WO2021166900A1 - Élément électroluminescent organique, dispositif d'affichage el organique et éclairage el organique - Google Patents

Élément électroluminescent organique, dispositif d'affichage el organique et éclairage el organique Download PDF

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WO2021166900A1
WO2021166900A1 PCT/JP2021/005683 JP2021005683W WO2021166900A1 WO 2021166900 A1 WO2021166900 A1 WO 2021166900A1 JP 2021005683 W JP2021005683 W JP 2021005683W WO 2021166900 A1 WO2021166900 A1 WO 2021166900A1
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group
substituent
ring
formula
light emitting
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PCT/JP2021/005683
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Japanese (ja)
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良子 梶山
延軍 李
中井　敏光
一毅 岡部
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三菱ケミカル株式会社
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Priority to CN202180015866.8A priority Critical patent/CN115136339A/zh
Priority to JP2022501902A priority patent/JPWO2021166900A1/ja
Priority to KR1020227027066A priority patent/KR20220143826A/ko
Publication of WO2021166900A1 publication Critical patent/WO2021166900A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21S—NON-PORTABLE LIGHTING DEVICES; SYSTEMS THEREOF; VEHICLE LIGHTING DEVICES SPECIALLY ADAPTED FOR VEHICLE EXTERIORS
    • F21S2/00—Systems of lighting devices, not provided for in main groups F21S4/00 - F21S10/00 or F21S19/00, e.g. of modular construction
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21Y—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES F21K, F21L, F21S and F21V, RELATING TO THE FORM OR THE KIND OF THE LIGHT SOURCES OR OF THE COLOUR OF THE LIGHT EMITTED
    • F21Y2115/00—Light-generating elements of semiconductor light sources
    • F21Y2115/10—Light-emitting diodes [LED]
    • F21Y2115/15—Organic light-emitting diodes [OLED]
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to an organic electroluminescent element, an organic EL display device having the organic electroluminescent element, and organic EL lighting.
  • Examples of the method for forming the organic layer in the organic electroluminescent device include a vacuum vapor deposition method and a wet film deposition method. Since the vacuum vapor deposition method is easy to stack, it has the advantages of improving charge injection from the anode and / or cathode and facilitating containment of excitons in the light emitting layer. On the other hand, the wet film forming method does not require a vacuum process, it is easy to increase the area, and by using a coating liquid in which a plurality of materials having various functions are mixed, a plurality of materials having various functions can be easily obtained. There are advantages such as being able to form a layer containing the above materials. However, since the wet film deposition method is difficult to stack, the drive stability is inferior to that of the device by the vacuum vapor deposition method, and the drive stability has not reached the practical level except for a part.
  • Patent Document 1 discloses an organic EL produced by laminating a plurality of layers by a wet film forming method.
  • the stacking by the conventional wet film formation method has a problem in the hole transport efficiency between the laminated layers, for example, the light emitting layer and the hole transport layer.
  • Patent Document 1 discloses that the host compound of the light emitting layer should have a structure common to that of the compound constituting the hole transport layer from the viewpoint of charge transport.
  • the disclosed structure is only a small part, and it is not clear what other structure can exert this effect.
  • An object of the present invention is to provide an organic electroluminescent device having high brightness and long drive life.
  • an organic electroluminescent element having an anode, a cathode, and an organic layer between the anode and the cathode on a substrate
  • the present inventor has a light emitting layer in which the organic layer is adjacent to a hole transport layer and a hole transport layer.
  • the gist of the present invention is as follows [1] to [19].
  • An organic electroluminescent device having an anode, a cathode, and an organic layer between the anode and the cathode on a substrate, wherein the organic layer is adjacent to a hole transport layer and the hole transport layer. At least one of the materials contained in the hole transport layer and at least one of the materials contained in the light emitting layer both have the same partial structure A represented by the following formula (31).
  • An organic electroluminescent element having.
  • Ring HA represents an aromatic heterocycle of a monocyclic ring or a 2-6 condensed ring which may have a substituent.
  • the benzene ring in formula (31) may have a substituent.
  • Ar 0 is an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent and Represents a monovalent group in which a plurality of two or more groups selected from aromatic heterocyclic groups which may have a substituent are linked.
  • n1 represents an integer less than or equal to the number in which Ar 0 can be replaced with 0 or ring HA. When n1 is 2 or more, a plurality of Ar 0s may be the same or different.
  • Ar 0 and n1 are synonymous with those in the equation (31).
  • the benzene ring in the formulas (33) to (35) may have a substituent.
  • X and Y each independently represent a C atom or an N atom. When X and Y are C atoms, Ar 0 may be bonded.
  • A represents a partial structure A.
  • G represents an aromatic hydrocarbon group that may have a substituent, or an N atom.
  • Ar 2 may have a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or a substituent.
  • a divalent group in which a plurality of two or more groups selected from a good divalent aromatic hydrocarbon group and a divalent aromatic heterocyclic group which may have a substituent are directly or via a linking group are linked.
  • Ar 20 is directly bonded, has a divalent aromatic hydrocarbon group which may have a substituent, or a plurality of divalent aromatic hydrocarbon groups which may have a substituent are linked. Represents a divalent group.
  • the G is a group consisting of any of a benzene ring which may have a substituent, a fluorene ring which may have a substituent, and a spirofluorene ring which may have a substituent.
  • the organic electric field light emitting element according to [5].
  • A is synonymous with A in the above formula (1).
  • Q represents -C (R 5 ) (R 6 )-, -N (R 7 )-or -C (R 11 ) (R 12 ) -C (R 13 ) (R 14 )-.
  • R 1 to R 4 each independently represent an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an aralkyl group which may have a substituent.
  • R 5 to R 7 and R 11 to R 14 may independently have an alkyl group which may have a substituent, an alkoxy group which may have a substituent, and a substituent.
  • a and b are independently integers of 0 to 4.
  • c1 to c5 are independently integers of 0 to 3. However, at least one of c3 and c5 is 1 or more.
  • d1 to d4 are independently integers of 1 to 4. When there are a plurality of R 1 , R 2 , R 3 , and R 4 in the repeating unit, R 1 , R 2 , R 3 , and R 4 may be the same or different. )
  • X and Y each independently represent a C atom or an N atom.
  • the ring having X, Y and N corresponds to the ring HA in the formula (31).
  • Ar 1 is a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic hydrocarbon group in which two or more divalent aromatic hydrocarbon groups which may have a substituent are linked.
  • Ar 3 and Ar 4 may independently have an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent.
  • the structure bonded to the ring HA is a benzene ring. * Represents the binding site with G.
  • X, Y, and * are synonymous with those in the above equation (15).
  • the ring having X, Y and N corresponds to ring HA as in the formula (15).
  • Ar 1 ' is the direct bond or the formula (15) represents the residue of a case structure of bonding to the ring of HA
  • Ar 1 is a benzene ring.
  • Ar 3 ', Ar 4', in the hydrogen atom or each said formula (15) represents the residue of a case structure that binds to Ar 3, Ar 4 rings HA is a benzene ring.
  • Ar 13 represents an aromatic hydrocarbon group which does not contain a partial structure A and may have a substituent or an aromatic heterocyclic group which may have a substituent.
  • Ar 14 may have a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or a substituent.
  • a divalent group in which a plurality of two or more groups selected from a good divalent aromatic hydrocarbon group and a divalent aromatic heterocyclic group which may have a substituent are directly or via a linking group are linked.
  • the light emitting layer contains a low molecular weight compound having the partial structure A, and the low molecular weight compound is a compound having a molecular weight of 5,000 or less represented by any of the following formulas (10) to (12).
  • the organic electric field light emitting element according to [1] to [11].
  • A is the partial structure A.
  • B represents a single bond or any substructure.
  • na, nb and nc represent integers from 1 to 5.
  • the plurality of A, B, and AB may be the same or different.
  • HA represents any of the trivalent aromatic heterocyclic groups represented by the following structural formulas (10A-a), (10A-b) and (10A-c).
  • Xa 1 , Ya 1 , and Za 1 each independently have a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have a substituent, or a carbon which may have a substituent.
  • Each of Xa 2 , Ya 2 and Za 2 independently has a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon number which may have a substituent. Represents 3 to 30 aromatic heterocyclic groups.
  • g11, h11, and j11 each independently represent an integer of 0 to 6. At least one of g11, h11, and j11 is an integer of 1 or more. When g11, h11, and j11 are 2 or more, Xa 1 , Ya 1 , and Za 1 may be the same or different.
  • R 31 represents a hydrogen atom or a substituent, and the four R 31s may be the same or different.
  • Xa 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 , and Za 2 are synonymous with those in equation (10).
  • R 33 represents a hydrogen atom or a substituent, and a plurality of R 33 may be the same or different.
  • g11', h11' and j11'independently represent integers from 0 to 5.
  • the plurality of Xa 1 , Ya 1 , and Za 1 may be the same or different.
  • A has the same meaning as in the above formula (10).
  • Xb 1 , Yb 1 , and Zb 1 each independently may have a substituent or a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a carbon which may have a substituent.
  • p12, q12, and r12 each independently represent an integer of 0 to 6. When p12, q12, and r12 are 2 or more, the plurality of Xb 1 , Yb 1 , and Zb 1 may be the same or different.
  • q13 and r13 independently represent 0 or 1, respectively.
  • q12 and q13 are not 0 at the same time, and r12 and r13 are not 0 at the same time.
  • Yb 2 when q13 is 0 and Zb 2 when r13 is 0 independently have a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a substituent. Represents an aromatic heterocyclic group having 3 to 30 carbon atoms which may have.
  • q13 1, Yb 2 is a direct bond.
  • r13 is 1, Zb 2 is a direct bond.
  • A, Xb 1 , Yb 1 , Zb 1 , Yb 2 , Zb 2 , q13, and r13 are synonymous with those in the above formula (10B).
  • p12', q12' and r12'independently represent integers from 0 to 5.
  • a plurality of Xb 1 , Yb 1 , and Zb 1 may be the same or different.
  • q15 and r15 are 4 or 5 independently, respectively.
  • R 33 is a hydrogen atom or a substituent.
  • the plurality of R 33s in the formula (10B-1) may be the same or different.
  • Rings HA and Ar 0 are synonymous with those in the above formula (31).
  • nc has the same meaning as in the above formula (12).
  • Each of Xc 1 and Yc 1 independently has a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or 3 to 30 carbon atoms which may have a substituent. Represents a divalent aromatic heterocyclic group of.
  • Each of Xc 2 and Yc 2 has a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent. Represents an aromatic heterocyclic group.
  • Each of s11 and t11 independently represents an integer of 0 to 6. When s11 and t11 are 2 or more, the plurality of Xc 1 and Yc 1 may be the same or different.
  • R 31 represents a hydrogen atom or a substituent.
  • u11 is the number of substitutable substituents R 31.
  • u12 is a number in which the substituent Ar 0 can be substituted. If u11 is 2 or more, plural R 31 may be different even in the same. )
  • An organic EL display device including the organic electroluminescent device according to any one of [1] to [17].
  • an organic electroluminescent device having high brightness and a long drive life.
  • the organic electroluminescent element of the present invention has a specific structure including an aromatic heterocyclic group having a monocyclic ring or a 2 to 6 fused ring, which is a structure having electron attraction (in the present invention, "partial structure A". (Hereinafter referred to as "partial structure A-containing material") is included in both the hole transport layer and the light emitting layer.
  • partial structure A LUMO is easily localized and the electronic durability is high. Therefore, it is considered that the deterioration of the hole transport layer due to the electrons leaking from the light emitting layer to the hole transport layer is suppressed.
  • the electrons localized near the interface of the light emitting layer of the hole transport layer are considered to contribute to recombination in the light emitting layer, and the luminous efficiency is considered to be improved. Furthermore, it is considered that the voltage is lowered by efficiently transporting electrons and holes.
  • the organic electroluminescent device of the present invention is an organic electroluminescent device having an anode, a cathode, and an organic layer between the anode and the cathode on a substrate, and the organic layer is a hole transport layer and the above. It has a light emitting layer adjacent to the hole transport layer, and at least one of the materials contained in the hole transport layer and at least one of the materials contained in the light emitting layer are both represented by the following formula (31). It is characterized by having the same partial structure A.
  • Ring HA represents an aromatic heterocycle of a monocyclic ring or a 2-6 condensed ring which may have a substituent.
  • the benzene ring in formula (31) may have a substituent.
  • Ar 0 is an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent and Represents a monovalent group in which a plurality of two or more groups selected from aromatic heterocyclic groups which may have a substituent are linked.
  • n1 represents an integer less than or equal to the number in which Ar 0 can be replaced with 0 or ring HA. When n1 is 2 or more, a plurality of Ar 0s may be the same or different.
  • the partial structure A-containing material contained in the hole transport layer and the partial structure A-containing material contained in the light emitting layer are partial structures A represented by the above formula (31) and have the same partial structure A. This is an important constituent requirement of the present invention.
  • the effect of the present invention can be obtained when the material contained in the hole transport layer and the material contained in the light emitting layer have a common partial structure A represented by the formula (31).
  • either one or both of the partial structure A-containing material contained in the hole transport layer and the partial structure A-containing material contained in the light emitting layer is a partial structure A-containing material having two or more partial structures A.
  • the partial structure A-containing material contained in the hole transport layer and the partial structure A-containing material contained in the light emitting layer are both partial structure A-containing materials having the same partial structure A.
  • the partial structure A-containing material having two or more of the same partial structure A is the same portion in one compound when the partial structure A-containing material having two or more of the same partial structure A is a small molecule compound. It means having two or more structures A.
  • the partial structure A-containing material having two or more of the same partial structure A is a polymer compound, it means having two or more of the same partial structure A in one repeating unit.
  • the partial structure A-containing material contained in the hole transport layer and the partial structure A-containing material contained in the light emitting layer contains two or more kinds of materials having the partial structure A. ..
  • the electronic durability of the organic electroluminescent device will be further improved, and the organic electroluminescent device will have high brightness and long life.
  • the partial structure A-containing material contained in the hole transport layer is not particularly limited, but is preferably a polymer compound.
  • a polymer compound having a repeating unit represented by the formula (1) described later can be preferably mentioned.
  • the partial structure A-containing material contained in the light emitting layer is not particularly limited, but is preferably a small molecule compound.
  • the number of the partial structures A contained in the polymer compound is preferably equal to or greater than the number of the partial structures A contained in the repeating unit of the polymer compound.
  • the number of the partial structures A contained in the polymer compound is the repeating unit of the polymer compound ⁇ 2.
  • the polymer compound has a plurality of repeating units, at least one repeating unit may have a partial structure A.
  • the bonding method of the partial structure A in the partial structure A-containing material contained in the hole transport layer and the partial structure A-containing material contained in the light emitting layer is not particularly limited.
  • the partial structure A is represented by the following formula (31) -2 in any of the partial structure A-containing materials of the hole transport layer and the light emitting layer. It is preferable that the benzene ring in A is bonded in the material containing the partial structure A.
  • HA represents an aromatic heterocycle which may have a substituent of a monocyclic ring or a 2 to 6 condensed ring.
  • the ring-forming atom of the aromatic heterocycle is preferably any of a nitrogen atom, an oxygen atom, and a sulfur atom in addition to the carbon atom.
  • a dibenzofuran ring, a dibenzothiophene ring, a pyridine ring, a pyrimidine ring, and a 1,3,5-triazine ring are preferable, and a 1,3,5-triazine ring is particularly preferable.
  • Ar 0 is an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent. It represents a monovalent group in which a plurality of two or more groups selected from an aromatic hydrocarbon group which may have a group and an aromatic heterocyclic group which may have a substituent are linked.
  • the aromatic hydrocarbon group preferably has 6 or more carbon atoms and 60 or less carbon atoms.
  • 6-membered rings such as benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring.
  • Examples thereof include a monovalent group of a monocyclic ring or a 2 to 5 fused ring, or a monovalent group in which 2 to 10 rings selected from these are linked.
  • it is a monovalent group in which a benzene ring, a naphthalene ring, a fluorene ring or a ring selected from these is linked by 2 to 10.
  • the aromatic heterocyclic group preferably has 3 or more carbon atoms and 60 or less carbon atoms.
  • Examples thereof include a monovalent group of a fused ring or a monovalent group in which 2 to 10 of these are linked.
  • the same group is a plurality of monovalent groups in which two or more groups selected from an aromatic hydrocarbon group which may have a substituent and an aromatic heterocyclic group which may have a substituent are linked. It may be a linked group, or a group in which a plurality of different groups are linked may be used.
  • the total number of linked aromatic hydrocarbon groups and / or aromatic heterocyclic groups is preferably 2 to 10.
  • Ar 0 is preferably an aromatic hydrocarbon group which may have a substituent or an aromatic hydrocarbon group substituted with an aromatic heterocyclic group which may have a substituent.
  • the partial structure A represented by the formula (31) is preferably a structure represented by the following formulas (33) to (35) from the viewpoint of charge transportability and electron durability.
  • Ar 0 and n1 are synonymous with those in the equation (31).
  • the benzene ring in the formulas (33) to (35) may have a substituent.
  • X and Y each independently represent a C atom or an N atom. When X and Y are C atoms, Ar 0 may be bonded.
  • the above formula (35) is preferably represented by the following formula (36) from the viewpoint of charge transportability and electron durability, and more preferably represented by the following formula (37).
  • the structure represented by the formula (37) electrons are transferred by the biphenyl structure having high electron resistance, the electron durability of the compound is further improved, and as a result, the drive life of the organic electric field light emitting device is extended. It is thought that.
  • the three benzene rings may have a substituent.
  • the four benzene rings may have a substituent.
  • the structure represented by the above formula (37) is more preferably the structure represented by the following formula (37-2).
  • “*” And “* 1” in the formula (37-2) are bond positions in the partial structure A-containing material contained in the hole transport layer or the partial structure A-containing material contained in the light emitting layer, or a bond of a substituent. Represents a position.
  • at least "* 1" is the bond position in the partial structure A-containing material contained in the hole transport layer or the partial structure A-containing material contained in the light emitting layer, or the bond position of the substituent.
  • the S1 level and the T1 level are high because the conjugation of the electronically durable biphenyl structure does not spread, the excitons in the light emitting layer are not easily deactivated, and the luminous efficiency is high. From this point of view, it is more preferable that a substance other than a hydrogen atom is bonded to "* 1" and at least one "*".
  • the partial structures represented by the above equations (36) and (37) are the structures represented by the following equations (TzP) and (TzP-2) (hereinafter, "partial structure (TzP)” and “partial structure”, respectively. It may be referred to as “structure (TzP-2)”), which is preferable from the viewpoint of electrification transportability and stability.
  • the three benzene rings of the partial structure (TzP) and the four benzene rings of the partial structure (TzP-2) may have substituents.
  • the formula (TzP-2) is more preferably a structure represented by the following formula (TzP-3).
  • the reason why the structure represented by the following formula (TzP-3) is preferable is the same as the reason why the structure represented by the above formula (37-2) is preferable.
  • “*” And “* 1” in the formula (37-2) are bond positions in the partial structure A-containing material contained in the hole transport layer or the partial structure A-containing material contained in the light emitting layer, or a bond of a substituent. Represents a position.
  • the partial structure A-containing material contained in the hole transport layer and the partial structure A-containing material contained in the light emitting layer have similar skeletons of a common structure as the partial structure A.
  • a high degree of similarity of the skeletons of the common structure as the partial structure A means that the molecular weights of the matching partial structures A are large.
  • the partial structure A represented by the formula (31) is any of the formulas (33) to (35), the partial structure A contained in the hole transport layer or the partial structure contained in the light emitting layer.
  • the benzene ring portion of the partial structure A is preferably a bonding position in the partial structure A-containing material contained in the hole transport layer or the partial structure A-containing material contained in the light emitting layer.
