Compound, light-emitting material, and light-emitting element

Abstract

The invention relates to a compound, a light-emitting material and a light-emitting element. A compound represented by the following general formula is used as a light-emitting material. R is a hydrogen atom, a deuterium atom, an aryl group or a heteroaryl group bonded via a carbon atom, Ar is an aryl group or a heteroaryl group bonded via a carbon atom, D1 and D2 are donor groups and at least one is a heterocyclic fused carbazole-9-group. # imgabs0 #

Description

[0001] This application is a divisional application. The international application number of the original application is PCT / JP2021 / 019431, the Chinese national application number is 202180036659.0, the application date is May 21, 2021, and the name of the invention is “Compounds, luminescent materials and luminescent elements”. Technical Field

[0002] The present invention relates to a compound useful as a light-emitting material and a light-emitting device using the same. Background Art

[0003] Research is actively being conducted to improve the luminous efficiency of light-emitting elements such as organic electroluminescent elements (organic EL elements). In particular, much effort has been put into improving the luminous efficiency by newly developing and combining electron transport materials, hole transport materials, luminescent materials, etc. that constitute organic electroluminescent elements. Among them, research on organic electroluminescent elements using delayed fluorescence materials has also been seen.

[0004] Delayed fluorescence materials are materials that emit fluorescence when returning to the ground state after reverse intersystem crossing from the excited triplet state to the excited singlet state in the excited state. Because the fluorescence generated by this pathway is observed later than the fluorescence from the excited singlet state directly generated from the ground state (normal fluorescence), it is called delayed fluorescence. Here, for example, when a luminescent compound is excited by the injection of a carrier, because the probability of the generation of the excited singlet state and the excited triplet state is statistically 25%:75%, if only the fluorescence from the directly generated excited singlet state is used, there is a limit to the improvement of the luminous efficiency. On the other hand, because the delayed fluorescence material can use the excited triplet state for fluorescence luminescence through the pathway via reverse intersystem crossing in addition to the excited singlet state, a high luminous efficiency can be obtained compared to normal fluorescent materials.

[0005] After this principle was clarified, various delayed fluorescence materials were discovered through various studies. However, not all materials that emit delayed fluorescence can be immediately useful as luminescent materials. Among delayed fluorescence materials, there are materials that are relatively difficult to produce reverse intersystem crossing, and there are also materials with long delayed fluorescence lifetimes. In addition, there are materials that accumulate excitons in high current density areas and reduce luminous efficiency or cause rapid degradation if driven continuously for a long time. Therefore, the actual situation is that there is room for improvement in the practicality of many delayed fluorescence materials. Therefore, it has been pointed out that there are also problems in benzonitrile compounds known as delayed fluorescence materials. For example, although the compound with the following structure is a material that emits delayed fluorescence (reference patent document 1), there are problems such as long delayed fluorescence lifetime and insufficient component durability.

[0006] [Chemical formula 1]

[0007]

[0008] Previous technical literature

[0009] Patent Literature

[0010] Patent document 1: WO2014 / 208698A1 Summary of the invention

[0011] Technical issues to be solved by the invention

[0012] Although such problems have been pointed out, it is difficult to say that the relationship between the chemical structure and properties of delayed fluorescent materials has been fully elucidated. Therefore, it is difficult to generalize the chemical structure of compounds useful as light-emitting materials at present, and there are many unclear points.

[0013] Under such circumstances, the present inventors have repeatedly conducted research with the purpose of providing a compound more useful as a light-emitting material for a light-emitting element. Furthermore, the present inventors have conducted intensive research with the purpose of deriving a general formula of a compound more useful as a light-emitting material and generalizing it.

[0014] Means for solving technical problems

[0015] As a result of intensive studies to achieve the above object, the present inventors have found that compounds having a structure satisfying specific conditions among isophthalonitrile derivatives are useful as light-emitting materials. The present invention has been proposed based on this finding and specifically has the following structure.

[0016] [1] A compound represented by the following general formula (1).

[0017] [Chemical formula 2]

[0018] General formula (1)

[0019]

[0020] [In the general formula (1),

[0021] R is a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded via a carbon atom,

[0022] Ar is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded via a carbon atom,

[0023] D 1 and D 2 Each independently represents a donor group, but at least one of them is a heterocyclic fused carbazole-9-yl group (the heterocyclic ring and the carbazole may be substituted).]

[0024] [2] The compound according to [1], wherein the compound is represented by the following general formula (2).

[0025] [Chemical formula 3]

[0026] General formula (2)

[0027]

[0028] [3] The compound according to [1], wherein the compound is represented by the following general formula (3).

[0029] [Chemical formula 4]

[0030]

[0031] [4] The compound according to any one of [1] to [3], wherein D 1 and D 2 same.

[0032] [5] The compound according to any one of [1] to [3], wherein D 1 and D 2 different.

[0033] [6] The compound according to any one of [1] to [5], wherein the heterocyclic ring fused to the carbazole-9-yl group of the heterocyclic-fused carbazole-9-yl group is a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring or a substituted or unsubstituted pyrrole ring, and another ring may be further fused to the furan ring, the thiophene ring and the pyrrole ring.

[0034] [7] The compound according to any one of [1] to [6], wherein the heterocyclic-fused carbazole-9-yl group has any one of the following structures.

[0035] [Chemical formula 5]

[0036]

[0037] [In each of the above structures, hydrogen atoms may be substituted, but no heterocyclic ring may be further fused.]

[0038] [8] The compound according to any one of [1] to [6], wherein the heterocyclic-fused carbazole-9-yl group has any one of the following structures.

[0039] General formula (3)

[0040] [Chemical formula 6]

[0041]

[0042] [In each of the above structures, hydrogen atoms may be substituted, but no heterocyclic ring may be further fused.]

[0043] [9] The compound according to any one of [1] to [6], wherein the heterocyclic-fused carbazole-9-yl group has any one of the following structures.

[0044] [Chemical formula 7]

[0045]

[0046] [In each of the above structures, a hydrogen atom may be substituted, but no heterocyclic ring is further fused. R' represents a hydrogen atom, a deuterium atom or a substituent.]

[0047]

[10] A compound according to any one of [1] to [9], wherein the carbazole-9-yl group of the heterocyclic-fused carbazole-9-yl group is fused with two heterocyclic rings selected from the group consisting of a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring and a substituted or unsubstituted pyrrole ring (the furan ring, the thiophene ring and the pyrrole ring may be further fused with other rings).

[0048]

[11] The compound according to any one of [1] to

[10] , wherein the heterocyclic-fused carbazole-9-yl group has a structure in which a heterocyclic ring is fused at the 1 and 2 positions of the carbazole ring.

[0049]

[12] The compound according to any one of [1] to

[10] , wherein the heterocyclic-fused carbazole-9-yl group has a structure in which a heterocyclic ring is fused at the 2- and 3-positions of the carbazole ring.

[0050]

[13] The compound according to any one of [1] to

[10] , wherein the heterocyclic-fused carbazole-9-yl group has a structure in which a heterocyclic ring is fused at the 3- and 4-positions of the carbazole ring.

[0051]

[14] The compound according to any one of [1] to

[13] , wherein R and Ar are different.

[0052]

[15] The compound according to any one of [1] to

[13] , wherein R is a hydrogen atom or a deuterium atom.

[0053]

[16] The compound according to any one of [1] to

[15] , wherein Ar is a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group.

[0054]

[17] The compound according to any one of [1] to

[16] , which is composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

[0055]

[18] A light-emitting material comprising the compound described in any one of [1] to

[17] .

[0056]

[19] A light-emitting element comprising the compound according to any one of [1] to

[17] .

[0057]

[20] The light-emitting element according to

[19] , wherein the light-emitting element has a light-emitting layer, and the light-emitting layer contains the compound and a host material.

[0058]

[21] The light-emitting element according to

[20] , wherein the light-emitting element has a light-emitting layer, the light-emitting layer contains the compound and a light-emitting material, and emits light mainly from the light-emitting material.

[0059] Effects of the Invention

[0060] The compound of the present invention is useful as a light-emitting material. Furthermore, the compound of the present invention includes a compound having a short delayed fluorescence lifetime. In addition, an organic light-emitting device using the compound of the present invention has high device durability and is useful. BRIEF DESCRIPTION OF THE DRAWINGS

[0061] Figure 1 It is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescent element. DETAILED DESCRIPTION

[0062] The content of the present invention is described in detail below. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In addition, in this article, the numerical range represented by "to" means a range that includes the numerical values ​​described before and after "to" as the lower limit and upper limit. In addition, part or all of the hydrogen atoms present in the molecules of the compounds used in the present invention can be replaced by deuterium atoms ( 2 H, deuterium D). In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the representation of atoms that form carbon atom bonds with the ring skeleton of the benzene ring is omitted, H forms carbon atom bonds with the ring skeleton at the omitted position. In the chemical structural formulas herein, deuterium atoms are represented by D.

[0063] [Compound represented by general formula (1)]

[0064] [Chemical formula 8]

[0065] General formula (1)

[0066]

[0067] D in the general formula (1) 1 and D2 At least one of represents a heterocyclic-fused carbazole-9-yl group. The heterocyclic ring and the carbazole ring constituting the heterocyclic-fused carbazole-9-yl group may be substituted or unsubstituted.

[0068] The number of heterocyclic rings fused to the carbazole-9-yl group is one or more, preferably one or two, and more preferably one. When two or more heterocyclic rings are fused, the heterocyclic rings may be the same or different. In one aspect of the present invention, the heterocyclic rings are fused to the 1 and 2 positions of the carbazole-9-yl group. In another aspect of the present invention, the heterocyclic rings are fused to the 2 and 3 positions of the carbazole-9-yl group. In yet another aspect of the present invention, the heterocyclic rings are fused to the 3 and 4 positions of the carbazole-9-yl group.

[0069] The heterocyclic ring fused to the carbazole-9-yl group is a ring containing heteroatoms. The heteroatoms are preferably selected from oxygen atoms, sulfur atoms, nitrogen atoms and silicon atoms, and more preferably selected from oxygen atoms, sulfur atoms and nitrogen atoms. In a preferred aspect, the heteroatom is an oxygen atom. In another preferred aspect, the heteroatom is a sulfur atom. In another preferred aspect, the heteroatom is a nitrogen atom. The number of heteroatoms contained in the ring skeleton constituting atoms of the heterocycle is 1 or more, preferably 1 to 3, and more preferably 1 or 2. In a preferred aspect, the number of heteroatoms is one. When the number of heteroatoms is two or more, it is preferably the same heteroatom, but it can also be composed of different types of heteroatoms. For example, two or more heteroatoms can all be nitrogen atoms. The ring skeleton constituting atoms other than heteroatoms are carbon atoms.

[0070] The number of atoms constituting the ring skeleton of the heterocyclic ring fused with the carbazole-9-yl is preferably 4 to 8, more preferably 5 to 7, and further preferably 5 or 6. In a preferred aspect, the number of atoms constituting the ring skeleton of the heterocyclic ring is 5. Preferably, there are two or more conjugated double bonds in the heterocyclic ring, and the conjugated system of the carbazole ring is preferably expanded by fusion of the heterocyclic ring (preferably with aromaticity). Preferred examples of the heterocyclic ring may include a furan ring, a thiophene ring, and a pyrrole ring.

