlet energies and excited triplet energies, at least one of which is higher than those of the light-emitting materials of the present invention.
  • the singlet and triplet excitons generated in the luminescent material of the invention are confined within the molecules of the luminescent material of the invention. In certain embodiments, singlet and triplet excitons are sufficiently confined to improve light emission efficiency.
  • singlet and triplet excitons are not sufficiently confined even though high light emission efficiency is still obtained, i.e., host materials that can achieve high light emission efficiency can be used in the present invention without particular limitation.
  • light emission occurs in the emissive material in the emissive layer of the device of the invention.
  • emitted light includes both fluorescence and delayed fluorescence.
  • the emitted light includes emitted light from the host material.
  • the emitted light consists of emitted light from the host material.
  • the emitted light includes emitted light from the compound represented by general formula (1) and emitted light from the host material.
  • a TADF molecule and a host material are used.
  • TADF is an assisting dopant and has a lower excited singlet energy than the host material in the emissive layer and a higher excited singlet energy than the emissive material in the emissive layer.
  • the luminescent material preferably fluorescent material
  • examples of such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, Derivatives or the like containing metals (Al, Zn) can be used.
  • skeletons may or may not have a substituent. Also, these exemplary skeletons may be combined. Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by formula (1) are given below.
  • 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 joined together to form an acceptor group, or R 2 and R 3 are joined together to form an acceptor group.
  • R3 and R4 , R4 and R5 , R5 and R6 , R6 and R7 , R7 and R8 , R9 and R10 , R10 and R11 , R11 and R12 , R12 and R13 , R13 and R14 , R14 and R15 , R15 and R16 are They may be combined 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 rest may be O or NR or may not be linked.
  • both ends independently represent a hydrogen atom, a deuterium atom or a substituent.
  • CR 1 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 and CR 16 in general formula (1) are substituted with N. may have been
  • a compound represented by the following general formula (E2) can also be mentioned as a more preferable light-emitting material.
  • 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.
  • R1 and R3 , R3 and R4 , R4 and R5 , R5 and R6 , R6 and R7 , R7 and R8 , R8 and R9 , R9 and R2 , R2 and R10, R10 and R11 , R11 and R12 , R12 and R13 , R13 and R 14 , R 14 and R 15 , R 15 and R 16 , and R 16 and R 1 may combine with each other to form a cyclic structure .
  • CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 and CR 16 in general formula (1) may be substituted with N.
  • Further preferable light-emitting materials include compounds represented by the following general formula (E3).
  • Z 1 and Z 2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring
  • R 1 to R 9 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 may combine with each other to form a cyclic structure.
  • Substitutable carbon atoms among the benzene ring skeleton-constituting carbon atoms constituting the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted with a nitrogen atom.
  • CR 1 , CR 2 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 and CR 9 in general formula (1) may be substituted with N.
  • a compound represented by the following general formula (E4) can also be mentioned as a more preferable luminescent material.
  • Z 1 represents a furan ring condensed with a substituted or unsubstituted benzene ring, a thiophene ring condensed with a substituted or unsubstituted benzene ring , or an N-substituted pyrrole ring condensed 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; or a substituted or unsubstituted heteroaryl group.
  • Z 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 may combine with each other to form a cyclic structure. However, at least one pair of R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 are bonded to each other to form a cyclic structure.
  • Further preferable light-emitting materials include compounds represented by the following general formula (E5).
  • 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.
  • R 1 , R 2 , Z 1 and Z 2 includes a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and 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 , R9 and R1 may be bonded to each other to form a cyclic structure.
  • Substitutable carbon atoms among the benzene ring skeleton-constituting carbon atoms constituting the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted with a nitrogen atom.
  • CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 and CR 9 in general formula (1) may be substituted with N.
  • Further preferable light-emitting materials include compounds represented by the following general formula (E6).
  • one of X 1 and X 2 is a nitrogen atom and the other is a boron atom.
  • R 1 to R 26 , A 1 and A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.
  • X1 is a nitrogen atom
  • R17 and R18 are bonded together to form a single bond to form a pyrrole ring
  • R21 and R22 are bonded to each other to
  • R 1 to R 6 is a substituted or unsubstituted aryl group, or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R Either 5 and R6 are bonded together to form an aromatic or heteroaromatic ring.
  • a compound represented by the following general formula (E7) can also be mentioned as a more preferable luminescent material.
  • R 201 to R 221 each independently represent a hydrogen atom, a deuterium atom or a substituent, preferably a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, or a group in which an alkyl group and an aryl group are bonded.