  • a good substituent can be selected from the following substituent group Z.
  • substituent group Z examples include the following substituents. For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, dodecyl group and the like.
  • an alkenyl group such as a vinyl group having a carbon number of usually 2 or more, usually 24 or less, preferably 12 or less
  • an alkoxy group such as a methoxy group or an ethoxy group having a carbon number of usually 1 or more, usually 24 or less, preferably 12 or less
  • an alkoxycarbonyl group such as a methoxy
  • Aromatic hydrocarbon groups of 24 or less For example, a monovalent group in which a plurality of aromatic heterocycles of the same or different monocyclic or condensed rings are linked, such as a thienyl group, usually has 3 or more carbon atoms, preferably 5 or more carbon atoms, and usually 36 or less, preferably 36 or less carbon atoms.
  • aromatic heterocyclic groups A monovalent aromatic group in which an aromatic hydrocarbon ring and an aromatic heterocyclic group are linked, and when there are a plurality of aromatic hydrocarbon rings or aromatic heterocyclic groups, they may be the same or different.
  • a monovalent aromatic in which the above-mentioned alkyl group, alkoxy group, aromatic hydrocarbon group, aromatic heterocyclic group, aromatic hydrocarbon ring and aromatic heterocyclic group are linked is a group. From the viewpoint of charge transportability, it has no substituent or has a monovalent aromatic group in which an aromatic hydrocarbon group, an aromatic heterocyclic group, an aromatic hydrocarbon ring and an aromatic heterocyclic group are linked. Is even more preferable.
  • Each substituent of the above-mentioned Substituent Group Z may further have a Substituent.
  • substituents include the same substituents as the above-mentioned substituents (substituent group Z).
  • it does not have a further substituent, or has an alkyl group having 6 or less carbon atoms, an alkoxy group having 6 or less carbon atoms, a phenyl group, or a crosslinkable group described later as a further substituent. From the viewpoint of charge transportability, it is more preferable to have no additional substituent.
  • the polymer compound which is a partial structure A-containing material contained in the hole transport layer, which is one form of the present invention, is a polymer compound containing a repeating unit represented by the following formula (1) (hereinafter, “the present invention”. It may be referred to as a "polymer of the embodiment").
  • A represents a partial structure A.
  • G represents an aromatic hydrocarbon group that may have a substituent, or an N atom.
  • Ar 2 may have a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or a substituent.
  • a divalent group in which a plurality of two or more groups selected from a good divalent aromatic hydrocarbon group and a divalent aromatic heterocyclic group which may have a substituent are directly or via a linking group are linked.
  • Ar 20 is directly bonded, has a divalent aromatic hydrocarbon group which may have a substituent, or a plurality of divalent aromatic hydrocarbon groups which may have a substituent are linked. Represents a divalent group.
  • G represents an aromatic hydrocarbon group which may have a substituent or an N atom.
  • G is a benzene ring, which may have a substituent, from the viewpoint of excellent charge transportability and the separation of LUMO distributed around the partial structure A and HOMO distributed in the main chain.
  • a group consisting of a fluorene ring which may have a group or a spirofluorene ring which may have a substituent is preferable, and the structure shown in the following scheme 1 is more preferable.
  • the following structure may have a substituent.
  • "-*" represents a binding site with Ar 20.
  • G is an aromatic hydrocarbon group which may have a substituent
  • the substituent which may have is the substituent group Z, an aralkyl group having 7 to 40 carbon atoms, or an aralkyl group having 4 to 37 carbon atoms.
  • the heterocyclic aralkyl groups of the above, or a combination thereof are the same or different each time they appear, and they are an alkyl group having 1 to 24 carbon atoms, an aromatic group having 7 to 40 carbon atoms, and an aromatic group having a heterocycle having 3 to 37 carbon atoms.
  • the viewpoint of charge transportability it is the same or different each time it appears, and it is preferably an aromatic hydrocarbon group having 6 to 24 carbon atoms or an aromatic heterocyclic group having 3 to 24 carbon atoms, preferably phenyl. More preferably, it is a group, a naphthyl group, a fluorenyl group, a carbazolyl group, an indolocarbazolyl group, an indenocarbazolyl group, or an indenofluorenyl group.
  • LUMO distributed in the partial structure A and HOMO distributed in the main chain are further localized into fluorenyl groups and indenofluorenyl groups. Is preferable. It is most preferable that G has no substituent because of ease of synthesis and charge transport stability.
  • G is preferably an N atom (nitrogen atom) from the viewpoint of excellent charge transportability, particularly excellent hole transportability.
  • Ar 2 is a divalent aromatic hydrocarbon group which may have a substituent and a divalent aromatic which may have a substituent.
  • Ar 20 is directly bonded, has a divalent aromatic hydrocarbon group which may have a substituent, or a plurality of divalent aromatic hydrocarbon groups which may have a substituent are linked. Represents a divalent group.
  • the aromatic hydrocarbon groups of Ar 2 and Ar 20 preferably have 6 or more carbon atoms and 60 or less carbon atoms.
  • 6-membered rings such as benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring.
  • Examples thereof include a divalent group of a monocyclic ring or a 2 to 5 fused ring, or a divalent group in which 2 to 10 rings selected from these are linked.
  • the aromatic heterocyclic group of Ar 2 preferably has 3 or more carbon atoms and 60 or less carbon atoms.
  • a divalent group in which a plurality of two or more groups selected from an aromatic hydrocarbon group which may have a substituent of Ar 2 and an aromatic heterocyclic group which may have a substituent are linked.
  • the same group may be a group in which a plurality of the same groups are linked, or a group in which a plurality of different groups are linked may be used.
  • the groups are linked by 2 to 10.
  • Ar 2 has a divalent aromatic hydrocarbon group which may have a substituent and a divalent aromatic complex which may have a substituent because of its excellent charge transport property and durability. It is preferable that one or more groups selected from the ring groups are divalent groups bonded directly or via a linking group. If it has a linking group, an oxygen atom or a carbonyl group is preferable. Since the triplet level can be increased by forming a non-conjugated structure with the aromatic ring, a structure in which the phenylene rings are linked by an oxygen atom or a carbonyl group is preferable. A benzene ring or a fluorene ring is preferable from the viewpoint of improving charge transportability and excellent stability by expanding the ⁇ -conjugated system.
  • the main chain structure is such that the spread of the ⁇ -conjugated system is inhibited, the excited singlet energy level (S 1 ) and the excited triplet energy level (T 1 ) are increased, and quenching due to energy transfer from the luminescent exciter is suppressed. Therefore, from the viewpoint of excellent quenching efficiency, a twisted structure that bonds with a fluorene ring and phenylene having an alkyl group is particularly preferable. Among them, a structure containing a phenylene group having a methyl group is particularly preferable from the viewpoint of difficulty in synthesizing or purifying a monomer intermediate.
  • Ar 20 has one divalent aromatic hydrocarbon group which may have a direct bond or a substituent from the viewpoint of localizing LUMO distributed in the partial structure A and HOMO distributed in the main chain, respectively.
  • a group having to 9 linked groups is preferable, and a group having 1 to 7 linked divalent aromatic hydrocarbon groups which may have a direct bond or a substituent is more preferable.
  • a group in which 1 to 5 benzene rings which may have a substituent are linked is more preferable, and 3 benzene rings which may have a substituent are linked, and together with the benzene ring contained in A, Kur A terphenylene group is particularly preferred.
  • At least one benzene ring linked at the 1st and 3rd positions is provided. It is preferable to include it, and it is more preferable to include 2 or more. In the case of a group in which a plurality of divalent aromatic hydrocarbon groups which may have a substituent are linked, it is preferable that all of them are directly bonded and linked from the viewpoint of charge transportability or durability.
  • an aromatic hydrocarbon group which may have a substituent is preferable, and the substituent is used.
  • a phenylene group which may have a substituent or a fluorenylene group which may have a substituent is more preferable, and a phenylene group which may have a substituent is particularly preferable.
  • a benzene ring or a fluorene ring is preferably bonded to the benzene ring directly bonded to G, which is a nitrogen atom, and one or more phenylene groups are further between the benzene ring directly bonded to the nitrogen atom and the fluorene ring.
  • a structure in which fluorene is connected is also preferable.
  • the substituents that Ar 2 and Ar 20 may have in cases other than direct bonding are the same as the substituents that may be possessed when G is an aromatic hydrocarbon group. From the viewpoint of ease of synthesis and charge transport stability, it is most preferable that Ar 2 and Ar 20 do not have a substituent.
  • -Ar 20- A in the repeating unit represented by the above formula (1) is preferably represented by the following formula (15), and is represented by the formula (16) described later. It is more preferable to be done.
  • X and Y each independently represent a C atom or an N atom.
  • the ring having X, Y and N corresponds to the ring HA in the formula (31).
  • Ar 1 is a divalent aromatic hydrocarbon group which may have a substituent or a divalent group in which two or more divalent aromatic hydrocarbon groups which may have a substituent are linked.
  • Ar 3 and Ar 4 may independently have an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent.
  • the structure bonded to the ring HA is a benzene ring. * Represents the binding site with G. )
  • Ar 1 is a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic hydrocarbon group in which two or more divalent aromatic hydrocarbon groups which may have a substituent are linked. Represents a group.
  • the aromatic hydrocarbon preferably has 6 or more carbon atoms and 60 or less carbon atoms.
  • 6-membered rings such as benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring.
  • a divalent group of a monocyclic ring or a 2 to 5 fused ring, or a divalent group in which 2 to 10 rings selected from these are linked is preferable.
  • the substituent that Ar 1 may have, any one of the substituent group Z or a combination thereof can be used. From the viewpoint of durability and charge transportability, it is preferable to select from the same substituents that Ar 2 may have.
  • Ar 3 and Ar 4 may independently have an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent.
  • a monovalent group in which a plurality of two or more groups selected from a good aromatic hydrocarbon group and an aromatic heterocyclic group which may have a substituent are linked is preferable.
  • the aromatic hydrocarbon group preferably has 6 or more carbon atoms and 60 or less carbon atoms.
  • 6-membered rings such as benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring.
  • a monovalent group of a monocyclic ring or a 2 to 5 fused ring, or a monovalent group in which 2 to 10 rings selected from these are linked is preferable.
  • the aromatic heterocyclic group preferably has 3 or more carbon atoms and 60 or less carbon atoms.
  • a monovalent group in which a plurality of two or more groups selected from an aromatic hydrocarbon group and an aromatic heterocyclic group are linked, 2 to 10 structures selected from the aromatic hydrocarbon and the aromatic heterocyclic ring are linked.
  • a monovalent group is preferred.
  • Ar 3 and Ar 4 are independently a-1 to a-4, b-1 to b-9, c-1 to c-5, and d-1 shown in Scheme 2 below. It is preferable to have a structure selected from ⁇ d-17 and e-1 to e-4. Furthermore, from the viewpoint of promoting the spread of LUMO of the molecule by having an electron-attracting group, a-1 to a-4, b-1 to b-9, c-1 to c-5, d-1 to A structure selected from d-13 and e-1 to e-4 is preferable.
  • a-1 to a-4, d-1 to d-13, and e-1 to e-4 from the viewpoint of the effect of confining excitons formed in the light emitting layer, which has a higher triplet level.
  • the structure is preferred. Structures selected from d-1 to d-13 and e-1 to e-4 are more preferred in order to prevent molecular aggregation.
  • "-*" represents a binding site with ring HA. When there are a plurality of "-*", one of them represents a site that binds to the ring HA.
  • R 3A and R 3B of the above scheme 2 are linear, branched or cyclic alkyl groups which may independently have a substituent.
  • the number of carbon atoms of the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, the number of carbon atoms is preferably 1 or more and 6 or less, more preferably 3 or less, and further preferably a methyl group or an ethyl group. ..
  • R 3A and R 3B may be the same or different. It is preferable that all R 3A and R 3B have the same group because the charge can be uniformly distributed around the nitrogen atom and the synthesis is easy.
  • any one of the substituent group Z or a combination thereof can be used. From the viewpoint of durability and charge transportability, it is preferable to select from the same substituents that Ar 2 may have.
  • X, Y, and * are synonymous with those in the above equation (15).
  • the ring having X, Y and N corresponds to ring HA as in the formula (15).
  • Ar 1 ' is the direct bond or the formula (15) represents a residue when X corresponding to rings HA of Ar 1, a structure bonding to the ring with Y and N is a benzene ring.
  • the repeating unit represented by the formula (1) is preferably a repeating unit represented by any of the following formulas (2) -1 to (2) -3.
  • A is synonymous with A in the above formula (1).
  • Q represents -C (R 5 ) (R 6 )-, -N (R 7 )-or -C (R 11 ) (R 12 ) -C (R 13 ) (R 14 )-.
  • R 1 to R 4 each independently represent an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an aralkyl group which may have a substituent.
  • R 5 to R 7 and R 11 to R 14 may independently have an alkyl group which may have a substituent, an alkoxy group which may have a substituent, and a substituent.
  • a and b are independently integers of 0 to 4.
  • c1 to c5 are independently integers of 0 to 3. However, at least one of c3 and c5 is 1 or more.
  • d1 to d4 are independently integers of 1 to 4. When there are a plurality of R 1 , R 2 , R 3 , and R 4 in the repeating unit, R 1 , R 2 , R 3 , and R 4 may be the same or different. )
  • R 1 and R 2 each independently have an alkyl group and a substituent which may have a substituent. It is an alkoxy group which may be present, or an aralkyl group which may have a substituent.
  • R 1 and R 2 are preferably linear, branched or cyclic alkyl groups, each of which may independently have a substituent.
  • the number of carbon atoms of the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, the number of carbon atoms is preferably 1 or more and 6 or less, more preferably 3 or less, and further preferably a methyl group or an ethyl group. ..
  • R 1 and R 2 may be the same or different. It is preferable that all R 1 and R 2 are the same group because the charge can be uniformly distributed around the nitrogen atom and the synthesis is easy.
  • R 3 and R 4 in the repeating unit represented by the above formulas (2) -1 to (2) -3 each independently have an alkyl group and a substituent which may have a substituent. It is an alkoxy group which may be present, or an aralkyl group which may have a substituent. It is preferable that R 3 and R 4 are linear, branched or cyclic alkyl groups each independently which may have a substituent.
  • the carbon number of the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, the carbon number is preferably 1 or more, more preferably 4 or more, preferably 12 or less, and further preferably 8. The following is particularly preferable, and it is a hexyl group.
  • R 5 to R 7 and R 11 to R 14 may independently have an alkyl group which may have a substituent, an alkoxy group which may have a substituent, and a substituent. It is an aromatic hydrocarbon group which may have an aralkyl group or a substituent. R 5 to R 7 and R 11 to R 14 may independently have an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aralkyl group which may have a substituent. It is preferably a good aromatic hydrocarbon group.
  • the alkyl group is not particularly limited, but a long one is preferable in order to easily improve the solubility of the polymer, and a short one is preferable in order to improve the stability of the film and the charge transportability.
  • the alkyl group preferably has 1 or more and 24 or less carbon atoms, more preferably 12 or less, further preferably 8 or less, particularly preferably 6 or less, more preferably 2 or more, still more preferably 3 or more, and particularly preferably 4 or more. preferable. Further, the alkyl group may have a linear, branched or cyclic structure.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group and n-hexyl.
  • examples include a group, an n-octyl group, a cyclohexyl group, a dodecyl group and the like.
  • the alkoxy group is not particularly limited, but since it is easy to improve the solubility of the polymer, the number of carbon atoms is preferably 1 or more and 24 or less, more preferably 12 or less, further preferably 8 or less, particularly preferably 6 or less, and 2 or more. Is more preferable, 3 or more is further preferable, and 4 or more is particularly preferable.
  • Specific examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, a tert-butoxy group, a hexyloxy group and the like.
  • the aralkyl group is not particularly limited, but since it is easy to improve the solubility of the polymer, the number of carbon atoms is preferably 7 or more and 60 or less, more preferably 40 or less, more preferably 8 or more, further preferably 10 or more, and 12 or more. Is particularly preferable.
  • Specific examples of the aralkyl group include 1,1-dimethyl-1-phenylmethyl group, 1,1-di (n-butyl) -1-phenylmethyl group, and 1,1-di (n-hexyl).
  • -1-phenylmethyl group 1,1-di (n-octyl) -1-phenylmethyl group, phenylmethyl group, phenylethyl group, 3-phenyl-1-propyl group, 4-phenyl-1-n-butyl Group, 1-methyl-1-phenylethyl group, 5-phenyl-1-n-propyl group, 6-phenyl-1-n-hexyl group, 6-naphthyl-1-n-hexyl group, 7-phenyl-1 Examples thereof include -n-heptyl group, 8-phenyl-1-n-octyl group and 4-phenylcyclohexyl group.
  • the aromatic hydrocarbon group is not particularly limited, but the number of carbon atoms is preferably 6 or more and 60 or less, more preferably 30 or less, further preferably 24 or less, and 14 or less because it is easy to improve the solubility of the polymer. Especially preferable.
  • aromatic hydrocarbon group examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysen ring, a triphenylene ring, an acenaphthene ring, and a fluorene ring.
  • Examples thereof include monovalent groups of 6-membered monocyclic rings or 2 to 5 fused rings, such as fluorene rings, or groups in which 2 to 8 ring structures selected from these are linked. It is preferably a single ring or a group in which 2 to 4 or less are linked.
  • R 5 to R 7 are preferably an alkyl group or an aromatic hydrocarbon group
  • R 5 and R 6 are more preferably an alkyl group
  • R 7 is an aromatic hydrocarbon. It is more preferably a group, and the preferred number of carbon atoms is as described above.
  • R 5 and R 6 are preferably an alkyl group having 3 or more and 8 or less carbon atoms or an aralkyl group having 9 or more and 40 or less carbon atoms in terms of improving solubility and excellent charge transportability.
  • Alkyl group of the R 1 ⁇ R 4, alkoxy group, aralkyl group, the alkyl group of R 5 ⁇ R 7 and R 11 ⁇ R 14, alkoxy groups, aralkyl groups and aromatic hydrocarbon groups may further have a substituent May be. Further, the substituent which may be possessed is a group listed as a preferable group of the alkyl group of R 5 to R 7 and R 11 to R 14 , an alkoxy group, an aralkyl group and an aromatic hydrocarbon group, or a cross-linking group described later. Sex groups can be mentioned.
  • R 5 to R 7 and R 11 to R 14 may further have are insoluble in a solvent when the polymer of the present embodiment is formed into a film and then another layer is applied to form a film and laminated. From the viewpoint of improvement, it is preferable to use a crosslinkable group described later. Among them, it is preferable that any one of R 5 , R 6 , and R 11 to R 14 has a cross-linking group described later as a further substituent because it does not hinder the charge transport property, and at least of R 5 and R 6. It is more preferable that one has a crosslinkable group described later as a further substituent.
  • a and b are independently integers of 0 to 4. It is preferable that a and b are 2 or less, respectively, and it is more preferable that both a and b are 0 or 1 at the same time.
  • c1 to c5 are independently integers of 0 to 3. However, at least one of c3 and c5 is 1 or more, and d1 to d4 are independently integers of 1 to 4. It is preferable that c1 to c5 and d1 to d4 are independently 2 or less. It is more preferable that both c1 and c2 are 0 or 1 at the same time. It is more preferable that c1 and c2 are 1 or more. It is preferable that at least one of c3 or c4, or both c3 and c4 are 1 or more. It is more preferable that both c3 and c4 are 1. c5 is preferably 1 or more.
  • c1 and c2, c3 and c4, and d1 to d4 are equal to each other. It is more preferable that all of c1 to c5 and d1 to d4 are 1 or 2. It is particularly preferable that all of c1 to c5 and d1 to d4 are 1.