[0071] Other rings may be further fused to the heterocyclic ring fused to the carbazole-9-base. Furthermore, the fused ring may be a monocyclic ring or a fused ring. The fused ring may include an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring. The aromatic hydrocarbon ring may include a benzene ring. The aromatic heterocyclic ring may include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a pyrrole ring, a pyrazole ring, and an imidazole ring. The aliphatic hydrocarbon ring may include a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. The aliphatic heterocyclic ring may include a piperidine ring, a pyrrolidine ring, and an imidazoline ring. Specific examples of fused rings may include a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyran ring, a tetracene ring, an indole ring, an isoindole ring, a benzimidazole ring, a benzotriazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, and a cinnoline ring.

[0072] In a preferred aspect of the present invention, the heterocyclic fused carbazole-9-yl is a benzofuran fused carbazole-9-yl, a benzothiophene fused carbazole-9-yl, an indole fused carbazole-9-yl or a silane indene fused carbazole-9-yl. In a more preferred aspect of the present invention, the heterocyclic fused carbazole-9-yl is a benzofuran fused carbazole-9-yl, a benzothiophene fused carbazole-9-yl or an indole fused carbazole-9-yl.

[0073] In the present invention, the benzofuran-fused carbazole-9-yl group may be a substituted or unsubstituted benzofuran[2,3-a]carbazole-9-yl group. Also, a substituted or unsubstituted benzofuran[3,2-a]carbazole-9-yl group may be used. Also, a substituted or unsubstituted benzofuran[2,3-b]carbazole-9-yl group may be used. Also, a substituted or unsubstituted benzofuran[3,2-b]carbazole-9-yl group may be used. Also, a substituted or unsubstituted benzofuran[2,3-c]carbazole-9-yl group may be used. Also, a substituted or unsubstituted benzofuran[3,2-c]carbazole-9-yl group may be used.

[0074] A preferred benzofuran-fused carbazole-9-yl group is a carbazole-9-yl group having only one benzofuran ring fused at the 2 and 3 positions and no heterocyclic ring fused at other positions (the benzene ring may be fused). Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, a structure in which a part of the hydrogen atoms in the following structure are substituted by deuterium atoms or a structure in which all the hydrogen atoms in the following structure are substituted by deuterium atoms may be preferably exemplified. An unsubstituted structure may be preferably used.

[0075] [Chemical formula 9]

[0076]

[0077] Also preferably, a carbazole-9-yl group (the benzene ring may be fused) having two benzofuran rings fused at the 2 and 3 positions and no heterocyclic ring fused at other positions is used. Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, a structure in which a part of the hydrogen atoms in the following structure are substituted by deuterium atoms or a structure in which all the hydrogen atoms in the following structure are substituted by deuterium atoms can be preferably exemplified. An unsubstituted structure can be preferably used.

[0078] [Chemical formula 10]

[0079]

[0080] In the present invention, the benzothiophene-fused carbazole-9-yl group may be a substituted or unsubstituted benzothieno[2,3-a]carbazole-9-yl group. Also, a substituted or unsubstituted benzothieno[3,2-a]carbazole-9-yl group may be used. Also, a substituted or unsubstituted benzothieno[2,3-b]carbazole-9-yl group may be used. Also, a substituted or unsubstituted benzothieno[3,2-b]carbazole-9-yl group may be used. Also, a substituted or unsubstituted benzothieno[2,3-c]carbazole-9-yl group may be used. Also, a substituted or unsubstituted benzothieno[3,2-c]carbazole-9-yl group may be used.

[0081] A preferred benzothiophene-fused carbazole-9-yl group is a carbazole-9-yl group having only one benzothiophene ring fused at the 2 and 3 positions and no heterocyclic ring fused at other positions (the benzene ring may be fused). Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, a structure in which a part of the hydrogen atoms in the following structure are substituted by deuterium atoms or a structure in which all the hydrogen atoms in the following structure are substituted by deuterium atoms can be preferably exemplified. An unsubstituted structure can be preferably used.

[0082] [Chemical formula 11]

[0083]

[0084] Also preferably, a carbazole-9-yl group (the benzene ring may be fused) having two benzothiophene rings fused at the 2 and 3 positions and no heterocyclic ring fused at other positions is used. Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, a structure in which a part of the hydrogen atoms in the following structure are substituted by deuterium atoms or a structure in which all the hydrogen atoms in the following structure are substituted by deuterium atoms can be preferably exemplified. An unsubstituted structure can be preferably used.

[0085] [Chemical formula 12]

[0086]

[0087] In the present invention, the indole-fused carbazole-9-yl group may be a substituted or unsubstituted indolo[2,3-a]carbazole-9-yl group. In addition, a substituted or unsubstituted indolo[3,2-a]carbazole-9-yl group may be used. In addition, a substituted or unsubstituted indolo[2,3-b]carbazole-9-yl group may be used. In addition, a substituted or unsubstituted indolo[3,2-b]carbazole-9-yl group may be used. In addition, a substituted or unsubstituted indolo[2,3-c]carbazole-9-yl group may be used. In addition, a substituted or unsubstituted indolo[3,2-c]carbazole-9-yl group may be used.

[0088] The preferred indole-fused carbazole-9-yl group is a carbazole-9-yl group having only one indole ring fused at the 2 and 3 positions and no heterocyclic ring fused at other positions (the benzene ring may be fused). Specifically, it is a group having any of the following structures, wherein R' in the following structure represents a hydrogen atom, a deuterium atom or a substituent (preferably R' is a substituent). R' is preferably a substituted or unsubstituted aryl group. The hydrogen atoms in the following structure may be substituted. For example, a structure in which a part of the hydrogen atoms in the following structure are substituted by deuterium atoms or a structure in which all the hydrogen atoms in the following structure are substituted by deuterium atoms may be preferably exemplified. An unsubstituted structure may be preferably used.

[0089] [Chemical formula 13]

[0090]

[0091] The heterocyclic ring and carbazole ring constituting the heterocyclic fused carbazole-9-base can be substituted respectively. When substituted, it can be substituted by a deuterium atom or by a substituent other than this. The substituent described herein can include an alkyl, alkenyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, cyano. These substituents can be further substituted by another substituent. For example, it can include aspects substituted by a deuterium atom, an alkyl, an aryl, an alkoxy, and an alkylthio.

[0092] The "alkyl" described herein can be any one of a straight chain, a branched chain, or a cyclic chain. Furthermore, two or more of the straight chain part, the cyclic part, and the branched chain part can be mixed. The number of carbon atoms of the alkyl group can be set to, for example, more than 1, more than 2, or more than 4. Furthermore, the number of carbon atoms can be set to less than 30, less than 20, less than 10, less than 6, or less than 4. Specific examples of alkyl groups can 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-decyl, isododecyl, cyclopentyl, cyclohexyl, and cycloheptyl. The alkyl group as a substituent can be further substituted by a deuterium atom, an aryl, an alkoxy group, an aryloxy group, or a halogen atom.

[0093] "Alkenyl" can be any one of straight chain, branched chain, and cyclic. Furthermore, two or more of the straight chain part, cyclic part, and branched chain part can be mixed. The number of carbon atoms of the alkenyl group can be set to, for example, more than 2 or more than 4. Furthermore, the number of carbon atoms can be set to less than 30, less than 20, less than 10, less than 6, or less than 4. Specific examples of alkenyl groups can include vinyl, n-propenyl, isopropenyl, n-butenyl, isobutenyl, n-pentenyl, isopentenyl, n-hexenyl, isohexenyl, and 2-ethylhexenyl. The alkenyl group as a substituent can be further substituted.

[0094] "Aryl" and "heteroaryl" may be a single ring or a condensed ring formed by condensing two or more rings. When it is a condensed ring, the number of condensed rings is preferably 2 to 6, for example, it can be selected from 2 to 4. Specific examples of rings may include a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a quinoline ring, a pyrazine ring, a quinoxaline ring, and a naphthyridine ring. Specific examples of arylene or heteroarylene groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 2-pyridyl, 3-pyridyl, and 4-pyridyl.

[0095] Regarding the alkyl part of "alkoxy" and "alkylthio", the description and specific examples of the alkyl group described above can be referred to. Regarding the aryl part of "aryloxy" and "arylthio", the description and specific examples of the aryl group described above can be referred to. Regarding the heteroaryl part of "heteroaryloxy" and "heteroarylthio", the description and specific examples of the heteroaryl group described above can be referred to.

[0096] The number of atoms of the heterocyclic fused carbazole-9-yl group excluding hydrogen atoms and deuterium atoms is preferably 16 or more, more preferably 20 or more, and can be, for example, 16 or more. Also, the number is preferably 80 or less, more preferably 50 or less, and even more preferably 30 or less.

[0097] In the general formula (1), the heterocyclic fused carbazole-9-yl group may be only D 1 , or just D 2 In a preferred aspect of the present invention, D 1 and D 2 All of them are heterocyclic fused carbazole-9-yl. 1 and D 2 The structures may be the same or different heterocyclic ring-condensed carbazole-9-yl groups.

[0098] When D 1 and D 2 When only one of them is a heterocyclic fused carbazole-9-yl group, the other is a donor group other than the heterocyclic fused carbazole-9-yl group (hereinafter referred to as "other donor group"). The other donor group described herein is a group with a negative Hammett's σp value. Here, "Hammett's σp value" is a value proposed by L.P. Hammett, which is a value that quantifies the effect of the substituent on the reaction rate or equilibrium of the para-substituted benzene derivative. Specifically, it is the following formula established between the substituent in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant:

[0099] log(k / k 0 )=ρσp

[0100] or

[0101] log(K / K 0 )=ρσp

[0102] In the above formula, k represents the rate constant of the benzene derivative without substituents, k 0 represents the rate constant of the benzene derivative substituted with a substituent, K represents the equilibrium constant of the benzene derivative without a substituent, and K 0 represents the equilibrium constant of the benzene derivative substituted by the substituent, and ρ represents the reaction constant determined by the type and conditions of the reaction. Regarding the description of the "Hammett's σp value" and the number of each substituent in the present invention, reference can be made to the description of the σp value of Hansch, C. et.al., Chem. Rev., 91, 165-195 (1991). There is a tendency that a group with a negative Hammett's σp value shows electron donating property (donor property), and a group with a positive Hammett's σp value shows electron withdrawing property (acceptor property).

[0103] Other donor groups in the present invention are preferably groups containing substituted amino groups. The substituent bonded to the nitrogen atom of the 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 donor group in the present invention may be a group bonded to the nitrogen atom of the substituted amino group, or a group bonded to a group bonded to a substituted amino group. The group bonded to the substituted amino group is preferably a π-conjugated group. More preferably, it is a group bonded to the nitrogen atom of the substituted amino group. With regard to the alkyl, alkenyl, aryl and heteroaryl groups as substituents described herein, reference can be made to the above corresponding descriptions of the substituents of the aromatic hydrocarbon ring group and the aromatic heterocyclic group.

[0104] As other donor groups in the present invention, a particularly preferred group is a substituted or unsubstituted carbazole-9-yl. A benzene ring or a heterocyclic ring (wherein, except a benzofuran ring, a benzothiophene ring, an indole ring, an indene ring, and a silane indene ring) may be further fused to the carbazole-9-yl. The substituents of the carbazole-9-yl may include alkyl, alkenyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, substituted amino, and preferred substituents may include alkyl, aryl, substituted amino. For the description of the substituted amino, reference may be made to the description of the previous paragraph. Furthermore, the substituted amino described herein includes a substituted or unsubstituted carbazole-3-yl and a substituted or unsubstituted carbazole-9-yl.

[0105] The number of atoms of the other donor groups in the present invention other than hydrogen atoms and deuterium atoms is preferably 8 or more, more preferably 12 or more, for example, 16 or more, and preferably 80 or less, more preferably 60 or less, and further preferably 40 or less.

