WO2014168101A1 - Matériau luminescent, élément électroluminescent organique, et composé - Google Patents

Matériau luminescent, élément électroluminescent organique, et composé Download PDF

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WO2014168101A1
WO2014168101A1 PCT/JP2014/060051 JP2014060051W WO2014168101A1 WO 2014168101 A1 WO2014168101 A1 WO 2014168101A1 JP 2014060051 W JP2014060051 W JP 2014060051W WO 2014168101 A1 WO2014168101 A1 WO 2014168101A1
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セヨン イ
琢麿 安田
安達　千波矢
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国立大学法人九州大学
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Definitions

  • the present invention relates to a compound useful as a light emitting material and an organic light emitting device using the compound.
  • organic light emitting devices such as organic electroluminescence devices (organic EL devices)
  • organic electroluminescence devices organic electroluminescence devices
  • various efforts have been made to increase the light emission efficiency by newly developing and combining electron transport materials, hole transport materials, light emitting materials, and the like constituting the organic electroluminescence element.
  • research on organic electroluminescence devices using fluorenone derivatives can also be found.
  • Non-Patent Document 1 describes the results of studying the solution emission characteristics of a compound in which a diarylamino group is introduced into at least one of 2-position or 7-position of fluorenone. According to this document, it is described that when a hexane or acetonitrile solution of a fluorenone derivative having the following structure was irradiated with excitation light, light emission was observed in the visible region. However, Patent Document 1 does not describe the light emission characteristics of compounds having a similar skeleton other than fluorenone.
  • Patent Document 1 discloses an example in which a compound represented by the following general formula is used as a host material in a light emitting layer existing between a pair of electrodes constituting an organic electroluminescent element, or a hole injection layer. Examples used are described in.
  • R 1 to R 24 in the following general formula are each a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group, an aliphatic heterocyclic group, an aromatic heterocyclic group, a cyano group, an alkoxyl group, an aryl group, It is defined to represent a ruoxy group, an alkylthio group, an arylthio group, a substituted amino group, an acyl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group.
  • Patent Document 1 does not describe the light emission characteristics of the compound represented by this general formula.
  • Non-Patent Document 1 describes that a compound in which a diarylamino group is introduced into a fluorenone skeleton can be used as a light emitting material.
  • the present inventors actually evaluated the light emission characteristics of a compound in which a diarylamino group was introduced into the fluorenone skeleton, the light emission characteristics were not sufficiently satisfactory (see Comparative Example 1 below), which was more excellent. It has been found that there is a need to provide a luminescent material having good luminescent properties.
  • Patent Document 1 describes that a compound having a benzophenone skeleton is useful as a host material for a light emitting layer of an organic electroluminescence device or a hole transport material for a hole injection layer.
  • a compound having a benzophenone skeleton is useful as a host material for a light emitting layer of an organic electroluminescence device or a hole transport material for a hole injection layer.
  • no investigation has been made as to whether or not the compound described in Patent Document 1 can function as a light-emitting material.
  • Patent Document 1 Since the light-emitting material is different in required properties and functions from the host material and the hole transport material, the usefulness of the compound represented by the general formula of Patent Document 1 as the light-emitting material is unknown. Patent Document 1 does not describe a compound in which a substituted amino group other than carbazol-9-yl group is bonded to benzophenone. For this reason, some benzophenone derivatives substituted with a substituted amino group other than the carbazol-9-yl group have not been synthesized, and their usefulness as a light-emitting material cannot be predicted.
  • the present inventors have further studied the usefulness of benzophenone derivatives as luminescent materials, and have conducted research aimed at finding compounds with excellent luminescent properties. And the general formula of the compound useful as a luminescent material was derived, and the earnest examination was advanced for the purpose of generalizing the structure of the organic light emitting element with high luminous efficiency.
  • a light emitting material comprising a compound represented by the following general formula (1).
  • R 1 to R 10 each independently represents a hydrogen atom or a substituent. However, at least one of R 1 to R 10 is each independently a group represented by the following general formula (2).
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 are bonded to each other. Thus, a ring structure may be formed.
  • R 11 to R 20 each independently represents a hydrogen atom or a substituent.
  • R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 And R 20 may be bonded to each other to form a cyclic structure.
  • Ph represents a substituted or unsubstituted phenylene group.
  • n1 represents 0 or 1.
  • Ph represents a substituted or unsubstituted phenylene group.
  • n1 represents 0 or 1.
  • [3] It is characterized in that at least one of R 1 to R 5 of the general formula (1) and at least one of R 6 to R 10 are a group represented by the general formula (2).
  • [4] The luminescent material according to [3], wherein R 3 and R 8 in the general formula (1) are groups represented by the general formula (2).
  • [5] The luminescence according to any one of [1] to [4], wherein the group represented by the general formula (2) is a group represented by the general formula (4) material.
  • An organic light emitting device comprising the light emitting material according to any one of [1] to [9].
  • [12] [2] The organic light-emitting device according to [11], wherein the organic light-emitting device includes two or more light-emitting materials represented by the general formula (1) having different emission peak wavelengths.
  • the organic light-emitting device according to any one of [11] to [13], wherein the organic light-emitting device is an organic electroluminescence device.
  • R 1 ′ to R 10 ′ each independently represents a hydrogen atom or a substituent. However, at least one of R 1 ′ to R 10 ′ is independently a group represented by the following general formula (2 ′).
  • R 1 'and R 2', R 2 'and R 3', R 3 'and R 4', R 4 'and R 5', R 6 'and R 7', R 7 'and R 8', R 8 'And R 9 ' and R 9 'and R 10 ' may be bonded to each other to form a cyclic structure.
  • R 11 ′ to R 20 ′ each independently represents a hydrogen atom or a substituent.
  • R 11 'and R 12', R 12 'and R 13', R 13 'and R 14', R 14 'and R 15', 'R 16 and' R 15, R 16 'and R 17', R 17 'And R 18 ', R 18 'and R 19 ', R 19 'and R 20 ' may be bonded to each other to form a cyclic structure.
  • R 13 ′ and R 18 ′ are each independently a hydrogen atom or any one of the general formulas (4) to (8).
  • At least one of the groups is a group represented by any one of the general formulas (4) to (8).
  • Ph ′ represents a substituted or unsubstituted phenylene group.
  • n1 ′ represents 0 or 1.
  • the compound of the present invention is useful as a light emitting material.