  • Both c1 and c2 in the repeating unit represented by the formula (2) -1 is 1 or 2 simultaneously, and, when both a and b is 2 or 1, R 1 and R 2 are, Most preferably, they are connected to each other at symmetrical positions.
  • Specific examples of the preferred repeating unit structure include the following structures.
  • the terminal group refers to the structure of the terminal portion of the polymer formed by the end cap agent used at the end of the polymerization of the polymer.
  • the terminal group of the polymer of this embodiment is usually a hydrocarbon group. From the viewpoint of charge transportability, the hydrocarbon group preferably has 1 or more and 60 or less carbon atoms, more preferably 1 or more and 40 or less, and further preferably 1 or more and 30 or less.
  • the terminal group preferably includes the following. For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, dodecyl group and the like.
  • an alkenyl group such as a vinyl group having a carbon number of usually 2 or more, usually 24 or less, preferably 12 or less;
  • hydrocarbon groups may further have a substituent.
  • the substituent which may be possessed is preferably an alkyl group or an aromatic hydrocarbon group. When there are a plurality of these substituents which may be further present, they may be bonded to each other to form a ring.
  • the substituent that the hydrocarbon group of the terminal group may further have is preferably an alkyl group or an aromatic hydrocarbon group from the viewpoint of charge transportability and durability, and more preferably an aromatic hydrocarbon. It is a group.
  • the polymer of the present embodiment preferably has a soluble group for soluble expression in a solvent.
  • the soluble group in the present embodiment is a group having a linear or branched alkyl group or alkylene group having 3 or more and 24 or less carbon atoms, preferably 12 or less carbon atoms.
  • an alkyl group, an alkoxy group, or an aralkyl group is preferable, and for example, an n-propyl group, a 2-propyl group, an n-butyl group, an isobutyl group, an n-hexyl group, an n-octyl group and the like. .. More preferably, it is an n-hexyl group or an n-octyl group.
  • the soluble group may have a substituent.
  • the number of soluble groups contained in the polymer of the present embodiment is large in that it is easy to obtain a polymer solution that can be used in the wet film forming method.
  • the film thickness is less reduced due to the lower layer being dissolved in the solvent. Less is preferable.
  • the number of soluble groups contained in the polymer of the present embodiment can be expressed by the number of moles per gram of the polymer.
  • the number of soluble groups contained in the polymer of the present embodiment is expressed in terms of the number of moles per 1 g of the polymer, it is usually 4.0 mmol or less, preferably 3.0 mmol or less, more preferably 3.0 mmol or less per 1 g of the polymer. It is 2.0 mmol or less, and usually 0.1 mmol or more, preferably 0.5 mmol or more.
  • the number of soluble groups is within the above range, the polymer is easily dissolved in a solvent, and a composition containing a polymer suitable for a wet film forming method can be easily obtained. Further, since the soluble group density is appropriate and the solubility in an organic solvent after drying with a heating solvent is sufficient, a multilayer laminated structure can be formed by a wet film forming method.
  • the number of soluble groups per gram of the polymer can be calculated from the molar ratio of the charged monomer at the time of synthesis and the structural formula by removing the terminal group from the polymer.
  • the molecular weight of the repeating unit excluding the terminal group is 748 on average.
  • the average number of hexyl groups, which is 4 and is a soluble group, is 1.3 per repeating unit.
  • the number of soluble groups per 1 g of molecular weight is calculated to be 1.74 mmol.
  • the polymer of this embodiment may have a crosslinkable group.
  • the crosslinkable group in the polymer of the present embodiment may be present in the repeating unit represented by the formula (1), and is in a repeating unit different from the repeating unit represented by the formula (1). May be present in.
  • By having a crosslinkable group it is possible to make a large difference in solubility in an organic solvent before and after a reaction (poor solubility reaction) caused by irradiation with heat and / or active energy rays.
  • a crosslinkable group is a group that forms a new chemical bond by reacting with a group constituting another molecule located in the vicinity of the crosslinkable group by irradiation with heat and / or active energy rays.
  • the reacting group may be the same group as the crosslinkable group or a different group.
  • crosslinkable group a cyclobutene ring fused to the aromatic ring and a group containing an alkenyl group bonded to the aromatic ring are preferable, and a group selected from the following crosslinkable group group K is more preferable. It is preferable that the crosslinkable group is contained in the polymer in a form further substituted with the substituent having each structure.
  • Crosslinkable group K The crosslinkable group K has the structure shown below.
  • R 21 to R 23 each independently represent a hydrogen atom or an alkyl group.
  • R 24 to R 26 each independently represent an alkyl group or an alkoxy group.
  • p represents an integer of 1 to 4
  • q represents an integer of 1 to 4
  • r represents an integer of 1 to 4.
  • the plurality of R 24s may be the same or different, and adjacent R 24s may be bonded to each other to form a ring.
  • a plurality of R 25s may be the same or different, and adjacent R 25s may be bonded to each other to form a ring.
  • the plurality of R 26s may be the same or different, and adjacent R 26s may be bonded to each other to form a ring.
  • Ar 21 and Ar 22 each independently represent an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent. "-*" Is a binding site.
  • Examples of the alkyl group of R 21 to R 26 include a linear or branched chain alkyl group having 6 or less carbon atoms.
  • Examples of the alkoxy group of R 24 to R 26 include a linear or branched chain alkoxy group having 6 or less carbon atoms.
  • the number of carbon atoms of R 24 to R 26 is 6 or less, it is considered that the film formed by the polymer of the present embodiment is likely to be insolubilized without sterically inhibiting the cross-linking reaction.
  • Examples of the aromatic hydrocarbon group which may have a substituent of Ar 21 and Ar 22 include a single ring of a 6-membered ring such as a benzene ring and a naphthalene ring having one free valence, or 2 to 2 to. Examples include a 5-fused ring. In particular, a benzene ring having one free valence is preferable.
  • Ar 22 may be a group in which two or more aromatic hydrocarbon groups which may have a substituent are bonded. Examples of such a group include a biphenylene group and a terphenylene group, and a 4,4'-biphenylene group is preferable.
  • Examples of the aromatic heterocyclic group which may have a substituent of Ar 21 and Ar 22 include a single ring of a 6-membered ring having one free valence, such as a pyridine ring and a triazine ring, or 2 to 2 to Examples include a 5-fused ring. In particular, a triazine ring having one free valence is preferable.
  • the substituents that Ar 21 and Ar 22 may have are the same as those of the above-mentioned substituent group Z.
  • arylvinylcarbonyl groups such as cinnamoyl groups, benzocyclobutene rings having a monovalent free valence, and 1,2-dihydrocyclobuta [a] naphthalene rings having a monovalent free valence as crosslinkable groups.
  • a group that undergoes an addition reaction is preferable in that it further improves the electrochemical stability of the device.
  • the cyclobutene ring fused to an aromatic ring having a monovalent free valence and the 1,2-dihydrocyclobutane having a monovalent free valence are particularly stable in the structure after cross-linking.
  • a group containing a naphthalene ring is preferable, and among them, a benzocyclobutene ring or a 1,2-dihydrocyclobuta [a] naphthalene ring having a monovalent free valence is more preferable.
  • a 1,2-dihydrocyclobuta [a] naphthalene ring having a monovalent free valence in that the crosslinking reaction temperature is low is particularly preferable.
  • the crosslinkable group contained in the polymer of the present embodiment is sufficiently insolubilized by crosslinking, and it becomes easy to form another layer on the crosslinkable group by a wet film forming method.
  • the number of crosslinkable groups is small in that cracks are unlikely to occur in the formed layer, unreacted crosslinkable groups are unlikely to remain, and the organic electroluminescent device tends to have a long life.
  • the number of crosslinkable groups present in one polymer chain is preferably 1 or more, more preferably 2 or more, and preferably 200 or less, more preferably 100 or less. ..
  • the number of crosslinkable groups contained in the polymer of the present embodiment can be represented by the number per 1000 molecular weight of the polymer.
  • the number of crosslinkable groups contained in the polymer of the present embodiment is expressed by the number per 1000 molecular weight of the polymer, it is usually 3.0 or less, preferably 2.0 or less, more preferably 2.0 or less per 1000 molecular weight.
  • the number is 1.0 or less, and usually 0.01 or more, preferably 0.05 or more.
  • the number of crosslinkable groups is within the above range, cracks and the like are unlikely to occur, and a flat film can be easily obtained from the polymer of the present embodiment. Further, since the cross-linking density is appropriate, there are few unreacted cross-linking groups remaining in the layer after the cross-linking reaction, and it is unlikely to affect the life of the obtained device. Further, since the poor solubility in the organic solvent after the crosslinking reaction is sufficient, it is easy to form a multilayer laminated structure by the wet film forming method.
  • the number of crosslinkable groups per 1000 molecular weight of the polymer can be calculated from the molar ratio of the charged monomer at the time of synthesis and the structural formula by removing the terminal group from the polymer.
  • the polymer 1 represented by the formula (HT-1) used in Example 1 described later in the polymer 1, the molecular weight of the repeating unit excluding the terminal group is 748.4 on average, and cross-linking is performed.
  • the number of sex groups is 0.15 per repeating unit. When this is calculated by simple proportionality, the number of crosslinkable groups per 1000 molecular weight is calculated to be 0.20.
  • the content of the repeating unit represented by the formula (1) is not particularly limited, but it is usually contained in the polymer in an amount of 5 mol% or more, preferably 10 mol% or more, and 15 It is more preferably contained in an amount of mol% or more, and particularly preferably contained in an amount of 20 mol% or more.
  • the repeating unit may be composed of only the repeating unit represented by the formula (1), but for the purpose of balancing various performances when the organic electroluminescent device is used, the formula (1) It may have a repeating unit different from that of 1). In that case, the content of the repeating unit represented by the formula (1) in the polymer is usually 99 mol% or less, preferably 95 mol% or less.
  • the polymer of the present embodiment further contains a repeating unit represented by the following formula (3).
  • the repeating unit represented by the formula (3) is preferably a repeating unit represented by any of the following (3) -1, formula (3) -2 or formula (3) -3.
  • Ar 13 represents an aromatic hydrocarbon group which does not contain a partial structure A and may have a substituent or an aromatic heterocyclic group which may have a substituent.
  • Ar 14 may have a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or a substituent.
  • a divalent group in which a plurality of two or more groups selected from a good divalent aromatic hydrocarbon group and a divalent aromatic heterocyclic group which may have a substituent are directly or via a linking group are linked.
  • Ar 7 represents an aromatic hydrocarbon group which does not contain a partial structure A and may have a substituent or an aromatic heterocyclic group which may have a substituent.
  • Q represents -C (R 5 ) (R 6 )-, -N (R 7 )-or -C (R 11 ) (R 12 ) -C (R 13 ) (R 14 )-.
  • R 1 to R 4 each independently represent an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an aralkyl group which may have a substituent.
  • R 5 to R 7 and R 11 to R 14 may independently have an alkyl group which may have a substituent, an alkoxy group which may have a substituent, and a substituent.
  • a and b are independently integers of 0 to 4.
  • c1 to c5 are independently integers of 0 to 3. However, at least one of c3 and c5 is 1 or more.
  • d1 to d4 are independently integers of 1 to 4. When there are a plurality of R 1 , R 2 , R 3 , and R 4 in the repeating unit, R 1 , R 2 , R 3 , and R 4 may be the same or different.
  • Ar 7 may independently have a substituent containing no partial structure A in each repeating unit. Represents an aromatic heterocyclic group which may have an aromatic hydrocarbon group or a substituent.
  • the aromatic hydrocarbon group preferably has 6 or more carbon atoms and 60 or less carbon atoms.
  • 6-membered rings such as benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, and fluorene ring.
  • Examples thereof include a monocyclic ring, a 2 to 5 fused ring, or a monovalent group in which a plurality of rings selected from these are linked. When a plurality of them are linked, a monovalent group in which 2 to 10 are linked is preferable.
  • the aromatic heterocyclic group preferably has 3 or more carbon atoms and 60 or less carbon atoms.
  • Ar 7 is preferably an aromatic hydrocarbon group which may have a substituent from the viewpoint of excellent charge transportability and durability.
  • a monovalent group of a benzene ring or a fluorene ring which may have a substituent that is, a phenyl group or a fluorenyl group which may have a substituent is more preferable, and a substituent may be provided.
  • a fluorenyl group is more preferred, and a 2-fluorenyl group, which may have a substituent, is particularly preferred.
  • the substituent that the aromatic hydrocarbon group of Ar 7 may have is not particularly limited as long as it does not significantly reduce the characteristics of the polymer of the present embodiment.
  • a group selected from the substituent group Z or the crosslinkable group is mentioned.
  • an alkyl group, an alkoxy group, an aromatic hydrocarbon group, an aromatic heterocyclic group not corresponding to the partial structure A or the crosslinkable group is preferable, and an alkyl group is more preferable.
  • Ar 7 is preferably a fluorenyl group substituted with an alkyl group having 1 to 24 carbon atoms, and particularly a 2-fluorenyl group substituted with an alkyl group having 4 to 12 carbon atoms. preferable. Further, a 9-alkyl-2-fluorenyl group in which the alkyl group is substituted at the 9-position of the 2-fluorenyl group is preferable, and a 9,9'-dialkyl-2-fluorenyl group in which the alkyl group is 2-substituted is particularly preferable.
  • the solubility in a solvent and the durability of the fluorene ring are likely to be improved. Further, since both the 9-position and the 9'-position are substituted with an alkyl group, the solubility in a solvent and the durability of the fluorene ring are likely to be further improved. It is preferable that Ar 7 contains the crosslinkable group because the insolubility in the solvent is improved when the film is laminated and coated after the film formation.
  • the further substituent contains a repeating unit represented by the formulas (3) -1 to (3) -3 containing at least one of the above-mentioned crosslinkable groups.
  • the crosslinkable group is preferably further substituted with a substituent which the aromatic hydrocarbon group represented by Ar 7 may have.
  • repeating unit structure represented by the formulas (3) -1 to (3) -3 include the following structures.
  • the polymer of the present embodiment may further contain a repeating unit represented by the following formula (4) or the following formula (5) in terms of charge transportability and durability.
  • R 8 and R 9 are each independently a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, or a substituent. Represents an aromatic heterocyclic group which may have a group.
  • Ar 10 has a divalent aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent. Two or more groups selected from a divalent aromatic hydrocarbon group which may be present and a divalent aromatic heterocyclic group which may have a substituent are linked directly or via a linking group. Represents a valence group.
  • R 8 and R 9 examples of the alkyl group, aromatic hydrocarbon group and aromatic heterocyclic group of R 8 and R 9 include the alkyl group exemplified as the substituent group Z, the aromatic hydrocarbon group and the aromatic heterocyclic group.
  • the substituents that these groups may have are preferably a group similar to the substituent group Z or the crosslinkable group.
  • Ar 10 As a specific structure of Ar 10, a divalent group similar to Ar 2 in the above formula (1) can be mentioned.
  • the substituents that these groups may have are preferably a group similar to the substituent group Z or the crosslinkable group.
  • the weight average molecular weight (Mw) of the polymer of the present embodiment is usually 3,000,000 or less, preferably 1,000,000 or less, more preferably 500,000 or less, still more preferably 200,000 or less, particularly preferably. Is 100,000 or less, usually 10,000 or more, preferably 15,000 or more.
  • the weight average molecular weight of the polymer When the weight average molecular weight of the polymer is not more than the above upper limit value, solubility in a solvent is obtained, and the film forming property tends to be excellent. When the weight average molecular weight of the polymer is at least the above lower limit value, the decrease in the glass transition temperature, the melting point and the vaporization temperature of the polymer may be suppressed, and the heat resistance may be improved. In addition, the coating film after the cross-linking reaction may be sufficiently insoluble in the organic solvent.
  • the number average molecular weight (Mn) of the polymer of the present embodiment is usually 2.5 million or less, preferably 750,000 or less, more preferably 400,000 or less, particularly preferably 100,000 or less, and usually 2 It is 3,000 or more, preferably 4,000 or more, more preferably 8,000 or more, and even more preferably 20,000 or more.
  • the dispersity (Mw / Mn) in the polymer of the present embodiment is preferably 3.5 or less, more preferably 2.5 or less, and particularly preferably 2.0 or less.
  • the dispersity of the polymer is not more than the above upper limit value, purification is easy, and solubility in a solvent and charge transporting ability are good.
  • the weight average molecular weight and the number average molecular weight of the polymer are determined by SEC (size exclusion chromatography) measurement.
  • SEC size exclusion chromatography
  • the weight average molecular weight and the number average molecular weight are calculated.
  • the polymer of the present embodiment is most preferably represented by any of the following formulas (6a) to (6h).
  • A, Q, R 1 , R 2 , R 3 , and R 4 are the same as those in the formulas (2) -1 to (2) -3.
  • Ar 7 is the same as in the above equations (3) -1 to (3) -3.
  • At least one A or Ar 7 in each polymer preferably has the above-mentioned crosslinkable group.
  • n and m represent the number of repetitions.
  • a specific example of coalescence is shown.
  • the polymer of the present embodiment is not limited to these.
  • the numbers in the following chemical formulas represent the molar ratio of repeating units. These polymers may be any of a random copolymer, an alternating copolymer, a block copolymer, a graft copolymer and the like, and the arrangement order of the repeating units is not limited.
  • the method for producing the polymer of the present embodiment is not particularly limited.
  • it can be produced by a polymerization method by Suzuki reaction, a polymerization method by Grignard reaction, a polymerization method by Yamamoto reaction, a polymerization method by Ullmann reaction, a polymerization method by Buchwald-Hartwig reaction, or the like.
  • the aryl dihalide represented by the following formula (1a) (E represents a halogen atom such as I, Br, Cl, F) and the formula.
  • the polymer of the present embodiment is synthesized by reacting with the primary aminoaryl represented by (1b) and further reacting with the dial halide represented by the formula (2a).
  • A, R 1 ⁇ R 2 , Q, a, b, c1, d1 has the same meaning as the formula (2) -1 to (2) -3.
  • n and m represent the number of repetitions.
  • the reaction for forming an N-aryl bond is usually carried out in the presence of a base such as potassium carbonate, tert-butoxysodium or triethylamine. It can also be carried out in the presence of a transition metal catalyst such as a copper or palladium complex.
  • a base such as potassium carbonate, tert-butoxysodium or triethylamine. It can also be carried out in the presence of a transition metal catalyst such as a copper or palladium complex.
  • the partial structure A-containing material contained in the light emitting layer which is one embodiment of the present invention, is preferably a small molecule compound.
  • the partial structure A-containing material of the small molecule compound is a compound having a molecular weight of 5,000 or less represented by the following formula (10), the following formula (11), or the following formula (12) (hereinafter, these compounds are referred to as “these compounds”. It may be referred to as a "small molecule compound of the present embodiment").
  • A is the partial structure A.
  • B represents a single bond or any substructure.
  • na, nb and nc represent integers from 1 to 5.
  • the plurality of A, B, and AB may be the same or different.
  • (B) B in the above formula (10) and the above formula (11) is not particularly limited, but preferably a functional group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, and the like. It is selected from an aromatic heterocyclic group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent and an aromatic heterocyclic group which may have a substituent 2 Examples thereof include a group in which a plurality of the above groups are directly linked or linked via a linking group.
  • Functional groups include a structure having hole transportability, a structure having electron transportability, a structure that suppresses charge transport, a structure that imparts solubility in an organic solvent, a structure that inhibits crystallization and improves amorphousness, and a structure.
  • a group containing a structure having luminescence is preferable.
  • an aromatic amine structure that is, a group containing at least one aromatic hydrocarbon group bonded to a nitrogen atom of the amine is preferable.