[0106] The following is the D of the general formula (1): 1 and D 2 Specific examples of donor groups that can be used. D13 to D78, D84 to D119, D150 to D161, D168 to D209, D215 to D268, D270 to D324 are specific examples of heterocyclic condensed carbazole-9-yl groups, and D1 to D12, D79 to 83, D120 to 149, D162 to D167, D210 to D214, D269 are specific examples of other donor groups. In the following structural formulas, Ph represents a phenyl group, and * represents a bonding position.

[0107] [Chemical formula 14-1]

[0108]

[0109] [Chemical formula 14-2]

[0110]

[0111] [Chemical formula 14-3]

[0112]

[0113] [Chemical formula 14-4]

[0114]

[0115] [Chemical formula 14-5]

[0116]

[0117] [Chemical formula 14-6]

[0118]

[0119] [Chemical formula 14-7]

[0120]

[0121] [Chemical formula 14-8]

[0122]

[0123] [Chemical formula 14-9]

[0124]

[0125] [Chemical formula 14-10]

[0126]

[0127] [Chemical formula 14-11]

[0128]

[0129] [Chemical formula 14-12]

[0130]

[0131] [Chemical formula 14-13]

[0132]

[0133] [Chemical formula 14-14]

[0134]

[0135] R in the general formula (1) is a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded via a carbon atom. In a preferred aspect of the present invention, R is a hydrogen atom or a deuterium atom. Among them, the aspect in which R is a substituted or unsubstituted aryl group and the aspect in which R is a substituted or unsubstituted heteroaryl group bonded via a carbon atom can also be adopted. When R is an aryl group, it is preferably a substituted aryl group. And, when R is a heteroaryl group, it is preferably a substituted heteroaryl group.

[0136] Ar in the general formula (1) is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded via a carbon atom. In a preferred aspect of the present invention, Ar is a substituted or unsubstituted aryl group. Among them, the aspect in which Ar is a substituted or unsubstituted heteroaryl group can also be adopted.

[0137] The description and preferred range of the aryl and heteroaryl groups that can be used for R and Ar can refer to the description of the aryl and heteroaryl groups in the substituents of the heterocyclic fused carbazole-9-base. Wherein, the heteroaryl group is a heteroaryl group bonded to a carbon atom. The substituents of the aryl group and the substituents of the heteroaryl group can include alkyl, alkenyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, cyano. These substituents can be further substituted by another substituent. The preferred substituent group can include alkyl, aryl, alkoxy, alkylthio, cyano.

[0138] In a preferred aspect of the present invention, R is a hydrogen atom or a deuterium atom, and Ar is a substituted or unsubstituted phenyl group (on the phenyl group, one or more rings selected from a benzene ring, a pyridine ring, a furan ring, a thiophene ring, and a pyrrole ring may be fused). In another preferred aspect of the present invention, R is a hydrogen atom or a deuterium atom, and Ar is a substituted or unsubstituted pyridyl group (on the pyridyl group, one or more rings selected from a benzene ring, a pyridine ring, a furan ring, a thiophene ring, and a pyrrole ring may be fused). In another preferred aspect of the present invention, R is a hydrogen atom or a deuterium atom, and Ar is a substituted phenyl group (on the phenyl group, one or more groups selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted pyridyl group are substituted). In another preferred aspect of the present invention, R is a hydrogen atom or a deuterium atom, and Ar is a substituted pyridyl group (on the pyridyl group, one or more groups selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted pyridyl group are substituted).

[0139] Specific examples of substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups bonded via a carbon atom that can be used for R and Ar in the general formula (1) are shown below. In the following structural formulae, * indicates a bonding position.

[0140] [Chemical formula 15-1]

[0141]

[0142] [Chemical formula 15-2]

[0143]

[0144] [Chemical formula 15-3]

[0145]

[0146] The compound represented by the general formula (1) may be a compound consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms. In a preferred aspect of the present invention, the compound represented by the general formula (1) may be a compound consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms. In addition, the compound represented by the general formula (1) may be a compound consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and sulfur atoms. In addition, the compound represented by the general formula (1) may be a compound that does not contain hydrogen atoms but contains deuterium atoms. For example, the compound represented by the general formula (1) may be a compound consisting only of atoms selected from the group consisting of carbon atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

[0147] In one aspect of the present invention, the compound represented by the general formula (1) has a symmetrical structure.

[0148] In a preferred aspect of the present invention, the compound represented by the general formula (1) has a structure represented by the following general formula (2).

[0149] [Chemical formula 16]

[0150] General formula (2)

[0151]

[0152] In a preferred aspect of the present invention, the compound represented by the general formula (1) has a structure represented by the following general formula (3).

[0153] [Chemical formula 17]

[0154] General formula (3)

[0155]

[0156] Regarding R, Ar, and D in the general formula (2) and the general formula (3): 1 and D 2 For the definition and explanation of , reference can be made to the corresponding description of general formula (1).

[0157] Specific examples of the compounds represented by the general formula (1) are shown below. 1 ~R 4 R in the general formula (1) corresponds to R in the following general formula 1 , D of general formula (1) 1 Equivalent to R in the following general formula 2 In addition, when rotational isomers exist in the following compounds, both the mixture of rotational isomers and the separated individual rotational isomers are disclosed herein.

[0158] [Chemical formula 18]

[0159]

[0160] [Table 1-1]

[0161]

[0162] [Table 1-2]

[0163]

[0164] [Table 1-3]

[0165]

[0166] [Table 1-4]

[0167]

[0168] [Table 1-5]

[0169]

[0170] [Table 1-6]

[0171]

[0172] [Table 1-7]

[0173]

[0174] [Table 1-8]

[0175]

[0176] [Table 1-9]

[0177]

[0178] [Table 1-10]

[0179]

[0180] [Table 1-11]

[0181]

[0182] [Table 1-12]

[0183]

[0184] [Table 1-13]

[0185]

[0186] [Table 1-14]

[0187]

[0188] [Table 1-15]

[0189]

[0190] [Table 1-16]

[0191]

[0192] [Table 1-17]

[0193]

[0194] [Table 1-18]

[0195]

[0196] [Table 1-19]

[0197]

[0198] [Table 1-20]

[0199]

[0200] [Table 1-21]

[0201]

[0202] [Table 1-22]

[0203]

[0204] [Table 1-23]

[0205]

[0206] [Table 1-24]

[0207]

[0208] [Table 1-25]

[0209]

[0210] [Table 1-26]

[0211]

[0212] [Table 1-27]

[0213]

[0214] R in compounds 1 to 6300 1 Compounds wherein H is replaced by D are disclosed herein in order as Compounds 6301 to 12600. 1 , R 4 Replace with R 4 , R 1 Compounds of the invention are disclosed herein as compounds 12601 to 18900. 2 Compounds wherein H is replaced by D are disclosed herein in order as compounds 18901 to 25200. 1 , R 2 , R 3 , R4 Set to R in sequence 3 , R 1 , R 4 , R 2 Compounds of the invention are disclosed herein as compounds 25201 to 31500. 3 Compounds wherein H is replaced by D are disclosed herein in order as compounds 31501 to 37800. 1 , R 2 , R 3 , R 4 Set to R in sequence 4 , R 1 , R 2 , R 3 Compounds of the invention are disclosed herein as compounds 37801 to 44100. 4 Compounds wherein H is replaced by D are disclosed herein in order as compounds 44101 to 50400. 1 , R 3 , R 4 Replace with R 3 , R 4 , R 1 Compounds of the invention are disclosed herein as compounds 50401 to 56700. 3 Compounds wherein H is replaced by D are disclosed herein in order as compounds 56701 to 63000. 3 , R 4 Replace with R 4 , R 3 Compounds of the invention are disclosed herein as compounds 63001 to 69300. 1 Compounds wherein H is replaced by D are disclosed herein in sequence as compounds 69301 to 75600. Each structure of the above compounds 901 to 75600 is individually determined and described herein as a specific compound.

[0215] 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 further preferably 900 or less when an organic layer containing the compound represented by the general formula (1) is used, for example, by vapor deposition. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1). It is preferably 624 or more.

[0216] The compound represented by the general formula (1) can be formed into a film by a coating method regardless of its molecular weight. If the coating method is used, even a compound with a relatively large molecular weight can be formed into a film. The compound represented by the general formula (1) has the advantage of being easily soluble in an organic solvent among cyanobenzene compounds. Therefore, the compound represented by the general formula (1) is easily applicable to the coating method and is easily purified to improve the purity.

[0217] It is also conceivable that the present invention can be applied to using a compound containing a plurality of structures represented by the general formula (1) in the molecule as a light-emitting material.

[0218] For example, it is conceivable to use a polymer obtained by pre-existing a polymerizable group in the structure represented by the general formula (1) and polymerizing the polymerizable group as a light-emitting material. 1 , D 2 A monomer containing a polymerizable functional group in any one of the general formula (1) is polymerized alone or copolymerized with other monomers to obtain a polymer having a repeating unit, and the polymer is used as a light-emitting material. Alternatively, it is also conceivable to obtain a dimer or trimer by coupling compounds having a structure represented by the general formula (1) with each other, and use it as a light-emitting material.

[0219] Examples of the polymer having a repeating unit including a structure represented by the general formula (1) may include a polymer including a structure represented by the following general formula (4) or (5).

[0220] [Chemical formula 19]

[0221]

[0222] In the general formula (4) or (5), Q represents a group including a structure represented by the general formula (1), and L 1 and L 2 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 -X 11 -L 11 - a connecting group of a structure represented by. Here, X 11 represents an oxygen atom or a sulfur atom, preferably an oxygen atom. 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.

[0223] In the general formula (4) or (5), R 101 , R 102 , R103 and R 104 Each independently represents a substituent. Preferably, it is 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 further preferably an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms.

[0224] L 1 and L 2 The connecting group represented by can be connected with Ar, D 1 , D 2 Two or more linking groups may be linked to one Q to form a cross-linked structure or a network structure.

[0225] Specific structural examples of the repeating unit may include structures represented by the following formulae (6) to (9).

[0226] [Chemical formula 20]

[0227]

[0228] The polymer having repeating units of the formulae (6) to (9) can be synthesized by preliminarily isolating Ar, D 1 , D 2 A hydroxyl group is introduced into any one of the following compounds, which is used as a linking group to react with the following compound to introduce a polymerizable group, and the polymerizable group is polymerized.

[0229] [Chemical formula 21]

[0230]

[0231] The polymer containing the structure represented by the general formula (1) in the molecule may be a polymer consisting only of repeating units having the structure represented by the general formula (1), or may be a polymer containing repeating units having structures other than the above. Furthermore, the repeating units having the structure represented by the general formula (1) contained in the polymer may be a single type or two or more types. The repeating units not having the structure represented by the general formula (1) may include repeating units derived from monomers commonly used for copolymerization. For example, repeating units derived from monomers having ethylenically unsaturated bonds such as ethylene and styrene may be included.

[0232] In one embodiment, the compound represented by the general formula (1) is a light-emitting material.

[0233] In one embodiment, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence.

[0234] In one embodiment of the present invention, when excited by thermal or electronic means, the compound represented by general formula (1) is capable of emitting light in the UV region, the blue, green, yellow, orange, red region (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) in the visible spectrum, or in the near-infrared region.

[0235] In one embodiment of the present invention, when excited by thermal or electronic means, the compound represented by general formula (1) can emit light in the red or orange region (eg, about 620 nm to about 780 nm, about 650 nm) of the visible spectrum.

[0236] In one embodiment of the present invention, when excited by thermal or electronic means, the compound 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).

[0237] In one embodiment of the present invention, the compound represented by general formula (1) can emit light in the green region (eg, about 490 nm to about 575 nm, about 510 nm) of the visible spectrum when excited by thermal or electronic means.

