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WO2014088047A1 - Dérivé d'amine, matériau électroluminescent organique et élément électroluminescent organique l'utilisant - Google Patents

Dérivé d'amine, matériau électroluminescent organique et élément électroluminescent organique l'utilisant Download PDF

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WO2014088047A1
WO2014088047A1 PCT/JP2013/082647 JP2013082647W WO2014088047A1 WO 2014088047 A1 WO2014088047 A1 WO 2014088047A1 JP 2013082647 W JP2013082647 W JP 2013082647W WO 2014088047 A1 WO2014088047 A1 WO 2014088047A1
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group
substituted
amine derivative
unsubstituted
general formula
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Japanese (ja)
Inventor
純太 渕脇
裕美 大山
康生 宮田
直也 坂本
雅嗣 上野
高田　一範
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Samsung Display Co Ltd
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Samsung Display Co Ltd
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Priority claimed from JP2013248003A external-priority patent/JP2014131987A/ja
Application filed by Samsung Display Co Ltd filed Critical Samsung Display Co Ltd
Priority to KR1020177018061A priority Critical patent/KR20170081718A/ko
Priority to KR1020157002270A priority patent/KR20150090021A/ko
Publication of WO2014088047A1 publication Critical patent/WO2014088047A1/fr
Priority to US14/731,180 priority patent/US9780317B2/en
Anticipated expiration legal-status Critical
Priority to US15/716,613 priority patent/US10629830B2/en
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    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a novel amine derivative suitably used as an organic light-emitting material, particularly an organic light-emitting material such as a hole transport material, and an organic electroluminescence device using the same.
  • an organic electroluminescent display device displays a light emitting material containing an organic compound in a light emitting layer by emitting light and recombining holes and electrons injected from an anode and a cathode in the light emitting layer. This is a so-called self-luminous display device.
  • organic electroluminescent elements which are composed of a plurality of layers having different characteristics, such as a light emitting layer and a layer for transporting carriers (holes, electrons) to the light emitting layer.
  • the hole transport layer is required to have excellent hole transport ability and carrier resistance. From such a viewpoint, various hole transport materials have been proposed.
  • Patent Document 1 and Patent Document 6 Various materials such as aromatic amine compounds are known as materials used for each layer of the organic electroluminescence element.
  • a carbazole derivative is proposed as a hole transport material or a hole injection material.
  • an amine compound having a terphenyl group is proposed as a hole transport material and a host material in a light emitting layer.
  • an amine compound having a fluorenyl group is proposed as a hole transport material or a hole injection material.
  • Patent Document 4 an amine derivative having a dibenzofuryl group is proposed as a hole transport material or a host material of a light emitting layer.
  • Patent Document 5 an amine derivative having a silyl group is proposed as a hole transport material.
  • Patent Document 7 and Patent Document 8 carbazole derivatives substituted with a condensed ring are proposed.
  • a triarylamine derivative is proposed as a light emitting layer material or a hole injecting and transporting material.
  • Patent Document 10 a tri (p-terphenyl-4-yl) amine compound is proposed as a hole transport material.
  • Patent Document 11 a diamine compound is proposed as a hole transport material.
  • Patent Document 12 and Patent Document 13 an amine compound having a silyl group is proposed as a light emitting layer material.
  • Patent Document 14 an amine compound having a silyl group is proposed as an electron blocking layer material or a light emitting layer material.
  • organic electroluminescence elements using these materials also have a sufficient light emission lifetime. At present, the organic electroluminescence elements can be driven with higher efficiency and lower voltage and have a longer light emission life. Is desired.
  • the organic light emitting material is required to have a long lifetime.
  • the device using the compound proposed so far in the hole injection layer or the hole transport layer has not been sufficiently resistant to electrons, an improvement in device lifetime has been demanded.
  • the present invention provides an organic electroluminescence device having an improved device lifetime by suppressing a deterioration mechanism of the device caused by electrons entering the hole transport layer, and an organic light emitting device that realizes the organic electroluminescence device It is an object to provide materials.
  • An amine derivative according to an embodiment of the present invention is represented by the following general formula (1).
  • Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Ar 1 , Ar 2 , and Ar 3 At least one of them is substituted with a substituted or unsubstituted silyl group.