  • Two or more groups selected directly from an aromatic hydrocarbon group, an aromatic heterocyclic group, an aromatic hydrocarbon group which may have a substituent and an aromatic heterocyclic group which may have a substituent are directly Alternatively, as a plurality of groups linked via a linking group, those based on the same structure as Ar 0 in the above formula (31) are preferable.
  • the small molecule compound of this embodiment is preferably a charge transport material in the light emitting layer.
  • the small molecule compound of the present embodiment is preferably a compound represented by the above formula (10) or the above formula (12).
  • the compound represented by the formula (10) is preferably a compound represented by the following formula (10A) or the following formula (10B).
  • the compound represented by the formula (12) is preferably a compound represented by the following formula (12A).
  • HA represents any of the trivalent aromatic heterocyclic groups represented by the following structural formulas (10A-a), (10A-b) and (10A-c).
  • Xa 1 , Ya 1 , and Za 1 each independently have a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have a substituent, or a carbon which may have a substituent.
  • Each of Xa 2 , Ya 2 and Za 2 independently has a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon number which may have a substituent. Represents 3 to 30 aromatic heterocyclic groups.
  • g11, h11, and j11 each independently represent an integer of 0 to 6. At least one of g11, h11, and j11 is an integer of 1 or more. When g11, h11, and j11 are 2 or more, Xa 1 , Ya 1 , and Za 1 may be the same or different.
  • R 31 represents a hydrogen atom or a substituent. The four R 31s may be the same or different. )
  • A has the same meaning as in the above formula (10).
  • Xb 1 , Yb 1 , and Zb 1 each independently may have a substituent or a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a carbon which may have a substituent.
  • p12, q12, and r12 each independently represent an integer of 0 to 6. When p12, q12, and r12 are 2 or more, the plurality of Xb 1 , Yb 1 , and Zb 1 may be the same or different.
  • q13 and r13 independently represent 0 or 1, respectively.
  • q12 and q13 are not 0 at the same time, and r12 and r13 are not 0 at the same time.
  • Yb 2 when q13 is 0 and Zb 2 when r13 is 0 independently have a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a substituent. Represents an aromatic heterocyclic group having 3 to 30 carbon atoms which may have.
  • q13 1, Yb 2 is a direct bond.
  • r13 is 1, Zb 2 is a direct bond.
  • Rings HA and Ar 0 are synonymous with those in the above formula (31).
  • nc has the same meaning as in the above formula (12).
  • Each of Xc 1 and Yc 1 independently has a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or 3 to 30 carbon atoms which may have a substituent. Represents a divalent aromatic heterocyclic group of.
  • Each of Xc 2 and Yc 2 has a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 3 to 30 carbon atoms which may have a substituent. Represents an aromatic heterocyclic group.
  • Each of s11 and t11 independently represents an integer of 0 to 6. When s11 and t11 are 2 or more, the plurality of Xc 1 and Yc 1 may be the same or different.
  • R 31 represents a hydrogen atom or a substituent.
  • u11 is the number of substitutable substituents R 31.
  • u12 is a number in which the substituent Ar 0 can be substituted. If u11 is 2 or more, plural R 31 may be different even in the same. )
  • the aromatic hydrocarbon ring of the aromatic hydrocarbon group having 6 to 30 carbon atoms is preferably a 6-membered single ring or a 2 to 5 condensed ring. .. Specific examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, and a fluoranthene ring.
  • it is a monocyclic ring or a 2-3 condensed ring, and specific examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a fluorene ring.
  • a benzene ring, a naphthalene ring, a phenanthrene ring, and a fluorene ring are preferable, and a benzene ring or a fluorene ring is more preferable.
  • the aromatic heterocycle of the aromatic heterocyclic group having 3 to 30 carbon atoms is a 5- or 6-membered single ring, or a 2 to 5 condensation thereof. Rings are preferred. Specifically, furan ring, benzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, pyrol ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, indolocarbazole ring, Pyrroylmidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, flopyrol ring, flofuran ring, thienofuran ring, benzoisoxazole ring, benzoisothiazole ring, benzoisothiazole ring, benzo
  • the thiophene ring, pyrrole ring, imidazole ring, pyridine ring, pyrimidine ring, triazine ring, quinoline ring, quinazoline ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, indolocarbazole ring, phenanthroline ring, or indolocarbazole ring are preferable.
  • a pyridine ring it is more preferably a pyridine ring, a pyrimidine ring, a triazine ring, a quinoline ring, a quinazoline ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, or an indolocarbazole ring, and more preferably a carbazole ring, a dibenzofuran ring, or a dibenzo ring. It is a thiophene ring or an indolocarbazole ring.
  • a particularly preferable aromatic hydrocarbon ring is a benzene ring, a naphthalene ring or a phenanthrene ring, and a particularly preferable aromatic heterocycle is a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, or an indolocarbazole ring, which is aromatic.
  • Group hydrocarbon rings are more preferred.
  • R 31 is preferably an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent or an aromatic having 3 to 30 carbon atoms which may have a substituent. It is a group heterocyclic group. From the viewpoint of improving durability and charge transportability, it is more preferable that the aromatic hydrocarbon group may have a substituent. When there are a plurality of R 31s as substituents, they may be different from each other.
  • the above-mentioned hydrocarbon aromatic ring having 6 to 30 carbon atoms may have a substituent, a heteroaromatic ring having 3 to 30 carbon atoms may have a substituent, and the substituent R 31 has.
  • the substituents may be the same as the substituents listed in the substituent group Z or the crosslinkable group in the polymer of the present embodiment, and the preferred substituents are also the same. The same applies to the substituents that the substituents may further have.
  • the compound represented by the formula (10A) is more preferably a compound represented by the following general formulas (10A-1) to (10A-3).
  • R 33 represents a hydrogen atom or a substituent.
  • the plurality of R 33s may be the same or different.
  • g11', h11' and j11'independently represent integers from 0 to 5.
  • the plurality of Xa 1 , Ya 1 , and Za 1 may be the same or different.
  • R 33 which can be regarded as the structure A and is bonded to the benzene ring constituting the partial structure A, corresponds to R 31 in the formula (10A).
  • the compound represented by the formula (10B) is preferably a compound represented by the following formula (10B-1).
  • A, Xb 1 , Yb 1 , Zb 1 , Yb 2 , Zb 2 , q13, and r13 are synonymous with those in the above formula (10B).
  • p12', q12' and r12'independently represent integers from 0 to 5.
  • a plurality of Xb 1 , Yb 1 , and Zb 1 may be the same or different.
  • q15 and r15 are 4 or 5 independently, respectively.
  • R 33 is a hydrogen atom or a substituent.
  • the plurality of R 33s in the formula (10B-1) may be the same or different.
  • R 33 is a substituent in the formulas (10A-1) to (10A-3) and (10B-1), and a substitution which may be further possessed when R 33 is a substituent. group is the same as the R 31.
  • the molecular weight of the small molecule compound of the present embodiment is usually 5,000 or less, preferably 4,000 or less, particularly preferably 3,000 or less, most preferably 2,000 or less, usually 300 or more, preferably 350 or more. , More preferably 400 or more. Since the molecular weight of the small molecule compound of the present embodiment contains the required partial structure A, the molecular weight is usually equal to or higher than the above lower limit.
  • the partial structure A-containing material which is a small molecule compound contained in the light emitting layer according to one embodiment of the present invention, is a light emitting dopant.
  • the light emitting dopant is preferably a compound represented by the following formula (40).
  • the ring HA in the partial structure A represented by the formula (31) corresponds to the triazine ring
  • Ar 0 corresponds to the pyridine ring.
  • R 44 in the formula (40) may have an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aromatic which may have a substituent.
  • n1 is 2 and the other Ar. 0 is R 44 .
  • R 41 , R 42 , and R 43 independently have an alkyl group having 1 to 20 carbon atoms, a (hetero) aralkyl group having 7 to 40 carbon atoms, and an alkoxy having 1 to 20 carbon atoms.
  • R 44 independently has a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 20 carbon atoms, a (hetero) arylyl group having 7 to 40 carbon atoms, and an alkoxy group having 1 to 20 carbon atoms.
  • L 1 represents an organic ligand
  • m40 is an integer of 1 to 3.
  • R 41 to R 44 are independent of each other, and from the viewpoint of durability, an alkyl group having 1 to 20 carbon atoms, a (hetero) aralkyl group having 7 to 40 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a carbon. More preferably, it is a (hetero) aryl group having 3 to 30 carbon atoms or a (hetero) aryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a (hetero) aralkyl group having 7 to 40 carbon atoms, or the like.
  • R 41 to R 44 may further have is preferably a substituent selected from the substituent group Z. When a40 is 2 or more, two adjacent R 41s may be combined with each other to form a ring.
  • Examples of a plurality of R 41s in which adjacent R 41s are bonded to each other to form a ring include fluorene, naphthalene, dibenzothiophene, and dibenzofuran. From the viewpoint of stability, fluorene is particularly preferable. From the viewpoint of lengthening the emission wavelength, it is preferable that adjacent R 41s are bonded to each other to form a ring.
  • the adjacent R 41s do not bond with each other to form a ring. That is, it is preferable that a40 in the formula (40) is 1, or a40 is 2 or more, and adjacent R 41s do not have a ring bonded to each other.
  • the a40 is preferably 0 from the viewpoint of easy production, preferably 1 or 2 from the viewpoint of enhancing durability and solubility, and further preferably 1.
  • b40 is preferably 0 from the viewpoint of easy production, and preferably 1 from the viewpoint of enhancing solubility. Since there are many structures having a high electron acceptability including a triazine ring and LUMO is more stabilized, m40 is preferably 2 or 3, and more preferably 3.
  • L 1 is an organic ligand and is not particularly limited, but is preferably a monovalent bidentate ligand, and is more preferably selected from the following chemical formulas.
  • the broken line in the following chemical formula represents a coordination bond.
  • the organic ligand L 1 may have a different structure from each other.
  • L 1 does not exist.
  • L 1 is represented by the following formula (3), Equation (4), and preferably has at least one structure selected from the group consisting of Formula (5).
  • R 49 and R 50 are synonymous with R 41 in the above formula (40). That is, it is selected from the same group as the substituent selected as R 41 , and the preferred example is also the same, and may further have a substituent. When a plurality of R 49 and R 50 exist, they may be the same or different from each other.
  • R 51 to R 53 are independently substituted with an alkyl group having 1 to 20 carbon atoms which may be substituted with a hydrogen atom and a fluorine atom, a phenyl group which may be substituted with an alkyl group having 1 to 20 carbon atoms, or a phenyl group which may be substituted with an alkyl group having 1 to 20 carbon atoms. It is a halogen atom.
  • G is an integer from 0 to 4.
  • h is an integer from 0 to 4.
  • Ring B 40 is a pyridine ring, a pyrimidine ring, an imidazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, an azatriphenylene ring, a carboline ring, a benzothiazole ring, or a benzoxazole ring. Ring B 40 may further have a substituent.
  • R 49 , R 50 , and ring B 40 may further have are preferably substituents selected from the substituent group Z.
  • R 49 and R 50 are independently alkyl groups having 1 to 20 carbon atoms or aryl groups having 6 to 30 carbon atoms which may be substituted with alkyl groups having 1 to 20 carbon atoms.
  • the aryl group having 6 to 30 carbon atoms is a group in which a plurality of monocyclic, bicyclic condensed rings, tricyclic condensed rings, monocyclic, dicyclic fused rings, or tricyclic condensed rings are linked.
  • G and h are preferably 0 from the viewpoint of easy production, preferably 1 or 2 from the viewpoint of enhancing solubility, and even more preferably 1.
  • R 51 to R 53 are independently substituted with an alkyl group having 1 to 20 carbon atoms which may be substituted with a hydrogen atom and a fluorine atom, and a phenyl group or a halogen which may be substituted with an alkyl group having 1 to 20 carbon atoms, respectively.
  • R 51 and R 53 are methyl or t-butyl groups
  • R 52 is a hydrogen atom, an alkyl or phenyl group having 1 to 20 carbon atoms.
  • the ring B 40 is preferably a pyridine ring, a pyrimidine ring, or an imidazole ring, and more preferably a pyridine ring.
  • Hydrogen atoms on the ring B 40 from the point of viewpoint and solubility of durability is enhanced, an alkyl group having 1 to 20 carbon atoms, having 7 to 40 carbon atoms (hetero) aralkyl group or a C 3-20, It is preferably substituted with a (hetero) aryl group.
  • the hydrogen atom on ring B 40 is preferably not substituted from the viewpoint of easy production.
  • a phenyl group or a naphthyl group which may have a substituent may be used from the viewpoint of increasing the luminous efficiency. It is preferably replaced with.
  • the substituent that the phenyl group or the naphthyl group may have is preferably a substituent selected from the above-mentioned Substituent Group Z.
  • Ring B 40 is preferably a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, an azatriphenylene ring, or a carboline ring from the viewpoint of increasing the luminous efficiency because excitons are easily generated on the assist dopant. ..
  • a quinoline ring, an isoquinoline ring, and a quinazoline ring are more preferable in terms of durability and red emission.
  • a more preferred substituent of ring B 40 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 20 carbon atoms.
  • the aryl group having 6 to 20 carbon atoms is a group in which a plurality of monocyclic, bicyclic condensed rings, tricyclic condensed rings, monocyclic, dicyclic fused rings, or tricyclic condensed rings are linked.
  • R 44 is a phenyl group which may have a substituent group, i.e., the following formula It is preferably the compound represented by (40-1).
  • R 41, R 42, R 43, a40, b40, c40, L 1, m40 is, R 41 in formula (40), R 42, R 43, a40, b40, c40, and L 1, m40
  • R 45 has the same meaning as R 43, R 43 and R 45 may be different even in the same. When a plurality of R 43 and R 45 exist, they may be the same or different from each other.
  • d40 is an integer from 0 to 5.
  • R 43 and R 45 have an alkyl group having 1 to 20 carbon atoms, a (hetero) aralkyl group having 7 to 40 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or an arylamino group having 3 to 30 carbon atoms. It is preferably an alkyl group having 1 to 20 carbon atoms, a (hetero) aralkyl group having 7 to 40 carbon atoms, or a (hetero) aryl group having 3 to 20 carbon atoms. , An alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 40 carbon atoms is more preferable.
  • the substituent that R 43 and R 45 may further have is preferably a substituent selected from the substituent group Z.
  • C40 and d40 are preferably 0 from the viewpoint of easy production, preferably 1 or 2 from the viewpoint of enhancing durability and solubility, and further preferably 1.
  • b40 is preferably 0 from the viewpoint of easy production, and preferably 1 from the viewpoint of enhancing solubility.
  • the light emitting dopant represented by the formula (40) contained in the light emitting layer according to one embodiment of the present invention preferably has a structure in which a40 is 2 or more and adjacent R 41s are bonded to each other to form a fluorene ring.
  • the compound represented by the following formula (40-2) is preferable.
  • R 42 ⁇ R 44, b40, c40, L 1, m40 are each the R 42 ⁇ R 44, b40, c40, L 1, m40 synonymous in the formula (40).
  • R 54 to R 56 are substituents. When a plurality of R 54 to R 56 exist, they may be the same or different from each other.
  • i40 is an integer from 0 to 4.
  • R 54 is a substituent that substitutes for R 51 when R 51 is a phenyl group, and is preferably a substituent selected from the substituent group Z.
  • R 54 is more preferably an aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted with an alkyl group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms.
  • the aromatic hydrocarbon group having 6 to 30 carbon atoms is a monocyclic, 2 to 4 ring fused ring, or a group in which a plurality of monocyclic or 2 to 4 ring fused rings are linked.
  • R 54 is more preferably an alkyl group having 1 to 20 carbon atoms, and even more preferably an alkyl group having 1 to 8 carbon atoms.
  • R 55, R 56 is a substituent in which a part or R 41 in R 41 is substituted on R 41 when there was a methyl group, preferably each independently, an alkyl group having 1 to 20 carbon atoms, carbon atoms It may be substituted with an alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms. It is an aromatic hydrocarbon group having 6 to 30 carbon atoms.
  • the aromatic hydrocarbon group having 6 to 30 carbon atoms is a monocyclic, 2 to 4 ring fused ring, or a group in which a plurality of monocyclic or 2 to 4 ring fused rings are linked.
  • R 55 and R 56 are more preferably aromatic hydrocarbon groups having 6 or 12 carbon atoms which may be substituted with an alkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms. More preferably, it is an alkyl group having 1 to 8 carbon atoms or an aromatic hydrocarbon group having 6 carbon atoms which may be substituted with an alkyl group having 1 to 8 carbon atoms.
  • the aromatic hydrocarbon structure having 6 carbon atoms has a benzene structure
  • the aromatic hydrocarbon structure having 12 carbon atoms has a biphenyl structure.
  • preferable alkyl groups in R 54 to R 56 include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-octyl group, isopropyl group and isobutyl.
  • examples thereof include a group, an isopentyl group, a t-butyl group, a cyclohexyl group, a 2-ethylhexyl group and the like.
  • preferable aromatic hydrocarbon groups in R 54 to R 56 include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, and a fluorantene ring.
  • R 54 to R 56 Specific examples of the preferred alkoxy group in R 54 to R 56 include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a hexyloxy group, a cyclohexyloxy group, an octadecyloxy group and the like.
  • the compound that becomes the light emitting dopant represented by the formula (40-1) contained in the light emitting layer which is one form of the present invention is more preferably the compound represented by the following formula (40-3).
  • R 42, R 43, R 45, b40, c40, d40, L 1 m40 is, R 42 in the formula (40-1), R 43, R 45, b40, c40, d40, L 1, It is synonymous with m40.
  • R 54 ⁇ R 56, i40 are each synonymous with R 54 ⁇ R 56, i40 in Equation (40-2).
  • the hole transport layer of the organic electroluminescent device of the present invention (hereinafter, may be referred to as “hole transport layer of the present embodiment”) is preferably a material containing a partial structure A of the polymer of the present embodiment described above. Include as.
  • the hole transport layer of the present embodiment may contain one type of the polymer of the present embodiment, or may contain two or more types in any combination and in any ratio.
  • the content of the polymer of the present embodiment in the hole transport layer of the present embodiment is usually 1 to 100% by weight, preferably 5 to 100% by weight, and more preferably 10 to 100% by weight.
  • the above range is preferable because the charge transportability of the hole transport layer of the present embodiment is improved, the drive voltage is reduced, and the drive stability is improved.
  • examples of the components constituting the hole transport layer of the present embodiment include hole transporting compounds described later. Be done.
  • the polymer of the present embodiment is preferably used for the hole transport layer of the present embodiment formed by the wet film forming method.
  • the method of forming the hole transport layer by the wet film formation method and the like will be described later.
  • the hole transport layer forming composition for forming the hole transport layer of the present embodiment by the wet film forming method contains the polymer of the present embodiment.
  • the composition for forming a hole transport layer of the present embodiment may contain one kind of the above polymer, or may contain two or more kinds in any combination and any ratio. ..
  • the content of the polymer in the composition for forming a hole transport layer of the present embodiment is usually 0.01 to 70% by weight, preferably 0.1 to 60% by weight, and more preferably 0.5 to 50% by weight. By weight%. When it is within the above range, defects are unlikely to occur in the formed hole transport layer, and uneven film thickness is unlikely to occur, which is preferable.
  • the composition for forming a hole transport layer of the present embodiment may contain a solvent or the like in addition to the above polymer.
  • the composition for forming a hole transport layer of the present embodiment usually contains a solvent.
  • the solvent is preferably one that dissolves the above polymer.
  • a solvent that dissolves the polymer in an amount of usually 0.05% by weight or more, preferably 0.5% by weight or more, and more preferably 1% by weight or more at room temperature is preferable.