[0238] In one embodiment of the present invention, the compound represented by general formula (1) can emit light in the blue region (eg, about 400 nm to about 490 nm, about 475 nm) of the visible spectrum when excited by thermal or electronic means.

[0239] In one embodiment of the present invention, the compound represented by general formula (1) is capable of emitting light in the ultraviolet spectral region (eg, 280-400 nm) when excited by thermal or electronic means.

[0240] In one embodiment of the present invention, the compound represented by general formula (1) is capable of emitting light in the infrared spectral region (eg, 780 nm to 2 μm) when excited by thermal or electronic means.

[0241] The electronic properties of a chemical library of small molecules can be calculated using quantum chemical calculations based on known ab initio. For example, as a basis, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) can be analyzed using density functional theory using a time-dependent function group known as 6-31G* and Becke's three-parameter, Lee-Yang-Parr hybrid density functional (hybrid functional), and molecular fragments (parts) with a HOMO above a specific threshold and a LUMO below a specific threshold can be screened.

[0242] Thus, for example, when having a HOMO energy (e.g., ionization potential) of -6.5 eV or more, the donor part ("D") can be selected. And, for example, when having a LUMO energy (e.g., electron affinity) of -0.5 eV or less, the acceptor part ("A") can be selected. The bridge part ("B") is, for example, a strongly conjugated system that can strictly restrict the acceptor and donor parts to a specific stereostructure, thereby preventing duplication between the π-conjugated systems of the donor and acceptor parts.

[0243] In certain embodiments, a compound library is screened using one or more of the following properties.

[0244] 1. Emitting light near a specific wavelength

[0245] 2. Calculated triplet states above a specific energy level

[0246] 3. ΔE below a certain value ST value

[0247] 4. Quantum yield above a certain value

[0248] 5.HOMO level

[0249] 6.LUMO level

[0250] In one embodiment, the difference between the lowest excited singlet state and the lowest excited triplet state at 77K (ΔE S T ) 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. In one embodiment, ΔE ST The 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.

[0251] In one embodiment, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, for example, 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.

[0252] [Method for synthesizing the compound represented by general formula (1)]

[0253] The compound represented by the general formula (1) is a novel compound.

[0254] The compound represented by the general formula (1) can be synthesized by combining known reactions. For example, it can be synthesized by reacting the D to be introduced in the presence of sodium hydride. 1 , D 2 The position of difluoroisophthalonitrile substituted by fluorine atom and D 1 -H and D 2 -H in tetrahydrofuran. 1 and D 2 When different from each other, 1 -H, D 2 The reaction of -H can be carried out in two stages. For the specific conditions and reaction steps of the reaction, reference can be made to the synthesis examples described below.

[0255] [Composition using a compound represented by the general formula (1)]

[0256] In one embodiment, the compound represented by the general formula (1) is combined, the compound represented by the general formula (1) is dispersed, the compound represented by the general formula (1) is covalently bonded, the compound represented by the general formula (1) is coated, the compound represented by the general formula (1) is supported, or it is used together with one or more materials (such as small molecules, polymers, metals, metal complexes, etc.) that are combined with the compound represented by the general formula (1) to form a solid film or layer. For example, the compound represented by the general formula (1) can be combined with an electroactive material to form a film. In some cases, the compound represented by the general formula (1) can be combined with a hole transport polymer. In some cases, the compound represented by the general formula (1) can be combined with an electron transport polymer. In some cases, the compound represented by the general formula (1) can be combined with a hole transport polymer and an electron transport polymer. In some cases, the compound represented by the general formula (1) can be combined with a copolymer having both a hole transport portion and an electron transport portion. According to the above-described embodiments, electrons and / or holes formed in a solid film or layer can interact with the compound represented by the general formula (1).

[0257] [Film formation]

[0258] In one embodiment, a film of the compound of the present invention represented by the general formula (1) can be formed in a wet process. In the wet process, a solution obtained by dissolving a composition containing the compound of the present invention is applied to a surface, and after removing the solvent, a film is formed. The wet process may include spin coating, slit coating, inkjet (spraying), gravure printing, offset printing, flexographic printing, but is not limited to these. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In one embodiment, a substituent (e.g., an alkyl group) that improves solubility relative to an organic solvent can be introduced into the compound contained in the composition.

[0259] In one embodiment, a film containing the compound of the present invention can be formed in a dry process. In one embodiment, a vacuum deposition method can be used as a dry process, but it is not limited thereto. When the vacuum deposition method is used, the compounds constituting the film can be co-deposited from a separate deposition source, or co-deposited from a single deposition source in which the compounds are mixed. When a single deposition source is used, a mixed powder formed by mixing the powders of the compounds can be used, a compressed molded body formed by compressing the mixed powder can be used, or a mixture after heating, melting and cooling each compound can be used. In one embodiment, by co-depositing under conditions where the vapor deposition rates (weight reduction rates) of multiple compounds contained in a single deposition source are consistent or approximately consistent, a film with a composition ratio corresponding to the composition ratio of multiple compounds contained in the deposition source can be formed. If multiple compounds are mixed in a composition ratio identical to the composition ratio of the formed film and used as a deposition source, a film with a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-deposited compound becomes the same weight reduction rate can be determined, and this temperature is used as the temperature during co-deposition.

[0260] [Use Examples of Compounds Represented by General Formula (1)]

[0261] Organic Light Emitting Diodes:

[0262] One aspect of the present invention relates to the use of a compound represented by the general formula (1) of the present invention in the form of a light-emitting material for an organic light-emitting element. In one embodiment, the compound represented by the general formula (1) of the present invention can be effectively used as a light-emitting material in a light-emitting layer of an organic light-emitting element. In one embodiment, the compound represented by the general formula (1) contains a delayed fluorescence (delayed fluorescence body) that emits delayed fluorescence. In one embodiment, the present invention provides a delayed fluorescence body having a structure represented by the general formula (1). In one embodiment, the present invention relates to the use of a compound represented by the general formula (1) as a delayed fluorescence body. In one embodiment, the compound represented by the general formula (1) of the present invention can be used as a host material and can be used together with one or more light-emitting materials, which can be fluorescent materials, phosphorescent materials or TADF. In one embodiment, the compound represented by the general formula (1) can also be used as a hole transport material. In one embodiment, the compound represented by the general formula (1) can be used as an electron transport material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from a compound represented by the general formula (1). In one embodiment, an organic light-emitting element containing the compound as a light-emitting material emits delayed fluorescence and shows high luminous efficiency.

[0263] In one embodiment, the light-emitting layer comprises a compound represented by the general formula (1), and the compound represented by the general formula (1) is oriented parallel to the substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by the general formula (1) on the film-forming surface affects or determines the propagation direction of light emitted by the arranged compound. In one embodiment, by arranging the compound represented by the general formula (1) in the propagation direction of light emitted, the light extraction efficiency from the light-emitting layer is improved.

[0264] One aspect of the present invention refers to an organic light-emitting element. In one embodiment, the organic light-emitting element includes a light-emitting layer. In one embodiment, the light-emitting layer includes a compound represented by the general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting element is an organic photoluminescent element (organic PL element). In one embodiment, the organic light-emitting element is an organic electroluminescent element (organic EL element). In one embodiment, the compound represented by the general formula (1) assists the emission of other light-emitting materials contained in the light-emitting layer (as a so-called auxiliary dopant). In one embodiment, the compound represented by the general formula (1) contained in the light-emitting layer is in its lowest excited singlet energy level, which is contained between the lowest excited singlet energy level of the main material contained in the light-emitting layer and the lowest excited singlet energy level of another light-emitting material contained in the light-emitting layer.

[0265] In one embodiment, the organic photoluminescent element comprises at least one light-emitting layer. In one embodiment, the organic electroluminescent element comprises at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer comprises at least a light-emitting layer. In one embodiment, the organic layer comprises only a light-emitting layer. In one embodiment, the organic layer comprises one or more organic layers other than 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 one embodiment, the hole transport layer may be a hole injection and transport layer having a hole injection function, and the electron transport layer may be an electron injection and transport layer having an electron injection function. Examples of organic electroluminescent elements are shown in Figure 1 middle.

[0266] Luminous layer:

[0267] In a certain embodiment, the light emitting layer is a layer in which holes and electrons injected from the anode and the cathode, respectively, are re-bonded to form excitons. In a certain embodiment, the layer emits light.

[0268] In one embodiment, only the luminescent material is used as the luminescent layer. In one embodiment, the luminescent layer comprises a luminescent material and a host material. In one embodiment, the luminescent material is one or more compounds of the general formula (1). In one embodiment, in order to make the organic electroluminescent element and the organic photoluminescent element exhibit high luminescence efficiency, the singlet excitons and triplet excitons generated in the luminescent material are constrained in the luminescent material. In one embodiment, a host material is used in addition to the luminescent material in the luminescent layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has an excited singlet energy and an excited triplet energy, at least one of which is higher than those of the luminescent material of the present invention. In one embodiment, the singlet excitons and triplet excitons generated in the luminescent material of the present invention are constrained in the molecules of the luminescent material of the present invention. In one embodiment, the singlet and triplet excitons are sufficiently constrained to promote luminescence efficiency. In one embodiment, the singlet excitons and triplet excitons are not sufficiently constrained, but still obtain a higher luminescence efficiency, that is, the host material capable of achieving a higher luminescence efficiency can be used in the present invention without special restrictions. In one embodiment, light emission occurs in the light-emitting material in the light-emitting layer of the element of the present invention. In one embodiment, the emitted light includes both fluorescence and delayed fluorescence. In one embodiment, the emitted light includes light emitted from the host material. In one embodiment, the emitted light consists of light emitted from the host material. In one embodiment, the emitted light includes light emitted from the compound represented by the general formula (1) and light emitted from the host material. In one embodiment, TADF molecules and host materials are used. In one embodiment, TADF is an auxiliary dopant.

[0269] When the compound represented by the general formula (1) is used as an auxiliary dopant, various compounds can be used as luminescent materials (preferably fluorescent materials). Such luminescent materials can be composed of anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, 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 with metals (Al, Zn), etc. These exemplary skeletons may have substituents or may not have substituents. Furthermore, these exemplary skeletons may be combined with each other.

[0270] The following are examples of light-emitting materials that can be used in combination with the assisting dopant represented by the general formula (1).

[0271] [Chemical formula 22-1]

[0272]

[0273] [Chemical formula 22-2]

[0274]

[0275] [Chemical formula 22-3]

[0276]

[0277] [Chemical formula 22-4]

[0278]

[0279] In addition, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be preferably used as the light-emitting material used together with the auxiliary dopant represented by the general formula (1).

[0280] In one embodiment, when a host material is used, the amount of the compound of the present invention in the form of a luminescent material contained in the luminescent 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 in the form of a luminescent material contained in the luminescent layer is 1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of the present invention in the form of a luminescent material contained in the luminescent 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 in the form of a luminescent material contained in the luminescent layer is 20% by weight or less. In one embodiment, when a host material is used, the amount of the compound of the present invention in the form of a luminescent material contained in the luminescent layer is 10% by weight or less.

[0281] In one embodiment, the host material in the light-emitting layer is an organic compound having a hole transport function and an electron transport function. In one embodiment, the host material in the light-emitting layer is an organic compound that prevents the wavelength of the emitted light from increasing. In one embodiment, the host material in the light-emitting layer is an organic compound having a relatively high glass transition temperature.