  • At least one pair of 8 and R 219 , R 219 and R 220 , and R 220 and R 221 are bonded to each other to form a benzofuro structure or a benzothieno structure.
  • R201 and R202 , R202 and R203 , R203 and R204 , R205 and R206 , R206 and R207, R207 and R208, and R214 and R215, R215 and R216, R216 and R 217 , R 218 and R 219 , R 219 and R 220 , R 220 and R 221 are bonded together to form a benzofuro structure or a benzothieno structure.
  • R 203 and R 204 are bonded together to form a benzofuro structure or benzothieno structure, and even more preferably R 203 and R 204 and R 216 and R 217 are bonded together to form a benzofuro structure or benzothieno structure.
  • R 203 and R 204 , R 216 and R 217 are bonded to each other to form a benzofuro structure or a benzothieno structure
  • R 206 and R 219 are a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably an unsubstituted phenyl group).
  • the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 1% or more by weight. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 50% by weight or less. In one embodiment, when a host material is used, the amount of the compound of the present invention as the light-emitting material contained in the light-emitting layer is 20% by weight or less.
  • the amount of the compound of the invention as the light-emitting material contained in the light-emitting layer is 10% by weight or less.
  • the host material of the emissive layer is an organic compound with hole-transporting and electron-transporting functionality.
  • the host material of the emissive layer is an organic compound that prevents the wavelength of emitted light from increasing.
  • the host material of the emissive layer is an organic compound with a high glass transition temperature.
  • the host material is selected from the group consisting of:
  • the emissive layer comprises two or more structurally different TADF molecules.
  • the light-emitting layer can be made to contain three kinds of materials in which the excited singlet energy level is higher in the order of the host material, the first TADF molecule, and the second TADF molecule.
  • the difference ⁇ EST between the lowest excited singlet energy level and the lowest excited triplet energy level at 77K 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, further preferably 0.1 eV or less, even more preferably 0.07 eV or less, It is further preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less.
  • the concentration of the first TADF molecules in the light-emitting layer is higher than the concentration of the second TADF molecules.
  • the concentration of the host material in the light-emitting layer is preferably higher than the concentration of the second TADF molecules.
  • the concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material.
  • the composition within the emissive layer may be 10-70% by weight of the host material, 10-80% by weight of the first TADF molecule, and 0.1-30% by weight of the second TADF molecule. In some embodiments, the composition within the emissive layer may be 20-45% by weight of the host material, 50-75% by weight of the first TADF molecule, and 5-20% by weight of the second TADF molecule.
  • the emissive layer can include three structurally different TADF molecules.
  • the compound of the present invention can be any of a plurality of TADF compounds contained in the emissive layer.
  • the emissive layer can be composed of materials selected from the group consisting of host materials, assisting dopants, and emissive materials. In some embodiments, the emissive layer does not contain metallic elements. In some embodiments, the emissive layer can be composed of a material consisting only of 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 composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms.
  • the light-emitting layer can be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms.
  • the TADF material may be a known delayed fluorescence material.
  • Preferred delayed fluorescence materials include 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 WO20.
  • the organic electroluminescent device of the present invention is held by a substrate, and the substrate is not particularly limited, and any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon, may be used.
  • the anode of the organic electroluminescent device is made from metals, alloys, conductive compounds, or combinations thereof.
  • the metal, alloy or conductive compound has a high work function (4 eV or greater).
  • the metal is Au.
  • the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2 and ZnO. Some embodiments use amorphous materials that can form transparent conductive films, such as IDIXO (In 2 O 3 —ZnO).
  • the anode is a thin film. In some embodiments, the thin film is made by evaporation or sputtering.
  • the film is patterned by photolithographic methods. In some embodiments, if the pattern does not need to be highly precise (eg, about 100 ⁇ m or greater), the pattern may be formed using a mask with a shape suitable for vapor deposition or sputtering onto the electrode material. In some embodiments, wet film forming methods such as printing and coating methods are used when coating materials such as organic conductive compounds can be applied.
  • 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 thickness of the anode is 10-1,000 nm. In some embodiments, the thickness of the anode is 10-200 nm. In some embodiments, the thickness of the anode varies depending on the materials used.
  • the cathode is made of electrode materials such as metals with a low work function (4 eV or less) (referred to as electron-injecting metals), alloys, conductive compounds, or combinations 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 ( Al2O3 ) mixtures, indium, lithium-aluminum mixtures , and rare earth elements.
  • a mixture of an electron-injecting metal and a second metal that is a stable metal with a higher work function than the electron-injecting metal is used.