  • the solvent include aromatic solvents such as toluene, xylene, mesityrene and cyclohexylbenzene; halogen-containing solvents such as 1,2-dichloroethane, chlorobenzene and o-dichlorobenzene; ethylene glycol dimethyl ether, ethylene glycol diethyl ether and propylene.
  • Aliper ethers such as glycol-1-monomethyl ether acetate (PGMEA), 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetol, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, Ether-based solvents such as aromatic ethers such as 2,3-dimethylanisole and 2,4-dimethylanisole; aliphatic ester-based solvents such as ethyl acetate, n-butyl acetate, ethyl lactate and n-butyl lactate; phenyl acetate, Ester-based solvents such as phenyl propionate, methyl benzoate, ethyl benzoate, isopropyl benzoate, propyl benzoate, n-butyl benzoate and other aromatic esters; Examples thereof include organic solvents used in the composition for forming a hole transport layer and the
  • One type of solvent may be used, or two or more types may be used in any combination and in any ratio.
  • the surface tension at 20 ° C. is usually less than 40 dyn / cm, preferably 36 dyn / cm or less, more preferably 33 dyn / cm or less. Certain solvents are preferred.
  • the affinity between the solvent and the substrate is high. Is preferable. This is because the uniformity of the film quality greatly affects the uniformity and stability of the light emission of the organic electroluminescent device. Therefore, the composition for forming a hole transport layer used in the wet film forming method is required to have a low surface tension so that a uniform coating film having higher leveling property can be formed. Therefore, by using a solvent having a low surface tension as described above, a uniform layer containing the polymer can be formed, and a uniform crosslinked layer can be formed, which is preferable.
  • the low surface tension solvent examples include the above-mentioned aromatic solvents such as toluene, xylene, mesityrene and cyclohexylbenzene, aromatic ester solvents such as ethyl benzoate, aromatic ether solvents such as anisole, and trifluoro. Examples thereof include methoxyanisole, pentafluoromethoxybenzene, 3- (trifluoromethyl) anisole, and ethyl (pentafluorobenzoate).
  • aromatic solvents such as toluene, xylene, mesityrene and cyclohexylbenzene
  • aromatic ester solvents such as ethyl benzoate
  • aromatic ether solvents such as anisole, and trifluoro. Examples thereof include methoxyanisole, pentafluoromethoxybenzene, 3- (trifluoromethyl) anisole, and ethyl (pentafluorobenzoate).
  • a solvent having a vapor pressure at 25 ° C. of usually 10 mmHg or less, preferably 5 mmHg or less, and usually 0.1 mmHg or more is used.
  • a composition for forming a hole transport layer suitable for a process of producing a hole transport layer by a wet film forming method and suitable for the properties of the polymer of the present embodiment is prepared. Can be done.
  • the solvent evaporates at an appropriate rate from the liquid film immediately after the film formation. Therefore, as described above, the boiling point of the solvent used is usually 80 ° C. or higher, preferably 100 ° C. or higher, more preferably 120 ° C. or higher, usually 350 ° C. or lower, preferably 300 ° C. or lower, more preferably 280 ° C. or lower.
  • Specific examples of such a solvent include the above-mentioned aromatic solvents such as mesitylene and cyclohexylbenzene, aromatic ether solvents and aromatic ester solvents.
  • Moisture may cause performance deterioration of the organic electroluminescent element, and in particular, it may promote a decrease in brightness during continuous driving. Therefore, in order to reduce the water content remaining during the wet film formation as much as possible, among the above-mentioned solvents, those having a water solubility at 25 ° C. of 1% by weight or less are preferable, and those having a solubility of 0.1% by weight or less are preferable. Is more preferable.
  • the content of the solvent contained in the composition for forming a hole transport layer of the present embodiment is usually 10% by weight or more, preferably 30% by weight or more, and particularly preferably 50% by weight or more.
  • the content of the solvent is at least the above lower limit, the flatness and uniformity of the formed layer can be improved.
  • the composition for forming a hole transport layer of the present embodiment may further contain an electron-accepting compound from the viewpoint of reducing resistance.
  • an electron-accepting compound a compound having an oxidizing power and an ability to accept one electron from the above polymer is preferable.
  • a compound having an electron affinity of 4 eV or more is preferable, and a compound having an electron affinity of 5 eV or more is more preferable.
  • Examples of such an electron-accepting compound include a triarylboron compound, a metal halide, a Lewis acid, an organic acid, an onium salt, a salt of an arylamine and a metal halide, and a salt of an arylamine and a Lewis acid.
  • Examples thereof include one kind or two or more kinds of compounds selected from the group consisting of two or more kinds.
  • onium salts substituted with organic groups such as 4-isopropyl-4'-methyldiphenyliodonium tetrakis (pentafluorophenyl) borate, triphenylsulfonium tetrafluoroborate (International Publication No. 2005/089024), ( International Publication No. 2017/164268); High valence inorganic compounds such as iron chloride (III) (Japanese Patent Laid-Open No. 11-251067), ammonium peroxodisulfate; cyano compounds such as tetracyanoethylene; tris (pentafluorophenyl) Examples include aromatic boron compounds such as borane (Japanese Patent Laid-Open No. 2003-31365); fullerene derivatives, iodine and the like.
  • organic groups such as 4-isopropyl-4'-methyldiphenyliodonium tetrakis (pentafluorophenyl) borate, triphen
  • composition for forming a hole transport layer of the present embodiment may contain one kind of the above-mentioned electron-accepting compound alone, or may contain two or more kinds in any combination and ratio. good.
  • the content of the electron-accepting compound is usually 0.0005% by weight or more, preferably 0.001% by weight or more, and is usually used. It is 20% by weight or less, preferably 10% by weight or less.
  • the ratio of the electron-accepting compound to the polymer in the hole transport layer forming composition is usually 0.5% by weight or more, preferably 1% by weight or more, more preferably 3% by weight or more, and usually 80% by weight. % Or less, preferably 60% by weight or less, more preferably 40% by weight or less.
  • the electron acceptor accepts electrons from the polymer and the formed hole transport layer has low resistance, which is preferable.
  • the content of the electron-accepting compound in the composition for forming a hole transport layer is not more than the above upper limit, defects are unlikely to occur in the formed hole transport layer, and uneven film thickness is unlikely to occur, which is preferable.
  • the composition for forming a hole transport layer of the present embodiment may further contain a cationic radical compound.
  • a cationic radical compound an ionic compound composed of a cation radical, which is a chemical species obtained by removing one electron from a hole transporting compound, and a counter anion is preferable.
  • the cation radical is derived from a hole-transporting polymer compound, the cation radical has a structure in which one electron is removed from the repeating unit of the polymer compound.
  • the cation radical is preferably a chemical species obtained by removing one electron from the hole transporting compound described later.
  • a chemical species obtained by removing one electron from a preferable compound as a hole transporting compound is preferable from the viewpoints of amorphousness, visible light transmittance, heat resistance, solubility and the like.
  • the cationic radical compound can be produced by mixing the hole transporting compound described later and the electron accepting compound described above. That is, by mixing the hole transporting compound and the electron accepting compound, electron transfer occurs from the hole transporting compound to the electron accepting compound, and the hole transporting compound is composed of a cationic radical and a counter anion. A cationic ion compound is produced.
  • the content of the cation radical compound in the composition for forming a hole transport layer is usually 0.0005% by weight or more, preferably 0. It is 001% by weight or more, usually 40% by weight or less, preferably 20% by weight or less.
  • the content of the cationic radical compound is at least the lower limit, the formed hole transport layer has low resistance, which is preferable.
  • the content of the cationic radical compound is not more than the upper limit, defects are less likely to occur in the formed hole transport layer, and uneven film thickness is less likely to occur, which is preferable.
  • composition for forming a hole transport layer of the present embodiment in addition to the above-mentioned components, the components contained in the composition for forming a hole injection layer and the composition for forming a hole transport layer, which will be described later, are contained in the composition described below. It may be contained in.
  • the light emitting layer of the organic electroluminescent device of the present invention (hereinafter, may be referred to as “light emitting layer of the present embodiment”) preferably contains the above-mentioned low molecular weight compound of the present embodiment as a partial structure A-containing material.
  • the light emitting layer of the present embodiment may contain one kind of the small molecule compound of the present embodiment, or may contain two or more kinds in any combination and any ratio.
  • the light emitting layer of the present embodiment contains at least the low molecular weight compound of the present embodiment and the light emitting material, and the low molecular weight compound of the present embodiment functions as a host material of the light emitting material.
  • the light emitting material a phosphorescent light emitting material or a fluorescent light emitting material can be used.
  • the content of the light emitting material contained in the light emitting layer of the present invention is usually 0.1 to 50% by weight, preferably 0.2 to 40% by weight, and more preferably 0.5 to 35% by weight. When the content of the light emitting material is within the above range, high luminous efficiency can be obtained.
  • the content of the small molecule compound of the present embodiment in the light emitting layer of the present embodiment is usually 5% by weight or more, preferably 10% by weight or more, more preferably 20% by weight, as the content in the material other than the light emitting material. As described above, it is particularly preferably 30% by weight or more, usually 100% by weight or less, preferably 90% by weight or less, still more preferably 80% by weight or less, and particularly preferably 70% by weight or less.
  • the above range is preferable because it is considered that the charge transportability of the light emitting layer of the present embodiment is improved, the driving voltage is reduced, and the driving stability is improved.
  • the other components include a charge transport material described later.
  • the content of other components such as the charge transport material described later in the light emitting layer of the present embodiment is usually 0% by weight or more, preferably 10% by weight or more, more preferably 10% by weight or more, as the content in the material other than the light emitting material. It is 20% by weight or more, particularly preferably 30% by weight, usually 95% by weight or less, preferably 90% by weight or less, still more preferably 80% by weight or less, and particularly preferably 70% by weight or less.
  • the above range is preferable because it is considered that the carrier balance of electrons and holes in the light emitting layer is good, the luminous efficiency is improved, the charge transportability is improved, the voltage is lowered, and the drive stability is improved.
  • the small molecule compound of the present embodiment is preferably used for the light emitting layer of the present embodiment formed by the wet film formation method. The method of forming the light emitting layer by the wet film forming method will be described later.
  • composition for forming a light emitting layer contains the low molecular weight compound of the present embodiment.
  • the composition for forming a light emitting layer of the present embodiment may contain one kind of the above-mentioned small molecule compound, or may contain two or more kinds in any combination and any ratio.
  • the total content of solids such as the small molecule compound, the light emitting material, and the charge transport material in the composition for forming a light emitting layer of the present embodiment is usually 0.01 to 70% by weight, preferably 0.1 to 0.1. It is 60% by weight, more preferably 0.5 to 50% by weight. When it is within the above range, defects are unlikely to occur in the formed light emitting layer, and uneven film thickness is unlikely to occur, which is preferable.
  • the composition for forming a light emitting layer of the present embodiment may contain a solvent or the like in addition to the components such as the small molecule compound, the light emitting material, and the charge transport material.
  • composition for forming a light emitting layer of the present embodiment usually contains a solvent.
  • the same solvent as the solvent contained in the composition for forming a hole transport layer can be selected and used.
  • the properties required for the solvent are similar, and so are the preferred solvents.
  • the amount of the solvent used is arbitrary as long as the effect of the present invention is not significantly impaired, but the content in the light emitting layer forming composition is preferably 1% by mass or more, more preferably 10% by mass or more, and particularly preferably 50. It is 9% by mass or more, preferably 99.99% by mass or less, more preferably 99.9% by mass or less, and particularly preferably 99% by mass or less.
  • the light emitting layer of the present embodiment is a phosphorescent light emitting layer containing a phosphorescent light emitting material as a light emitting material, the following materials are preferable as the phosphorescent light emitting material.
  • the phosphorescent material refers to a material that emits light from an excited triplet state.
  • a metal complex compound having Ir, Pt, Eu, etc. is a typical example, and a material containing a metal complex is preferable as the structure of the material.
  • a phosphorescent organic metal complex that emits light via a triple term state it is a long-periodic periodic table (hereinafter, unless otherwise specified, the term "periodic table” refers to the long-periodic table.
  • a Werner-type complex or an organic metal complex compound containing a metal selected from Groups 7 to 11 as a central metal can be mentioned.
  • a compound represented by the formula (201) or a compound represented by the following formula (205) is preferable, and a compound represented by the following formula (201) is more preferable.
  • the ring A1 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.
  • Ring A2 represents an aromatic heterocyclic structure which may have a substituent.
  • R 201 and R 202 are structures independently represented by the equation (202). “*” Represents a binding site with ring A1 or ring A2.
  • R 201 and R 202 may be the same or different. When there are a plurality of R 201 and R 202 , they may be the same or different.
  • Ar 201 and Ar 203 each independently represent an aromatic hydrocarbon structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.
  • Ar 202 has an aromatic hydrocarbon structure which may have a substituent, an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent. show. Substituents bonded to ring A1, substituents bonded to ring A2, or substituents bonded to ring A1 and substituents bonded to ring A2 may be bonded to each other to form a ring.
  • B 201- L 200- B 202 represents an anionic bidentate ligand.
  • B 201 and B 202 each independently represent a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring.
  • L 200 represents a single bond, or represents an atomic group together with B 201 and B 202 constituting the bidentate ligand. When there are a plurality of B 201- L 200- B 202 , they may be the same or different.
  • i1 and i2 independently represent integers of 0 or more and 12 or less.
  • i3 is an integer of 0 or more up to a number substitutable for Ar 202.
  • j1 is an integer of 0 or more up to a number substitutable for Ar 201.
  • k1 and k2 are independently integers of 0 or more, up to a number substitutable for rings A1 and A2, respectively.
  • m1 is an integer of 1 to 3.
  • Aryl group An alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, further preferably an alkyl group having 1 to 8 carbon atoms, and particularly preferably an alkyl group having 1 to 6 carbon atoms.
  • -Aalkoxy group An alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 12 carbon atoms, further preferably an alkoxy group having 1 to 6 carbon atoms, and an aryloxy group: preferably 6 to 20 carbon atoms.
  • Aryloxy group more preferably an aryloxy group having 6 to 14 carbon atoms, further preferably an aryloxy group having 6 to 12 carbon atoms, particularly preferably an aryloxy group having 6 carbon atoms or a heteroaryloxy group: preferably carbon.
  • Amino group / arylamino group preferably an arylamino group having 6 to 36 carbon atoms, more preferably an arylamino group / aralkyl group having 6 to 24 carbon atoms: preferably an aralkyl group having 7 to 40 carbon atoms, more preferably carbon.
  • An aryl group having 6 to 18 carbon atoms particularly preferably an aryl group having 6 to 14 carbon atoms or a heteroaryl group: preferably a heteroaryl group having 3 to 30 carbon atoms, more preferably having 3 to 24 carbon atoms.
  • an alkylsilyl group / arylsilyl group having an alkyl group having 1 to 12 carbon atoms preferably an arylcy having an aryl group having 6 to 20 carbon atoms.
  • Arylsilyl group / alkylcarbonyl group having 6 to 14 carbon atoms more preferably an aryl group: preferably an alkylcarbonyl group having 2 to 20 carbon atoms, an arylcarbonyl group: preferably an aryl having 7 to 20 carbon atoms.
  • Substituents having a carbonyl group or more may have one or more hydrogen atoms replaced with fluorine atoms, or one or more hydrogen atoms may have been replaced with heavy hydrogen atoms.
  • the aryl group is an aromatic hydrocarbon group and the heteroaryl group is an aromatic heterocyclic group.
  • substituent group Z' Of the above substituent group Z', Preferable group in substituent group Z', Preferably, an alkyl group, an alkoxy group, an aryloxy group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, and one or more hydrogen atoms of these groups are present.
  • a group replaced by a fluorine atom, a fluorine atom, a cyano group, -SF 5 More preferably, an alkyl group, an alkoxy group, an aryloxy group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, a heteroaryl group, and a group in which one or more hydrogen atoms of these groups are replaced with fluorine atoms.
  • Fluorine atom, cyano group, -SF 5 More preferably, it is an alkyl group, an alkoxy group, an aryloxy group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group or a heteroaryl group. Particularly preferred are an alkyl group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, and a heteroaryl group. Most preferably, it is an alkyl group, an arylamino group, an aralkyl group, an aryl group, or a heteroaryl group.
  • substituent group Z' may further have a substituent selected from the substituent group Z'as a substituent.
  • the preferred group, the more preferable group, the more preferable group, the particularly preferable group, and the most preferable group of the substituents which may be possessed are the same as the preferable groups in the substituent group Z'.
  • Ring A1 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.
  • the aromatic hydrocarbon ring of ring A1 is preferably an aromatic hydrocarbon ring having 6 to 30 carbon atoms. Specifically, a benzene ring, a naphthalene ring, an anthracene ring, a triphenylyl ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring are preferable.
  • an aromatic heterocycle of ring A1 an aromatic heterocycle having 3 to 30 carbon atoms containing any of a nitrogen atom, an oxygen atom, and a sulfur atom as a heteroatom is preferable, and a furan ring and a benzofuran ring are more preferable.
  • the ring A1 is more preferably a benzene ring, a naphthalene ring, or a fluorene ring, particularly preferably a benzene ring or a fluorene ring, and most preferably a benzene ring.
  • Ring A2 represents an aromatic heterocyclic structure which may have a substituent.
  • the aromatic heterocycle of ring A2 is preferably an aromatic heterocycle having 3 to 30 carbon atoms, which contains any of a nitrogen atom, an oxygen atom, or a sulfur atom as a hetero atom.
  • Ar 201 and Ar 203 each independently represent an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.
  • Ar 202 has an aromatic hydrocarbon ring structure which may have a substituent, an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent. Represents.
  • Aromatic hydrocarbon rings of Ar 201 , Ar 202 , Ar 203 When any one of Ar 201 , Ar 202 , and Ar 203 has an aromatic hydrocarbon structure which may have a substituent, the aromatic hydrocarbon structure is preferably an aromatic hydrocarbon having 6 to 30 carbon atoms. It is a ring.
  • benzene ring examples include a benzene ring, a naphthalene ring, an anthracene ring, a triphenylyl ring, an acenaphthene ring, a fluoranthene ring and a fluorene ring, more preferably a benzene ring, a naphthalene ring and a fluorene ring, and most preferably a benzene ring. ..
  • Ar 201 or Ar 202 is a benzene ring which may have a substituent
  • at least one benzene ring is preferably bonded to an adjacent structure at the ortho-position or the meta-position, and at least one. It is more preferable that one benzene ring is bonded to an adjacent structure at the meta position.
  • Ar 201 , Ar 202 , and Ar 203 are aromatic heterocyclic structures which may have a substituent
  • the aromatic heterocyclic structure is preferably a nitrogen atom, an oxygen atom, or a heteroatom as a heteroatom. It is an aromatic heterocycle containing any of the sulfur atoms and having 3 to 30 carbon atoms.
  • N position of carbazole If any of Ar 201 , Ar 202 , and Ar 203 is a carbazole ring which may have a substituent, the N-position of the carbazole ring may have a substituent or be bonded to an adjacent structure. preferable.
  • Ar 202 is an aliphatic hydrocarbon structure which may have a substituent, it is an aliphatic hydrocarbon structure having a straight chain, a branched chain, or a cyclic structure, preferably having 1 or more and 24 or less carbon atoms. Yes, more preferably the carbon number is 1 or more and 12 or less, and more preferably the carbon number is 1 or more and 8 or less.
  • i1 represents an integer of 0 to 12, preferably an integer of 1 to 12, more preferably 1 to 8, and even more preferably an integer of 1 to 6. Within this range, the solubility and charge transportability are expected to be improved.
  • i3 preferably represents an integer of 0 to 5, more preferably 0 to 2, more preferably 0 or 1.
