WO2019031605A1 - 縮合環化合物 - Google Patents

縮合環化合物 Download PDF

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WO2019031605A1
WO2019031605A1 PCT/JP2018/030086 JP2018030086W WO2019031605A1 WO 2019031605 A1 WO2019031605 A1 WO 2019031605A1 JP 2018030086 W JP2018030086 W JP 2018030086W WO 2019031605 A1 WO2019031605 A1 WO 2019031605A1
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森中裕太
田中剛
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東ソー株式会社
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Priority to KR1020207003370A priority Critical patent/KR102556378B1/ko
Priority to CN201880051882.0A priority patent/CN110997648B/zh
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Definitions

  • the present disclosure relates to fused ring compounds.
  • dibenzo [g, p] chrysene compound may be used as a material for an organic electroluminescent element, there are few reported examples of the dibenzo [g, p] chrysene compound, and the study has not been sufficiently conducted.
  • Patent Document 1 discloses various monoamine derivatives, and a dibenzo [g, p] chrysene compound substituted with a diphenylamino group as one of them. Furthermore, Patent Document 2 and Patent Document 3 disclose dibenzo [g, p] chrysene compounds substituted with an aromatic hydrocarbon group and a triazyl group, respectively.
  • one aspect of the present disclosure is directed to providing a fused ring compound that exhibits excellent driving voltage, luminous efficiency, and / or device life.
  • the fused ring compound according to one aspect of the present disclosure is a fused ring compound represented by Formula (1):
  • One of these rings represents a ring fused to a substituted or unsubstituted benzene ring;
  • Each of A 1 to A 3 independently represents a charge transporting group;
  • k1 to k3 are each independently an integer of 0 or more and 4 or less; When k1 to k3 are integers of 2 or more, the plurality of A 1 to A 3 may be the same or different.
  • FIG. 6 is a schematic cross-sectional view showing an example of another laminated configuration of the organic electroluminescent device according to an embodiment of the present disclosure (a configuration of Device Example 1).
  • the arylaminodibenzo [g, p] chrysene according to Patent Document 1 has a low glass transition temperature and a poor device life.
  • the drive voltage exhibits sufficient performance but a low triplet excitation level and / or from a light emitting layer. It was found that the current efficiency is inferior due to the low electron stopping power, and an improvement is necessary.
  • the fused ring compound according to an aspect of the present disclosure is a skeleton in which one benzene ring in the skeleton of dibenzo [g, p] chrysene is replaced with a furan-based or thiophene-based ring or the like.
  • This skeleton has the effect of expanding the ⁇ conjugated system of dibenzo [g, p] chrysene, and since more ⁇ electron systems than dibenzo [g, p] chrysene contribute to charge transport, the electron transport material, hole
  • the present inventors speculate that the present invention is applicable to various materials such as transport materials and light emitting materials. That is, it is inferred that the fused ring compound according to one aspect of the present disclosure has a specific skeleton, and is derived from this skeleton to exert various effects required for each layer constituting the organic electroluminescent element. Ru.
  • the fused ring compound according to one aspect of the present disclosure is a fused ring compound represented by Formula (1):
  • One of these rings represents a ring fused to a substituted or unsubstituted benzene ring;
  • Each of A 1 to A 3 independently represents a charge transporting group;
  • k1 to k3 are each independently an integer of 0 or more and 4 or less; When k1 to k3 are integers of 2 or more, the plurality of A 1 to A 3 may be the same or different.
  • a 1 to A 3 , k 1 to k 3 and X in the fused ring compound represented by the formula (1) are as follows.
  • Each of A 1 to A 3 independently represents a charge transporting group.
  • the charge transporting group is a substituent having a function of transporting a charge.
  • the charge is a hole, an electron, or both.
  • charge transporting group each independently, (A-1) deuterium atom, (a-2) fluorine atom, bromine atom, iodine atom, (a-3) trifluoromethyl group, (a-4) hexafluoroethyl group, (a-5) cyano group (A-6) nitro group, (a-7) hydroxyl group, (a-8) thiol group, (A-9) an optionally substituted monocyclic hydrocarbon ring having 6 to 30 carbon atoms, a linked or fused aromatic hydrocarbon group, (A-10) a C3-C36 monocyclic, linked or fused heteroaromatic group which may have a substituent, (A-11) phosphine oxide group which may have a substituent, (A-12) silyl group which may have a substituent, (A-13) a boronyl group which may have a saturated hydrocarbon group having 2 to 10 carbon atoms, (A-14) a linear or branched alkyl group having
  • R 1 to R 3 are each independently (R-1) hydrogen atom, (r-2) deuterium atom, (R-3) an optionally substituted monocyclic hydrocarbon ring having 6 to 30 carbon atoms, a linked or fused aromatic hydrocarbon group, (R-4) a C3-C36 monocyclic, linked, or fused heteroaromatic group which may have a substituent, or (R-5) represents a linear or branched alkyl group having 1 to 18 carbon atoms; Y is each independently A phenylene group which may be substituted by a methyl group or a phenyl group, Naphthylene group which may be substituted by methyl group or phenyl group, A biphenylene group which may be substituted by a methyl group or a phenyl group, or Represents a single bond; n represents 1 or 2; When Y is a single bond, n is 1 and When Y is not a single bond, n is 1 or 2; When n
  • a 1 to A 3 may be substituted by one substituent or may be substituted by two or more substituents.
  • the hydrogen group is not particularly limited, and examples thereof include phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, triphenylenyl group, spirobifluorene. Nyl group, diphenylfluorenyl group, and dibenzo [g, p] chrysenyl group, and the like.
  • the C6 to C30 monocyclic, linked or fused aromatic hydrocarbon group is a C6 to C18 monocyclic, linked or fused aromatic hydrocarbon group.
  • each of the substituents is independently a fluorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a hydroxyl group or a thiol group.
  • a phosphine oxide group which may have a substituent, a silyl group which may have a substituent, a boronyl group which may have a saturated hydrocarbon group having 2 to 10 carbon atoms, It is preferable that it is an 18 linear or branched alkyl group, or a linear or branched alkoxy group having 1 to 18 carbon atoms.
  • phosphine oxide group an unsubstituted phosphine oxide group and a phosphine oxide group having a substituent can be mentioned. It is preferably a phosphine oxide group having a substituent.
  • the phosphine oxide group having a substituent is preferably a monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 18 carbon atoms, or a phosphine oxide group having a condensed heteroaromatic group. Although it does not specifically limit specifically, For example, the group substituted by two aryl groups, such as diphenyl phosphine oxide, is mentioned.
  • silyl group examples include unsubstituted silyl groups and silyl groups having a substituent. It is preferable that it is a silyl group having a substituent.
  • the silyl group having a substituent is preferably a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 18 carbon atoms, or a silyl group having a fused heteroaromatic group. Although it does not specifically limit specifically, For example, the group substituted by three aryl groups, such as a triphenyl silyl group, is mentioned.