  • L represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • the amine derivative is an aryl group in which Ar 1 in the general formula (1) is substituted with a silyl group exhibiting strong electron resistance. Therefore, the electron resistance is improved, and the organic electroluminescent element is improved. Improvement of luminous efficiency and long life can be realized.
  • At least one of Ar 1 , Ar 2 , and Ar 3 may be a substituted or unsubstituted heteroaryl group.
  • Ar 1 and Ar 2 may each independently be a substituted or unsubstituted aryl group.
  • Ar 1 and Ar 2 are each independently an aryl group having 6 to 18 ring carbon atoms, and Ar 3 is substituted or unsubstituted. It may be a dibenzoheteroyl group.
  • the amine derivative according to one embodiment of the present invention is an aryl derivative in which in the general formula (1), a silyl group that substitutes at least one of Ar 1 , Ar 2 , and Ar 3 is substituted with the silyl group.
  • the group may be a triarylsilyl group having 6 to 18 ring carbon atoms, or a trialkylsilyl group having 1 to 6 carbon atoms in the alkyl group substituted by the silyl group.
  • Ar 1 and Ar 2 may each be substituted with one silyl group.
  • Ar 1 , Ar 2 , and Ar 3 in the general formula (1) may be substituted with one silyl group.
  • L may be a single bond or an arylene group having 6 to 14 ring carbon atoms.
  • Ar 3 in the general formula (1) may be a substituted or unsubstituted dibenzofuryl group.
  • the introduction of a dibenzofuryl group further improves the electron resistance and increases the glass transition temperature. For this reason, the improvement of the luminous efficiency of an organic electroluminescent element, low voltage, and lifetime improvement are realizable.
  • L in the general formula (1) may not include a single bond.
  • L is a phenylene group, and a dibenzofuryl group that is Ar 3 may be bonded to L at the 3-position.
  • the hole transportability is improved, whereby the light emission efficiency of the organic electroluminescence device can be improved, the voltage can be lowered, and the life can be extended.
  • the amine derivative according to one embodiment of the present invention represented by the general formula (1) may be a compound represented by the following general formula (2).
  • An organic electroluminescence device includes any one of the above-described amine derivatives in a light emitting layer.
  • an organic electroluminescence device that achieves improved luminous efficiency, lower voltage, and longer life is provided.
  • An organic electroluminescence device includes any one of the above-described amine derivatives in one of the laminated films between the light emitting layer and the anode.
  • an organic electroluminescence device that achieves improved luminous efficiency, lower voltage, and longer life is provided.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, At least one of Ar 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted dibenzofuryl group, and L may be a single bond. .
  • the dibenzofuryl group exhibits strong electron resistance and high planarity, and thus exhibits a high glass transition point. For this reason, it is possible to improve the light emission efficiency of the organic electroluminescence element, and to realize a lower driving voltage and a longer life. Moreover, when producing an organic electroluminescent element, improvement of film forming property can be expected.
  • the dibenzofuryl group may be bonded to the L at the 3-position.
  • the dibenzofuryl group is bonded to the L at the 3-position, that is, bonded to the nitrogen atom (N) of the amine site, thereby expanding the ⁇ -electron conjugated system of the entire molecule. Therefore, improvement in hole transportability is expected, and further improvement in light emission efficiency and longer life of the organic electroluminescence element can be realized.
  • An organic electroluminescence device includes the amine derivative in a light emitting layer.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • the organic electroluminescence device includes the amine derivative in one of the laminated films between the light emitting layer and the anode.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Ar At least one of 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted fluorenyl group, L is a substituted or unsubstituted arylene group, or substituted or unsubstituted It may be an unsubstituted heteroarylene group.
  • a conjugated group of ⁇ electrons is expanded by bonding a fluorenyl group to an amine moiety via L as a linking group, so that hole transportability and molecular stability are improved.
  • L a linking group
  • the substituted or unsubstituted arylene group or the substituted or unsubstituted heteroarylene group as the linking group L is planarized, whereby the hole transport property of the amine derivative is improved. Thereby, the improvement of the luminous efficiency and lifetime improvement of an organic electroluminescent element are realizable.
  • An organic electroluminescence device includes the amine derivative in a light emitting layer.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • the organic electroluminescence device includes the amine derivative in one of the laminated films between the light emitting layer and the anode.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • An amine derivative according to an embodiment of the present invention is represented by the following general formula (3), wherein Ar 3 is a substituted or unsubstituted fluorenyl group and L is a single bond in the general formula (1). It may be.