  • j1 preferably represents an integer of 0 to 2, and is more preferably 0 or 1.
  • k1 and k2 preferably represent an integer of 0 to 3, more preferably 1 to 3, more preferably 1 or 2, and particularly preferably 1.
  • the substituents that Ar 201 , Ar 202 , and Ar 203 may have can be arbitrarily selected, but preferably one or a plurality of substituents selected from the substituent group Z'.
  • the preferred group is also the same as that of the substituent group Z', but more preferably a hydrogen atom, an alkyl group or an aryl group, particularly preferably a hydrogen atom or an alkyl group, and most preferably an unsubstituted (hydrogen atom). be.
  • Ar 201 is an aromatic hydrocarbon structure or an aromatic heterocyclic structure, i1 is 1 to 6, Ar 202 is an aliphatic hydrocarbon structure, i2 is 1 to 12, preferably 3 to 8, and Ar 203 is a benzene ring structure. , I3 is 0 or 1.
  • Ar 201 has the aromatic hydrocarbon structure, more preferably a structure in which 1 to 5 benzene rings are linked, and more preferably one benzene ring. With this structure, it is expected that the solubility is improved and the charge transportability is improved.
  • (Dendron) A structure in which dendron is bound to ring A1 or ring A2.
  • Ar and Ar 202 have a benzene ring structure
  • Ar 203 has a biphenyl or terphenyl structure
  • i1 and i2 have 1 to 6
  • i3 has 2
  • j has 2.
  • B 201- L 200- B 202 > B 201- L 200- B 202 represents an anionic bidentate ligand.
  • B 201 and B 202 each independently represent a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring.
  • L 200 represents a single bond, or represents an atomic group together with B 201 and B 202 constituting the bidentate ligand. When there are a plurality of B 201- L 200- B 202 , they may be the same or different.
  • the structure represented by B 201- L 200- B 202 is preferably a structure represented by the following formula (203) or (204).
  • R 211 , R 212 , and R 213 represent substituents.
  • ring B3 represents an aromatic heterocyclic structure containing a nitrogen atom, which may have a substituent. Ring B3 is preferably a pyridine ring.
  • the phosphorescent material represented by the formula (201) is not particularly limited, and specific examples thereof include the following structures. In the following, “Ph” represents a “phenyl group” and “Me” represents a "methyl group”.
  • M 2 represents a metal.
  • T represents a carbon atom or a nitrogen atom.
  • R 92 to R 95 each independently represent a substituent. However, when T is a nitrogen atom, there are no R 94 and R 95.
  • M 2 represents a metal.
  • the above-mentioned metal can be mentioned as a metal selected from the 7th to 11th groups of the periodic table.
  • ruthenium, rhodium, palladium, silver, renium, osmium, iridium, platinum or gold are preferable, and divalent metals such as platinum and palladium are particularly preferable.
  • R 92 and R 93 are independently hydrogen atom, halogen atom, alkyl group, aralkyl group, alkenyl group, cyano group, amino group, acyl group, alkoxycarbonyl group, carboxyl group and alkoxy group, respectively. , Alkylamino group, aralkylamino group, haloalkyl group, hydroxyl group, aryloxy group, aromatic hydrocarbon group or aromatic heterocyclic group.
  • R 94 and R 95 independently represent substituents represented by the same examples as R 92 and R 93, respectively.
  • R 92 to R 95 may further have a substituent.
  • the substituent can be the above-mentioned substituent. Any two or more groups of R 92 to R 95 may be connected to each other to form a ring.
  • the molecular weight of the phosphorescent material is preferably 5000 or less, more preferably 4000 or less, particularly preferably 3000 or less, usually 800 or more, preferably 1000 or more, still more preferably 1200 or more. Within this molecular weight range, it is considered that the phosphorescent materials do not aggregate and are uniformly mixed with the charge transport material, so that a light emitting layer having high luminous efficiency can be obtained.
  • the molecular weight of the phosphorescent material is high in Tg, melting point, decomposition temperature, etc., and the phosphorescent material and the formed light emitting layer are excellent in heat resistance, and the film quality due to gas generation, recrystallization, molecular migration, etc. It is preferable that it is large in that it is unlikely that a decrease in the concentration of impurities or an increase in the concentration of impurities due to thermal decomposition of the material will occur. On the other hand, the molecular weight of the phosphorescent material is preferably small in that the organic compound can be easily purified.
  • the light emitting layer of the present embodiment contains the low molecular weight compound of the present embodiment as a host material, but when the light emitting layer is a phosphorescent light emitting layer, it is preferable to include the following materials as other host materials.
  • the host material of the light emitting layer is a material having a skeleton excellent in charge transportability, and is preferably selected from an electron transporting material, a hole transporting material, and a bipolar material capable of transporting both electrons and holes.
  • skeleton with excellent charge transport Specific examples of the skeleton having excellent charge transport properties include an aromatic structure, an aromatic amine structure, a triarylamine structure, a dibenzofuran structure, a naphthalene structure, a phenanthrene structure, a phthalocyanine structure, a porphyrin structure, a thiophene structure, and a benzylphenyl structure.
  • Examples thereof include a fluorene structure, a quinacridone structure, a triphenylene structure, a carbazole structure, a pyrene structure, an anthracene structure, a phenanthrene structure, a quinoline structure, a pyridine structure, a pyrimidine structure, a triazine structure, an oxadiazole structure or an imidazole structure.
  • Electrode transportable material As the electron transporting material, a compound having a pyridine structure, a pyrimidine structure, and a triazine structure is more preferable, and a compound having a pyrimidine structure and a triazine structure is preferable from the viewpoint of being a material having excellent electron transportability and a relatively stable structure. Is more preferable.
  • the hole transporting material is a compound having a structure excellent in hole transporting property, and among the central skeletons having excellent hole transporting property, a carbazole structure, a dibenzofuran structure, a triarylamine structure, a naphthalene structure, a phenanthrene structure or
  • the pyrene structure is preferable as a structure having excellent hole transportability, and a carbazole structure, a dibenzofuran structure or a triarylamine structure is more preferable.
  • the host material of the light emitting layer preferably has a condensed ring structure of 3 or more rings, and is further preferably a compound having 2 or more condensed ring structures of 3 or more rings or a compound having at least one condensed ring structure of 5 or more rings.
  • the rigidity of the molecule is increased, and the effect of suppressing the degree of molecular motion in response to heat can be easily obtained.
  • the condensed ring having 3 or more rings and the condensed ring having 5 or more rings have an aromatic hydrocarbon ring or an aromatic heterocycle in terms of charge transportability and material durability.
  • fused ring structure having three or more rings include anthracene structure, phenanthrene structure, pyrene structure, chrysene structure, naphthacene structure, triphenylene structure, fluorene structure, benzofluorene structure, indenofluorene structure, and indolofluorene structure.
  • fused ring structure having three or more rings include anthracene structure, phenanthrene structure, pyrene structure, chrysene structure, naphthacene structure, triphenylene structure, fluorene structure, benzofluorene structure, indenofluorene structure, and indolofluorene structure.
  • examples thereof include a carbazole structure, an indenocarbazole structure, an indolocarbazole structure, a dibenzofuran structure, and a dibenzothiophene structure.
  • At least one selected from the group consisting of phenanthrene structure, fluorene structure, indenofluorene structure, carbazole structure, indenocarbazole structure, indolocarbazole structure, dibenzofuran structure and dibenzothiophene structure is selected.
  • a carbazole structure or an indolocarbazole structure is more preferable from the viewpoint of resistance to electric charge.
  • At least one of the host materials of the light emitting layer is a material having a pyrimidine skeleton or a triazine skeleton.
  • the host material of the light emitting layer is preferably a polymer material from the viewpoint of excellent flexibility.
  • a light emitting layer formed by using a material having excellent flexibility is preferable as a light emitting layer of an organic electroluminescent element formed on a flexible substrate.
  • the molecular weight is preferably 5,000 or more and 1,000,000 or less, more preferably 10,000 or more and 500,000 or less, and more preferably 10,000 or more. It is 100,000 or less.
  • the host material of the light emitting layer is a small molecule in terms of ease of synthesis and purification, ease of designing electron transport performance and hole transport performance, and ease of viscosity adjustment when dissolved in a solvent. Is preferable.
  • the molecular weight is preferably 5,000 or less, more preferably 4,000 or less, particularly preferably 3,000 or less, and most preferably 2,. It is 000 or less, usually 300 or more, preferably 350 or more, and more preferably 400 or more.
  • the light emitting layer of the present embodiment is a fluorescent light emitting layer
  • the light emitting layer is a blue fluorescent light emitting layer using the following blue fluorescent light emitting material as the fluorescent light emitting material.
  • the light emitting material for the blue fluorescent light emitting layer is not particularly limited, but a compound represented by the following formula (211) is preferable.
  • Ar 241 represents an aromatic hydrocarbon condensed ring structure which may have a substituent.
  • Ar 242 and Ar 243 represent an alkyl group which may independently have a substituent, an aromatic hydrocarbon group, or a group to which these are bonded.
  • n41 is an integer of 1 to 4.
  • Ar 241 preferably represents an aromatic hydrocarbon condensed ring structure having 10 to 30 carbon atoms.
  • Specific structures include naphthalene ring, acenaphthene ring, fluorene ring, anthracene ring, phenatren ring, fluoranthene ring, pyrene ring, tetracene ring, chrysene ring, perylene ring and the like. More preferably, it has an aromatic hydrocarbon condensed ring structure having 12 to 20 carbon atoms.
  • Specific structures include an acenaphthene ring, a fluorene ring, an anthracene ring, a phenatren ring, a fluoranthene ring, a pyrene ring, a tetracene ring, a chrysene ring, and a perylene ring. More preferably, it has an aromatic hydrocarbon condensed ring structure having 16 to 18 carbon atoms.
  • Specific structures include a fluoranthene ring, a pyrene ring, and a chrysene ring.
  • N41 is an integer of 1 to 4, preferably 1 to 3, more preferably 1 to 2, and most preferably 2.
  • the substituents that Ar 241 , Ar 242 , and Ar 243 may have are preferably a group selected from the substituent group Z', more preferably a hydrocarbon group contained in the substituent group Z', and further. It is preferably a hydrocarbon group among the groups preferred as the substituent group Z'.
  • the small molecule compound of the present embodiment is used as the host material of the light emitting material, but when the blue fluorescent light emitting material is used, the following materials are preferable as the other host materials.
  • the host material for the blue fluorescent light emitting layer is not particularly limited, but a compound represented by the following formula (212) is preferable.
  • R 241 and R 242 have structures independently represented by the following formula (213).
  • R243 represents a substituent. When there are a plurality of R 243s , they may be the same or different.
  • n43 is an integer from 0 to 8.
  • Ar 244 and Ar 245 independently represent an aromatic hydrocarbon structure which may have a substituent or a heteroaromatic ring structure which may have a substituent. When a plurality of Ar 244 and Ar 245 exist, they may be the same or different.
  • n44 is an integer from 1 to 5.
  • n45 is an integer from 0 to 5.
  • Ar 244 is preferably an aromatic hydrocarbon structure which is a monocyclic or condensed ring having 6 to 30 carbon atoms, which may have a substituent, and more preferably it may have a substituent.
  • An aromatic hydrocarbon structure which is a monocyclic or condensed ring having 6 to 12 carbon atoms.
  • Ar 245 preferably has an aromatic hydrocarbon structure which is a monocyclic or fused ring having 6 to 30 carbon atoms, which may have a substituent, or may have a substituent, which has 6 carbon atoms. It has an aromatic heterocyclic structure which is a fused ring of to 30 and more preferably has an aromatic hydrocarbon structure which is a monocyclic ring or a fused ring having 6 to 12 carbon atoms or which may have a substituent. It is an aromatic heterocyclic structure which is a fused ring having 12 carbon atoms which may have a substituent.
  • N44 is preferably an integer of 1 to 3, and more preferably 1 or 2.
  • n45 is preferably 0 to 3, more preferably 0 to 2.
  • the substituents R 243 and Ar 244 and Ar 245 may have a substituent preferably a group selected from the substituent group Z', and more preferably a hydrocarbon contained in the substituent group Z'. It is a group, more preferably a hydrocarbon group among the groups preferred as the substituent group Z'.
  • the molecular weight of the light emitting material for the blue fluorescent light emitting layer and its host material is preferably 5,000 or less, more preferably 4,000 or less, particularly preferably 3,000 or less, and most preferably 2,000 or less. , Usually 300 or more, preferably 350 or more, more preferably 400 or more.
  • the organic electroluminescent device of the present embodiment is an organic electroluminescent device having an anode, a cathode, and an organic layer between the anode and the cathode on a substrate, and the organic layer is a hole transport layer and a hole transport layer.
  • a partial structure A having a light emitting layer adjacent to the hole transport layer, and at least one of the materials contained in these hole transport layers and at least one of the materials contained in the light emitting layer have the same partial structure A. It is characterized by being a contained material.
  • the preferred embodiments of the hole transport layer of the present embodiment containing the partial structure A-containing material and the light emitting layer of the present embodiment containing the partial structure A-containing material are as described above.
  • FIG. 1 shows a schematic view (cross section) of a structural example of the organic electroluminescent device 10.
  • 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 a hole blocking layer
  • 7 is an electron transport layer
  • 8 is an electron injection layer.
  • 9 represents each cathode.
  • the wet film forming method is a film forming method, that is, as a coating method, for example, a spin coating method, a dip coating method, a die coating method, a bar coating method, a blade coating method, a roll coating method, a spray coating method, and the like.
  • a method of forming a film by adopting a wet film forming method such as a capillary coating method, an inkjet method, a nozzle printing method, a screen printing method, a gravure printing method, or a flexographic printing method, and drying the coating film.
  • a spin coating method, a spray coating method, an inkjet method, a nozzle printing method and the like are preferable.
  • the substrate 1 serves as a support for an organic electroluminescent element, and usually a quartz or glass plate, a metal plate, a metal foil, a plastic film, a sheet, or the like is used. Of these, a glass plate or a transparent synthetic resin plate such as polyester, polymethacrylate, polycarbonate, or polysulfone is preferable.
  • the substrate is preferably made of a material having a high gas barrier property because the organic electroluminescent element is unlikely to be deteriorated by the outside air. Therefore, particularly when a material having a low gas barrier property such as a synthetic resin substrate is used, it is preferable to provide a dense silicon oxide film or the like on at least one surface of the substrate to improve the gas barrier property.
  • the anode 2 has a function of injecting holes into the layer on the light emitting layer 5 side.
  • the anode 2 is usually a metal such as aluminum, gold, silver, nickel, palladium, platinum; a metal oxide such as an oxide of indium and / or tin; a metal halide such as copper iodide; carbon black and poly (3). -Methylthiophene), polypyrrole, polyaniline and other conductive polymers.
  • the anode 2 is usually formed by a dry method such as a sputtering method or a vacuum vapor deposition method.
  • a dry method such as a sputtering method or a vacuum vapor deposition method.
  • metal fine particles such as silver, fine particles such as copper iodide, carbon black, conductive metal oxide fine particles, conductive polymer fine powder, etc.
  • disperse them in an appropriate binder resin solution it can also be formed by applying it on a substrate.
  • a conductive polymer a thin film can be formed directly on the substrate by electrolytic polymerization, or an anode can be formed by applying the conductive polymer on the substrate (Appl. Phys. Lett., Volume 60, 2711 p., 1992).
  • the anode 2 usually has a single-layer structure, but may have a laminated structure as appropriate. When the anode 2 has a laminated structure, different conductive materials may be laminated on the first-layer anode.
  • the thickness of the anode 2 may be determined according to the required transparency, material, and the like. When particularly high transparency is required, a thickness having a visible light transmittance of 60% or more is preferable, and a thickness having a visible light transmittance of 80% or more is more preferable.
  • the thickness of the anode 2 is usually 5 nm or more, preferably 10 nm or more, and usually 1000 nm or less, preferably 500 nm or less. When transparency is not required, the thickness of the anode 2 may be arbitrarily set according to the required strength and the like. In this case, the anode 2 may have the same thickness as the substrate.
  • impurities on the anode 2 are removed and the ionization potential thereof is formed by treating the surface of the anode 2 with ultraviolet rays / ozone, oxygen plasma, argon plasma, or the like. It is preferable to improve the hole injection property.
  • the layer having a function of transporting holes from the anode 2 side to the light emitting layer 5 side is usually called a hole injection transport layer or a hole transport layer.
  • the layer closer to the anode side may be referred to as the hole injection layer 3.
  • the hole injection layer 3 is preferably formed in terms of enhancing the function of transporting holes from the anode 2 to the light emitting layer 5.
  • the hole injection layer 3 is usually formed on the anode 2.
  • the film thickness of the hole injection layer 3 is usually 1 nm or more, preferably 5 nm or more, usually 1000 nm or less, preferably 500 nm or less.
  • the hole injection layer may be formed by either a vacuum vapor deposition method or a wet film deposition method. In terms of excellent film forming property, it is preferably formed by a wet film forming method.
  • the hole injection layer 3 preferably contains a hole transporting compound, and more preferably contains a hole transporting compound and an electron accepting compound. Further, it is preferable to contain a cationic radical compound in the hole injection layer, and it is particularly preferable to contain a cationic radical compound and a hole transporting compound.
  • the hole injection layer is preferably formed by a wet film forming method using the composition for an organic electroluminescent device.
  • the composition for forming a hole injection layer usually contains a hole transporting compound that becomes the hole injection layer 3.
  • the composition for forming a hole injection layer usually also contains a solvent.
  • the composition for forming a hole injection layer preferably has high hole transportability and can efficiently transport the injected holes. Therefore, it is preferable that the hole mobility is high and impurities that serve as traps are unlikely to be generated during production or use. Further, it is preferable that the stability is excellent, the ionization potential is small, and the transparency to visible light is high.
  • the hole injection layer 3 when the hole injection layer 3 is in contact with the light emitting layer 5, those that do not quench the light emitted from the light emitting layer 5 or those that form an exciplex with the light emitting layer 5 and do not reduce the luminous efficiency are preferable.
  • hole transporting compound a compound having an ionization potential of 4.5 eV to 6.0 eV is preferable from the viewpoint of a charge injection barrier from the anode 2 to the hole injection layer 3.
  • hole-transporting compounds include aromatic amine compounds, phthalocyanine compounds, porphyrin compounds, oligothiophene compounds, polythiophene compounds, benzylphenyl compounds, compounds in which a tertiary amine is linked with a fluorene group, and hydrazone. Examples thereof include system compounds, silazane compounds, and quinacridone compounds.
  • aromatic amine compounds are preferable, and aromatic tertiary amine compounds are particularly preferable, from the viewpoint of amorphousness and visible light transmission.
  • the aromatic tertiary amine compound is a compound having an aromatic tertiary amine structure, and also includes a compound having a group derived from an aromatic tertiary amine.
  • the type of the aromatic tertiary amine compound is not particularly limited, but a polymer compound having a weight average molecular weight of 1000 or more and 1000,000 or less (polymerized compound in which repeating units are continuous) is easy to obtain uniform light emission due to the surface smoothing effect. ) Is preferably used.
  • the hole injecting layer 3 can improve the conductivity of the hole injecting layer by oxidizing the hole transporting compound, the hole injecting layer 3 contains the above-mentioned electron-accepting compound and the above-mentioned cationic radical compound. Is preferable.
  • Cationic radical compounds derived from polymer compounds such as PEDOT / PSS (Adv. Mater., 2000, Vol. 12, p. 481) and emeraldine hydrochloride (J. Phys. Chem., 1990, Vol. 94, p. 7716) It is also produced by oxidative polymerization (dehydrogenation polymerization).
  • the oxidative polymerization referred to here is to chemically or electrochemically oxidize a monomer in an acidic solution using peroxodisulfate or the like.