  • the boronyl group which may have a saturated hydrocarbon group having 2 to 10 carbon atoms is not particularly limited, and examples thereof include dihydroxyboryl group (-B (OH) 2 ), 4, 4, 5 And 5-tetramethyl- [1,3,2] -dioxabororanyl group, 5,5-dimethyl- [1,3,2] -dioxaborinane group and the like.
  • the linear or branched alkyl group having 1 to 18 carbon atoms is not particularly limited, and examples thereof include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, sec- Examples thereof include butyl, tert-butyl, pentyl, n-hexyl, cyclohexyl, octyl, decyl, dodecyl and octadecyl groups.
  • the linear or branched alkoxy group having 1 to 18 carbon atoms is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, and a sec- Examples include butoxy, tert-butoxy, pentyloxy, n-hexyloxy, cyclohexyloxy, octyloxy, decyloxy, dodecyloxy, octadecyloxy and the like.
  • C3-C36 monocyclic, linked or fused heteroaromatic group Is not particularly limited, and is a single ring having 3 to 36 carbon atoms, which contains at least one atom selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom on an aromatic ring, a linkage, or It is a fused heteroaromatic group.
  • the heteroaromatic group is not particularly limited, and examples thereof include pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, and phenyl.
  • each of the substituents is independently a cyano group, a fluorine atom, a trifluoromethyl group, a linear or branched chain having 1 to 18 carbon atoms. It is preferable that it is an alkyl group of the above, or a linear or branched alkoxy group having 1 to 18 carbon atoms.
  • the linear or branched alkyl group having 1 to 18 carbon atoms is not particularly limited, but is the same as the linear or branched alkyl group having 1 to 18 carbon atoms exemplified in (a-9) described above The thing is mentioned.
  • the linear or branched alkoxy group having 1 to 18 carbon atoms is not particularly limited, but is the same as the linear or branched alkoxy group having 1 to 18 carbon atoms exemplified in (a-9) described above The thing is mentioned.
  • examples of the phosphine oxide group include unsubstituted phosphine oxide groups and phosphine oxide groups having a substituent. It is preferably a phosphine oxide group having a substituent.
  • the phosphine oxide group having a substituent is not particularly limited, and examples thereof include the same as the phosphine oxide group exemplified in (a-9) described above.
  • silyl group examples include unsubstituted silyl groups and silyl groups having a substituent. It is preferable that it is a silyl group having a substituent.
  • the silyl group having a substituent is not particularly limited, and examples thereof include the same as the silyl group exemplified in (a-9) described above.
  • the group is not particularly limited, and examples thereof include the same as the boronyl group exemplified in (a-9) described above.
  • the linear alkyl group having 1 to 18 carbon atoms is not particularly limited. The same ones as the linear or branched alkyl group having 1 to 18 carbon atoms exemplified in the above (a-9) can be mentioned.
  • the linear or branched alkoxy group having 1 to 18 carbon atoms is not particularly limited, For example, the same ones as the linear or branched alkoxy group having 1 to 18 carbon atoms exemplified in the above (a-9) can be mentioned.
  • R 1 to R 3 each independently have (r-1) hydrogen atom, (r-2) deuterium atom, (r-3) substituent A monocyclic, linked or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, (r-4) a monocyclic, linked or fused heteroaromatic group having 3 to 36 carbon atoms, Or (r-5) represents a linear or branched alkyl group having 1 to 18 carbon atoms.
  • R 1 to R 3 may be substituted by one substituent or may be substituted by two or more substituents.
  • R 1 to R 3 each represent an aromatic hydrocarbon group having a substituent or a heteroaromatic group having a substituent
  • the substituents each independently represent a deuterium atom, a fluorine atom, or a carbon number It is preferably a linear or branched alkyl group of 1 to 18, a linear or branched alkoxy group of 1 to 18 carbon atoms, 9-carbazolyl group, a dibenzothienyl group or a dibenzofuranyl group.
  • (R-3) monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms
  • a monocyclic, linked, or fused ring having 6 to 30 carbon atoms The definition of the aromatic hydrocarbon group of the ring is, except for the definition of the substituent thereof, the definition of the monocyclic, linked or fused aromatic hydrocarbon group having 6 to 30 carbon atoms shown in the above (a-9) Is the same as
  • the aromatic hydrocarbon group of (r-3) has a substituent
  • the substituent is preferably a deuterium atom, a fluorine atom, a linear or branched alkyl group having 1 to 18 carbon atoms, or 1 to 18 carbon atoms.
  • the linear or branched alkyl group having 1 to 18 carbon atoms is not particularly limited, but is the same as the linear alkyl group having 1 to 18 carbon atoms exemplified in (a-9) described above It can be mentioned.
  • the linear or branched alkoxy group having 1 to 18 carbon atoms is not particularly limited, but is the same as the linear or branched alkoxy group having 1 to 18 carbon atoms exemplified in (a-9) described above The thing is mentioned.
  • (R-4) C3-C36 monocyclic, linked or fused heteroaromatic group
  • C3-C36 monocyclic, linked or fused ring The definition of the heteroaromatic group is the same as the C3-C36 monocyclic, linked or fused heteroaromatic group exemplified in (a-10) above, except for the definition of the substituent It can be mentioned. Further, it is more preferable that the heteroaromatic group is a C3-C20 monocyclic, linked or fused heteroaromatic group.
  • the substituent is preferably a deuterium atom, a fluorine atom, a linear or branched alkyl group having 1 to 18 carbon atoms, or 1 to 18 carbon atoms. Linear or branched alkoxy group, 9-carbazolyl group, dibenzothienyl group, dibenzofuranyl group, N, N-diphenylamino group, or N, N-bis (4-biphenylyl) -amino group preferable.
  • These substituents are not particularly limited, and for example, have the same definition as the substituent of (r-3) described above.
  • R-5 linear or branched alkyl group having 1 to 18 carbon atoms
  • the definition of the linear or branched alkyl group having 1 to 18 carbon atoms is the same as the above (a) Same as the definition shown in -9).
  • Y is a phenylene group which may be substituted by a methyl group or a phenyl group; a naphthylene group which may be substituted by a methyl group or a phenyl group; a methyl group or a phenyl group Or a single bond.
  • the phenylene group is not particularly limited, and examples thereof include a 1,2-phenylene group, a 1,3-phenylene group, and a 1,4-phenylene group.
  • the above-mentioned naphthylene group is not particularly limited, and examples thereof include naphthalene-1,2-diyl group, naphthalene-1,4-diyl group, naphthalene-1,8-diyl group, and naphthalene-2,3- Diyl group etc. are mentioned.
  • the biphenylene group is not particularly limited.
  • biphenyl-4,4'-diyl group, biphenyl-4,3'-diyl group, biphenyl-4,2'-diyl group, biphenyl-3 for example.
  • 3'-diyl group, biphenyl-3,2'-diyl group, biphenyl-2,2'-diyl group and the like are mentioned.
  • n 1 or 2.
  • n 1 or 2.
  • Y is not a single bond
  • n is 1 or 2.