  • 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 manufactured by depositing or sputtering the electrode material as a thin film. In some embodiments, the cathode has a sheet resistance of no more than several hundred ohms per unit area.
  • the thickness of said cathode is between 10 nm and 5 ⁇ m. In some embodiments, the thickness of the cathode is 50-200 nm. In some embodiments, either one of the anode and cathode of the organic electroluminescent device is transparent or translucent to allow transmission of emitted light. In some embodiments, transparent or translucent electroluminescent elements enhance light radiance. In some embodiments, the cathode is formed of a conductive transparent material as described above for the anode, thereby forming a transparent or translucent cathode. In some embodiments, the device includes an anode and a cathode, both transparent or translucent.
  • the injection layer is the layer between the electrode and the organic layer. In some embodiments, the injection layer reduces drive voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be placed between the anode and the light-emitting layer or hole-transporting layer and between the cathode and the light-emitting layer or electron-transporting layer. In some embodiments, an injection layer is present. In some embodiments, there is no injection layer. 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 out of the light-emitting layer.
  • an electron blocking layer is present between the emissive layer and the hole transport layer to block electrons from passing through the emissive layer to the hole transport layer.
  • a hole blocking layer is between the emissive layer and the electron transport layer and blocks holes from passing through the emissive layer to the electron transport layer.
  • the barrier layer prevents excitons from diffusing out of the emissive layer.
  • the electron blocking layer and the hole blocking layer constitute an exciton blocking layer.
  • the terms "electron blocking layer” or “exciton blocking layer” include layers that have both the functionality of an electron blocking layer and an exciton blocking layer.
  • Hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer blocks holes from reaching the electron transport layer during electron transport. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the emissive layer.
  • the materials used for the hole blocking layer can be the same materials as 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, the electron blocking layer prevents electrons from reaching the hole transport layer during hole transport. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the emissive layer.
  • the materials used for the electron blocking layer may be the same materials as described above for the hole transport layer. Specific examples of preferred compounds that can be used as the electron barrier material are given below.
  • Exciton barrier layer The exciton blocking layer prevents excitons generated through 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 effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, an exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides thereof. In some embodiments, when an exciton blocking layer is present on the anode side, it may be present between and adjacent to the hole-transporting layer and the light-emitting layer.
  • an exciton blocking layer when an exciton blocking layer is present on the cathode side, it may be between and adjacent to the emissive layer and the cathode. In some embodiments, a hole-injection layer, electron-blocking layer, or similar layer is present between the anode and an exciton-blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, electron blocking layer, hole blocking layer or similar layer is present between the cathode and an exciton blocking layer adjacent to the emissive 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 triplet energy, respectively, of the emissive material.
  • the hole-transporting layer comprises a hole-transporting material.
  • the hole transport layer is a single layer.
  • the hole transport layer has multiple layers.
  • the hole transport material has one property of a hole injection or transport property and an electron barrier 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 the hole-transporting material are given below.
  • the electron transport layer includes an electron transport material.
  • the electron transport layer is a single layer.
  • the electron transport layer has multiple layers.
  • the electron-transporting material need only function to transport electrons injected from the cathode to the emissive layer.
  • the electron transport material also functions as a hole blocking material.
  • electron-transporting 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 the electron-transporting material are given below.
  • examples of preferred compounds as materials that can be added to each organic layer are given.
  • it may be added as a stabilizing material.
  • Preferred materials that can be used in organic electroluminescence elements are specifically exemplified, but materials that can be used in the present invention are not limitedly interpreted by the following exemplified compounds. Moreover, even compounds exemplified as materials having specific functions can be used as materials having other functions.
  • the emissive layer is incorporated into the device.
  • devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones and tablets.
  • an electronic device includes an OLED having at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.
  • compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices.
  • the composition may be useful in facilitating charge or energy transfer within a device and/or as a hole transport material.
  • Such devices include, for example, 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
  • O-TFTs organic thin film transistors
  • O-LETs organic light emitting transistors
  • O-SCs organic solar cells
  • organic optical detectors organic photoreceptors
  • O-FQDs organic field-quench devices
  • LOCs light emitting fuel cells
  • O-lasers organic laser diodes
  • an electronic device includes an OLED including at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.
  • the device includes OLEDs of different colors.
  • the device includes an array including combinations of OLEDs.
  • said combination of OLEDs is a combination of three colors (eg RGB).
  • the combination of OLEDs is a combination of colors other than red, green, and blue (eg, orange and yellow-green).