  • a cation radical obtained by removing one electron from a repeating unit of a polymer, which is polymerized by oxidizing a monomer and has an anion derived from an acidic solution as a counter anion, is generated. Generate.
  • the material to be the hole injection layer 3 is usually mixed with a soluble solvent (solvent for the hole injection layer) to form a composition for film formation (positive).
  • a composition for forming a hole injection layer is prepared, and this composition for forming a hole injection layer is applied onto a layer corresponding to the lower layer of the hole injection layer 3 (usually, an anode 2) to form a film, and then dried. It is formed by letting it.
  • the concentration of the hole-transporting compound in the composition for forming a hole injection layer is arbitrary as long as the effect of the present invention is not significantly impaired, but it is preferably low in terms of film thickness uniformity, and hole injection Higher is preferable in that defects are less likely to occur in the layer.
  • it is preferably 0.01% by weight or more, more preferably 0.1% by weight or more, particularly preferably 0.5% by weight or more, and 70% by weight or less. Is more preferable, and it is more preferably 60% by weight or less, and particularly preferably 50% by weight or less.
  • solvent examples include ether solvents, ester solvents, aromatic hydrocarbon solvents, amide solvents and the like.
  • ether-based solvent examples include aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA), and 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, and anisole. , Fenetol, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole and other aromatic ethers.
  • aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA), and 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, and anisole.
  • PGMEA propylene glycol-1-monomethyl ether acetate
  • Fenetol 2-methoxyto
  • ester-based solvent examples include aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate.
  • aromatic hydrocarbon solvent examples include toluene, xylene, cyclohexylbenzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, cyclohexylbenzene, methylnaphthalene and the like. Be done.
  • amide-based solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide and the like. In addition to these, dimethyl sulfoxide and the like can also be used.
  • the formation of the hole injection layer 3 by the wet film formation method is usually performed on the layer corresponding to the lower layer of the hole injection layer 3 (usually, the anode 2) after preparing the composition for forming the hole injection layer. It is carried out by applying a film to the film and drying it. In the hole injection layer 3, the coating film is usually dried by heating, vacuum drying, or the like after the film formation.
  • the hole injection layer 3 is formed by the vacuum deposition method
  • the constituent materials of the hole injection layer 3 the above-mentioned hole transporting compound, electron accepting compound, etc.
  • Place in a crucible installed inside the container when using two or more materials, usually put each in a separate crucible, exhaust the inside of the vacuum container to about 10-4 Pa with a vacuum pump, and then heat the crucible.
  • each crucible is usually heated
  • the material in the crucible is evaporated while controlling the amount of evaporation (when two or more types of materials are used, each is usually independent).
  • a mixture thereof can be placed in a crucible and heated and evaporated to form a hole injection layer.
  • the degree of vacuum during vapor deposition is not limited as long as the effect of the present invention is not significantly impaired, but is usually 0.1 ⁇ 10 -6 Torr (0.13 ⁇ 10 -4 Pa) or more, 9.0 ⁇ 10 -6 Torr ( It is 12.0 ⁇ 10 -4 Pa) or less.
  • the vapor deposition rate is not limited as long as the effect of the present invention is not significantly impaired, but is usually 0.1 ⁇ / sec or more and 5.0 ⁇ / sec or less.
  • the film formation temperature at the time of vapor deposition is not limited as long as the effect of the present invention is not significantly impaired, but is preferably 10 ° C. or higher and 50 ° C. or lower.
  • the hole injection layer 3 may be crosslinked in the same manner as the hole transport layer 4 described later.
  • the hole transport layer 4 is a layer that has a function of transporting holes from the anode 2 side to the light emitting layer 5.
  • the hole transport layer 4 of the present embodiment preferably contains the polymer of the present embodiment as the partial structure A-containing material.
  • the hole transport layer 4 is usually formed between the anode 2 and the light emitting layer 5.
  • the hole transport layer 4 is formed between the hole injection layer 3 and the light emitting layer 5.
  • the film thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more, usually 300 nm or less, preferably 100 nm or less.
  • the hole transport layer 4 may be formed by either a vacuum vapor deposition method or a wet film deposition method. In terms of excellent film forming property, it is preferably formed by a wet film forming method.
  • the general method for forming the hole transport layer will be described below.
  • the hole transport layer of the present embodiment is preferably formed by a wet film forming method using the above-mentioned hole transport layer forming composition.
  • the hole transport layer 4 usually contains a hole transport compound.
  • the hole-transporting compound contained in the hole-transporting layer 4 the polymer of the present embodiment or, when the polymer has a crosslinkable group, a polymer in which the polymer is crosslinked is preferable.
  • two or more 3 represented by the hole transporting compound preferably 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl.
  • Aromatic diamine containing a secondary amine in which two or more fused aromatic rings are replaced with nitrogen atoms Japanese Patent Laid-Open No.
  • Aromatic amine compounds having a starburst structure such as amines (J. Lumin., 72-74, pp. 985, 1997), aromatic amine compounds consisting of triphenylamine tetramers (Chem. Commun., 2175). P. 1996), Spiro compounds such as 2,2', 7,7'-tetrax- (diphenylamino) -9,9'-spirobifluorene (Synth. Metals, Vol. 91, p.
  • It may contain a carbazole derivative such as 4,4'-N, N'-dicarbazolebiphenyl and the like. Further, it contains polyvinylcarbazole, polyvinyltriphenylamine (Japanese Patent Laid-Open No. 7-53953), polyarylene ether sulfone containing tetraphenylbenzidine (Polym. Adv. Tech., Vol. 7, p. 33, 1996) and the like. But it may be.
  • the hole transport layer 4 is formed by the wet film forming method, usually, in the same manner as when the hole injection layer 3 is formed by the wet film forming method, instead of the hole injection layer forming composition. It is formed using a composition for forming a hole transport layer.
  • the hole transport layer forming composition usually further contains a solvent.
  • the solvent used in the hole transport layer forming composition the same solvent as the solvent used in the hole injection layer forming composition described above can be used.
  • the concentration of the hole-transporting compound in the composition for forming a hole-transporting layer can be in the same range as the concentration of the hole-transporting compound in the composition for forming a hole-injecting layer.
  • the hole transport layer 4 can be formed by the wet film formation method in the same manner as the hole injection layer 3 film formation method described above.
  • the light emitting layer 5 is a layer having a function of emitting light by being excited by recombination of holes injected from the anode 2 and electrons injected from the cathode 9 when an electric field is applied between the pair of electrodes. ..
  • the light emitting layer 5 is a layer formed between the anode 2 and the cathode 9.
  • the light emitting layer 5 is formed between the hole transport layer 4 and the cathode 9.
  • the film thickness of the light emitting layer 5 is arbitrary as long as the effect of the present invention is not significantly impaired, but a thicker one is preferable in that defects are less likely to occur in the film. On the other hand, a thinner one is preferable because it is easy to obtain a low drive voltage. Therefore, the film thickness of the light emitting layer 5 is preferably 3 nm or more, more preferably 5 nm or more, usually 200 nm or less, and further preferably 100 nm or less.
  • the light emitting layer 5 contains at least a material having a light emitting property (light emitting material) and preferably a material having a charge transporting property (charge transporting material).
  • the light emitting layer of the present embodiment contains at least a light emitting material and a small molecule compound of the present embodiment as a partial structure A-containing material.
  • the light emitting layer is preferably formed by a wet film forming method using the above-mentioned composition for forming a light emitting layer.
  • the light emitting material is not particularly limited as long as it emits light at a desired light emitting wavelength and the effect of the present invention is not impaired, and a known light emitting material can be applied.
  • the light emitting material may be either a fluorescent light emitting material or a phosphorescent light emitting material, but a material having good luminous efficiency is preferable, and a phosphorescent light emitting material is preferable from the viewpoint of internal quantum efficiency.
  • Examples of the fluorescent light emitting material include the following materials.
  • fluorescent light emitting material blue fluorescent light emitting material
  • examples of the fluorescent light emitting material that gives blue light emission include naphthalene, perylene, pyrene, anthracene, coumarin, chrysene, p-bis (2-phenylethenyl) benzene, and derivatives thereof.
  • the fluorescent light-emitting material giving green luminescence for example, quinacridone derivatives, coumarin derivatives, Al (C 9 H 6 NO ) aluminum complex such as 3.
  • Examples of the fluorescent light emitting material that gives yellow light emission include rubrene, a perimidone derivative, and the like.
  • red fluorescent light emitting material examples include DCM (4- (dimethyanomethylene) -2-methyl-6- (p-dimethylaminostylyl) -4H-pyran) compounds, benzopyran derivatives, and rhodamine derivatives. , Benzothioxanthene derivatives, azabenzothioxanthene and the like.
  • Examples of the phosphorescent material include an organometallic complex containing a metal selected from Groups 7 to 11 of the long periodic table.
  • Preferred metals selected from Groups 7 to 11 of the periodic table include ruthenium, rhodium, palladium, silver, renium, osmium, iridium, platinum, gold and the like.
  • a ligand in which a (hetero) aryl group such as a (hetero) arylpyridine ligand or a (hetero) arylpyrazole ligand is linked to a pyridine, pyrazole, phenanthroline or the like is preferable.
  • a phenylpyridine ligand and a phenylpyrazole ligand are preferable.
  • the (hetero) aryl represents an aryl group or a heteroaryl group.
  • Specific preferred phosphorescent materials include tris (2-phenylpyridine) iridium, tris (2-phenylpyridine) ruthenium, tris (2-phenylpyridine) palladium, bis (2-phenylpyridine) platinum, and tris (2).
  • Examples thereof include phenylpyridine complexes such as -phenylpyridine) osmium and tris (2-phenylpyridine) renium, and porphyrin complexes such as octaethyl platinum porphyrin, octaphenyl platinum porphyrin, octaethyl palladium porphyrin, and octaphenyl palladium porphyrin.
  • Polymer-based luminescent materials include poly (9,9-dioctylfluorene-2,7-diyl) and poly [(9,9-dioctylfluorene-2,7-diyl) -co- (4,4'-).
  • the charge transporting material is a material having a positive charge (hole) or negative charge (electron) transport property.
  • the charge transporting material is not particularly limited as long as the effects of the present invention are not impaired, and known charge transporting materials can be applied.
  • the charge transporting material a compound or the like conventionally used for the light emitting layer of the organic electroluminescent device can be used, and a compound used as a host material for the light emitting layer is particularly preferable.
  • the charge transporting material other than the low molecular weight compound of the present embodiment include aromatic amine compounds, phthalocyanine compounds, porphyrin compounds, oligothiophene compounds, and polythiophene compounds containing the polymer of the present embodiment.
  • a hole transporting compound in the hole injection layer such as a compound, a benzylphenyl compound, a compound in which a tertiary amine is linked with a fluorene group, a hydrazone compound, a silazane compound, a silanamine compound, a phosphamine compound, a quinacridone compound, etc. Examples thereof include the exemplified compounds.
  • electron-transporting compounds such as anthracene-based compounds, pyrene-based compounds, carbazole-based compounds, pyridine-based compounds, phenanthroline-based compounds, oxadiazole-based compounds, and silol-based compounds can be mentioned.
  • two or more fused aromatic rings containing two or more tertiary amines represented by 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl are used as nitrogen atoms.
  • Aromatic amine compounds having a starburst structure such as substituted aromatic diamines (Japanese Patent Laid-Open No. 5-234681), 4,4', 4''-tris (1-naphthylphenylamino) triphenylamine, etc. Lumin., 72-74, 985, 1997), aromatic amine compounds consisting of triphenylamine tetramers (Chem.
  • PyPySPyPy phenanthroline compounds
  • BPhen vasophenanthroline
  • BCP bathocuproine
  • the light emitting layer 5 may be formed by a vacuum vapor deposition method or a wet film deposition method.
  • the wet film forming method is preferable, and the spin coating method and the inkjet method are more preferable because of the excellent film forming property.
  • the hole transport layer 4 to be the lower layer of the light emitting layer 5 is formed by using the composition for forming the hole transport layer described above, laminating by the wet film formation method is easy. It is preferable to adopt it.
  • the light emitting layer 5 is formed by the wet film forming method
  • the above-mentioned composition is used. It is formed using a composition for forming a light emitting layer.
  • heating or depressurization can be used as a method for removing the solvent after the wet film formation.
  • heating or depressurization can be used as the heating means used in the heating method.
  • a clean oven and a hot plate are preferable because heat is evenly applied to the entire film.
  • the heating temperature in the heating step is arbitrary as long as the effect of the present invention is not significantly impaired.
  • a high temperature is preferable in terms of shortening the drying time, and a low temperature is preferable in terms of less damage to the material.
  • the upper limit of the heating temperature is usually 250 ° C. or lower, preferably 200 ° C. or lower, and more preferably 150 ° C. or lower.
  • the lower limit of the heating temperature is usually 30 ° C. or higher, preferably 50 ° C. or higher, and more preferably 80 ° C. or higher.
  • a temperature at which the heating temperature exceeds the above upper limit is higher than the heat resistance of a commonly used charge transporting material or phosphorescent material, and may be decomposed or crystallized, which is not preferable.
  • the heating time in the heating step is appropriately determined by the boiling point and vapor pressure of the solvent in the composition for forming the light emitting layer, the heat resistance of the material, and the heating conditions.
  • the constituent materials of the light emitting layer 5 are usually used. Place in a crucible installed in a vacuum vessel (when using two or more materials, usually put each in a separate crucible), exhaust the inside of the vacuum vessel to about 10-4 Pa with a vacuum pump, and then remove the crucible. Heat (usually heat each crucible when using two or more materials) and evaporate while controlling the amount of evaporation of the material in the crucible (usually each when using two or more materials).
  • a mixture thereof can be placed in a crucible and heated and evaporated to form the light emitting layer 5.
  • the degree of vacuum during vapor deposition is not limited as long as the effect of the present invention is not significantly impaired, but is usually 0.1 ⁇ 10 -6 Torr (0.13 ⁇ 10 -4 Pa) or more, 9.0 ⁇ 10 -6 Torr ( It is 12.0 ⁇ 10 -4 Pa) or less.
  • the vapor deposition rate is not limited as long as the effect of the present invention is not significantly impaired, but is usually 0.1 ⁇ / sec or more and 5.0 ⁇ / sec or less.
  • the film formation temperature at the time of vapor deposition is not limited as long as the effect of the present invention is not significantly impaired, but is preferably 10 ° C. or higher and 50 ° C. or lower.
  • a hole blocking layer 6 may be provided between the light emitting layer 5 and the electron injection layer 8 described later.
  • the hole blocking layer 6 is a layer laminated on the light emitting layer 5 so as to be in contact with the interface of the light emitting layer 5 on the cathode 9 side.
  • the hole blocking layer 6 has a role of blocking holes moving from the anode 2 from reaching the cathode 9 and a role of efficiently transporting electrons injected from the cathode 9 toward the light emitting layer 5.
  • the physical properties required for the material constituting the hole blocking layer 6 are high electron mobility and low hole mobility, a large energy gap (difference between HOMO and LUMO), and an excited triplet level (T1). Is high.
  • Examples of the material of the hole blocking layer 6 satisfying such conditions include bis (2-methyl-8-quinolinolato) (phenolato) aluminum and bis (2-methyl-8-quinolinolato) (triphenylsilanorat) aluminum.
  • Mixed ligand complexes such as, bis (2-methyl-8-quinolato) aluminum- ⁇ -oxo-bis- (2-methyl-8-quinolilato) aluminum dinuclear metal complexes and other metal complexes, distyrylbiphenyl derivatives, etc.
  • Styryl compounds Japanese Patent Laid-Open No.
  • the hole blocking layer 6 There is no limitation on the method of forming the hole blocking layer 6. Therefore, it can be formed by a wet film forming method, a thin film deposition method, or another method.
  • the film thickness of the hole blocking layer 6 is arbitrary as long as the effect of the present invention is not significantly impaired, but is usually 0.3 nm or more, preferably 0.5 nm or more, and usually 100 nm or less, preferably 50 nm or less.
  • the electron transport layer 7 is provided between the light emitting layer 5 and the electron injection layer 8 for the purpose of further improving the current efficiency of the device.
  • the electron transport layer 7 is formed of a compound capable of efficiently transporting electrons injected from the cathode 9 in the direction of the light emitting layer 5 between the electrodes to which an electric field is applied.
  • the electron-transporting compound used in the electron-transporting layer 7 has high electron-injection efficiency from the cathode 9 or the electron-injection layer 8 and high electron mobility, and efficiently transports the injected electrons. It needs to be a compound that can.
  • the electron-transporting compound used in the electron-transporting layer include metal complexes such as an aluminum complex of 8-hydroxyquinolin (Japanese Patent Laid-Open No. 59-194393), 10-hydroxybenzo [h] quinoline. Metal Complex, Oxaziazole Derivative, Distyrylbiphenyl Derivative, Sirol Derivative, 3-Hydroxyflavon Metal Complex, 5-Hydroxyflavon Metal Complex, Benzoxazole Metal Complex, Benthiazole Metal Complex, Trisbenzimidazolylbenzene (US Patent No. 5645948) Specified specification), quinoxalin compound (Japanese Patent Laid-Open No.
  • phenanthroline derivative Japanese Patent Laid-Open No. 5-331459
  • 2-t-butyl-9,10-N, N'-dicyanoanthraquinone diimine examples thereof include hydride amorphous silicon carbide, n-type zinc sulfide, and n-type zinc selenium.
  • the film thickness of the electron transport layer 7 is usually 1 nm or more, preferably 5 nm or more, and usually 300 nm or less, preferably 100 nm or less.
  • the electron transport layer 7 is formed by laminating on the hole blocking layer 6 by a wet film deposition method or a vacuum vapor deposition method in the same manner as described above. Usually, the vacuum deposition method is used.
  • the electron injection layer 8 plays a role of efficiently injecting the electrons injected from the cathode 9 into the electron transport layer 7 or the light emitting layer 5.
  • the material forming the electron injection layer 8 is preferably a metal having a low work function.
  • alkali metals such as sodium and cesium, alkaline earth metals such as barium and calcium, and the like are used.
  • the film thickness of the electron injection layer 8 is usually preferably 0.1 nm or more and 5 nm or less.
  • Materials for forming the electron injection layer 8 include organic electron transport materials typified by nitrogen-containing heterocyclic compounds such as basophenanthroline and metal complexes such as aluminum complexes of 8-hydroxyquinoline, and sodium, potassium, cesium, and the like.
  • Dope with an alkali metal such as lithium or rubidium also improves electron injection and transportability and is excellent. It is preferable because it makes it possible to achieve both film quality and film quality.
  • the film thickness of the electron injection layer 8 is usually 5 nm or more, preferably 10 nm or more, and usually 200 nm or less, preferably 100 nm or less.
  • the electron injection layer 8 is formed by laminating on the light emitting layer 5 or the hole blocking layer 6 or the electron transport layer 7 on the light emitting layer 5 by a wet film forming method or a vacuum vapor deposition method.
  • the details in the case of the wet film forming method are the same as in the case of the light emitting layer described above.
  • the cathode 9 plays a role of injecting electrons into a layer on the light emitting layer 5 side (electron injection layer 8 or light emitting layer 5 or the like).
  • the material used for the anode 2 can be used.
  • a metal having a low work function for example, a metal such as tin, magnesium, indium, calcium, aluminum, silver or an alloy thereof is used.
  • Specific examples include alloy electrodes having a low work function such as magnesium-silver alloy, magnesium-indium alloy, and aluminum-lithium alloy.
  • a metal layer having a high work function and stable with respect to the atmosphere on the cathode 9 to protect the cathode made of a metal having a low work function.
  • the metal to be laminated include metals such as aluminum, silver, copper, nickel, chromium, gold, and platinum.