  • two R 1 and two R 2 are present, but they may be identical to or different from each other.
  • Each of k1 to k3 is independently an integer of 0 to 4. In the case k1 ⁇ k3 is an integer of 2 or more, but A 1 ⁇ A 3 there are a plurality, the plurality of A 1 ⁇ A 3 may be the same as each other or may be different.
  • the sum (k1 + k2 + k3) of k1 to k3 is preferably 3 or less, more preferably 2 or less, and particularly preferably 0 or 1.
  • the molecular weight decreases as compared to the compound in which the sum of k1 to k3 is 4 or more. As a result, the sublimation temperature of the compound is lowered, and the heat stability at the time of sublimation is improved, which is preferable.
  • k1 and k2 are preferably 0 or 1, and more preferably 0 from the viewpoint of achieving excellent charge transportability in the organic electroluminescent device.
  • k3 is preferably 0, 1 or 2 and more preferably 1 from the viewpoint of achieving excellent charge transportability in the organic electroluminescent device.
  • the fused ring compound represented by the above formula (1) is particularly preferably one in which k1 and k2 are 0 and k3 is 1 from the viewpoint of realizing excellent charge transportability in an organic electroluminescent device.
  • X is A furan ring which may have a substituent, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring or a dibenzothiophene ring; or One of these rings represents a ring fused to a substituted or unsubstituted benzene ring.
  • the substituent which the above furan ring, thiophene ring, benzofuran ring, benzothiophene ring, dibenzofuran ring or dibenzothiophene ring may have is not particularly limited, but, for example, the above-mentioned (a-1) And the substituents shown in (a-16) can be mentioned.
  • Examples of the substituted benzene ring include a benzene ring substituted with a phenyl group, a biphenylyl group, or a pyridyl group.
  • the fused ring compound represented by the formula (1) is preferably a fused ring compound represented by any one of the formulas (3) to (22).
  • a 1 to A 3 and k 1 to k 3 have the same definitions as A 1 to A 3 and k 1 to k 3 in the formula (1), respectively;
  • Each of A 4 and A 5 independently represents a charge transporting group; k4 is an integer of 0 or more and 4 or less; k5 is an integer of 0 or more and 2 or less; When k1 to k5 are integers of 2 or more, the plurality of A 1 to A 5 may be the same or different.
  • k4 is an integer of 0 or more and 4 or less.
  • k5 is an integer of 0 or more and 2 or less.
  • k4 is preferably 0, 1 or 2 and more preferably 0 from the viewpoint of realizing excellent charge transportability in the organic electroluminescent device.
  • k5 is preferably 0 or 1, and more preferably 0, from the viewpoint of realizing excellent charge transportability in the organic electroluminescent device.
  • the sum (k1 + k2 + k3) of k1 to k3 is preferably 3 or less, more preferably 2 or less, 0 or 1. Being particularly preferred.
  • k1, k2, k4 and k5 are 0 and k3 is 1 from the viewpoint of realizing excellent charge transportability in organic electroluminescent devices. Is preferred.
  • the charge transporting group represented by A 4 and A 5 has the same definition as the charge transporting group represented by A 1 to A 3 in the formula (1), and the same applies to a preferable range.
  • a 1 to A 5 may be substituted by one substituent or may be substituted by two or more substituents.
  • a 1 to A 5 are an aromatic hydrocarbon group having a substituent or a heteroaromatic group having a substituent
  • the substituents are each independently exemplified in the above (a-9) The same thing as a substituent is mentioned.
  • a 1 to A 5 are not particularly limited, and examples of the groups (1) to (24) shown below can be given as preferable examples.
  • a 1 to A 5 are each independently from the viewpoint of easy availability of raw materials: Phenyl group, biphenylyl group, pyridylphenyl group, terphenylyl group, naphthyl group, phenanthryl group, pyrenyl group, 9,9-spirobi [9H-fluorenyl] group, triphenylenyl group, dibenzothienyl group, dibenzofuranyl group, pyridyl group, pyrimidyl group Or a group in which these groups are substituted with a cyano group, a nitro group, a hydroxyl group, a thiol group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group or a methoxy group; A fluorenyl group, a benzofluorenyl group, an anthryl group,
  • the fused ring compound represented by the formula (1) is shown below, but the fused ring compound is not limited to these compounds.
  • Tables B-1 to B-7 have the skeletons of (3A) to (22B) shown in Table A-1 to Table A-4, and the substituent A 3 which the skeleton has is Table B
  • m represents an arbitrary integer of 1 to 251. That is, the compound of (NA-m) indicates the compounds of (NA-1) to (NF-251).
  • N represents an arbitrary integer of 3 to 22.
  • N 3 ⁇ 6, (NA -1), (NB-1), (NC-1) is, A 3 is deuterium (D) atoms.
  • D deuterium
  • ND -1 ND -1
  • NE-1 NE-1
  • NF-1 A 3 is hydrogen (H) atoms.
  • N 7 ⁇ 22, (NA -1) is, A 3 is deuterium (D) atoms.
  • N 7 ⁇ 22, (NB -1) is, A 3 is hydrogen (H) atoms.
  • the fused ring compound represented by the formula (1) is synthesized according to the following route using a compound represented by the formula (23a) or (23b) described later as a starting material from the viewpoint of yield and purity at the time of production Is preferred.
  • a 1 to A 3 , and k 1 to k 3 have the same definitions as in the above formula (1); ⁇ and ⁇ are mutually different and each represent a boronyl group which may have a saturated hydrocarbon group of 2 to 10 carbon atoms, or a halogen atom (chlorine, bromine or iodine).
  • X, A 1 ⁇ A 3, and the preferred range of k 1 ⁇ k 3 is, X in Formula (1), the same as the preferable range of A 1 ⁇ A 3, and k 1 ⁇ k 3.
  • a phenanthrene compound represented by the formula (23a) and a compound represented by the formula (23c), or a phenanthrene compound represented by the formula (23b) and a compound represented by the formula (23d) Is coupled in the presence of a palladium catalyst, optionally using a base, to obtain a phenanthrene compound represented by the formula (23).
  • the phenanthrene compound represented by Formula (23) obtained can be intramolecularly cyclized, and the fused ring compound represented by said Formula (1) can be obtained.
  • the phenanthrene compound be oxidized or irradiated with an oxidizing agent to cause an intramolecular cyclization reaction.
  • Formula (1) obtained by the above route has a halogen atom (fluorine, chlorine, bromine or iodine) or a boronyl group which may have a saturated hydrocarbon group having 2 to 10 carbon atoms If necessary, additional coupling reactions may be performed.
  • halogen atom fluorine, chlorine, bromine or iodine
  • boronyl group which may have a saturated hydrocarbon group having 2 to 10 carbon atoms If necessary, additional coupling reactions may be performed.
  • the boronyl group which may have a saturated hydrocarbon group having 2 to 10 carbon atoms is not particularly limited, but the saturated hydrocarbon having 2 to 10 carbon atoms exemplified in (a-9) described above The same thing as the boronyl group which may have a group is mentioned.