  • the compounds of the present invention include those that emit delayed fluorescence.
  • An organic light emitting device using the compound of the present invention as a light emitting material can realize high luminous efficiency.
  • FIG. 2 is an emission spectrum of Compound 1 of Example 1.
  • 2 is a transient decay curve of a thin film type organic photoluminescence device of Compound 1 of Example 1.
  • FIG. 2 is a transient decay curve of a thin film type organic photoluminescence device of Compound 1 of Example 1.
  • FIG. 2 is an emission lifetime spectrum of Compound 1 of Example 1.
  • 2 is a cyclic voltammogram of Compound 1 of Example 1.
  • FIG. 2 is an emission spectrum of Compound 2 of Example 2.
  • 2 is a transient decay curve of a thin film type organic photoluminescence device of Compound 2 of Example 2.
  • 2 is a transient decay curve of a thin film type organic photoluminescence device of Compound 2 of Example 2.
  • 2 is a transient decay curve of a thin film type organic photoluminescence device of Compound 2 of Example 2.
  • 2 is an emission lifetime spectrum of Compound 2 of Example 2.
  • 2 is a cyclic voltammogram of Compound 2 of Example 2.
  • 2 is an emission spectrum of compound 3 of Example 3.
  • 4 is a transient decay curve of a solution of compound 3 of Example 3. 4 is a transient decay curve of a thin film type organic photoluminescence device of Compound 3 of Example 3.
  • 2 is an emission lifetime spectrum of the compound 3 of Example 3.
  • 2 is a cyclic voltammogram of Compound 3 of Example 3. 2 is an emission spectrum of compounds 17 and 18 of Examples 4 and 5.
  • FIG. 2 is an emission lifetime spectrum of the compound 18 of Example 5.
  • 2 is a cyclic voltammogram of compound 18 of Example 5.
  • 3 is a transient decay curve of a thin film type organic photoluminescence device of Comparative Compound A of Comparative Example 1.
  • 2 is an emission spectrum of an organic electroluminescent element of Compound 1 of Example 6.
  • 6 is a graph showing voltage-current density-luminescence intensity characteristics of an organic electroluminescence device of Compound 1 of Example 6.
  • 6 is a graph showing current density-external quantum efficiency characteristics of an organic electroluminescence device of Compound 1 of Example 6.
  • FIG. 7 is an emission spectrum of an organic electroluminescent element of the compound 2 of Example 7.
  • 6 is a graph showing voltage-current density-luminescence intensity characteristics of an organic electroluminescent device of Compound 2 of Example 7.
  • 6 is a graph showing the current density-external quantum efficiency characteristics of the organic electroluminescence device of Compound 2 of Example 7.
  • 7 is an emission spectrum of an organic electroluminescent device of Compound 3 in Example 8.
  • FIG. 7 is a graph showing voltage-current density-luminescence intensity characteristics of an organic electroluminescence device of Compound 3 of Example 8.
  • 10 is a graph showing current density-external quantum efficiency characteristics of an organic electroluminescent device of Compound 3 of Example 8. It is an emission spectrum of the organic electroluminescent element of the compounds 17 and 18 of Examples 9 and 10.
  • 4 is a graph showing voltage-current density-luminescence intensity characteristics of organic electroluminescence elements of compounds 17 and 18 of Examples 9 and 10. It is a graph which shows the current density-external quantum efficiency characteristic of the organic electroluminescent element of the compounds 17 and 18 of Example 9, 10.
  • a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the isotope species of the hydrogen atom present in the molecule of the compound used in the present invention is not particularly limited. For example, all the hydrogen atoms in the molecule may be 1 H, or a part or all of them are 2 H. (Deuterium D) may be used.
  • the luminescent material of the present invention is characterized by comprising a compound represented by the following general formula (1).
  • R 1 to R 10 each independently represents a hydrogen atom or a substituent. However, at least one of R 1 to R 10 is each independently a group represented by the following general formula (2).
  • the group represented by the following general formula (2) may be only one of R 1 to R 10 , or may be two or more.
  • R 2 or R 3 is preferably a group represented by the following general formula (2).
  • R 3 is more preferably a group represented by the following general formula (2).
  • the group represented by the following general formula (2) is at least one of R 1 to R 5 .
  • R 6 to R 10 Preferably, one and at least one of R 6 to R 10 .
  • the group represented by the following general formula (2) is one-fourth of the R 1 to R 5, preferably 1 to be four of R 6 - R 10, R 1 More preferably, it is 1 or 2 of R 5 and 1 or 2 of R 6 to R 10 .
  • the number of groups represented by general formula (2) in R 1 to R 5 and the number of groups represented by general formula (2) in R 6 to R 10 may be the same or different. Good, but preferably the same.
  • at least one of R 2 to R 4 is preferably a group represented by the general formula (2), and at least R 3 is a group represented by the general formula (2). It is more preferable.
  • R 7 to R 9 is preferably a group represented by the general formula (2), and at least R 8 is a group represented by the general formula (2).
  • Preferred compounds are those in which R 3 and R 8 in the general formula (1) are groups represented by the general formula (2), and R 2 and R 9 in the general formula (1) are represented by the general formula (2).
  • the groups represented by the plurality of general formulas (2) present in the general formula (1) may be the same or different, but are preferably the same.
  • the group represented by the general formula (1) has a symmetrical structure. That is, R 1 and R 10 , R 2 and R 9 , R 3 and R 8 , R 4 and R 7 , and R 5 and R 6 are preferably the same.
  • R 11 to R 20 each independently represents a hydrogen atom or a substituent.
  • the number of substituents is not particularly limited, and all of R 11 to R 20 may be unsubstituted (that is, hydrogen atoms).
  • the plurality of substituents may be the same as or different from each other.
  • the substituent that R 11 to R 20 can take and the substituent that R 1 to R 10 can take include, for example, a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, and an alkoxy group having 1 to 20 carbon atoms.
  • substituents are a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, carbon A substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, and a dialkyl-substituted amino group having 1 to 20 carbon atoms.
  • substituents are a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, carbon A substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, and a dialkyl-substituted amino group having 1 to 20 carbon
  • substituents are a fluorine atom, a chlorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, and a substituted group having 6 to 15 carbon atoms.
  • it is an unsubstituted aryl group or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 11 And R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 may be bonded to each other to form a cyclic structure.