  • the hole transport property is improved, and the light emission efficiency of the organic electroluminescence device can be improved and the lifetime can be increased.
  • the substituents of the fluorenyl group are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or It may be a substituted or unsubstituted heteroaryl group.
  • the fluorenyl group may be bonded to L at the 2-position.
  • the fluorenyl group when the fluorenyl group is bonded to the nitrogen atom (N) of the amine moiety at the 2-position, the conjugated system of ⁇ electrons of the whole molecule is expanded, and the hole transport property is improved and Since the stability is improved, it is possible to improve the light emission efficiency and extend the life of the organic electroluminescence element.
  • Ar 1 and Ar 2 may each independently be a substituted or unsubstituted aryl group.
  • Ar 1 may be a substituted or unsubstituted aryl group
  • Ar 2 may be a substituted or unsubstituted dibenzoheteroyl group.
  • the amine derivative according to one embodiment of the present invention is a ring-forming carbon of an aryl group in which at least one of Ar 1 and Ar 2 in General Formula (3) is substituted with the silyl group. It may be a triarylsilyl group having 6 to 18 carbon atoms, or a trialkylsilyl group having 1 to 6 carbon atoms in each alkyl group substituted by the silyl group.
  • An organic electroluminescent element material according to an embodiment of the present invention contains the amine derivative.
  • the organic electroluminescent element material according to an embodiment of the present invention may be a hole transport material.
  • An organic electroluminescence device includes a light emitting layer and a hole transport layer disposed between a cathode and an anode, and the hole transport layer includes the amine derivative.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Ar At least one of 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted carbazolyl group, L is a substituted or unsubstituted arylene group, or substituted or unsubstituted It may be an unsubstituted heteroarylene group.
  • the amine derivative according to one embodiment of the present invention has improved hole transportability by introducing a carbazolyl group, and the amine derivative is substituted via a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • the level of HOMO is adjusted, and it is possible to improve the light emission efficiency and extend the lifetime of the organic electroluminescence element.
  • the substituted or unsubstituted carbazolyl group may be bonded to L at the 2-position or 3-position.
  • the carbazolyl group is bonded to L at the 2-position or 3-position, thereby expanding the ⁇ -electron conjugated system of the entire molecule, improving hole transportability and stability of the molecule.
  • L the carbazolyl group
  • An organic electroluminescence device includes the amine derivative in a light emitting layer.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • the organic electroluminescence device includes the amine derivative in one of the laminated films between the light emitting layer and the anode.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, At least one of Ar 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted carbazolyl group, L is a substituted or unsubstituted arylene group, or substituted Alternatively, it is an unsubstituted heteroarylene group and is represented by the following general formula (4).
  • R 1 to R 8 are a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • the hole transportability is improved by introducing a carbazolyl group, and the carbazolyl group is bonded to the amine moiety via the linking group L, whereby the HOMO level is adjusted.
  • the HOMO level is adjusted.
  • R 1 to R 8 may be bonded to each other to form a saturated or unsaturated ring.
  • L may be a phenylene group, a biphenylene group or a fluorenylene group.
  • the linking group L is a phenylene group, a biphenylene group, or a fluorenylene group, so that a conjugated system of ⁇ electrons in the whole molecule is expanded. It is possible to improve the emission efficiency and extend the life of the organic electroluminescence element.
  • Ar 1 and Ar 2 in the general formula (4) are aryl groups having 6 to 12 ring carbon atoms.
  • An organic electroluminescence device includes the amine derivative in a light emitting layer.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • the organic electroluminescence device includes the amine derivative in one of the laminated films between the light emitting layer and the anode.
  • an organic electroluminescence device that achieves improved luminous efficiency and longer life is provided.
  • Ar 1 is an aryl group represented by the following General Formula (5) substituted with a silyl group
  • Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • Ar 3 is an aryl group represented by the following general formula (6)
  • L is an arylene group represented by the following general formula (7),
  • o is an integer that satisfies 0 ⁇ o ⁇ 2
  • R 11 , R 12 , and R 13 are each independently an alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted ring formation.
  • each R 9 is independently a hydrogen atom, a halogen atom, or a carbon number of 1 or more.
  • An alkyl group having 15 or less, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, m is an integer satisfying 0 ⁇ m ⁇ 5, and in the general formula (7), each R 10 is independent.