  • the compounds represented by the formulas (23a) to (23d) can be synthesized based on known methods, or commercially available compounds can be used.
  • a known coupling reaction can be used, and as the base and the palladium catalyst, known ones can be used.
  • the phenanthrene compound represented by the formula (23) has a furan ring which may have a substituent, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring or a dibenzothiophene ring; or one of these rings is
  • X which is a ring ringed with a substituted or unsubstituted benzene ring.
  • X is a ring other than the above-mentioned ring (for example, X is a benzene ring or a naphthalene ring).
  • the intramolecular cyclization is preferably performed by oxidation with an oxidizing agent or oxidation with light irradiation.
  • an oxidizing agent ferric chloride (FeCl 3 ), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), molybdenum chloride (MoCl 5 ), aluminum chloride (AlCl 3 ), or [bis (Trifluoroacetoxy) iodo] benzene (PIFA) is preferred.
  • iodine (I 2 ) and 1,2-epoxypropane or 1,2-epoxybutane iodine (I 2 ) and 1,2-epoxypropane or 1,2-epoxybutane.
  • the phenanthrene compound according to one aspect of the present disclosure is a phenanthrene compound represented by Formula (23):
  • a furan ring which may have a substituent, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, or One of these rings represents a ring fused to a substituted or unsubstituted benzene ring;
  • Each of A 1 to A 3 independently represents a substituent;
  • k1 to k3 are each independently an integer of 0 or more and 4 or less; When k1 to k3 are integers of 2 or more, the plurality of A 1 to A 3 may be the same or different.
  • the phenanthrene compound represented by the formula (23) is specifically represented by the following formulas (3i) to (18i) from the viewpoint of obtaining the fused ring compound represented by the formula (1) in high yield and high purity.
  • the phenanthrene compound represented by these is preferable.
  • a 1 to A 5 and k 1 to k 5 have the same definitions as in the formulas (3) to (22), and the same applies to the preferred ranges.
  • Preferred phenanthrene compounds represented by formulas (3i) to (18i) are exemplified below based on the skeletons described in Tables C-1 to C-3, but this embodiment is limited to these compounds. It is not something to be done.
  • Preferred phenanthrene compounds have the skeletons of (3iA) to (18iB) shown in Tables C-1 to C-3, and the substituent A 3 which the skeleton has is shown in Tables B-1 to B-. It is a compound of (NiA-m) which is a group shown in 5.
  • m is an arbitrary integer of 1 to 167.
  • the (NiA-m) compound means a compound of (NiA-1) to (NiF-167).
  • N represents an arbitrary integer of 3 to 18.
  • N 3 ⁇ 6, (NiA -1), (NiB-1), (NiC-1) is, A 3 is deuterium (D) atoms.
  • N 3 ⁇ 6, (NiD -1), (NiE-1), (NiF-1) is, A 3 is hydrogen (H) atoms.
  • N 7 ⁇ 18, (NiA -1) is, A 3 is deuterium (D) atoms.
  • N 7 ⁇ 18, (NiB -1) is, A 3 is hydrogen (H) atoms.
  • the fused ring compound represented by the formula (1) can be used as a material for an organic electroluminescent device. Therefore, the material for an organic electroluminescent device according to an aspect of the present disclosure includes the fused ring compound represented by Formula (1).
  • the fused ring compound represented by the formula (1) is preferably highly pure in terms of charge transport properties and device life. Specifically, it is preferable that the amount of impurities such as halogen atoms and transition metal elements and impurities such as manufacturing raw materials and byproducts be as small as possible.
  • the material for an organic electroluminescent device containing the fused ring compound represented by the formula (1) is a hole transporting layer (each layer having a hole transporting property between the anode and the light emitting layer, specifically, A hole injection layer, a hole transport layer, etc., a light emitting layer, or an electron transporting layer (each layer having an electron transporting property between the cathode and the light emitting layer, specifically, electron injection Layer, an electron transport layer, etc. can be mentioned as a material which forms. Among these, it is particularly preferable to use as a material of the hole transport layer, the light emitting layer or the electron transport layer.
  • the fused ring compound represented by Formula (1) is 1st positive It may be used as a material for either or both of the hole transport layer (anode side) and the second hole transport layer (cathode side).
  • the fused ring compound represented by the formula (1) is used as a material of a hole transportable layer of an organic electroluminescent device, a material of a light emitting layer, or a material of an electron transportable layer, conventionally used Known fluorescent light emitting materials, phosphorescent light emitting materials, or thermally activated delayed fluorescent light emitting materials can be used for the light emitting layer.
  • the light emitting layer may be formed of only one kind of light emitting material, or one or more kinds of light emitting materials may be doped in the host material.
  • the hole transporting layer containing the fused ring compound represented by the formula (1) may be a single layer, or may be a laminated structure comprising a plurality of layers.
  • the hole transporting layer may be composed of the fused ring compound represented by the formula (1), and further contains one or more known materials in addition to the fused ring compound May be
  • a layer containing one or more known materials is further laminated.
  • Examples of such known materials include N, N, N ', N'-tetraphenyl-4,4'-diaminophenyl, N, N'-diphenyl-N, N'-bis (3-methylphenyl)- [1,1′-biphenyl] -4,4′-diamine (TPD), 2,2-bis (4-di-p-tolylaminophenyl) propane, 1,1-bis (4-di-p-tolyl Aminophenyl) cyclohexane, N, N, N ', N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis (4-di-p-tolylaminophenyl) -4-phenylcyclohexane Bis (4-dimethylamino-2-methylphenyl) phenylmethane, bis (4-di-p-tolylaminophenyl) phenylmethane, N, N'
  • the fused ring compound represented by the formula (1) When used as a material of the light emitting layer of the organic electroluminescent device, the fused ring compound may be used alone or may be doped in a known light emitting host material It may be used as it is, or may be used by doping a known light emitting dopant.
  • Examples of methods for forming an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, and a hole injection layer containing the fused ring compound represented by the formula (1) include a vacuum evaporation method and a spin coating method. Known methods such as cast method can be applied.
  • the material for an organic electroluminescent device used for coating methods such as spin coating and casting includes an organic solvent in addition to the fused ring compound represented by the formula (1).
  • the organic solvent is not particularly limited, and examples thereof include monochlorobenzene and orthodichlorobenzene.
  • the organic solvent may be a combination of two or more of these. It is preferable that an organic solvent is selected to exhibit a desired coating performance, and the viscosity and concentration of the material for an organic electroluminescent element be adjusted.
  • An organic electroluminescent device includes a layer including the fused ring compound represented by the above-described formula (1).
  • FIG. 1 is a schematic cross-sectional view showing an example of a laminated structure of an organic electroluminescent device according to an aspect of the present disclosure.
  • the organic electroluminescent device according to the present embodiment will be described with reference to FIG.
  • the organic electroluminescent element shown in FIG. 1 has a so-called bottom emission type element structure
  • the organic electroluminescent element according to one aspect of the present disclosure is limited to the bottom emission type element structure. is not. That is, the organic electroluminescent device according to one aspect of the present disclosure may be a top emission type device configuration, or may be another known device configuration.