  • the cyclic structure may be an aromatic ring or an alicyclic ring, may contain a hetero atom, and the cyclic structure may be a condensed ring of two or more rings.
  • the hetero atom here is preferably selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom.
  • cyclic structures formed include benzene ring, naphthalene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring, imidazoline ring, oxazole ring, isoxazole ring, thiazole And a ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentaene ring, a cycloheptatriene ring, a cycloheptadiene ring, and a cycloheptaene ring.
  • Ph represents a substituted or unsubstituted phenylene group.
  • the phenylene group may be any of 1,2-phenylene group, 1,3-phenylene group, and 1,4-phenylene group. More preferred is a 1,4-phenylene group.
  • the hydrogen atom of the phenylene group may be substituted with a substituent.
  • the substituents described above are the substituents that R 11 to R 20 can take and the substituents that R 1 to R 10 can take. A substituent can be mentioned.
  • n1 represents 0 or 1.
  • the group represented by the general formula (2) is preferably a group represented by any one of the following general formulas (3) to (8).
  • R 21 to R 24 , R 27 to R 38 , R 41 to R 48 , R 51 to R 58 , R 61 to R 65 , R 71 to R 79 , R 81 to R 90 each independently represents a hydrogen atom or a substituent.
  • R 21 to R 24 , R 27 to R 38 , R 41 to R 48 , R 51 to R 58 , R 61 to R 65 , R 71 to R 79 , R 81 to R 90 each independently represents a hydrogen atom or a substituent.
  • R 21 to R 24 , R 27 to R 38 , R 41 to R 48 , R 51 to R 58 , R 61 to R 65 , R 71 to R 79 , R 81 to R 90 A group represented by any one of formulas (3) to (8) is also preferred.
  • R 89 and R 90 are preferably a substituted or unsubstituted alkyl group, and more preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
  • the number of substituents in the general formulas (3) to (8) is not particularly limited. It is also preferred that all are unsubstituted (ie hydrogen atoms). Further, when each of the general formulas (3) to (8) has two or more substituents, these substituents may be the same or different.
  • the substituent is preferably any one of R 22 to R 24 and R 27 to R 29 in the case of the general formula (3). , R 23 and R 28 are more preferable.
  • any one of R 32 to R 37 is preferable, and in the general formula (5), R 42 to Any one of R 47 is preferable, and in the case of the general formula (6), any of R 52 , R 53 , R 56 , R 57 , R 62 to R 64 is preferable, and the general formula (7) If it is, it is preferably any one of R 72 to R 74 , R 77 and R 78 , and if it is general formula (8), it is preferably any one of R 82 to R 87 , R 89 and R 90. .
  • Ph represents a substituted or unsubstituted phenylene group
  • n1 represents 0 or 1.
  • the explanation of Ph and the preferred positional isomer can be referred to.
  • All the groups represented by the general formula (2) present in the general formula (1) are preferably groups represented by any one of the general formulas (3) to (8).
  • the case where it is group represented by General formula (3) and the case where all are represented by General formula (4) can be illustrated preferably.
  • the compound represented by the general formula (1) is preferably a compound represented by the general formulas (9) to (24), and the general formulas (9), (13), (16), (19 It is more preferable that it is a compound represented by.
  • R 105 to R 137 are each independently groups represented by the following formulas (25) to (32), and may be groups represented by the formula (27). preferable.
  • the plurality of R present in the general formulas (9), (10), (13) to (24) may be the same or different, but are preferably the same.
  • R 105 and R 106 in the general formula (9) may be the same or different, but are preferably the same.
  • R 138 to R 141 each independently represents a hydrogen atom or a substituent.
  • R 138 to R 141 each independently represents a hydrogen atom or a substituent.
  • the molecular weight of the compound represented by the general formula (1) is, for example, 1500 or less when the organic layer containing the compound represented by the general formula (1) is intended to be formed by vapor deposition. Preferably, it is preferably 1200 or less, more preferably 1000 or less, and even more preferably 800 or less.
  • the lower limit of the molecular weight is the molecular weight of the minimum compound represented by the general formula (1).
  • the compound represented by the general formula (1) may be formed by a coating method regardless of the molecular weight. If a coating method is used, a film can be formed even with a compound having a relatively large molecular weight.
  • a compound containing a plurality of structures represented by the general formula (1) in the molecule as a light emitting material.
  • a polymer obtained by previously polymerizing a polymerizable group in the structure represented by the general formula (1) and polymerizing the polymerizable group as a light emitting material.
  • a monomer containing a polymerizable functional group in any of R 1 to R 10 in the general formula (1) and polymerizing it alone or copolymerizing with other monomers, It is conceivable to obtain a polymer having a repeating unit and use the polymer as a light emitting material.
  • dimers and trimers are obtained by reacting compounds having a structure represented by the general formula (1) and used as a luminescent material.
  • Examples of the polymer having a repeating unit containing a structure represented by the general formula (1) include a polymer containing a structure represented by the following general formula (33) or (34).
  • Q represents a group including the structure represented by General Formula (1)
  • L 1 and L 2 represent a linking group.
  • the linking group preferably has 0 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and still more preferably 2 to 10 carbon atoms. And preferably has a structure represented by - linking group -X 11 -L 11.
  • X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
  • L 11 represents a linking group, preferably a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted group A phenylene group is more preferable.
  • R 101 , R 102 , R 103 and R 104 each independently represent a substituent.
  • 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, and a chlorine atom and more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms and an unsubstituted alkoxy group having 1 to 3 carbon atoms.
  • the linking group represented by L 1 and L 2 is any one of R 1 to R 10 in the structure of general formula (1) constituting Q, any of R 11 to R 20 in general formula (2), One of R 21 to R 24 and R 27 to R 30 having the structure of the formula (3), one of R 31 to R 38 having the structure of the general formula (4), R 41 to the structure of the general formula (5) Any of R 48 , any of R 51 to R 58 and R 61 to R 65 having the structure of the general formula (6), any of R 71 to R 78 having the structure of the general formula (7), general formula (8 ) Can be bonded to any one of R 81 to R 90 of the structure.
  • Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.
  • repeating unit examples include structures represented by the following formulas (35) to (38).
  • a hydroxy group is introduced into any one of R 1 to R 10 of the structure of the general formula (1), and this is used as a linker as described below. It can be synthesized by reacting a compound to introduce a polymerizable group and polymerizing the polymerizable group.