  • the amine derivative according to one embodiment of the present invention is an aryl group in which Ar 1 in the general formula (1) is substituted with a silyl group exhibiting strong electron resistance, so that the electron resistance is improved.
  • Ar 1 in the general formula (1) having an arylene group in which n is 2 or more spreads ⁇ electrons and exhibits good hole transport properties. Therefore, the amine derivative according to an embodiment of the present invention can improve the light emission efficiency and extend the life of the organic electroluminescence element.
  • the amine derivative by one Embodiment of this invention has an arylene group whose n is 2 or more in General formula (7), glass transition temperature (Tg) rises and film forming property improves.
  • the glass transition temperature of the amine derivative is preferably 120 ° C. or higher for production.
  • R 11 , R 12 and R 13 may each be a phenyl group.
  • o may be 0 or 1.
  • o in the general formula (5) when o in the general formula (5) is 0 or 1, the ability to prevent the penetration of electrons into the hole transport layer is increased. Deterioration can be suppressed, and the lifetime of the organic electroluminescence element can be extended.
  • n may be 2.
  • n in the general formula (7) is 2, the electron resistance of the amine derivative can be further improved.
  • the material for an organic electroluminescence device contains any of the amine derivatives described above.
  • an organic electroluminescent element material having strong electron resistance and good hole transportability.
  • An organic electroluminescent device includes the organic electroluminescent device material in any one of laminated films disposed between a light emitting layer and an anode.
  • an organic electroluminescence element with improved luminous efficiency and a long lifetime is provided.
  • an organic electroluminescent element with improved luminous efficiency and improved element lifetime, and an organic electroluminescent element material that makes it possible to realize it.
  • an amine derivative having a silyl group is used as a material for a hole transport layer in an organic electroluminescence device, and that the lifetime of the organic electroluminescence device can be extended. It was confirmed.
  • the amine derivative having a silyl group conceived by the present inventors will be described.
  • the organic electroluminescent material of the present invention and the organic electroluminescent element using the same can be implemented in many different modes, and should be interpreted as being limited to the description of the embodiments described below. is not.
  • the organic electroluminescent material according to the present invention is an amine derivative having a silyl group represented by the following general formula (1).
  • Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and the Ar 1 , Ar 2 , and Ar At least one of 3 is substituted with a substituted or unsubstituted silyl group.
  • L represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • the aryl group and heteroaryl group of the “substituted or unsubstituted aryl group” or “substituted or unsubstituted heteroaryl group” of Ar 1 , Ar 2 , and Ar 3 include phenyl group, naphthyl group, anthracenyl group, phenanthryl Group, biphenyl group, terphenyl group, fluorenyl group, triphenylene group, biphenylene group, pyrenyl group, benzothiazolyl group, thiophenyl group, thienothiophenyl group, thienothienothiophenyl group, benzothiophenyl group, dibenzothiophenyl group, dibenzofuryl Group, N-arylcarbazolyl group, N-heteroarylcarbazolyl group, N-alkylcarbazolyl group, phenoxazyl group, phenothiazyl group, pyri
  • At least one of the aryl groups and heteroaryl groups of Ar 1 , Ar 2 , and Ar 3 is substituted with a silyl group.
  • a silyl group it is preferably substituted by one to at least one of Ar 1 and Ar 2, in particular, Ar 1, Ar 2, and be substituted by one to at least one of Ar 3 Further preferred.
  • Ar 1 , Ar 2 , and Ar 3 is a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted carbazolyl group, dibenzothiophenyl group, dibenzofuryl group, etc. Dibenzoheteroyl group.
  • Ar 3 is preferably a substituted or unsubstituted heteroaryl group, and Ar 3 is particularly preferably a dibenzoheteroyl group.
  • Ar 1 and Ar 2 are preferably substituted or unsubstituted aryl groups, and particularly preferably Ar 3 is a dibenzoheteroyl group, and Ar 1 And Ar 2 is an aryl group having 6 to 18 ring carbon atoms.
  • the “substituted or unsubstituted arylene group” or “substituted or unsubstituted heteroarylene group” for L is the “substituted or unsubstituted aryl group” or “substituted” mentioned in Ar 1 , Ar 2 , and Ar 3. Or the thing similar to the aryl group and heteroaryl group of "an unsubstituted heteroaryl group” is mentioned.