[0282] In some embodiments, the host material is selected from the group consisting of: [Chemical Formula 23-1]

[0283]

[0284] [Chemical formula 23-2]

[0285]

[0286] In one embodiment, the light-emitting layer includes two or more TADF molecules with different structures. For example, the light-emitting layer may include three materials with high excited singlet energy levels in the order of host material, first TADF molecule, and second TADF molecule. In this case, the difference ΔE between the lowest excited singlet energy level of the first TADF molecule and the second TADF molecule and the lowest excited triplet energy level at 77K is STPreferably, it is less than 0.3eV, more preferably less than 0.25eV, more preferably less than 0.2eV, more preferably less than 0.15eV, further preferably less than 0.1eV, further preferably less than 0.07eV, further preferably less than 0.05eV, further preferably less than 0.03eV, and particularly preferably less than 0.01eV. The content of the first TADF molecule in the light-emitting layer is preferably greater than the content of the second TADF molecule. Furthermore, the content of the main material in the light-emitting layer is preferably greater than the content of the second TADF molecule. The content of the first TADF molecule in the light-emitting layer may be greater than the content of the main material, may be less than the content of the main material, or may be the same. In one embodiment, the composition in the light-emitting layer may be set as follows: the main material is set to 10 to 70 weight %, the first TADF molecule is set to 10 to 80 weight %, and the second TADF molecule is set to 0.1 to 30 weight %. In one embodiment, the composition of the light-emitting layer can be set as follows: the host material is set to 20-45 wt%, the first TADF molecule is set to 50-75 wt%, and the second TADF molecule is set to 5-20 wt%. In one embodiment, the light emission quantum yield φPL1(A) caused by the photoexcitation of the co-deposited film of the first TADF molecule and the host material (the content of the first TADF molecule in the co-deposited film = A wt%) and the light emission quantum yield φPL2(A) caused by the photoexcitation of the co-deposited film of the second TADF molecule and the host material (the content of the second TADF molecule in the co-deposited film = A wt%) satisfy the relationship φPL1(A)>φPL2(A). In one embodiment, the luminescence quantum yield φPL2(B) caused by the photoexcitation of the co-deposited film of the second TADF molecule and the host material (the content of the second TADF molecule in the co-deposited film = B weight %) and the luminescence quantum yield φPL2(100) caused by the photoexcitation of the single film of the second TADF molecule satisfy the relationship φPL2(B)>φPL2(100). In one embodiment, the light-emitting layer can contain three TADF molecules with different structures. The compound of the present invention can be any one of the multiple TADF compounds contained in the light-emitting layer.

[0287] In one embodiment, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an auxiliary dopant and a light-emitting material. In one embodiment, the light-emitting layer does not contain a metal element. In one embodiment, the light-emitting 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 also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms. Alternatively, the light-emitting layer can also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms.

[0288] When the light-emitting layer includes a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescent material. Preferred delayed fluorescent 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 paragraphs 0008 to 0073 of WO2013 / 081088. 1 and 0118 to 0133, 0009 to 0046 and 0093 to 0134 of Japanese Patent Application Publication No. 2013-256490, 0008 to 0020 and 0038 to 0040 of Japanese Patent Application Publication No. 2013-116975, 0007 to 0032 and 0079 to 0084 of WO2013 / 133359, 000 8 to 0054 and 0101 to 0121, JP-A-2014-9352, JP-A-2014-9352, JP-A-2014-9224, JP-A-2017-119663, JP-A-2017-119664 ...3, JP-A-2017-119664, JP-A-2017-119664, JP-A-2017-119664, JP-A-2017-119663, JP- The compound included in the general formula described in paragraphs 0012 to 0025 of Japanese Patent Application Publication No. 2017-222623, paragraphs 0010 to 0050 of Japanese Patent Application Publication No. 2017-226838, paragraphs 0012 to 0043 of Japanese Patent Application Publication No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, and in particular the exemplified compound and a material that can emit delayed fluorescence.In addition, Japanese Patent Application Publication No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 13312 1, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO20 15 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, Japanese Patent Application Publication No. 2015-129240, WO2015 / 129714, WO2015 / 1297 15, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, WO2015 / 159541, and materials capable of emitting delayed fluorescence. In addition, the above-mentioned publications described in this paragraph are incorporated herein as part of this article.

[0289] Hereinafter, each member of the organic electroluminescent element and each layer other than the light-emitting layer will be described.

[0290] Substrate:

[0291] In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, wherein the substrate is not particularly limited and may be any of those substrates that have been commonly used in organic electroluminescent elements, such as those formed of glass, transparent plastic, quartz, and silicon.

[0292] anode:

[0293] In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a large work function (above 4 eV). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO 2In some embodiments, an amorphous material such as IDIXO (In 2 O 3 -ZnO) and the like. In some embodiments, the anode is a thin film. In some embodiments, the thin film is made by vapor deposition or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, when the pattern may not require high precision (for example, about 100 μm or more), the pattern can be formed by vapor deposition or sputtering of the electrode material using a mask of the desired shape. In some embodiments, when a coating material (such as an organic conductive compound) can be applied, a wet film formation method such as a printing method and a coating method is used. In some embodiments, when the emitted light passes through the anode, the transmittance of the anode is greater than 10%, and the sheet resistance of the anode is less than hundreds of ohms per square. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0294] cathode:

[0295] In some embodiments, the cathode is made of a metal (less than 4 eV) (called an electron injection metal) having a small work function, an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, a magnesium-copper mixture, a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al 2 O 3 ) mixture, indium, lithium-aluminum mixture and rare earth metal. In some embodiments, a mixture of an electron injecting metal and a second metal is used, and the second metal is a stable metal with a larger work function than the electron injecting metal. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al 2 O 3 ) mixture, lithium-aluminum mixture and aluminum. In some embodiments, the mixture increases electron injection characteristics and durability against oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film by vapor deposition or sputtering. In some embodiments, the sheet resistance of the cathode is less than hundreds of ohms per square. In some embodiments, the thickness of the cathode is in the range of 10nm to 5μm. In some embodiments, the thickness of the cathode is in the range of 50 to 200nm. In some embodiments, in order to transmit the emitted light, any one of the anode and cathode of the organic electroluminescent element is transparent or translucent. In some embodiments, the transparent or translucent electroluminescent element enhances the luminous brightness.

[0296] In some embodiments, the cathode is formed with a conductive transparent material as described for the anode to form a transparent or translucent cathode. In some embodiments, the element comprises an anode and a cathode that are both transparent or translucent.

[0297] Injection layer:

[0298] The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the luminous brightness. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be configured 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. In some embodiments, there is an injection layer. In some embodiments, there is no injection layer.

[0299] Preferred examples of compounds that can be used as hole injection materials are included below.

[0300] [Chemical formula 24]

[0301]

[0302] Next, preferred examples of compounds that can be used as electron injecting materials are included.

[0303] [Chemical formula 25]

[0304]

[0305] Barrier layer:

[0306] The blocking layer is a layer that can inhibit the diffusion of charges (electrons or holes) and / or excitons in the light-emitting layer to the outside of the light-emitting layer. In some embodiments, the electron blocking layer is between the light-emitting layer and the hole transport layer, and inhibits electrons from passing through the light-emitting layer toward the hole transport layer. In some embodiments, the hole blocking layer is between the light-emitting layer and the electron transport layer, and inhibits holes from passing through the light-emitting layer toward the electron transport layer. In some embodiments, the blocking layer inhibits the diffusion of excitons to the outside of the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. The term "electron blocking layer" or "exciton blocking layer" used in this article includes a layer having the functions of both an electron blocking layer and an exciton blocking layer.

[0307] Hole blocking layer:

[0308] The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer inhibits holes from reaching the electron transport layer while transporting electrons. In some embodiments, the hole blocking layer enhances the probability of re-bonding of electrons and holes in the light-emitting layer. The material used for the hole blocking layer can be the same material as described for the electron transport layer.

[0309] The following are examples of preferred compounds that can be used in the hole blocking layer.

[0310] [Chemical formula 26]

[0311]

[0312] Electron blocking layer:

[0313] The holes are transported by the electron blocking layer. In some embodiments, the electron blocking layer inhibits electrons from reaching the hole transport layer while transporting holes. In some embodiments, the electron blocking layer enhances the probability of re-bonding of electrons and holes in the light-emitting layer. The material used for the electron blocking layer can be the same material as described for the hole transport layer.

[0314] Specific examples of preferred compounds that can be used as electron blocking materials are included below.

[0315] [Chemical formula 27]

[0316]

[0317] Exciton blocking layer:

[0318] The exciton blocking layer inhibits the diffusion of excitons generated by the rebonding of holes and electrons in the light-emitting layer to the electron transport layer. In some embodiments, the exciton blocking layer enables the excitons to be effectively confined in the light-emitting layer. In some embodiments, the luminescence efficiency of the device is enhanced. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side and the cathode side and on both sides. In some embodiments, when the exciton blocking layer is on the anode side, the layer may be between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, the layer may be between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, the hole injection layer, the electron blocking layer, or the same layer is between the anode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light-emitting layer on the anode side. In some embodiments, the hole injection layer, the electron blocking layer, the hole blocking layer, or the same layer is between the cathode and the exciton blocking layer, and the exciton blocking layer is 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 the excited triplet energy of the light-emitting material, respectively.

[0319] Hole transport layer:

[0320] The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers.

[0321] In some embodiments, the hole transport material has one of the injection or transport characteristics of holes and the blocking characteristics of electrons. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indole and carbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, aromatic amine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers and conductive polymer oligomers (especially thiophene oligomers) or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amines and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. The following includes specific examples of preferred compounds that can be used as hole transport materials.

[0322] [Chemical formula 28]

[0323]

[0324] Electron transport layer:

[0325] The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers.

[0326] In some embodiments, the electron transport material only needs to have the function of transporting electrons, which are injected from the cathode into the light-emitting layer. In some embodiments, the electron transport material also functions as a hole blocking material. Examples of electron transport layers that can be used in the present invention include (but are not limited to) fluorene derivatives substituted by nitro, dibenzoquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenyl methane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, oxazine derivatives or combinations thereof or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. The following includes specific examples of preferred compounds that can be used as electron transport materials.

[0327] [Chemical formula 29]

[0328]

[0329] In addition, examples of compounds that are preferable as materials that can be added to each organic layer are included. For example, it is conceivable that the compound can be added as a stabilizing material.

[0330] [Chemical formula 30]

[0331]

[0332] Preferred materials that can be used for organic electroluminescent elements are specifically exemplified, but the materials that can be used in the present invention are not limited to the following exemplified compounds. Furthermore, even compounds exemplified as materials having specific functions can be used as materials having other functions.

[0333] Device:

[0334] In some embodiments, the light emitting layer is incorporated into a device. Examples of devices include, but are not limited to, OLED bulbs, OLED lamps, television screens, computer monitors, mobile phones, and tablet computers.

[0335] In some embodiments, an electronic device includes an OLED having an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode.

[0336] In some embodiments, the compositions described herein can be incorporated into various light-sensitive or light-activated devices, such as OLEDs or photovoltaic devices. In some embodiments, the compositions can be suitable for promoting charge transfer or energy transfer within the device and / or for use as hole transport materials. The devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic photodetectors, organic photoreceptors, organic field-quenching devices (organic field-quench devices; O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0337] Bulb or Lamp:

[0338] In some embodiments, an electronic device includes an OLED including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode.

[0339] In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors.

[0340] In some embodiments, the device is an OLED lamp having:

[0341] A circuit substrate having a first surface having a mounting surface and a second surface opposite thereto and defining at least one opening;

[0342] At least one OLED is disposed on the mounting surface and has a structure in which the at least one OLED includes an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode and emits light;

[0343] A housing for a circuit substrate; and

[0344] At least one connector is disposed at an end of the housing, and the housing and the connector define a package suitable for mounting on a lighting device.