  • the polymer containing a structure represented by the general formula (1) in the molecule may be a polymer consisting only of a repeating unit having the structure represented by the general formula (1), or other structures may be used. It may be a polymer containing repeating units.
  • the repeating unit having a structure represented by the general formula (1) contained in the polymer may be a single type or two or more types. Examples of the repeating unit not having the structure represented by the general formula (1) include those derived from monomers used in ordinary copolymerization. Examples thereof include a repeating unit derived from a monomer having an ethylenically unsaturated bond such as ethylene and styrene.
  • R 1 ′ to R 10 ′ each independently represents a hydrogen atom or a substituent. However, at least one of R 1 ′ to R 10 ′ is independently a group represented by the following general formula (2 ′).
  • R 11 ′ to R 20 ′ each independently represents a hydrogen atom or a substituent.
  • R 13 ′ and R 18 ′ are each independently a hydrogen atom or any one of the above general formulas (4) to (8).
  • Ph ′ represents a substituted or unsubstituted phenylene group
  • n1 represents 0 or 1.
  • R 13 ′ and R 18 ′ are each independently represented by a hydrogen atom or any one of the general formulas (4) to (8). At least one of them is a group represented by any one of the general formulas (4) to (8).
  • R 1 ′ to R 10 ′, R 11 ′ to R 20 ′, and Ph ′ in the general formula (1 ′) refer to the description of the compound represented by the general formula (1). it can.
  • R 1 ′, R 2 ′, R 4 ′ to R 7 ′, R 9 ′ to R 20 ′ in the above reaction formula the corresponding description in the general formula (1 ′) can be referred to.
  • X represents a halogen atom, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a chlorine atom, a bromine atom, and an iodine atom are preferable.
  • the above reaction is an application of a known reaction, and known reaction conditions can be appropriately selected and used. The details of the above reaction can be referred to the synthesis examples described below.
  • the compound represented by the general formula (1 ′) can also be synthesized by combining other known synthesis reactions.
  • the compound represented by the general formula (1) of the present invention is useful as a light emitting material of an organic light emitting device. For this reason, the compound represented by General formula (1) of this invention can be effectively used as a luminescent material for the light emitting layer of an organic light emitting element.
  • the compound represented by the general formula (1) includes a delayed fluorescent material (delayed phosphor) that emits delayed fluorescence. That is, the present invention relates to a delayed phosphor having a structure represented by the general formula (1), an invention using a compound represented by the general formula (1) as a delayed phosphor, and a general formula (1).
  • An invention of a method for emitting delayed fluorescence using the represented compound is also provided.
  • An organic light emitting device using such a compound as a light emitting material emits delayed fluorescence and has a feature of high luminous efficiency. The principle will be described below by taking an organic electroluminescence element as an example.
  • the organic electroluminescence element carriers are injected into the light emitting material from both positive and negative electrodes to generate an excited light emitting material and emit light.
  • 25% of the generated excitons are excited to the excited singlet state, and the remaining 75% are excited to the excited triplet state. Therefore, the use efficiency of energy is higher when phosphorescence, which is light emission from an excited triplet state, is used.
  • the excited triplet state has a long lifetime, energy saturation occurs due to saturation of the excited state and interaction with excitons in the excited triplet state, and in general, the quantum yield of phosphorescence is often not high.
  • delayed fluorescent materials after energy transition to an excited triplet state due to intersystem crossing, etc., are then crossed back to an excited singlet state due to triplet-triplet annihilation or absorption of thermal energy, and emit fluorescence.
  • a thermally activated delayed fluorescent material by absorption of thermal energy is particularly useful.
  • excitons in the excited singlet state emit fluorescence as usual.
  • excitons in the excited triplet state absorb heat generated by the device and cross between the excited singlets to emit fluorescence.
  • the light is emitted from the excited singlet, the light is emitted at the same wavelength as the fluorescence, but the light lifetime (luminescence lifetime) generated by the reverse intersystem crossing from the excited triplet state to the excited singlet state is normal. Since the fluorescence becomes longer than the fluorescence and phosphorescence, it is observed as fluorescence delayed from these. This can be defined as delayed fluorescence. If such a heat-activated exciton transfer mechanism is used, the ratio of the compound in an excited singlet state, which normally generated only 25%, is increased to 25% or more by absorbing thermal energy after carrier injection. It can be raised.
  • the heat of the device will sufficiently cause intersystem crossing from the excited triplet state to the excited singlet state and emit delayed fluorescence. Efficiency can be improved dramatically.
  • the compound represented by the general formula (1) of the present invention as a light-emitting material of a light-emitting layer, excellent organic light-emitting devices such as an organic photoluminescence device (organic PL device) and an organic electroluminescence device (organic EL device) Can be provided.
  • the compound represented by the general formula (1) of the present invention may have a function of assisting light emission of another light emitting material included in the light emitting layer as a so-called assist dopant. That is, the compound represented by the general formula (1) of the present invention contained in the light emitting layer includes the lowest excitation singlet energy level of the host material contained in the light emitting layer and the lowest excitation of other light emitting materials contained in the light emitting layer.
  • the organic photoluminescence element has a structure in which at least a light emitting layer is formed on a substrate.
  • the organic electroluminescence element has a structure in which an organic layer is formed at least between an anode, a cathode, and an anode and a cathode.
  • the organic layer includes at least a light emitting layer, and may consist of only the light emitting layer, or may have one or more organic layers in addition to the light emitting layer.
  • examples of such other 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.
  • the hole transport layer may be a hole injection / transport layer having a hole injection function
  • the electron transport layer may be an electron injection / transport layer having an electron injection function.
  • 1, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light emitting layer, 6 is an electron transport layer, and 7 is a cathode.
  • each member and each layer of an organic electroluminescent element are demonstrated.
  • substrate and a light emitting layer corresponds also to the board
  • the organic electroluminescence device of the present invention is preferably supported on a substrate.
  • the substrate is not particularly limited and may be any substrate conventionally used for organic electroluminescence elements.
  • a substrate made of glass, transparent plastic, quartz, silicon, or the like can be used.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) that can form a transparent conductive film may be used.
  • a thin film may be formed by vapor deposition or sputtering of these electrode materials, and a pattern of a desired shape may be formed by photolithography, or when pattern accuracy is not so high (about 100 ⁇ m or more) ), A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • wet film-forming methods such as a printing system and a coating system, can also be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this for example, a magnesium / silver mixture
  • Suitable are a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3 ) mixture, a lithium / aluminum mixture, aluminum and the like.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • the emission luminance is advantageously improved.