  • the basic structure of the organic electroluminescent device 100 is as follows: substrate 1, anode 2, hole injection layer 3, charge generation layer 4, hole transport layer 5, light emitting layer 6, electron transport layer 7, electron injection layer 8, And the cathode 9 in this order.
  • some of these layers may be omitted, and conversely, other layers may be added.
  • the charge generation layer 4 may be omitted, and the hole transport layer 5 may be directly provided on the hole injection layer 3, and a hole blocking layer is provided between the light emitting layer 6 and the electron transport layer 7.
  • a single layer having a combination of functions of a plurality of layers such as an electron injection / transport layer having the function of the electron injection layer and the function of the electron transport layer in a single layer, It may be a configuration provided instead of
  • one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer have the formula (1)
  • the layer containing the fused ring compound represented by the formula (1) is a known material together with the fused ring compound. It may contain any one or more selected from the above. Further, among the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer, a layer not containing the fused ring compound represented by the formula (1) is selected from known materials. It is preferable to contain any 1 or more types.
  • the anode 2 and the cathode 9 of the organic electroluminescent element 100 are connected to a power supply via an electrical conductor. By applying a voltage between the anode 2 and the cathode 9, the organic electroluminescent device 100 operates and emits light.
  • Holes are injected into the organic electroluminescent device 100 at the anode 2 and electrons are injected into the organic electroluminescent device 100 at the cathode 9.
  • the anode 2 is provided in contact with the substrate 1.
  • the electrode in contact with the substrate is conveniently referred to as the lower electrode.
  • the present embodiment is not limited to such a configuration, and instead of the anode, a cathode may be provided in contact with the substrate to be a lower electrode, and the substrate and the anode or the cathode are not in contact.
  • the anode or the cathode may be laminated on the substrate through another layer.
  • the light transmittance of the substrate may be appropriately selected according to the light emission direction (the direction in which light is extracted) of the intended organic electroluminescent element. That is, the substrate may or may not be light transmissive (or may be opaque to light having a predetermined wavelength). Whether or not the substrate has optical transparency can be confirmed, for example, by whether or not light derived from the light emission of the organic electroluminescent element is observed from the substrate in a desired amount or more.
  • a transparent glass plate or a plastic plate is generally employed as a substrate having light transmittance.
  • the substrate is not limited to these.
  • the substrate may, for example, be a composite structure comprising multiple material layers.
  • Anode 2 is provided on the substrate 1.
  • the anode is formed of a material that transmits or substantially transmits the light.
  • the transparent material used for the anode is not particularly limited.
  • ITO Indium-tin oxide
  • IZO Indium-zinc oxide
  • tin oxide aluminum ⁇
  • Doped type tin oxide magnesium-indium oxide, nickel-tungsten oxide, other metal oxides; metal nitrides such as gallium nitride; metal selenides such as zinc selenide; and metal sulfides such as zinc sulfide Etc.
  • the anode can be modified with plasma deposited fluorocarbons.
  • transmission characteristic of an anode is unimportant, and arbitrary transparent, opaque or reflective electroconductive materials can be used as a material of an anode. Therefore, gold, iridium, molybdenum, palladium, platinum etc. are mentioned as an example of the material used for the anode in this case.
  • Hole transportable layer (hole injection layer 3, hole transport layer 5) >> A hole transportable layer is provided between the anode 2 and the light emitting layer 6.
  • the hole transporting layer is a layer having a hole transporting property provided between the anode and the light emitting layer, and is a hole injecting layer, a hole transporting layer or the like. A plurality of hole transporting layers may be provided between the anode and the light emitting layer.
  • the hole injection layer or the hole transport layer has a function of transferring holes injected from the anode to the light emitting layer. By interposing the layers between the anode and the light emitting layer, holes are injected into the light emitting layer with a lower electric field.
  • the hole transport layer is composed of a single layer in the embodiment shown in FIG.
  • first hole transport layer on the anode side and a second hole transport layer on the cathode side It may be composed of
  • the first hole transport layer is a layer having an excellent hole transportability compared to the second hole transport layer
  • the second hole transport layer is the first positive hole transport layer. It is preferable that it is a layer excellent in electron stopping power compared with a hole transport layer.
  • the second hole transport layer may also be generally referred to as an electron blocking layer.
  • a hole transport layer (which may be the above-described function-separated first hole transport layer and second hole transport layer), a hole injection layer, and One or more selected from the group consisting of the light emitting layer is one including the fused ring compound represented by the formula (1).
  • the hole transport layer containing the fused ring compound represented by the formula (1), the hole injection layer, and the fused ring compound are any one or more selected from materials having known hole transportability. May be contained.
  • the positive hole transport layer which does not contain the condensed ring compound represented by Formula (1) a positive hole injection layer contains arbitrary 1 or more types selected from the material which has a well-known hole transportability. Is preferred.
  • the material having a known hole transportability is not particularly limited, but, for example, a triazole derivative, an oxadiazole derivative, an imidazole Derivative, polyarylalkane derivative, pyrazoline derivative, pyrazolone derivative, phenylenediamine derivative, arylamine derivative, amino substituted chalcone derivative, oxazole derivative, styrylanthracene derivative, fluorenone derivative, hydrazone derivative, stilbene derivative, silazane derivative, aniline based copolymer And conductive polymer oligomers, in particular thiophene oligomers.
  • porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds are preferable, and aromatic tertiary amine compounds are particularly preferable.
  • aromatic tertiary amine compound and the styrylamine compound include the above-mentioned known hole transporting materials.
  • Inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
  • the hole injection layer and the hole transport layer may have a single layer structure composed of one or more selected from the above materials and the fused ring compound represented by the formula (1), and a plurality of layers having the same composition or different compositions.
  • the laminated structure which consists of these may be sufficient.
  • a charge generation layer may be provided between the hole injection layer 3 and the hole transport layer 5.
  • the material of the charge generation layer is not particularly limited, and, for example, dipyrazino [2,3-f: 2 ′, 3′-h] quinoxaline-2,3,6,7,10,11-hexa And carbonitrile (HAT-CN).
  • a light emitting layer 6 is provided between the hole transport layer 5 and the electron transport layer 7 or a hole blocking layer described later.
  • the light emitting layer comprises a fluorescent light emitting material, or a thermally activated delayed fluorescent light emitting material, and light emission occurs as a result of recombination of electron-hole pairs in this region.
  • the light emitting layer may consist of a single material containing both small molecules and polymers, but more generally consists of a host material doped with a guest compound.
  • the emission mainly originates from the dopant and can have any color.