  • said combination of OLEDs is a combination of two, four or more colors.
  • the device a circuit board having a first side with a mounting surface and a second opposite side and defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration, the at least one OLED comprising at least one organic layer comprising an anode, a cathode, and a light-emitting layer between the anode and the cathode; a housing for a circuit board; at least one connector disposed at an end of said housing, said housing and said connector defining a package suitable for attachment to a lighting fixture.
  • the OLED light comprises multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some light emitted in the first direction is polarized and emitted in the second direction. In some embodiments, a reflector is used to polarize light emitted in the first direction.
  • the emissive layers of the invention can be used in screens or displays.
  • the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, evaporation or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in two-sided etching to provide unique aspect ratio pixels.
  • Said screens also called masks
  • the corresponding artwork pattern design allows placement of very steep narrow tie-bars between pixels in the vertical direction as well as large and wide beveled openings in the horizontal direction.
  • the internal patterning of the pixels makes it possible to construct three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged "stripes" or halftone circles in pixel areas protects etching in specific areas until these specific patterns are undercut and removed from the substrate. All pixel areas are then treated with a similar etch rate, but their depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within the pixel, allowing for the localized deep etching necessary to form steep vertical bevels. A preferred material for the evaporation mask is Invar.
  • Invar is a metal alloy that is cold rolled into long thin sheets in steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask.
  • a suitable and low-cost method for forming the open areas in the deposition mask is by wet chemical etching.
  • the screen or display pattern is a matrix of pixels on a substrate.
  • screen or display patterns are fabricated using lithography (eg, photolithography and e-beam lithography).
  • the screen or display pattern is processed using wet chemical etching.
  • the screen or display pattern is fabricated using plasma etching.
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on a mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base material, coating the TFT with a planarizing film, sequentially forming a pixel electrode, a light emitting layer, a counter electrode and an encapsulation layer, and cutting from the mother panel.
  • TFT thin film transistor
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on a mother panel is formed by forming a thin film transistor (TFT) having an active layer and source/drain electrodes on a base material, coating the TFT with a planarizing film, sequentially forming a pixel electrode, a light emitting layer, a counter electrode and an encapsulation layer, and cutting from the mother panel.
  • TFT thin film transistor
  • an organic light emitting diode (OLED) display comprising: forming a barrier layer on the base substrate of the mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interfaces between the cell panels.
  • the barrier layer is an inorganic film, eg, made of SiNx, and the edges of the barrier layer are covered with an organic film, made of polyimide or acrylic.
  • the organic film helps the mother panel to be softly cut into cell panels.
  • a thin film transistor (TFT) layer has an emissive 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, wherein the organic film applied to the interface portion is formed of the same material as that of the planarization film and is formed at the same time as the formation of the planarization film.
  • the light-emitting unit is coupled to the TFT layer by a passivation layer, a planarizing 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 encapsulation layer.
  • each of the organic film and the planarizing film may include 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 comprise attaching a carrier substrate made of a glass material to another surface of a base substrate made of polyimide prior to forming the barrier layer on one 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 placed on the TFT layer to cover the TFT layer.
  • the planarizing film is an organic film formed over a passivation layer.
  • the planarizing film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarizing 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 the remaining portion of the organic film is in contact with the barrier layer surrounding the edge of the barrier layer.
  • the emissive layer comprises a pixel electrode, a counter electrode, and an organic emissive layer disposed between the pixel electrode and the counter electrode.
  • the pixel electrodes are connected to source/drain electrodes of the TFT layer.
  • a suitable voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image.
  • An image forming unit having a TFT layer and a light emitting unit is hereinafter referred to as a display unit.
  • the encapsulation layer that covers the display unit and prevents the penetration of external moisture may be formed into a thin encapsulation structure in which organic films and inorganic films are alternately laminated.
  • the encapsulation layer has a thin film-like encapsulation structure in which multiple thin films are stacked.
  • the organic film applied to the interface portion is spaced apart from each of the plurality of display units.
  • the organic film is formed 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 edges of the barrier layer.
  • the OLED display is flexible and uses a flexible base substrate made of polyimide.
  • the base substrate is formed on a carrier substrate made of glass material, and then the carrier substrate is separated.
  • a barrier layer is formed on the surface of the base substrate opposite the carrier substrate.
  • the barrier layer is patterned according to the size of each cell panel. For example, a base substrate is formed on all surfaces of a mother panel, while barrier layers are 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 groove.