  • a transparent or semi-transparent cathode can be produced. By applying this, an element in which both the anode and the cathode are transparent is used. Can be produced.
  • the light emitting layer is a layer that emits light after excitons are generated by recombination of holes and electrons injected from each of the anode and the cathode, and the light emitting material may be used alone for the light emitting layer. , Preferably including a luminescent material and a host material.
  • a luminescent material the 1 type (s) or 2 or more types chosen from the compound group of this invention represented by General formula (1) can be used.
  • a host material in addition to the light emitting material in the light emitting layer.
  • the host material an organic compound having at least one of excited singlet energy and excited triplet energy higher than that of the light emitting material of the present invention can be used.
  • singlet excitons and triplet excitons generated in the light emitting material of the present invention can be confined in the molecules of the light emitting material of the present invention, and the light emission efficiency can be sufficiently extracted.
  • high luminous efficiency can be obtained, so that host materials that can achieve high luminous efficiency are particularly limited. And can be used in the present invention.
  • the organic light emitting device or organic electroluminescent device of the present invention light emission is generated from the light emitting material of the present invention contained in the light emitting layer. This emission includes both fluorescence and delayed fluorescence. However, light emission from the host material may be partly or partly emitted.
  • the amount of the compound of the present invention, which is a light emitting material is preferably 0.1% by weight or more, more preferably 1% by weight or more, and 50% or more. It is preferably no greater than wt%, more preferably no greater than 20 wt%, and even more preferably no greater than 10 wt%.
  • the host material in the light-emitting layer is preferably an organic compound that has a hole transporting ability and an electron transporting ability, prevents the emission of longer wavelengths, and has a high glass transition temperature.
  • the injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the luminance of light emission.
  • the injection layer can be provided as necessary.
  • the blocking layer is a layer that can prevent diffusion of charges (electrons or holes) and / or excitons existing in the light emitting layer to the outside of the light emitting layer.
  • the electron blocking layer can be disposed between the light emitting layer and the hole transport layer and blocks electrons from passing through the light emitting layer toward the hole transport layer.
  • a hole blocking layer can be disposed between the light emitting layer and the electron transporting layer to prevent holes from passing through the light emitting layer toward the electron transporting layer.
  • the blocking layer can also be used to block excitons from diffusing outside the light emitting layer. That is, each of the electron blocking layer and the hole blocking layer can also function as an exciton blocking layer.
  • the term “electron blocking layer” or “exciton blocking layer” as used herein is used in the sense of including a layer having the functions of an electron blocking layer and an exciton blocking layer in one layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense.
  • the hole blocking layer has a role of blocking holes from reaching the electron transport layer while transporting electrons, thereby improving the recombination probability of electrons and holes in the light emitting layer.
  • the material for the hole blocking layer the material for the electron transport layer described later can be used as necessary.
  • the electron blocking layer has a function of transporting holes in a broad sense.
  • the electron blocking layer has a role to block electrons from reaching the hole transport layer while transporting holes, thereby improving the probability of recombination of electrons and holes in the light emitting layer. .
  • the exciton blocking layer is a layer for preventing excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer. It becomes possible to efficiently confine in the light emitting layer, and the light emission efficiency of the device can be improved.
  • the exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both can be inserted simultaneously.
  • the layer when the exciton blocking layer is provided on the anode side, the layer can be inserted adjacent to the light emitting layer between the hole transport layer and the light emitting layer, and when inserted on the cathode side, the light emitting layer and the cathode Between the luminescent layer and the light-emitting layer.
  • a hole injection layer, an electron blocking layer, or the like can be provided between the anode and the exciton blocking layer adjacent to the anode side of the light emitting layer, and the excitation adjacent to the cathode and the cathode side of the light emitting layer can be provided.
  • an electron injection layer, an electron transport layer, a hole blocking layer, and the like can be provided.
  • the blocking layer is disposed, at least one of the excited singlet energy and the excited triplet energy of the material used as the blocking layer is preferably higher than the excited singlet energy and the excited triplet energy of the light emitting material.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has any one of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
  • hole transport materials that can be used include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, Examples include amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • An aromatic tertiary amine compound and an styrylamine compound are preferably used, and an aromatic tertiary amine compound is more preferably used.
  • the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.
  • the electron transport material (which may also serve as a hole blocking material) may have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • Examples of the electron transport layer that can be used include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide oxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • the compound represented by the general formula (1) may be used not only for the light emitting layer but also for layers other than the light emitting layer.
  • the compound represented by General formula (1) used for a light emitting layer and the compound represented by General formula (1) used for layers other than a light emitting layer may be same or different.
  • the compound represented by the general formula (1) may be used for the injection layer, blocking layer, hole blocking layer, electron blocking layer, exciton blocking layer, hole transporting layer, electron transporting layer, and the like. .
  • the method for forming these layers is not particularly limited, and the layer may be formed by either a dry process or a wet process.
  • the preferable material which can be used for an organic electroluminescent element is illustrated concretely.
  • the material that can be used in the present invention is not limited to the following exemplary compounds. Moreover, even if it is a compound illustrated as a material which has a specific function, it can also be diverted as a material which has another function.
  • R and R 2 to R 7 each independently represent a hydrogen atom or a substituent.
  • n represents an integer of 3 to 5.
  • the organic electroluminescence device produced by the above-described method emits light by applying an electric field between the anode and the cathode of the obtained device. At this time, if the light is emitted by excited singlet energy, light having a wavelength corresponding to the energy level is confirmed as fluorescence emission and delayed fluorescence emission. In addition, in the case of light emission by excited triplet energy, a wavelength corresponding to the energy level is confirmed as phosphorescence. Since normal fluorescence has a shorter fluorescence lifetime than delayed fluorescence, the emission lifetime can be distinguished from fluorescence and delayed fluorescence.
  • the excited triplet energy is unstable and is converted into heat and the like, and the lifetime is short and it is immediately deactivated.
  • the excited triplet energy of a normal organic compound it can be measured by observing light emission under extremely low temperature conditions.
  • the organic electroluminescence element of the present invention can be applied to any of a single element, an element having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix.
  • an organic light emitting device with greatly improved light emission efficiency can be obtained by containing the compound represented by the general formula (1) in the light emitting layer.