  • Examples of the host material include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthranyl group. More specifically, DPVBi (4,4'-bis (2,2-diphenylvinyl) -1,1'-biphenyl), BCzVBi (4,4'-bis (9-ethyl-3-carbazovinylene) 1, 1′-biphenyl), TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene), ADN (9,10-di (2-naphthyl) anthracene), CBP (4,4′-bis) (Carbazol-9-yl) biphenyl), CDBP (4,4'-bis (carbazol-9-yl) -2,2'-dimethylbiphenyl), 2- (9-phenylcarbazol-3
  • the host material may be an electron transport material described later, a material having a hole transportability described above, another material that supports hole-electron recombination (support), or a combination of these materials.
  • the fluorescent dopant for example, anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylene pyran compound, thiopyran compound, polymethine compound, pyrilium, thiapyrilium compound, fluorene derivative, periflanthene derivative, indenoperylene Derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, carbostyril compounds, fused ring compounds represented by the formula (1) and the like can be mentioned.
  • the fluorescent dopant may be a combination of two or more selected from these.
  • phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.
  • the fluorescent dopant and the phosphorescent dopant include Alq 3 (tris (8-hydroxyquinoline) aluminum), DPAVBi (4,4′-bis [4- (di-p-tolylamino) styryl] biphenyl), perylene, bis [4 2- (4-n-Hexylphenyl) quinoline] (acetylacetonate) iridium (III), Ir (PPy) 3 (tris (2-phenylpyridine) iridium (III)), and FIrPic (bis (3,5-) Difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III)), 1,6-pyrenediamine, N 1 , N 6 -bis ([1,1′-biphenyl] -3-) Yl) -N 1 , N 6 -bis (4-dibenzofuranyl)-and the like.
  • Alq 3 tris (8-
  • the light emitting layer may have a single layer structure, or may have a laminated structure including a plurality of layers having the same composition or different compositions.
  • Electron Transportable Layer (Electron Transport Layer 7, Electron Injection Layer 8)
  • the electron transport layer 7 is provided between the electron injection layer 8 and the light emitting layer 6.
  • the electron transport layer has a function of transferring electrons injected from the electron injection layer to the light emitting layer. By interposing the electron transport layer between the electron injection layer and the light emitting layer, electrons are injected into the light emitting layer with a lower electric field.
  • the electron transport layer is composed of a single layer in the embodiment shown in FIG. 1, it is composed of a plurality of layers, for example, the first electron transport layer on the anode side and the second electron transport layer on the cathode side. It is also good.
  • the second electron transport layer is a layer excellent in electron transport ability as compared with the first hole transport layer, and the first electron transport layer is compared with the second electron transport layer It is preferable that the layer has an excellent hole blocking ability.
  • the first electron transport layer may be generally referred to as a hole blocking layer.
  • the hole blocking layer can improve carrier balance.
  • the electron transport layer contains an electron transport material.
  • Electron transporting materials include lithium 8-hydroxyquinolinate (Liq), zinc bis (8-hydroxyquinolinate), bis (8-hydroxyquinolinate) copper, bis (8-hydroxyquinolinate) manganese, Tris (8-hydroxyquinolinate) aluminum, tris (2-methyl-8-hydroxyquinolinate) aluminum, tris (8-hydroxyquinolinate) gallium, bis (10-hydroxybenzo [h] quinolinate) beryllium, Bis (10-hydroxybenzo [h] quinolinate) zinc, bis (2-methyl-8-quinolinate) chlorogallium, bis (2-methyl-8-quinolinate) (o-cresolate) gallium, bis (2-methyl-8) -Quinolinate) -1-naphtholate aluminum or bis (2- 2- (3-quinolinate) -2-naphtholate gallium, 2- [3- (9-phenanthrenyl) -5- (3-pyridinyl) phenyl] -4,6-diphenyl-1
  • the electron injection layer can improve the electron injection property, and can improve the device characteristics (for example, luminous efficiency, constant voltage drive, or high durability).
  • Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, Antron etc. are mentioned.
  • the above-mentioned metal complexes alkali metal oxides, alkaline earth oxides, rare earth oxides, alkali metal halides, alkaline earth halides, rare earth halides, SiO 2 , AlO, SiN, SiN, SiON, AlON, GeO, Inorganic compounds such as various oxides such as LiO, LiON, TiO, TiON, TaO, TaON, TaN, C, nitrides, or oxynitrides can also be used.
  • a cathode 9 is provided on the electron injection layer 8.
  • a cathode can be formed from arbitrary electroconductive materials.
  • Preferred cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.
  • the organic electroluminescent device 100 is selected from the group consisting of the hole injection layer 8, the hole transport layer 7, the light emitting layer 6, the electron transport layer 5, and the electron injection layer 3 as described above.
  • One or more of them include the fused ring compound represented by the formula (1).
  • the fused ring compound represented by the formula (1) is an organic electroluminescent device, particularly a phosphorescent organic electroluminescent device, as compared with the compound using dibenzo [g, p] chrysene described in Patent Documents 1 to 3.
  • organic electroluminescence excellent in driving voltage, light emitting efficiency, and / or element life depending on the layer used A device is obtained.
  • driving voltage and luminous efficiency can be obtained by replacing the dibenzo [g, p] chrysene compound in the conventional organic electroluminescent device with the fused ring compound represented by the formula (1). It is possible to provide an organic electroluminescent device excellent in device lifetime and / or device lifetime.
  • the material for an organic electroluminescent device according to still another aspect of the present disclosure is used as a hole transport material, adjacent light emission is obtained as compared with the case where conventional dibenzo [g, p] chrysene is used. It has the effect of preventing the leak of electrons from the layer. Therefore, according to the further another aspect of this indication, the material for organic electroluminescent elements which contributes to preparation of the organic electroluminescent element excellent in luminous efficiency can be provided.
  • the material for an organic electroluminescence device when used as a light emitting material, adjacent positive ones are used as compared with the case where conventional dibenzo [g, p] chrysene is used. It has the effect of more rapidly accepting holes from the hole transport layer and electrons from the electron transport layer. Therefore, according to the further another aspect of this indication, the material for organic electroluminescent elements which contributes to preparation of the organic electroluminescent element excellent in luminous efficiency can be provided.
  • the material for an organic electroluminescent device when used as an electron transport material, the material for electrons is used as compared to the case where conventional dibenzo [g, p] chrysene is used. It has the effect of improving the durability. Therefore, according to the further another aspect of this indication, the material for organic electroluminescent elements which contributes to preparation of the organic electroluminescent element excellent in element lifetime can be provided.
  • the fused ring compound according to one aspect of the present disclosure can be used as a material for an organic electroluminescent device, for example, a hole injection material, a hole transport material, a light emitting layer material, an electron transport material, and an electron injection material.
  • the organic electroluminescent device using the fused ring compound is excellent in driving voltage, luminous efficiency or device life.
  • the fused ring compound is not limited to use in organic electroluminescent devices, and can be applied to the field of organic photoconductive materials such as electrophotographic photosensitive members, photoelectric conversion devices, solar cells, and image sensors. is there.
  • a first aspect of the present disclosure is a fused ring compound represented by the formula (1):
  • X is A furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring which may have a substituent, or
  • One of these rings represents a ring fused to a substituted or unsubstituted benzene ring;
  • Each of A 1 to A 3 independently represents a charge transporting group;
  • k1 to k3 are each independently an integer of 0 or more and 4 or less; When k1 to k3 are integers of 2 or more, the plurality of A 1 to A 3 may be the same or different.