[0345] In some embodiments, the OLED lamp includes a plurality of OLEDs mounted on a circuit board so that light is emitted in a plurality of directions. In some embodiments, a portion of the light emitted in a first direction is deflected to be emitted in a second direction. In some embodiments, a reflector is used to deflect the light emitted in the first direction.

[0346] Monitor or Screen:

[0347] In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compounds involved in the present invention are deposited onto a substrate using methods including (but not limited to) vacuum evaporation, deposition, vapor deposition or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure suitable for double-sided etching, providing unique aspect ratio pixels. The screen (which may also be referred to as a mask) is used in a method for manufacturing an OLED display. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction, and promotes larger sweeping angle openings in the horizontal direction. Thus, the pixels required for high-definition displays are allowed to be tightly patterned while optimizing chemical vapor deposition onto the TFT backplane.

[0348] The internal patterning of the pixel allows the construction of 3-dimensional pixel openings with varying aspect ratios in the horizontal and vertical directions. In addition, etching in specific areas is suppressed using imaged "strips" or halftone circles within the pixel area until these specific patterns are undercut and leave the substrate. At this point, all pixel areas are processed at the same etching rate, but the depth varies depending on the halftone pattern. Changing the size and spacing of the halftone pattern allows etching to be suppressed at different rates within the pixel, allowing for localized deeper etching required to form steep vertical bevels.

[0349] The preferred material for the deposition mask is invar. Invar is a metal alloy that is cold rolled into long thin sheets in a steel mill. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. An appropriate and low-cost method for forming the opening area in the mask for vapor deposition is a method based on wet chemical etching.

[0350] In some embodiments, the screen or display pattern is a matrix of pixels on a substrate. In some embodiments, the screen or display pattern is manufactured using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is manufactured using wet chemical etching. In other embodiments, the screen or display pattern is manufactured using plasma etching.

[0351] Device manufacturing method:

[0352] OLED displays are generally manufactured by forming a large motherboard and then cutting the motherboard into unit board units. Generally speaking, each unit board on the motherboard is formed by forming a thin film transistor including an active layer and a source electrode / drain electrode on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light emitting layer, a counter electrode and an encapsulation layer, and cutting from the motherboard.

[0353] OLED displays are generally manufactured by forming a large motherboard and then cutting the motherboard into unit board units. Generally speaking, each unit board on the motherboard is formed by forming a thin film transistor including an active layer and a source electrode / drain electrode on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light emitting layer, a counter electrode and an encapsulation layer, and cutting from the motherboard.

[0354] In another aspect of the present invention, there is provided a method for manufacturing an organic light emitting diode (OLED) display, the method comprising:

[0355] The process of forming a barrier layer on the base substrate of the mother board;

[0356] A process of forming a plurality of display units from a unit panel unit on the barrier layer;

[0357] forming an encapsulation layer on each of the display units of the unit panel; and

[0358] A process of coating an organic film on the interface portion between the unit plates.

[0359] In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and an edge portion of the barrier layer is covered with an organic film formed of polyimide or acryl. In some embodiments, the organic film helps to gently cut the mother board into unit board units.

[0360] In some embodiments, the thin film transistor (TFT) layer has a light emitting layer, a gate electrode, and a source electrode / drain electrode. Each of the plurality of display units may include a thin film transistor (TFT), a planarization film formed on the TFT layer, and a light emitting unit formed on the planarization film, wherein the organic film applied to the interface portion is formed of the same material as the material of the planarization film and is formed at the same time as the planarization film is formed. In some embodiments, the light emitting unit is connected to the TFT layer with a passivation layer, a planarization film, and an encapsulation layer therebetween, and the encapsulation layer covers and protects the light emitting unit. In some embodiments of the manufacturing method, the organic film contacts neither the display unit nor the encapsulation layer.

[0361] Each of the organic film and the planarization film may include any one of polyimide and acryl. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include, before forming a barrier layer on one surface of the base substrate formed of polyimide, mounting a carrier substrate formed of a glass material on another surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display.

[0362] In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acryl, as is the organic film formed on the edge portion of the barrier layer. In some embodiments, when manufacturing an OLED display, the planarization film and the organic film are formed simultaneously. In some embodiments, the organic film may be formed on the edge portion of the barrier layer so 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 edge portion of the barrier layer.

[0363] In some embodiments, the light emitting layer comprises a pixel electrode, an opposite electrode and an organic light emitting layer disposed between the pixel electrode and the opposite electrode. In some embodiments, the pixel electrode is connected to a source electrode / drain electrode of a TFT layer.

[0364] In some embodiments, when a voltage is applied to the pixel electrode via the TFT layer, an appropriate voltage is formed between the pixel electrode and the opposite electrode, whereby the organic light-emitting layer emits light, thereby forming an image. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit is referred to as a display unit.

[0365] In some embodiments, the encapsulation layer that covers the display unit and prevents external moisture from penetrating can be formed to have a thin film encapsulation structure in which an organic film and an inorganic film are alternately stacked. In some embodiments, the encapsulation layer has a thin film encapsulation structure in which a plurality of thin films are stacked. In some embodiments, the organic film applied to the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed so 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 edge portion of the barrier layer.

[0366] In one embodiment, the OLED display is flexible and uses a soft base substrate formed of polyimide.In some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.

[0367] In some embodiments, a barrier layer is formed on a surface of a side of the base substrate opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit board. For example, while the base substrate is formed over the entire surface of the mother board, the barrier layer is formed according to the size of each unit board, thereby forming a groove at the interface portion between the unit board barrier layers. Each unit board can be cut along the groove.

[0368] In some embodiments, the manufacturing method further comprises a process of cutting along the interface portion, wherein a groove is formed in the barrier layer, wherein at least a portion of the organic film is formed in the groove, and the groove does not penetrate into the base substrate. In some embodiments, the TFT layer of each unit board is formed, and a passivation layer (i.e., an inorganic film) and a planarization film (i.e., an organic film) are arranged on the TFT layer to cover the TFT layer. While forming a planarization film formed of, for example, polyimide or acryl, the groove at the interface portion is covered with an organic film formed of, for example, polyimide or acryl. This is when cracking is prevented from occurring by allowing the organic film to absorb the impact, which is generated when each unit board is cut along the groove at the interface portion. That is, if the entire barrier layer is completely exposed without the organic film, the impact generated when each unit board is cut along the groove at the interface portion is transferred to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, because the groove at the interface portion between the barrier layers is covered with an organic film, and the organic film absorbs the impact that would otherwise be transferred to the barrier layer, each unit board can be cut gently, and cracking can be prevented from occurring in the barrier layer. In one embodiment, the organic film covering the groove at the interface portion is spaced apart from the planarization film. For example, if the organic film and the planarization film are connected to each other as a single layer, since external moisture may penetrate into the display unit through the planarization film and a portion where the organic film remains, the organic film and the planarization film are spaced apart from each other so that the organic film is spaced apart from the display unit.

[0369] In some embodiments, the display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the motherboard is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, when a laser beam is emitted toward the carrier 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.

[0370] In some embodiments, the mother board is cut into unit board units. In some embodiments, the mother board is cut along the interface portion between the unit boards by using a cutting machine. In some embodiments, because the groove at the interface portion along which the mother board is cut is covered with an organic film, the organic film absorbs impact during cutting. In some embodiments, cracking can be prevented from occurring in the barrier layer during cutting.

[0371] In some embodiments, the method reduces the defect rate of the product and stabilizes its quality.

[0372] 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 coated on an edge portion of the barrier layer.

[0373] Example

[0374] The following includes synthesis examples and embodiments and the features of the present invention are further specifically described. The materials, processing contents, processing steps, etc. shown below can be appropriately changed as long as they do not depart from the main purpose of the present invention. Therefore, the scope of the present invention should not be interpreted restrictively by the specific examples shown below. In addition, about the evaluation of luminescence characteristics, source meter (Keithley company system: 2400 series), semiconductor parameter analyzer (Agilent Technologies Japan, Ltd. system: E5273A), optical power meter measuring device (Newport Corporation system: 1930C), spectrometer (Ocean Optics company system: USB2000), spectroradiometer (TOPCON CORPORATION system: SR-3) and streak camera (Hamamatsu Photonics KK system C4334 type) are used for evaluation.

[0375] (Synthesis Example 1) Synthesis of Compound C1

[0376] [Chemical formula 31]

[0377]

[0378] Potassium carbonate (1.04 g, 7.5 mmol), benzofuran [2,3-c] carbazole (1.61 g, 6.3 mmol) and 4,6-difluoro-5-phenylisophthalonitrile (0.60 mmol, 2.5 mmol) were reacted in dimethylformamide (20 mL) at 100 ° C under a nitrogen stream for 9 hours. After that, the temperature was returned to room temperature, and water and methanol were added to stop the reaction. The precipitated yellow solid was filtered, and the filtrate was purified by silica gel column chromatography (toluene) and reprecipitation (toluene / methanol), thereby obtaining a yellow solid compound C1 (1.33 g, yield 76%).

[0379] 1 H NMR (400 MHz, CDCl 3,δ):8.49(s,1H),8.43(d,J=7.6Hz,2H),7.96-7.91(m,4H),7.70(d,J=7.6Hz,2H),7.47-7. 36(m,8H),7.14-7.11(m,2H),7.10-7.07(m,2H),6.52-6.46(m,3H),6.37(t,J=7.6Hz,2H).

[0380] MS(ASAP):715.34(M+H+).Calcd for C 50 H 26 N 4 O 2 :714.21.

[0381] (Synthesis Example 2) Synthesis of Compound C2

[0382] [Chemical formula 32]

[0383]

[0384] Under nitrogen flow, compound C1 (2.40 g, 3.4 mmol), 4-bromobenzonitrile (1.17 g, 5.0 mmol), potassium carbonate (0.93 g, 6.7 mmol), 2-ethylhexanoic acid (0.10 mg, 0.7 mmol), tricyclohexylphosphine (0.10 g, 0.5 mmol) and dichlorobis(triphenylphosphine)palladium (0.20 g, 0.3 mmol) were dissolved in xylene (30 mL) and stirred at 120° C. for 18 hours. The mixture was returned to room temperature and the insoluble substances were removed by diatomaceous earth filtration. After the filtrate was concentrated by vacuum distillation, the residue was purified by silica gel column chromatography (chloroform / hexane=2 / 1) and reprecipitation (toluene / methanol), thereby obtaining compound C2 (1.90 g, yield 68%) as a white solid.

[0385] 1 H NMR (400 MHz, CDCl 3 ,δ):8.43(d,J=7.6Hz,2H),8.00-7.92(m,8H),7.70(d,J=8.0Hz,2H),7.48-7.36(m,8H) ,7.19(d,J=8.0Hz,2H),7.14(d,J=8.0Hz,2H),6.54-6.50(m,3H),6.40(t,J=7.6Hz,2H).

[0386] MS(ASAP):816.45(M+H+).Calcd for C 57 H 29 N 5O 2 :815.23.

[0387] (Synthesis Example 3) Synthesis of Compound C3

[0388] [Chemical formula 33]

[0389]

[0390] Under nitrogen flow, potassium carbonate (1.22 g, 8.8 mmol), benzofuran [2,3-c] carbazole (2.00 g, 7.4 mmol) and 4,6-difluoro-5-phenylisophthalonitrile (0.77 mmol, 3.0 mmol) were reacted in dimethylformamide (36 mL) at 80 ° C for 2 hours. After that, the temperature was returned to room temperature and water was added to stop the reaction. Chloroform was added to the reaction mixture for liquid separation, and the organic layer was dried with magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (toluene), thereby obtaining compound C3 (2.25 g, yield 90%) as a yellow solid.