  • the organic light emitting device such as the organic electroluminescence device of the present invention can be further applied to various uses. For example, it is possible to produce an organic electroluminescence display device using the organic electroluminescence element of the present invention. For details, see “Organic EL Display” (Ohm Co., Ltd.) ) Can be referred to.
  • the organic electroluminescence device of the present invention can be applied to organic electroluminescence illumination and backlights that are in great demand.
  • source meter manufactured by Keithley: 2400 series
  • semiconductor parameter analyzer manufactured by Agilent Technologies: E5273A
  • optical power meter measuring device manufactured by Newport: 1930C
  • optical spectrometer Ocean Optics, USB2000
  • spectroradiometer Topcon, SR-3
  • streak camera Haamamatsu Photonics C4334
  • the organic layer and the aqueous layer were separated, sodium sulfate was added to the organic layer for drying, and suction filtration was performed to obtain a filtrate.
  • the obtained filtrate was purified by column chromatography, and 4,4-bis (10H-phenoxazine) benzophenone was obtained in a yield of 1.42 g and a yield of 88.7%.
  • the compound was identified by 1 H-NMR and elemental analysis.
  • This mixture was stirred at 100 ° C. for 5 hours under a nitrogen atmosphere. After a predetermined time, chloroform was added to the mixture and stirred. After stirring, the mixture was suction filtered through celite, Florisil, and alumina to obtain a filtrate. The obtained filtrate was transferred to a separatory funnel and washed with water and saturated brine. After washing, magnesium sulfate was added to the organic layer and dried. After drying, the mixture was suction filtered to obtain a filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography.
  • the solid obtained by concentrating the obtained fraction was recrystallized with a mixed solvent of acetone and isopropanol. As a result, 1.98 g, 71.2%, of the desired pale yellow powdery solid was obtained.
  • the compound was identified by 1 H-NMR and elemental analysis.
  • 1,3-bis ⁇ 4- (10H-phenoxazin-10-yl) benzoyl ⁇ benzene is a method for synthesizing 1,4-bis (4-bromo) instead of 1,3-bis (4-bromobenzoyl) benzene. Synthesis was performed using benzoyl) benzene, and 1.4-bis [4- (10-phenoxazin-10-yl) benzoyl] benzene was obtained in a yield of 1.20 g and a yield of 84.0%. The compound was identified by 1 H-NMR and elemental analysis.
  • the compound 1 was synthesized using 1,3-bis (4-bromobenzoyl) benzene in place of 4,4′-dibromobenzophenone, and 1,3-bis [4- (10-phenoxazine) was synthesized.
  • -10-yl) benzoyl] benzene was obtained in a yield of 1.40 g and a yield of 96.0%.
  • the compound was identified by 1 H-NMR and elemental analysis.
  • Example 1 Production and Evaluation of Organic Photoluminescence Element Using Compound 1
  • a toluene solution of compound 1 (concentration 10 ⁇ 4 mol / L) was prepared in a glove box under an Ar atmosphere. Further, a thin film of Compound 1 having a thickness of 50 nm was formed on a quartz substrate by a vacuum vapor deposition method under a vacuum degree of 10 ⁇ 4 Pa or less to obtain an organic photoluminescence device.
  • a compound 1 and CBP or mCP are deposited from a different deposition source on a quartz substrate by a vacuum deposition method under a vacuum degree of 10 ⁇ 4 Pa or less, and the concentration of the compound 1 is 6.0 weight.
  • FIG. 2 shows the results of measuring the emission spectrum of the sample using these compounds 1 with 290 nm excitation light.
  • the photoluminescence quantum efficiency is 28.0% for the toluene solution without bubbling, 43.7% for the toluene solution bubbling with nitrogen, 38.0% for the organic photoluminescence device having a thin film of only Compound 1, and the compound 1 and CBP. It was 60.2% for an organic photoluminescence device having a thin film, and 70.2% for an organic photoluminescence device having a thin film of Compound 1 and mCP.
  • FIG. 2 shows the results of measuring the emission spectrum of the sample using these compounds 1 with 290 nm excitation light.
  • the photoluminescence quantum efficiency is 28.0% for the toluene solution without bubbling, 43.7% for the toluene solution bubbling with nitrogen, 38.0% for the organic photoluminescence device having a thin film of only Compound 1, and the compound 1 and CBP. It was 60.2% for an organic photolumin
  • FIG. 3 shows a transient attenuation curve of an organic photoluminescence device having a thin film of only a toluene solution and Compound 1.
  • This transient decay curve shows the result of measuring the luminescence lifetime obtained by measuring the process in which the emission intensity is deactivated by applying excitation light to the compound.
  • the light emission intensity decays in a single exponential manner. This means that if the vertical axis of the graph is semi-log, it will decay linearly.
  • the transient decay curve of Compound 1 shown in FIG. 3 such a linear component (fluorescence) is observed at the beginning of observation, but a component deviating from linearity appears after several ⁇ sec.
  • FIG. 4 shows transient decay curves at 300K, 250K, 200K, 150K, 100K, 50K, and 5K of the organic photoluminescence device having the thin film of Compound 1 and mCP, and the emission lifetime spectrum at 300K is shown in FIG. Shown in From FIG. 4, it was confirmed that the delayed fluorescence component was a thermally activated delayed fluorescence with an increase in temperature.
  • FIG. 6 shows a cyclic voltammogram of Compound 1 in a methylene chloride solution (0.1 mol / L concentration) of tetrabutylammonium perchlorate (TBAP). From FIG. 6, it was confirmed that Compound 1 has good redox characteristics and can realize a good device life.
  • TBAP tetrabutylammonium perchlorate
  • Example 2 Production and Evaluation of Organic Photoluminescence Device Using Compound 2
  • the emission spectrum shown in FIG. 7 was obtained by the same method as in Example 1 except that Compound 2 was used instead of Compound 1. .
  • DPEPO was used without using CBP.
  • the photoluminescence quantum efficiency is 15.2% with a toluene solution without bubbling, 38.3% with a toluene solution bubbling nitrogen, 16.1% with an organic photoluminescence device having a thin film of only Compound 2, and the compound 1 and mCP.
  • the organic photoluminescence device having a thin film was 16.5%
  • the organic photoluminescence device having a thin film of Compound 2 and DPEPO was 57.2% in the air, and 72.7% in a nitrogen atmosphere.