  • the second aspect of the present disclosure is A 1 to A 3 are each independently Deuterium atom, fluorine atom, bromine atom, iodine atom, cyano group, nitro group, hydroxyl group, thiol group, An aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have a substituent, 6 to 30 carbon atoms, a linkage, or a fused ring, A C3-C36 monocyclic, linked, or fused heteroaromatic group which may have a substituent, Phosphine oxide group which may have a substituent, Silyl group which may have a substituent, A boronyl group optionally having a saturated hydrocarbon group of 2 to 10 carbon atoms, A linear or branched alkyl group having 1 to 18 carbon atoms, a linear or branched alkoxy group having 1 to 18 carbon atoms, or
  • the fused ring compound according to the first aspect is a group represented by the above formula (2) or the above (2 ′):
  • a third aspect of the present disclosure is the fused ring compound according to the first or second aspect, wherein the total of k1 to k3 is 3 or less.
  • a fourth aspect of the present disclosure is the fused ring compound according to any one of the first to third, which is a fused ring compound represented by any one of the formulas (3) to (22).
  • a 1 to A 3 and k 1 to k 3 have the same definitions as A 1 to A 3 and k 1 to k 3 in the formula (1), respectively;
  • Each of A 4 and A 5 independently represents a charge transporting group; k4 is an integer of 0 or more and 4 or less; k5 is an integer of 0 or more and 2 or less; When k1 to k5 are integers of 2 or more, the plurality of A 1 to A 5 may be the same or different.
  • aqueous layer and the organic layer are separated, and the obtained organic layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a viscous liquid containing 4- (2-bromo-4-chlorophenyl) dibenzothiophene. I got .6g. Next, 22.6 g of the viscous liquid, 12.4 g (55.9 mmol) of 9-phenanthreneboronic acid, and 464 mg of tetrakis (triphenylphosphine) palladium (0) were added to a 300 mL two-necked round bottom flask under a nitrogen stream.
  • the precipitated solid was collected by filtration and washed with pure water and methanol. The residue was recrystallized (o-xylene / methanol) to isolate 985 mg (1.60 mmol) of a yellow powder of compound (10B-154) (yield 88.9%, HPLC purity 98.8%) .
  • the sublimation temperature of the compound (10B-154) was 350 ° C., and it was confirmed that the compound (10B-154) of the sublimation product was in the form of powder.
  • the precipitated solid was collected by filtration and washed with pure water and methanol.
  • the yellow powder of compound (11A-154) was isolated by recrystallization (o-xylene / methanol) of the residue to isolate 652 mg (1.00 mmol) of a yellow powder (yield 73.7%, HPLC purity 99.0%) .
  • the sublimation temperature of the compound (11A-154) was 360 ° C., and it was confirmed that the compound of sublimate (11A-154) was in the form of powder.
  • the precipitated solid was collected by filtration and washed with pure water and methanol. 0.90 g (1.39 mmol) of yellow powder of compound (11B-154) was isolated by recrystallization (o-xylene / methanol) of the residue (yield 69.6%, HPLC purity 96.6) %).
  • the sublimation temperature of the compound (11B-154) was 360 ° C., and it was confirmed that the compound (11B-154) of the sublimation product was in the form of powder.
  • the precipitated solid was collected by filtration and washed with pure water and methanol. The residue was recrystallized (o-xylene / methanol) to isolate 1.46 g (2.20 mmol) of a yellow powder of compound (12B-154) (yield 85.1%, HPLC purity 99.4). %).
  • the sublimation temperature of the compound (12B-154) was 355 ° C., and it was confirmed that the compound (12B-154) of the sublimate was powdery.
  • the precipitated solid was collected by filtration and washed with pure water and methanol. The residue was recrystallized (o-xylene / methanol) to isolate 0.83 g (1.27 mmol) of a yellow powder of compound (15B-154) (yield 73.39%, HPLC purity 99.9). %).
  • the sublimation temperature of the compound (15B-154) was 355 ° C., and it was confirmed that the compound (15B-154) of the sublimation product was in the form of powder.
  • the precipitated solid was collected by filtration and washed with pure water and methanol. The residue was recrystallized (o-xylene / methanol) to isolate 1.04 g (1.56 mmol) of a yellow powder of compound (16B-154) (yield 83.7%, HPLC purity 99.8). %).
  • the sublimation temperature of the compound (16B-154) was 350 ° C., and it was confirmed that the compound (16B-154) of the sublimate was powdery.
  • the precipitated solid was collected by filtration and washed with pure water and methanol. The residue was recrystallized (toluene / methanol) to isolate 1.86 g (3.58 mmol) of a pale yellow powder of compound (7B-25) (yield 89.0%, HPLC purity 98.5%) .
  • the sublimation temperature of the compound (7B-25) was 315 ° C., and it was confirmed that the compound of the sublimation product (7B-25) was powdery.
  • the aqueous layer and the organic layer were separated, and the obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure.
  • the residue was recrystallized (o-xylene / methanol) to isolate 2.49 g (3.63 mmol) of a pale yellow powder of compound (7B-170) (yield 91%, HPLC purity 93.5%) .
  • the sublimation temperature of the compound (7B-170) was 350 ° C., and it was confirmed that the compound (7B-170) of the sublimate was glassy.
  • the aqueous layer and the organic layer were separated, and the obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure.
  • the residue was purified by silica gel column chromatography (toluene / hexane (1/1 (v / v))) to isolate 0.85 g (1.20 mmol) of a pale yellow powder of compound (7B-240). 60.1%, HPLC purity 97.4%).
  • the sublimation temperature of the compound (7B-240) was 350 ° C., and it was confirmed that the compound (7B-240) of the sublimate was in the form of powder.
  • the aqueous layer and the organic layer were separated, and the obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.
  • the residue was recrystallized (o-xylene / methanol) to isolate 1.46 g (1.98 mmol) of a yellow powder of compound (11A-170) (yield 79.2%, HPLC purity 99.6%) ).
  • the sublimation temperature of the compound (11A-170) was 360 ° C., and it was confirmed that the compound of sublimate (11A-170) was glassy.
  • Recrystallization Example 1 After dissolving 10 mg of a compound (4iF-1) having an HPLC purity of 92.6% in 2 mL of chloroform, 1 mL of the solution was withdrawn with a syringe and charged into a 5 mL sample tube through filter filtration. Next, 2 mL of methanol was added to the filtrate, and the mixture was stirred for 10 seconds to confirm that no precipitation had occurred. Thereafter, the sample tube was attached with a lid and sealed. After 24 hours, the presence or absence of precipitation of the compound (4iF-1) was confirmed in the solution in the sealed sample tube. The results are shown in Table 1.
  • the fused ring compound according to the present embodiment is high in crystallinity, and is advantageous for the production process using recrystallization.