  • the manufacturing method further includes cutting along the interface, wherein grooves are formed in the barrier layer, at least a portion of the organic film is formed with grooves, and the grooves do 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 placed on and cover the TFT layer.
  • the planarizing film eg made of polyimide or acrylic
  • the interface grooves are covered with an organic film, eg made of polyimide or acrylic. This prevents cracking by having the organic film absorb the impact that occurs when each cell panel is cut along the groove at the interface.
  • the grooves at the interfaces between the barrier layers may be coated with an organic film to absorb shocks that might otherwise be transmitted to the barrier layers, thereby softly cutting each cell panel and preventing the barrier layers from cracking.
  • the organic film covering the groove of the interface and the planarizing film are spaced apart from each other.
  • the organic film and the planarizing film are interconnected as a layer, the organic film and the planarizing film are spaced apart from each other such that the organic film is spaced from the display unit because external moisture may enter the display unit through the planarizing film and the remaining portion of the organic film.
  • the display unit is formed by forming a light-emitting unit and an encapsulating layer is placed over the display unit to cover the display unit.
  • the carrier substrate carrying the base substrate is separated from the base substrate.
  • the carrier substrate separates from the base substrate due to the difference in coefficient of thermal expansion between the carrier substrate and the base substrate.
  • the mother panel is cut into cell panels.
  • the mother panel is cut along the interfaces between the cell panels using a cutter.
  • the interface groove along which the mother panel is cut is coated with an organic film so that the organic film absorbs impact during cutting.
  • the barrier layer can be prevented from cracking during cutting. In some embodiments, the method reduces the reject rate of the product and stabilizes its quality.
  • Another embodiment 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 an edge of the barrier layer.
  • Example 1 Production and Evaluation of Thin Film Compound 3 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 3 with a thickness of 100 nm.
  • compound 3 and PYD2Cz were vapor-deposited from different vapor deposition sources on a quartz substrate at a vacuum degree of less than 1 ⁇ 10 ⁇ 3 Pa to form a doped thin film with a thickness of 100 nm with a concentration of compound 3 of 20% by weight.
  • compound 13773 and compound 19281 instead of compound 3, a neat thin film and a doped thin film were formed in the same manner.
  • Doped thin films were formed according to the method described above using comparative compounds 1 to 4 below.
  • DPEPO was used as the host material.
  • Compound 3, Compound 13773, and Compound 19281 represented by general formula (1) had a shorter delayed fluorescence lifetime than Comparative Compounds 1-3.
  • Comparative compound 4 had a delayed fluorescence lifetime equivalent to that of compound 13773, but had a low photoluminescence quantum yield (PLQY) of 26%, and did not exhibit superior emission characteristics as compared to compounds 3, 13773, and 19281.
  • the photoluminescence quantum yield (PLQY) of Compound 3, Compound 13773, and Compound 19281 was higher than that of Comparative Compound 1 and Comparative Compound 2, and it was confirmed that they had excellent light emission properties.
  • Example 2 Fabrication of organic electroluminescence element
  • ITO indium tin oxide
  • HAT-CN was formed to a thickness of 10 nm on ITO
  • NPD was formed thereon to a thickness of 35 nm
  • PTCz was formed thereon to a thickness of 10 nm.
  • PYD2Cz and compound 3 were co-deposited from different vapor deposition sources to form a layer with a thickness of 40 nm, which was used as a light-emitting layer.
  • the concentration of compound 3 in the light-emitting layer was 30% by mass.
  • Liq and SF3-TRZ were co-evaporated from different deposition sources to form a layer with a thickness of 20 nm.
  • the concentrations of Liq and SF3-TRZ in this layer were 30% and 70% by weight, respectively.
  • Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby forming an organic electroluminescence device.
  • the compound represented by general formula (1) has good luminescence performance. Therefore, by using the compound represented by the general formula (1), an excellent organic light-emitting device can be provided. Therefore, the present invention has high industrial applicability.

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Abstract

Un composé de formule générale possède d'excellentes propriétés électroluminescentes. A représente un groupe 2- ou 4-cyanophényle ou un groupe cyanopyridyle ; l'un de R2 et R3 représente un groupe accepteur ; l'autre R2 et R3 et au moins un R1, R4 et R5 représentent un groupe benzofluoro- ou benzothiéno-carbazol-9-yl à anneau fusionné ; et les autres R1 à R5 représentent un atome d'hydrogène, un atome de deutérium, un groupe aryle ou un groupe donneur.
PCT/JP2023/001844 2022-01-24 2023-01-23 Composé, matériau électroluminescent et élément électroluminescent WO2023140374A1 (fr)

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