  • the film thickness of the cathode 9 is usually the same as that of the anode 2.
  • the organic electroluminescent device of the present embodiment may further have another layer as long as the effect of the present invention is not significantly impaired. That is, any of the above-mentioned other layers may be provided between the anode 2 and the cathode 9.
  • the organic electroluminescent device of the present embodiment has a structure opposite to that described above, that is, the cathode 9, the electron injection layer 8, the electron transport layer 7, the hole blocking layer 6, the light emitting layer 5, and the holes on the substrate 1. It is also possible to stack the transport layer 4, the hole injection layer 3, and the anode 2 in this order. It is also possible to provide the organic electroluminescent device of the present invention between two substrates having at least one highly transparent substrate.
  • the organic electroluminescent device of the present embodiment When the organic electroluminescent device of the present embodiment is applied to an organic electroluminescent device, it may be used as a single organic electroluminescent device or may be used in a configuration in which a plurality of organic electroluminescent devices are arranged in an array. , The anode and the cathode may be arranged in an XY matrix.
  • Organic EL display device uses the above-mentioned organic electroluminescent element.
  • the model and structure of the organic EL display device of the present embodiment are not particularly limited, and can be assembled according to a conventional method using the above-mentioned organic electroluminescent element.
  • the organic EL display device of the present invention can be used by the method described in "Organic EL Display” (Ohmsha, published on August 20, 2004, by Shizushi Tokito, Chihaya Adachi, Hideyuki Murata). Can be formed.
  • Organic EL lighting uses the above-mentioned organic electroluminescent element.
  • the type and structure of the organic EL illumination of the present embodiment are not particularly limited, and can be assembled according to a conventional method using the above-mentioned organic electroluminescent element.
  • compound 5 (7.1 g, 14.87 mmol), commercially available 2-chloro-4,6-diphenyl-1,3,5-triazine (3.98 g, 14.87 mmol), potassium phosphate aqueous solution (2M, 23.0 ml), toluene (50 ml) and ethanol (25 ml) were placed in a flask, and the inside of the system was sufficiently replaced with nitrogen and heated to 65 ° C. Tetrakis (triphenylphosphine) palladium (0) (0.52 g, 0.45 mmol) was added thereto, and the mixture was stirred at 85 ° C. for 4.0 hours.
  • Compound 14 was synthesized by the same method as that for compound 12 except that 1-bromo-4-iodobenzene was used instead of 5-bromo-2-iodotoluene.
  • Solution B1 was added to solution A1 in a nitrogen stream, and a heating reflux reaction was carried out for 1.0 hour. After confirming that compounds 7, 10 and 13 had disappeared, compound 14 (1.78 g, 3.5 mmol) was added. After heating under reflux for 2 hours, bromobenzene (1.84 g, 11.7 mmol) was added, and the mixture was heated under reflux for 1 hour. The reaction mixture was allowed to cool and added dropwise to an ethanol / water (370 ml / 70 ml) solution to obtain an end-capped crude polymer. The end-capped crude polymer was dissolved in toluene, reprecipitated in acetone, and the precipitated polymer was filtered off.
  • the obtained polymer was dissolved in toluene, washed with dilute hydrochloric acid, and reprecipitated with ammonia-containing ethanol.
  • the polymer collected by filtration was purified by column chromatography to obtain the target polymer 1 (2.5 g).
  • the molecular weight and the like of the obtained polymer 1 were as follows.
  • Example 1 An organic electroluminescent device was manufactured by the following method.
  • a transparent conductive film of indium tin oxide (ITO) deposited on a glass substrate to a thickness of 70 nm (manufactured by Sanyo Vacuum Co., Ltd., sputter-deposited product) is 2 mm wide using ordinary photolithography technology and hydrochloric acid etching.
  • the stripes were patterned to form an anode.
  • the substrate on which the ITO pattern is formed is washed in the order of ultrasonic cleaning with an aqueous surfactant solution, water washing with ultrapure water, ultrasonic cleaning with ultrapure water, and water washing with ultrapure water, and then dried with compressed air. Finally, UV ozone cleaning was performed.
  • composition for forming the hole injection layer 100 parts by weight of the hole-transporting polymer compound having a repeating structure represented by the following formula (P-1) and the compound 20 represented by the following formula (HI-1). The parts by weight were weighed and dissolved in ethyl benzoate to prepare a composition having a solid content concentration of 3.0% by weight.
  • This composition for forming a hole injection layer is spin-coated on the substrate in the atmosphere and dried in the air at 240 ° C. for 30 minutes to form a uniform thin film having a film thickness of 40 nm, and hole injection is performed. Layered.
  • HT-1 charge-transporting polymer compound represented by the following formula (HT-1), which is the polymer 1 synthesized in Synthesis Example 1
  • cyclohexylbenzene 100 parts by weight of the charge-transporting polymer compound represented by the following formula (HT-1), which is the polymer 1 synthesized in Synthesis Example 1
  • HT-1 charge-transporting polymer compound represented by the following formula (HT-1)
  • cyclohexylbenzene 100 parts by weight of the charge-transporting polymer compound represented by the following formula (HT-1), which is the polymer 1 synthesized in Synthesis Example 1
  • a composition for forming a hole transport layer was prepared. This composition for forming a hole transport layer is spin-coated in a nitrogen glove box on a substrate coated with the hole injection layer and dried at 230 ° C. for 30 minutes on a hot plate in the nitrogen glove box to form a film.
  • a uniform thin film having a thickness of 40 nm was formed to form a hole transport layer.
  • the compound represented by the following formula (H-1) is 15 parts by weight
  • the compound represented by the following formula (H-2) is 15 parts by weight
  • the following formula (H-3) is used as the material of the light emitting layer.
  • This composition for forming a light emitting layer is spin-coated on a substrate coated with the hole transport layer in a nitrogen glove box, dried on a hot plate in the nitrogen glove box at 120 ° C. for 20 minutes, and has a film thickness of 70 nm. A uniform thin film was formed to form a light emitting layer.
  • the substrate on which the film was formed up to the light emitting layer was installed in a vacuum vapor deposition apparatus, and the inside of the apparatus was exhausted until it became 2 ⁇ 10 -4 Pa or less.
  • the compound represented by the following formula (HB-1) and 8-hydroxyquinolinolatrithium are co-deposited on the light emitting layer at a film thickness ratio of 2: 3 by a vacuum deposition method at a rate of 1 ⁇ / sec. Then, a hole blocking layer having a film thickness of 30 nm was formed.
  • a striped shadow mask having a width of 2 mm was brought into close contact with the substrate so as to be orthogonal to the ITO stripe of the anode as a mask for cathode vapor deposition, and installed in another vacuum vapor deposition apparatus.
  • aluminum was heated by a molybdenum boat to form an aluminum layer having a film thickness of 80 nm at a vapor deposition rate of 1 to 8.6 ⁇ / sec to form a cathode.
  • an organic electroluminescent device having a light emitting area portion having a size of 2 mm ⁇ 2 mm was obtained.
  • these organic electroluminescent elements are driven at 40 mA / cm 2 , the 15% luminance attenuation lifetime (LT85) is measured, and the ratio when the 15% attenuation lifetime of Comparative Example 1 is set to 1 (hereinafter, “relative attenuation lifetime”). ".) was requested. They are shown in Table 1.
  • the organic field light emitting device of the present invention containing a compound having the same partial structure A and a structure represented by the formula (TzP) in the hole transport layer and the light emitting layer has a lower voltage and a longer life.
  • the charge-transporting polymer compound represented by the formula (HT-1) and the compound represented by the formula (H-1) both used in Example 1 have a structure in which four benzene rings are linked to triazine. Therefore, it has a high degree of commonality, and this point is also considered to contribute to the extension of life.
  • Example 2 An organic electroluminescent device was manufactured by the following method. A 2 mm wide stripe of indium tin oxide (ITO) transparent conductive film deposited on a glass substrate to a thickness of 50 nm (a sputtered film product manufactured by Geomatec) using ordinary photolithography technology and hydrochloric acid etching. The anode was formed by patterning. The substrate on which the ITO pattern is formed is washed in the order of ultrasonic cleaning with an aqueous surfactant solution, water washing with ultrapure water, ultrasonic cleaning with ultrapure water, and water washing with ultrapure water, and then dried with compressed air. Finally, UV ozone cleaning was performed.
  • ITO indium tin oxide
  • composition for forming the hole injection layer 3.0% by weight of the hole-transporting polymer compound having a repeating structure represented by the formula (P-1) used in Example 1 and the formula (HI-1).
  • a composition was prepared in which 0.6% by weight of the compound represented by (1) was dissolved in ethyl benzoate.
  • This composition for forming a hole injection layer is spin-coated on the substrate in the atmosphere and dried on an atmospheric hot plate at 240 ° C. for 30 minutes to form a uniform thin film having a film thickness of 40 nm to form a hole injection layer. And said.
  • the hole transport layer material 100 parts by weight of the charge transport polymer compound represented by the following formula (HT-2) is dissolved in cyclohexylbenzene, and the hole transport layer is composed of a 3.0% by weight solution.
  • a composition for formation was prepared. This composition for forming a hole transport layer is spin-coated in a nitrogen glove box on a substrate coated with the hole injection layer and dried in a hot plate in a nitrogen glove box at 230 ° C. for 30 minutes to form a film. A uniform thin film having a thickness of 40 nm was formed to form a hole transport layer.
  • the material of the light emitting layer 50 parts by weight of the compound represented by the formula (H-1) used in Example 1, 50 parts by weight of the compound represented by the following formula (H-6), and the above.
  • the compound represented by the formula (D-1) was weighed in 15 parts by weight and dissolved in cyclohexylbenzene to prepare a solution having a solid content concentration of 5.0% by weight as a light emitting layer forming composition.
  • This composition for forming a light emitting layer is spin-coated on a substrate coated with the hole transport layer in a nitrogen glove box, dried on a hot plate in the nitrogen glove box at 120 ° C. for 20 minutes, and has a film thickness of 80 nm. A uniform thin film was formed to form a light emitting layer.
  • the substrate on which the film was formed up to the light emitting layer was installed in a vacuum vapor deposition apparatus, and the inside of the apparatus was exhausted until it became 2 ⁇ 10 -4 Pa or less.
  • the compound represented by the following formula (ET-1) and 8-hydroxyquinolinolatrithium are co-deposited on the light emitting layer at a film thickness ratio of 2: 3 by a vacuum deposition method at a rate of 1 ⁇ / sec. Then, a hole blocking layer having a film thickness of 30 nm was formed.
  • a striped shadow mask having a width of 2 mm was brought into close contact with the substrate so as to be orthogonal to the ITO stripe of the anode as a mask for cathode vapor deposition, and installed in another vacuum vapor deposition apparatus.
  • aluminum was heated by a molybdenum boat to form an aluminum layer having a film thickness of 80 nm at a vapor deposition rate of 1 to 8.6 ⁇ / sec to form a cathode.
  • an organic electroluminescent device having a light emitting area portion having a size of 2 mm ⁇ 2 mm was obtained.
  • the organic field light emitting device of the present invention containing a compound having the same partial structure A and a structure represented by the formula (TzP) in the hole transport layer and the light emitting layer has a lower voltage and a longer life.
  • Example 3 As the material of the light emitting layer, 50 parts by weight of the compound represented by the following formula (H-7), 50 parts by weight of the compound represented by the following formula (H-8), and the above formula (D-1) are represented.
  • the device was produced in the same manner as in Example 2 except that 15 parts by weight of the compound to be used was weighed and dissolved in cyclohexylbenzene to prepare a solution having a solid content concentration of 5.0% by weight as a composition for forming a light emitting layer. bottom.
  • Example 4 As the material of the light emitting layer, the compound represented by the formula (H-1) is represented by 50 parts by weight, the compound represented by the formula (H-8) is represented by 50 parts by weight, and the compound represented by the formula (D-1).
  • the device was produced in the same manner as in Example 2 except that 15 parts by weight of the compound to be used was weighed and dissolved in cyclohexylbenzene to prepare a solution having a solid content concentration of 5.0% by weight as a composition for forming a light emitting layer. bottom.
  • the compound represented by the formula (H-4) is represented by 50 parts by weight
  • the compound represented by the formula (H-8) is represented by 50 parts by weight
  • the device was produced in the same manner as in Example 2 except that 15 parts by weight of the compound to be used was weighed and dissolved in cyclohexylbenzene to prepare a solution having a solid content concentration of 5.0% by weight as a composition for forming a light emitting layer. bottom.
  • the time (LT95 (hr)) at which the brightness of the device drops to 95% of the initial brightness is measured by continuously energizing the device at a current density of 60 mA / cm 2, and Comparative Example 4
  • Table 3 shows the lifetimes of the LT95s of Example 3, Example 4, and Comparative Example 3 when the LT95 of 1 was set to 1, as relative lifetimes.
  • the organic field light emitting device of the present invention containing a compound having the same partial structure A and a structure represented by the formula (TzP) in the hole transport layer and the light emitting layer has a lower voltage and a longer life.
  • Example 5 As the material of the light emitting layer, 50 parts by weight of the compound represented by the following formula (H-9), 50 parts by weight of the compound represented by the above formula (H-6), and the following formula (D-2) are represented.
  • the device was prepared in the same manner as in Example 3 except that 15 parts by weight of the compound to be used was weighed and dissolved in cyclohexylbenzene to prepare a solution having a solid content concentration of 5.0% by weight as a composition for forming a light emitting layer. bottom.
  • the charge transport polymer compound represented by the formula (HT-3) was used instead of the charge transport polymer compound represented by the formula (HT-2), and the charge transport polymer compound represented by the formula (HT-3) was used.
  • the material of the light emitting layer 50 parts by weight of the compound represented by the formula (H-9), 50 parts by weight of the compound represented by the formula (H-6), and the following formula (D-3). 15 parts by weight of the compound to be used was weighed and dissolved in cyclohexylbenzene to prepare a solution having a solid content concentration of 5.0% by weight as a composition for forming a light emitting layer. bottom.
  • the organic field light emitting device of the present invention containing a compound having the same partial structure A and a structure represented by the formula (TzP) in the hole transport layer and the light emitting layer has a lower voltage and a longer life.
  • the charge transport polymer compound represented by the following formula (HT-4) was used instead of the charge transport polymer compound represented by the formula (HT-2).
  • the material of the light emitting layer 50 parts by weight of the compound represented by the following formula (H-10), 25 parts by weight of the compound represented by the following formula (H-11), and the following formula (H-12). 25 parts by weight of the compound to be used and 30 parts by weight of the compound represented by the following formula (D-4) are weighed and dissolved in cyclohexylbenzene to prepare a solution having a solid content concentration of 5.0% by weight for forming a light emitting layer.
  • the element was produced in the same manner as in Example 2 except that it was prepared as a product.
  • the time (LT90 (hr)) at which the brightness of the element decreases to 90% of the initial brightness is measured by continuously energizing the element at a current density of 15 mA / cm 2, and Comparative Example 6
  • the life of the LT90 of Example 6 when the LT90 of the above is set to 1 is shown in Table 5 as a relative life.
  • Substrate 2 Anode 3 Hole injection layer 4 Hole transport layer 5 Light emitting layer 6 Hole blocking layer 7 Electron transport layer 8 Electron injection layer 9 Cathode 10 Organic electric field light emitting device

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Abstract

La présente invention concerne un élément électroluminescent organique qui comprend, sur un substrat, une électrode positive, une électrode négative et une couche organique entre l'électrode positive et l'électrode négative. La couche organique a une couche de transport de trous et une couche électroluminescente adjacente à la couche de transport de trous. Au moins l'un des matériaux contenus dans la couche de transport de trous et au moins l'un des matériaux contenus dans la couche électroluminescente ont tous deux la même structure partielle A représentée par la formule (31). Le noyau HA est un noyau hétérocyclique aromatique, qui peut avoir un substituant, d'un seul anneau ou de 2-6 anneaux fusionnés. Ar0 est un groupe hydrocarboné aromatique qui peut avoir un substituant, un groupe hétérocyclique aromatique qui peut avoir un substituant ou un groupe monovalent obtenu par liaison d'une pluralité d'au moins deux groupes choisis parmi un groupe hydrocarboné aromatique qui peut avoir un substituant et un groupe hétérocyclique aromatique qui peut avoir un substituant. n1 est 0 ou un nombre entier égal ou inférieur au nombre dans lequel Ar0 peut être substitué à l'anneau HA.
PCT/JP2021/005683 2020-02-20 2021-02-16 Élément électroluminescent organique, dispositif d'affichage el organique et éclairage el organique WO2021166900A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113736080A (zh) * 2021-10-08 2021-12-03 中国地质大学（北京） 一种多级孔共价有机聚合物材料及其制备方法与应用

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002319491A (ja) * 2000-08-24 2002-10-31 Fuji Photo Film Co Ltd 発光素子及び新規重合体子
WO2004066685A1 (fr) * 2003-01-24 2004-08-05 Idemitsu Kosan Co., Ltd. Dispositif electroluminescent organique
JP2012062450A (ja) * 2010-09-17 2012-03-29 Idemitsu Kosan Co Ltd 新規重合性単量体と高分子化合物、それを用いた有機デバイス用材料、有機エレクトロルミネッセンス用材料、有機デバイス及び有機エレクトロルミネッセンス素子
JP2015005396A (ja) * 2013-06-20 2015-01-08 三菱化学株式会社 有機ｅｌ素子製造方法、有機ｅｌ素子、表示装置及び照明装置
WO2015105014A1 (fr) * 2014-01-08 2015-07-16 住友化学株式会社 Complexe métallique et élément d'émission de lumière utilisant celui-ci
JP2018104675A (ja) * 2016-12-27 2018-07-05 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 高分子化合物、組成物、液状組成物、薄膜、並びにエレクトロルミネッセンス素子用材料、及びエレクトロルミネッセンス素子
WO2020171190A1 (fr) * 2019-02-20 2020-08-27 三菱ケミカル株式会社 Polymère, élément électroluminescent organique, dispositif d'affichage el organique et éclairage el organique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013080696A1 (fr) 2011-11-29 2013-06-06 コニカミノルタ株式会社 Elément électroluminescente (el) organique

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002319491A (ja) * 2000-08-24 2002-10-31 Fuji Photo Film Co Ltd 発光素子及び新規重合体子
WO2004066685A1 (fr) * 2003-01-24 2004-08-05 Idemitsu Kosan Co., Ltd. Dispositif electroluminescent organique
JP2012062450A (ja) * 2010-09-17 2012-03-29 Idemitsu Kosan Co Ltd 新規重合性単量体と高分子化合物、それを用いた有機デバイス用材料、有機エレクトロルミネッセンス用材料、有機デバイス及び有機エレクトロルミネッセンス素子
JP2015005396A (ja) * 2013-06-20 2015-01-08 三菱化学株式会社 有機ｅｌ素子製造方法、有機ｅｌ素子、表示装置及び照明装置
WO2015105014A1 (fr) * 2014-01-08 2015-07-16 住友化学株式会社 Complexe métallique et élément d'émission de lumière utilisant celui-ci
JP2018104675A (ja) * 2016-12-27 2018-07-05 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 高分子化合物、組成物、液状組成物、薄膜、並びにエレクトロルミネッセンス素子用材料、及びエレクトロルミネッセンス素子
WO2020171190A1 (fr) * 2019-02-20 2020-08-27 三菱ケミカル株式会社 Polymère, élément électroluminescent organique, dispositif d'affichage el organique et éclairage el organique

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113736080A (zh) * 2021-10-08 2021-12-03 中国地质大学（北京） 一种多级孔共价有机聚合物材料及其制备方法与应用
CN113736080B (zh) * 2021-10-08 2022-04-26 中国地质大学（北京） 一种多级孔共价有机聚合物材料及其制备方法与应用

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