  • Comparative Example 2 3- (4,6-diphenyl-1,3,5-triazyl) dibenzo [g, p] chrysene (a compound disclosed in Patent Document 3) represented by the following formula (X2) was synthesized.
  • the sublimation temperature of the compound (X2) was 310 ° C., and it was confirmed that the compound (X2) of the sublimation product was in the form of powder.
  • Comparative Example 3 3- (1-biphenyl-4-yl) dibenzo [g, p] chrysene (a compound disclosed in Patent Document 2) represented by the following formula (X3) was synthesized.
  • the sublimation temperature of the compound (X3) was 310 ° C., and it was confirmed that the compound (X3) of the sublimate was glassy.
  • Comparative Example 4 3- (Diphenylamino) dibenzo [g, p] chrysene (a compound disclosed in Patent Document 1) represented by the following formula (X4) was synthesized.
  • the sublimation temperature of the compound (X4) was 310 ° C., and it was confirmed that the compound (X4) of the sublimate was glassy.
  • the fused ring compound according to this embodiment has a high glass transition temperature and a triplet excitation level.
  • FIG. 2 is a schematic cross-sectional view showing an example of another laminated configuration of the electroluminescent device according to an aspect of the present disclosure.
  • the structural formula of the compound used for preparation of an organic electroluminescent element and its abbreviation are as follows.
  • a glass substrate with an ITO transparent electrode in which an indium tin oxide (ITO) film (film thickness of 110 nm) having a width of 2 mm was patterned in stripes was prepared. Then, the substrate was washed with isopropyl alcohol and then subjected to surface treatment by ozone ultraviolet ray washing.
  • ITO indium tin oxide
  • Each layer was vacuum-deposited by a vacuum deposition method on the surface-treated substrate after cleaning to form each layer in layers.
  • Each organic material and metal material were deposited by resistance heating.
  • the glass substrate was introduced into a vacuum deposition tank, and the pressure was reduced to 1.0 ⁇ 10 ⁇ 4 Pa. Then, in accordance with the film forming conditions of each layer, they were manufactured in the following order.
  • HTL-1 was deposited to a thickness of 10 nm at a rate of 0.15 nm / sec to prepare a first hole transport layer.
  • HTL-2 was deposited to a thickness of 10 nm at a rate of 0.15 nm / sec to prepare a second hole transport layer (electron blocking layer).
  • the second hole transport layer is a layer that also functions as an electron blocking layer that blocks the inflow of electrons.
  • EML-1 and EML-2 were deposited to a thickness of 25 nm at a ratio of 5:95 (mass ratio) to prepare a light emitting layer.
  • the deposition rate was 0.18 nm / sec.
  • ETL-1 was deposited to a thickness of 5 nm at a rate of 0.15 nm / sec to prepare a first electron transport layer (hole blocking layer).
  • the first electron transport layer is a layer that also functions as a hole blocking layer that blocks the flow of holes.
  • An electron injecting layer was formed by depositing Liq at a rate of 0.01 nm / sec for 1 nm.
  • a metal mask was disposed to be orthogonal to the ITO stripes on the substrate, and a cathode (cathode layer) was formed.
  • the cathode was formed into a two-layer structure by depositing silver / magnesium (mass ratio 1/10) and silver in this order at 80 nm and 20 nm, respectively.
  • the deposition rate of silver / magnesium was 0.5 nm / sec, and the deposition rate of silver was 0.2 nm / sec.
  • an organic electroluminescent device having a light emitting area of 4 mm 2 having a laminated structure as shown in FIG. 2 was produced.
  • each film thickness was measured by a stylus type film thickness measurement meter (DEKTAK manufactured by Bruker).
  • this element was sealed in a glove box under a nitrogen atmosphere with an oxygen and water concentration of 1 ppm or less.
  • the sealing was performed using a glass sealing cap and a film formation substrate (element) using a bisphenol F-type liquid epoxy resin (manufactured by Nagase ChemteX Corp.).
  • a direct current was applied to the organic electroluminescent device produced as described above, and the light emission characteristic was evaluated using a luminance meter (LUMINANCE METER BM-9 manufactured by TOPCON).
  • V voltage
  • cd / A current efficiency
  • the device life (h) was measured by measuring the luminance decay time during continuous lighting when the prepared organic electroluminescent device was driven at an initial luminance of 1000 cd / m 2 , and it was necessary to reduce the luminance (cd / m 2 ) by 5%. The time taken was measured.
  • the obtained measurement results are shown in Table 2.
  • the voltage, current efficiency, and device life are relative values with the result in device comparison example 1 described later as a reference value (100).
  • Element Example 7 A device example-1 is the same as the device example-1, except that the compound (11A-25) is used instead of the EML-2, and ETL-2 is used instead of the compound (10B-154). An organic electroluminescent device was produced and evaluated. The obtained measurement results are shown in Table 6. The voltage, current efficiency, and device life are relative values with the result in device comparison example 2 described later as a reference value (100).
  • Element Example 11 The steps from (preparation of substrate 1 and anode 2) to (preparation of first hole transport layer 51) were conducted in the same manner as in Example 1.
  • Second Hole Transport Layer 52 The compound (7B-25) was deposited to a thickness of 40 nm at a rate of 0.15 nm / sec to prepare a second hole transport layer (electron blocking layer).
  • a light emitting layer was formed by depositing Hex-Ir (piq) 2 (acac) and EML-3 at a ratio of 8: 92 (mass ratio) to a thickness of 35 nm.
  • the deposition rate was 0.18 nm / sec.
  • ETL-2 and Liq were deposited to a thickness of 30 nm at a ratio of 50:50 (mass ratio) to prepare a first electron transport layer.
  • the deposition rate was 0.15 nm / sec.
  • Element Comparison Example 3 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example 11 except that the compound (X3) was used instead of the compound (7B-25) in Device Example 11. The obtained measurement results are shown in Table 7.
  • Element Example 12 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example 11 except that the compound (7B-170) was used instead of the compound (7B-25) in the device example-11. The obtained measurement results are shown in Table 8. The voltage and current efficiency are relative values with the result in the element comparative example 4 described later as a reference value (100).
  • Example 13 The steps from (Production of Substrate 1, Anode 2) to (Production of Charge Generating Layer 4) were carried out in the same manner as in Example 1.
  • HTL-1 was deposited to a thickness of 85 nm at a rate of 0.15 nm / sec to prepare a first hole transport layer.
  • Second Hole Transport Layer 52 The compound (7B-233) was deposited to a thickness of 60 nm at a rate of 0.15 nm / sec to prepare a second hole transport layer (electron blocking layer).
  • a light emitting layer was formed by depositing Hex-Ir (piq) 2 (acac) and EML-4 at a ratio of 2:98 (mass ratio) to a thickness of 35 nm.
  • the deposition rate was 0.18 nm / sec.
  • ETL-2 and Liq were deposited to a thickness of 30 nm at a ratio of 50:50 (mass ratio) to prepare a first electron transport layer.
  • the deposition rate was 0.15 nm / sec.

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