  • FIG. 8 shows a transient attenuation curve of an organic photoluminescence device having a thin film of only a toluene solution and compound 2.
  • FIG. 9 shows transient decay curves of the organic photoluminescence device having a thin film of Compound 2 and DPEPO at temperatures of 350K, 250K, 150K, and 77K, and 300K, 250K, 200K, 150K, 100K, 50K, and 5K.
  • the transient decay curve at each temperature is shown in FIG.
  • the emission lifetime spectrum at 300K is shown in FIG. 9 and 10, it was confirmed that the delayed fluorescence component is a thermally activated type in which the delayed fluorescence component increases with increasing temperature.
  • FIG. 12 shows a cyclic voltammogram of compound 1 in a methylene chloride solution (0.1 mol / L concentration) of tetrabutylammonium perchlorate (TBAP). From FIG. 12, it was confirmed that the compound 2 has good redox characteristics and can realize a good device lifetime.
  • TBAP tetrabutylammonium perchlorate
  • Example 3 Preparation and Evaluation of Organic Photoluminescence Device Using Compound 3
  • chloroform was used as a solvent without using toluene
  • DPEPO was used as a host material without using CBP or mCP.
  • the photoluminescence quantum efficiency is 15.6% in a chloroform solution without bubbling, 21.2% in a chloroform solution bubbling nitrogen, 24.4% in an organic photoluminescence device having a thin film of only Compound 3, and the compound 3 and DPEPO.
  • the organic photoluminescence device having a thin film had a content of 55.0%.
  • a transient decay curve of a methylene chloride solution of Compound 3 is shown in FIG. Further, FIG.
  • FIG. 15 shows transient decay curves at 300 K, 250 K, 200 K, 150 K, 100 K, 50 K, and 5 K of the organic photoluminescence device having the thin film of Compound 3 and DPEPO, and the emission lifetime spectrum at 300 K is shown in FIG. Shown in From FIG. 15, it was confirmed that the delayed fluorescence component is a thermally activated delayed fluorescence that increases with increasing temperature. The emission lifetime of the immediate fluorescence component was 0.02 ms, and the emission lifetime of the delayed fluorescence component was 0.5 ms.
  • FIG. 17 shows a cyclic voltammogram of Compound 3 in a methylene chloride solution (0.1 mol / L concentration) of tetrabutylammonium perchlorate (TBAP). From FIG. 17, it was confirmed that the compound 3 has good redox characteristics and can realize a good device life.
  • TBAP tetrabutylammonium perchlorate
  • Example 4 Production and Evaluation of Organic Photoluminescence Device Using Compound 17
  • a cyclohexane solution of compound 17 (concentration: 10 ⁇ 4 mol / L) was prepared in a glove box under an Ar atmosphere.
  • FIG. 18 shows the result of measuring the emission spectrum of this cyclohexane solution with 290 nm excitation light.
  • FIG. 18 also shows the measurement results of the emission spectra of the cyclohexane solutions (concentration 10 ⁇ 4 mol / L) of the compounds 1 to 3, 18 measured under the same conditions.
  • PL1 to PL3, PL17, and PL18 are emission spectra of cyclohexane solutions of compounds 1 to 3, 17, and 18, respectively.
  • UV1 to UV3, UV17, and UV18 are cyclohexane solutions of compounds 1 to 3, 17, and 18, respectively. It is an absorption spectrum of.
  • a toluene solution and an organic photoluminescence device were produced in the same manner as in Example 1 except that Compound 17 was used instead of Compound 1.
  • mCBP was used without using CBP or mCP as a host material. And the emission spectrum was measured about these samples.
  • the photoluminescence quantum efficiency is 9.1% for a nitrogen-bubbled toluene solution, 1.8% for an organic photoluminescence device having a thin film of compound 17 alone, and 35.9 for an organic photoluminescence device having a thin film of compound 17 and mCBP. %Met.
  • FIG. 19 shows a transient decay curve at 300K, 250K, 200K, 150K, 100K, 50K, and 5K of the organic photoluminescence device having the thin film of Compound 17 and mCBP
  • FIG. 20 shows the emission lifetime spectrum at 300K.
  • FIG. 19 it was confirmed that it was a thermally activated delayed fluorescence in which the delayed fluorescence component increased with increasing temperature.
  • the emission lifetime of the immediate fluorescence component was 0.03 ⁇ s, and the emission lifetime of the delayed fluorescence component was 0.6 ⁇ s.
  • FIG. 21 shows a cyclic voltammogram of compound 17 in a methylene chloride solution (0.1 mol / L concentration) of tetrabutylammonium perchlorate (TBAP). From FIG. 21, it was confirmed that the compound 17 has good redox characteristics and can realize a good device lifetime.
  • TBAP tetrabutylammonium perchlorate
  • Example 5 Production and Evaluation of Organic Photoluminescence Device Using Compound 18
  • a cyclohexane solution (concentration 10 ⁇ 4 mol / L) of compound 18 was prepared in a glove box under an Ar atmosphere.
  • FIG. 18 shows the result of measuring the emission spectrum of this cyclohexane solution with 290 nm excitation light.
  • the point which used the compound 18 instead of the compound 1 was changed, and the toluene solution and the organic photoluminescent element were produced by the same method as Example 1.
  • mCBP was used without using CBP or mCP as a host material. And the emission spectrum was measured about these samples.
  • the photoluminescence quantum efficiency is 36.0% for a toluene solution bubbled with nitrogen, 28.5% for an organic photoluminescence device having a thin film of only Compound 18, and 71.3 for an organic photoluminescence device having a thin film of Compound 18 and mCBP. %Met.
  • FIG. 22 shows a transient decay curve at 300K, 250K, 200K, 150K, 100K, 50K, and 5K of the organic photoluminescence device having the compound 18 and mCBP thin film
  • FIG. 23 shows the emission lifetime spectrum at 300K. . From FIG. 22, it was confirmed that the delayed fluorescence component is a thermally activated delayed fluorescence in which the delayed fluorescence component increases as the temperature rises.
  • FIG. 24 shows a cyclic voltammogram of Compound 17 in a methylene chloride solution (0.1 mol / L concentration) of tetrabutylammonium perchlorate (TBAP). From FIG. 24, it was confirmed that the compound 18 has good redox characteristics and can realize a good device lifetime.