[0391] 1 H NMR (400 MHz, CDCl 3 ,δ):8.44(s,1H),8.22(d,J=5.2Hz,2H),7.92(t,J=7.2Hz,2H),7.88-7.81(m,2H),7.69(d,J=8.0Hz,2H),7.45-7.40(m,2H),7.38-7. 33(m,2H),7.27-7.26(m,1H),7.22(t,J=8.4Hz,1H),7.07-6.95(m,4H),6.49-6.46(m,3H),6.40-6.36(m,2H),2.56(d,J=7.2Hz,6H).

[0392] MS(ASAP):743.28[(M+H)+,cal.C 52 H 31 N 4 O 2 ,743.24].

[0393] (Synthesis Example 4) Synthesis of Compound C4

[0394] [Chemical formula 34]

[0395]

[0396] Under nitrogen flow, sodium hydride (0.30 g, 7.5 mmol) and 11-phenyl-11,12-dihydroindole [2,3-a] carbazole (2.08 g, 6.3 mmol) were stirred in THF (20 mL) for 1 hour at room temperature, and 4,6-difluoro-5-phenylisophthalonitrile (1.50 g, 6.24 mmol) dissolved in tetrahydrofuran (50 ml) was added dropwise. After reacting at room temperature for 5 hours, water was added to stop the reaction. Chloroform was added to the reaction mixture for liquid separation, and the organic layer was dried with magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (toluene), thereby obtaining intermediate 1 (1.82 g, yield 53%) as a yellow solid.

[0397] 1 H NMR (400 MHz, CDCl 3 ,δ):8.10(d,J=8.4Hz,1H),7.99(d,J=7.6Hz,1H),7.78(s,1H),7.61(d,J=6.4Hz,1H),7.48-7.40(m,4H),7.36-7.2 0(m,7H),6.84-6.82(br,1H),6.70(t,J=7.6Hz,1H),6.40(t,J=7.6Hz,2H),6.06(br,1H); MS(ASAP):553.70[(M+H) + ,cal.C 38 H 22 FN 4 ,553.18].

[0398] Potassium carbonate (0.36 g, 2.6 mmol), benzofuran [2,3-c] carbazole (0.54 g, 2.1 mmol) and intermediate 1 (0.96 mmol, 1.7 mmol) were reacted in dimethylformamide (17 mL) for 4 hours at room temperature under nitrogen flow. The reaction was stopped by adding water, chloroform was added to the reaction mixture for liquid separation, and the organic layer was dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (toluene), thereby obtaining compound C4 (1.36 g, yield 99%) as a yellow solid.

[0399] 1 H NMR (400 MHz, CDCl 3,δ):8.78(s,1.00),8.55(d,J=8.8Hz,0.54),8.27-8.19(m,2.38),8.02-7.97(m,1.55),7.89-7.83(m,2. 85),7.94-7.75(m,1.99),7.70-7.62(m,1.98),7.59-7.43(m,6.17),7.39-7.34(m,0.51),7.29-7.26(m, 2.61),7.21-7.16(m,1.02),7.06-6.99(m,1.00),6.81(br,0.90),6.67-6.61(m,1.00),6.15(t,J=7.6Hz ,0.5),6.09(t,J=7.6Hz,0.5),5.91(br,1.87),5.57(br,0.90),5.29(br,0.90); MS(ASAP):790.31[(M+H) + ,cal.C 56 H 32 N 4 O,790.25].

[0400] (Synthesis Example 5) Synthesis of Compound C5

[0401] [Chemical formula 35]

[0402]

[0403] Under nitrogen flow, sodium hydride (0.30 g, 7.5 mmol) and 5-phenyl-5,12-dihydroindole [3,2-a] carbazole were stirred in THF (50 mL) at room temperature for 1 hour, and 4,6-difluoro-5-phenylisophthalonitrile (1.49 g, 6.20 mmol) dissolved in THF (50 ml) was added dropwise. After reacting at room temperature for 15 hours, the reaction was stopped with water. Chloroform was added to the reaction mixture for liquid separation, and the organic layer was dried with magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (toluene), thereby obtaining intermediate 2 (1.70 g, yield 50%) as a yellow solid.

[0404] 1 H NMR (400 MHz, CDCl 3,δ):9.05(d,J=6.4Hz,1H),8.16(d,J=8.8Hz,1H),8.09-8.07(m,1H),7.72-7.68(m,2H),7.61-7.57(m, 3H),7.37-7.29(m,2H),7.27-7.19(m,4H),7.14-7.02(m,2H),6.99-6.95(m,4H),6.21(d,J=8.0Hz,1H).

[0405] MS(ASAP):553.40[(M+H) + ,cal.C 38 H 22 FN 4 ,553.18].

[0406] Potassium carbonate (0.43 g, 3.1 mmol), benzofuran [2,3-c] carbazole (0.66 g, 2.6 mmol) and intermediate 2 (1.30 mmol, 2.4 mmol) were reacted in dimethylformamide (25 mL) for 4 hours at room temperature under nitrogen flow. The reaction was stopped by adding water, chloroform was added to the reaction mixture for liquid separation, and the organic layer was dried with magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (toluene), thereby obtaining compound C5 (1.63 g, yield 88%) as a yellow solid.

[0407] 1 H NMR (400 MHz, CDCl 3 ,δ):9.44(s,1H),8.22-8.17(m,1H),8.12-8.07(m,1H),7.76(d,J=8.0Hz,1H),7 .69-7.26(m,17H),7.08(d,J=8.4Hz,1H),6.54-6.49(m,1H),6.40-6.03(m,5H).

[0408] MS(ASAP):790.37[(M+H) + ,cal.C 56 H 32 N 4 O,790.25].

[0409] (Synthesis Example 6) Synthesis of Compound C6

[0410] [Chemical formula 36]

[0411]

[0412] Potassium phosphate (1.74 g, 8.2 mmol), 5-phenyl-5,12-dihydroindole [3,2-a] carbazole (2.28 g, 6.8 mmol) and 4,6-difluoro-5-phenylisophthalonitrile (0.66 g, 2.7 mmol) were reacted in dimethylformamide (30 mL) at 110°C under nitrogen flow for 6 hours. After the reaction, water was added at room temperature to stop the reaction, chloroform was added to the reaction mixture for liquid separation, and the organic layer was dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (toluene), thereby obtaining compound C6 (0.97 g, yield 41%) as a yellow solid.

[0413] 1 H NMR (400 MHz, CDCl 3 ,δ):9.57(s,1H),8.01(d,J=7.6Hz,2H),7.91(d,J=8.4Hz,2H),7.64-7.60(m,4H),7.54-7.50(m,4H),7.42-7.35(m,10H),7.26(t,J=8.0 Hz,2H),7.22-7.19(m,2H),6.91(d,J=8.4Hz,2H),6.52-6.49(m,2H),6.21(t,J=7.2Hz,1H),5.78(t,J=8.0Hz,2H),5.22(d,J=7.6Hz,2H).

[0414] MS(ASAP):865.47[(M+H) + ,cal.C 62 H 37 N 6 ,865.30].

[0415] (Synthesis Example 7) Synthesis of Compound C7

[0416] [Chemical formula 37]

[0417]

[0418] Under nitrogen flow, sodium hydride (0.19 g, 4.7 mmol) and benzofuran [3,2-c] carbazole (1.02 g, 4.0 mmol) were stirred in tetrahydrofuran (15 mL) at 0°C for 30 minutes, and then 4,6-difluoro-5-phenylisophthalonitrile was added. The reaction solution was heated to 40°C and reacted for 6 hours, then returned to room temperature and the reaction was stopped with water and methanol. The precipitated yellow solid was filtered and purified by silica gel column chromatography (toluene / hexane = 4 / 1) and reprecipitation (toluene / methanol), thereby obtaining compound C7 (0.98 g, yield 78%) as a yellow solid.

[0419] 1 H NMR (400 MHz, CDCl 3 ,δ):8.44(d,J=8.0Hz,2H),7.99-7.95(m,4H),7.89-7.86(m,2H),7.73-7.63(m,5H),7.49-7.45(m,4H),7 .42-7.37(m,4H),7.25(d,J=8.4Hz,2H),7.23(d,J=8.8Hz,2H),6.56-6.50(m,3H),6.40(t,J=7.6Hz,2H).

[0420] MS (ASAP): 791.26 (M+H + ).Calcd for C 56 H 30 N 4 O 2 :790.24

[0421] (Synthesis Example 8) Synthesis of Compound C8

[0422] [Chemical formula 38]

[0423]

[0424] Under nitrogen flow, sodium hydride (0.49 g, 11.8 mmol) and benzofuran [3,2-c] carbazole (2.54 g, 9.9 mmol) were stirred in tetrahydrofuran (20 mL) at 0°C for 30 minutes, and then 4,5-difluoro-6-phenylisophthalonitrile was added. The reaction solution was returned to room temperature and reacted at room temperature for 6 hours, and then the reaction was stopped with water and methanol. The precipitated yellow solid was filtered, and the filtrate was purified by silica gel column chromatography (toluene / chloroform = 10 / 1) and reprecipitation (toluene / methanol), thereby obtaining compound C8 (0.48 g, yield 17%) as a yellow solid.

[0425] 1 H NMR (400 MHz, CDCl 3,δ):(With the presence of stereoisomers in the sample, the proton number is displayed as a relative ratio.:When stereoisomers are present in the sample, the proton number is displayed as a relative ratio)8.53(s,1H),8.12(t,J=7.6Hz,1H),7.97-7.94(m,1H),7.89-7.74(m,2H),7.67(d,J=8.4Hz,0.5H),7.59-7.50(m,3H),7.45(d,J=8.4Hz,0.5H),7.41-7.28(m,4H),7.22-7.17(m,0.5H),7.14-6.97(m,10H),6.90-6.84(m,2.5H).

[0426] MS (ASAP): 715.38 (M+H + ).Calcd for C 50 H 26 N 4 O 2 :714.21

[0427] (Synthesis Example 9) Synthesis of Compound C9

[0428] [Chemical formula 39]

[0429]

[0430] Cesium carbonate (1.30 g, 4.0 mmol), 5-phenyl-5,11-dihydroindole [3,2-a] carbazole (0.78 g, 2.3 mmol) and 4,6-difluoro-5-phenylisophthalonitrile (0.24 g, 1.0 mmol) were reacted in dimethylformamide (20 mL) at 80°C under a nitrogen stream for 12 hours. After the reaction, water was added at room temperature to stop the reaction, chloroform was added to the reaction mixture for liquid separation, and the organic layer was dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (toluene) and reprecipitation (toluene / methanol), thereby obtaining compound C9 (0.17 g, yield 22%) as a yellow solid.

[0431] 1 H NMR (400 MHz, CDCl 3,δ):8.53(d,J=7.6Hz,1H),8.21(d,J=8.0Hz,1H),8.15(d,J=8.0Hz,1H),7.89-7.96(m,4H),7.85(s,1 H),7.78(s,1H),7.07-7.66(m,22H),6.95(d,J=8.0Hz,1H),6.40-6.58(m,3H),6.34(t,J=8.0Hz,2H).

[0432] MS (ASAP): 865.58 (M+H + ).Calcd for C 62 H 36 N 6 :864.30

[0433] (Synthesis Example 10) Synthesis of Compound C10

[0434] Compound C10 was synthesized by the same procedure as in Synthesis Example 1 (yield 84%).

[0435] [Chemical formula 40]

[0436]

[0437] 1 H NMR (400 MHz, CDCl 3 ,δ):8.62(s,2H),8.51(s,1H),7.99-7.90(m,4H),7.79-7.71(m,6H),7.69-7.64(m,2H),7.52-7.44(m, 6H),7.39-7.35(m,4H),7.21-7.18(m,2H),7.09-7.06(m,2H),6.58-6.50(m,3H),6.41(t,J=8.4Hz,2H).

[0438] MS (ASAP): 867.50 (M+H + ).Calcd for C 62 H 34 N 4 O 2 :866.27.

[0439] (Synthesis Example 11) Synthesis of Compound C11

[0440] Compound C11 was synthesized by the same procedure as in Synthesis Example 1 (yield 78%).

[0441] [Chemical formula 41]

[0442]

[0443] 1 H NMR (400 MHz, CDCl 3 ,δ):8.62(s,2H),8.51(s,1H),7.96-7.91(m,4H),7.72(d,J=8.2Hz,2H),7 .70-7.64(m,2H),7.46-7.37(m,2H),7.21-7.19(m,2H),7.09-7.06(m,2H),

[0444] MS(ASAP):882.21(M+H + ).Calcd for C 62 H 19 D 15 N 4 O 2 :881.36.

[0445] (Synthesis Example 12) Synthesis of Compound C12

[0446] Compound C12 was synthesized by the same procedure as in Synthesis Example 1 (yield 78%).

[0447] [Chemical formula 42]

[0448]

[0449] 1 H NMR (400MHz, DMSO, δ): 9.48 (s, 1H), 8.51 (s, 1H), 8.29 (d, J = 8.4H z,4H),8.19(d,J=8.4Hz,4H),7.91(mJ=8.4Hz,4H),7.84(t,J=6.8Hz,4H),7.45(t,J=6.8Hz,4H),6.73(t,J=7.2Hz,2H),6.38(t,J=7.2Hz,3H),

[0450] MS (ASAP): 895.35 (M+H + ).Calcd for C 62 H 3 0N 4 O 4 :894.23

[0451] (Synthesis Example 13) Synthesis of Compound C13

[0452] Compound C13 was synthesized by the same method as in Synthesis Example 1 (yield 64%).

[0453] [Chemical formula 43]

[0454]

[0455] 1 H NMR (400 MHz, CDCl 3 ,δ):8.82-8.76(m,4H),8.45(s,1H),7.64-7.32(m,22H),7.21(d,J=9.2Hz,2H),7.08-7.05(m,2H),6.47-6.44(m,3H),6.32(t,J=9.2Hz,2H).

[0456] MS(ASAP):865.27(M+H + ).Calcd for C 62 H 36 N 6 :864.30

[0457] (Synthesis Example 14) Synthesis of Compound C14

[0458] Compound C14 was synthesized by the same procedure as in Synthesis Example 1 (yield 47%).

[0459] [Chemical formula 44]

[0460]

[0461] 1 H NMR (400 MHz, CDCl 3 ,δ):8.47(s,1H),8.19-8.10(m,4H),7.68-7.51(m,10H),7.38-7.26(m,6H),7.20-7.14(m ,2H),7.06-6.98(m,4H),6.74(t,J=7.6Hz,2H),6.47-6.44(m,3H),6.31(t,J=7.6Hz,2H)..

[0462] MS (ASAP): 865.37 (M+H + ).Calcd for C 62 H 36 N 6 :864.30

[0463] (Examples 1 to 9, Comparative Examples 1 to 4) Preparation and Evaluation of Thin Films

[0464] Through vacuum deposition, the vacuum degree is less than 1×10 -3Pa, compound C1 and Host1 were vapor deposited from different deposition sources, and a thin film with a concentration of 20 wt % of compound C1 was formed on a quartz substrate with a thickness of 100 nm, which was used as the doped thin film of Example 1.

[0465] Compounds C2 to C9 were used instead of compound C1 to obtain thin films of Examples 2 to 9. Compound A and PPF were used to obtain a thin film of Comparative Example 1. In addition, each compound used as a luminescent material in the Examples and Comparative Examples was purified by sublimation before use.

[0466] Each of the obtained thin films was irradiated with 300 nm excitation light, and as a result, photoluminescence was observed in all the thin films. The lifetime (τ d ), and the relative value relative to Comparative Example 1 was calculated based on the lifetime of Comparative Example 1. The results are shown in the following table. It was confirmed that the delayed fluorescence lifetime (τ d )short.

[0467] [Table 2]

[0468]

[0469] (Examples 10 to 14, Comparative Example 2) Preparation of Organic Electroluminescent Element

[0470] By vacuum deposition method, the vacuum degree is 1×10 -6 Pa stacked each thin film on a glass substrate formed with an anode composed of indium / tin oxide (ITO) with a film thickness of 100nm. First, HATCN was formed on ITO with a thickness of 10nm, and NPD was formed thereon with a thickness of 30nm. Then, TrisPCz was formed thereon with a thickness of 10nm, and Host1 was further formed thereon with a thickness of 5nm. Then, compound C1 and Host1 were co-deposited from different deposition sources, respectively, to form a light-emitting layer with a thickness of 30nm. At this time, the concentration of compound C1 was set to 35 weight%. SF3TR Z was formed thereon with a thickness of 10nm, and SF3TRZ and Liq were co-deposited from different deposition sources to further form SF3TRZ and Liq thereon with a thickness of 30nm. At this time, SF3TRZ:Liq (weight ratio) was set to 7:3. In addition, Liq was formed to a thickness of 2nm, and then aluminum (Al) was vapor deposited to a thickness of 100nm, thereby forming a cathode. Through the above steps, the organic electroluminescent element of Example 10 was manufactured.

[0471] Organic electroluminescent elements of Examples 11 to 14 and Comparative Example 2 were prepared in this order by using Compound C2, Compound C3, Compound C4, Compound C6 and Comparative Compound A, respectively, instead of Compound C1.

[0472] (evaluate)

[0473] The CIE chromaticity coordinates x and y of the luminescence of the organic electroluminescent element of Example 10 were measured, and it was confirmed that x=0.26 and y=0.57, indicating a good chromaticity. In addition, the 12.6 mA / cm 2 The time until the luminous intensity under the condition of 95% is reduced (LT95), and the relative value is calculated when the LT95 of Comparative Example 2 is set to 1. The results are shown in the following table. The device life (device durability) of the organic electroluminescent device of Example 10 is greatly improved.

[0474] [Table 3]

[0475]

[0476] [Chemical formula 45]

[0477]

[0478] Explanation of symbols

[0479] 1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-light-emitting layer, 6-electron transport layer, 7-cathode.

Claims

1. A compound represented by the following general formula (1), wherein the hydrogen atoms of the compound are not substituted with deuterium atoms or a part or all of the hydrogen atoms are substituted with deuterium atoms, General formula (1) In the general formula (1), R is a hydrogen atom or an aryl group which is substituted or unsubstituted by a substituent selected from the group consisting of an alkyl group, an aryl group, an alkoxy group, an alkylthio group and a cyano group, Ar is an aryl group which may be substituted or unsubstituted by a substituent selected from the group consisting of an alkyl group, an aryl group, an alkoxy group, an alkylthio group and a cyano group, D 1 and D 2 The same as, and is a heterocyclic fused carbazole-9-yl group, wherein, The heterocyclic ring and the carbazole may have a substituent selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group and a cyano group, or may have no substituent, The number of carbon atoms in the alkyl group is 1 or more and 4 or less, The alkenyl group has 2 to 4 carbon atoms. The aryl group is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl and 9-anthryl, The heteroaryl group is selected from the group consisting of 2-pyridyl, 3-pyridyl and 4-pyridyl, The number of carbon atoms in the alkyl portion of each of the alkoxy group and the alkylthio group is the same as the number of carbon atoms in the alkyl group, The definition of the aryl moiety of each of the aryloxy group and the arylthio group is the same as that of the aryl group, The definition of the heteroaryl moiety of each of the heteroaryloxy group and the heteroarylthio group is the same as that of the heteroaryl group.

2. The compound according to claim 1, wherein The compound is represented by the following general formula (2): General formula (2) 3. The compound according to claim 1, wherein The compound is represented by the following general formula (3): General formula (3) 4. The compound according to claim 3, wherein R is a hydrogen atom or a deuterium atom, and Ar is a phenyl group which may be substituted or unsubstituted by a substituent selected from the group consisting of an alkyl group, an aryl group, an alkoxy group, an alkylthio group, and a cyano group.

5. The compound according to any one of claims 1 to 3, wherein The heterocyclic-condensed carbazole-9-yl group has an aryl group as a substituent.

6. The compound according to any one of claims 1 to 3, wherein The heterocyclic ring fused to the carbazole-9-yl group of the heterocyclic-fused carbazole-9-yl group is a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring or a substituted or unsubstituted pyrrole ring, and other rings may be further fused to the furan ring, the thiophene ring and the pyrrole ring or not.

7. The compound according to any one of claims 1 to 3, wherein The heterocyclic fused carbazole-9-yl group has any of the following structures, In the above structures, the hydrogen atoms may be substituted with a substituent selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group and a cyano group, or may be unsubstituted, but may not be further condensed with a heterocyclic ring.

8. The compound according to any one of claims 1 to 3, wherein The heterocyclic fused carbazole-9-yl group has any of the following structures, In the above structures, the hydrogen atoms may be substituted with a substituent selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group and a cyano group, or may be unsubstituted, but may not be further condensed with a heterocyclic ring.

9. The compound according to any one of claims 1 to 3, wherein The heterocyclic fused carbazole-9-yl group has any of the following structures, In the above structures, the hydrogen atom is substituted or unsubstituted by a substituent selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group and a cyano group, but is not further condensed with a heterocyclic ring, and R' represents a hydrogen atom or an aryl group substituted or unsubstituted by a substituent selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group and a cyano group.

10. The compound according to any one of claims 1 to 3, wherein The carbazole-9-yl group of the heterocyclic-fused carbazole-9-yl group has two heterocyclic rings selected from the group consisting of a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring and a substituted or unsubstituted pyrrole ring fused thereto, and other rings may or may not be further fused to the furan ring, the thiophene ring and the pyrrole ring.

11. The compound according to any one of claims 1 to 3, wherein The heterocyclic-fused carbazole-9-yl group has a structure in which a heterocyclic ring is fused at the 1 and 2 positions of the carbazole ring.

12. The compound according to any one of claims 1 to 3, wherein The heterocyclic-fused carbazole-9-yl group has a structure in which a heterocyclic ring is fused at the 2 and 3 positions of the carbazole ring.

13. The compound according to any one of claims 1 to 3, wherein The heterocyclic-fused carbazole-9-yl group has a structure in which a heterocyclic ring is fused at the 3 and 4 positions of the carbazole ring.

14. The compound according to any one of claims 1 to 3, wherein R and Ar are different.

15. The compound according to any one of claims 1 to 3, wherein R is a hydrogen atom or a deuterium atom.

16. The compound according to any one of claims 1 to 3, wherein Ar is a phenyl group which may be substituted by a substituent selected from the group consisting of an alkyl group, an aryl group, an alkoxy group, an alkylthio group, and a cyano group. 17 . The compound according to claim 1 , which is composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

18. Use of the compound according to any one of claims 1 to 17 as a light-emitting material.

19. A light emitting element, characterized in that: Comprising the compound according to any one of claims 1 to 17.

20. The light emitting element according to claim 19, wherein The light-emitting element includes a light-emitting layer containing the compound and a host material.

21. The light emitting element according to claim 20, wherein The light-emitting element has a light-emitting layer containing the compound and a light-emitting material, and emits light mainly from the light-emitting material.

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