  • TBAP tetrabutylammonium perchlorate
  • FIG. 25 shows a transient decay curve measured for each temperature of 300K and 5K for the organic photoluminescence device in which DPEPO and compound 3 (concentration 6% by weight) were co-evaporated. It was confirmed that the comparative compound A is not a thermally activated fluorescent material. Furthermore, when the photoluminescence quantum efficiency of this organic photoluminescence device was measured, it was as low as 9.4%.
  • Example 6 Production and evaluation of organic electroluminescence device using compound 1 Each thin film was formed by vacuum deposition on a glass substrate on which an anode made of indium tin oxide (ITO) having a thickness of 100 nm was formed. And a degree of vacuum of 5.0 ⁇ 10 ⁇ 4 Pa. First, ⁇ -NPD was formed to a thickness of 40 nm on ITO. Next, Compound 1 and mCP were co-evaporated from different vapor deposition sources to form a 20 nm thick layer as a light emitting layer. At this time, the concentration of Compound 1 was 6.0% by weight.
  • ITO indium tin oxide
  • TPBi is formed to a thickness of 40 nm
  • lithium fluoride (LiF) is further vacuum-deposited to 0.8 nm
  • aluminum (Al) is evaporated to a thickness of 80 nm to form a cathode.
  • a luminescence element was obtained.
  • the emission spectrum of the manufactured organic electroluminescence device is shown in FIG. 26, the voltage-current density-luminescence intensity characteristic is shown in FIG. 27, and the current density-external quantum efficiency characteristic is shown in FIG.
  • the organic electroluminescence device using Compound 1 as the light emitting material achieved a high external quantum efficiency of 10.7%.
  • Example 7 Preparation and evaluation of organic electroluminescence device using compound 2 Each thin film was formed by vacuum deposition on a glass substrate on which an anode made of indium tin oxide (ITO) having a thickness of 100 nm was formed. And a degree of vacuum of 5.0 ⁇ 10 ⁇ 4 Pa. First, ⁇ -NPD was formed on ITO to a thickness of 35 nm, and mCP was formed to a thickness of 5 nm. Next, Compound 2 and DPEPO were co-evaporated from different vapor deposition sources to form a 20 nm thick layer as a light emitting layer. At this time, the concentration of Compound 2 was 6.0% by weight.
  • ITO indium tin oxide
  • DPEPO is formed to a thickness of 10 nm
  • TPBi is formed to a thickness of 30 nm
  • lithium fluoride (LiF) is vacuum-deposited to 0.8 nm
  • aluminum (Al) is then deposited to a thickness of 80 nm.
  • a cathode was formed, and an organic electroluminescence element was obtained.
  • the emission spectrum of the produced organic electroluminescence device is shown in FIG. 29, the voltage-current density characteristic is shown in FIG. 30, and the current density-external quantum efficiency-luminescence intensity characteristic is shown in FIG.
  • the organic electroluminescence device using Compound 2 as the light emitting material achieved a high external quantum efficiency of 14.3%. This value greatly exceeds the theoretical limit value (7.5%) of the external quantum efficiency when a normal fluorescent material that does not exhibit delayed fluorescence is used as the light emitting material.
  • Example 8 Production and Evaluation of Organic Electroluminescence Device Using Compound 3
  • An organic electroluminescence device was produced in the same manner as in Example 5 using Compound 3 instead of Compound 2.
  • the emission spectrum of the produced organic electroluminescence device is shown in FIG. 32
  • the voltage-current density characteristic is shown in FIG. 33
  • the current density-external quantum efficiency-luminescence intensity characteristic is shown in FIG.
  • the organic electroluminescence device using Compound 3 as the light emitting material achieved a high external quantum efficiency of 8.1%. This value exceeds the theoretical limit value (7.5%) of the external quantum efficiency when a normal fluorescent material that does not exhibit delayed fluorescence is used as the light emitting material.
  • Example 9 Production and Evaluation of Organic Electroluminescence Device Using Compound 17
  • An organic electroluminescence device was produced in the same manner as in Example 6 using Compound 17 instead of Compound 1. However, when forming the light emitting layer, mCBP was used without using mCP.
  • the emission spectrum of the produced organic electroluminescence device is shown in FIG. 35
  • the voltage-current density-luminescence intensity characteristic is shown in FIG. 36
  • the current density-external quantum efficiency characteristic is shown in FIG.
  • the characteristic represented by a white symbol is a voltage-luminescence intensity characteristic
  • the characteristic represented by a black symbol is a voltage-current density characteristic.
  • the organic electroluminescence device using Compound 17 as the light emitting material achieved a high external quantum efficiency of 6.9%.
  • 35 to 37 show an organic electroluminescent device (compound 18) produced in the same manner except that compound 18 was used instead of compound 17, and an organic electroluminescent device using compound 18 described later (compound 18 alone). ) Characteristics are also shown.
  • Example 10 Production and Evaluation of Organic Electroluminescence Device Using Compound 18
  • An organic electroluminescence device was produced in the same manner as in Example 6 using Compound 18 instead of Compound 1. However, when forming the light emitting layer, a thin film of only compound 18 was formed without using mCP.
  • the emission spectrum of the produced organic electroluminescence device is shown in FIG. 35, the voltage-current density-luminescence intensity characteristic is shown in FIG. 36, and the current density-external quantum efficiency characteristic is shown in FIG. Light emission was observed from the organic electroluminescence device using Compound 18 as the light emitting material.
  • the compound of the present invention is useful as a luminescent material. For this reason, the compound of this invention is effectively used as a luminescent material for organic light emitting elements, such as an organic electroluminescent element. Since the compounds of the present invention include those that emit delayed fluorescence, it is also possible to provide an organic light-emitting device with high luminous efficiency. For this reason, this invention has high industrial applicability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Indole Compounds (AREA)

Abstract

L'invention concerne un composé représenté par la formule générale (1), utile comme matériau luminescent. R1 à R10 représentent des atomes d'hydrogène ou des substituants, mais au moins l'un de R1 à R10 est un groupe représenté par la formule générale (2). R21 à R30 représentent des atomes d'hydrogène ou des substituants, Ph représente un groupe phénylène, et n1 représente 0 ou 1.
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WO2020076796A1 (fr) 2018-10-09 2020-04-16 Kyulux, Inc. Nouvelle composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
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WO2021157642A1 (fr) 2020-02-04 2021-08-12 株式会社Ｋｙｕｌｕｘ Matériau hôte, composition, et élément luminescent organique
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