  • the arylene group and heteroarylene group of the “substituted or unsubstituted arylene group” or “substituted or unsubstituted heteroarylene group” of L include a phenylene group, a naphthylene group, a biphenylylene group, a thienothiophenylene group, and a pyridylene group. preferable. In particular, an arylene group having 6 to 14 ring carbon atoms is preferable, and a phenylene group and a biphenylylene group are more preferable.
  • L being a “single bond” means that in the amine derivative having a silyl group represented by the general formula (1) of the present invention, the nitrogen atom (N) at the amine site and Ar 3 are directly bonded. Represents the state.
  • Examples of the substituent substituted on the aryl group or heteroaryl group of Ar 1 , Ar 2 , and Ar 3 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group.
  • Illustrative examples of the aryl group and heteroaryl group are the same as the aryl group and heteroaryl group of Ar 1 , Ar 2 , and Ar 3 described above.
  • the alkyl group of the substituent substituted with the aryl group or heteroaryl group of Ar 1 , Ar 2 , and Ar 3 is not particularly limited, but a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a butyl group, Examples include isobutyl group, t-butyl group, cyclobutyl group, pentyl group, isopentyl group, neopentyl group, cyclopentyl group, hexyl group, cyclohexyl group, heptyl group, cycloheptyl group, octyl group, nonyl group, decyl group, etc. it can.
  • the alkoxy group of the substituent of the aryl group or heteroaryl group of Ar 1 , Ar 2 , and Ar 3 is not particularly limited, but is a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group T-butoxy group, n-pentyloxy group, neopentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7 -A dimethyloctyloxy group etc. can be illustrated.
  • Examples of the substituent for the arylene group or heteroarylene group of L include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Illustrative examples are the same as the alkyl group, alkoxy group, aryl group and heteroaryl group described as the substituents substituted on the aryl group or heteroaryl group of Ar 1 , Ar 2 and Ar 3 .
  • Examples of the substituent of the silyl group that is substituted with at least one of Ar 1 , Ar 2 , and Ar 3 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Illustrative examples are the same as the alkyl group, alkoxy group, aryl group and heteroaryl group mentioned as the substituents substituted on the aryl group or heteroaryl group of Ar 1 , Ar 2 , and Ar 3. Group and aryl group are preferable, and methyl group and phenyl group are particularly preferable.
  • the silyl group substituted with at least one of Ar 1 , Ar 2 , and Ar 3 is a trialkylsilyl group in which the alkyl group substituted with the silyl group has 1 to 6 carbon atoms, or the silyl group It is preferable that the aryl group to be substituted is a triarylsilyl group having 6 to 18 ring carbon atoms.
  • Examples of the amine derivative having a silyl group of the present invention represented by the formula (1) include compounds exemplified below, but are not limited thereto.
  • the above-mentioned compounds 1, 2, 3, 4, 5, 6, 8, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 37, 38, 40, 42, 44, 45, 46, 49, 50, 53, 54, 55, 56, 57, 59, 60, 61, 62, 63, 64, 74, 77, 79, 85, 87, 88, 89, 92, 96, 98, 101, 102, 107, and 110 are more preferable.
  • the amine derivative having a silyl group of the present invention can be used as a material for an organic electroluminescence device.
  • the amine derivative having a silyl group of the present invention represented by the general formula (1) is a substituted or unsubstituted group of Ar 1 , Ar 2 , and Ar 3 bonded to the nitrogen atom (N) or linker (L) of the amine.
  • At least one of the aryl group and the substituted or unsubstituted heteroaryl group is substituted with a substituted or unsubstituted silyl group exhibiting strong electron resistance.
  • the amine derivative having a silyl group of the present invention is stable with respect to electrons, and can be preferably used as a material for an organic electroluminescence device, particularly as a hole transport layer material adjacent to a light emitting layer.
  • the amine derivative having a silyl group of the present invention as a hole transport layer material, the electron transport resistance of the hole transport layer can be improved, and a hole transport material caused by electrons entering the hole transport layer It is possible to suppress the deterioration of the organic electroluminescence element and extend the life of the organic electroluminescence element.
  • the use of the amine derivative having a silyl group of the present invention is not limited to the hole transport material of the organic electroluminescence element.
  • it can be preferably used for the material of the hole injection layer.
  • an amine derivative having a silyl group is used as the material for the hole injection layer, the deterioration of the hole injection layer caused by electrons can be suppressed. Thus, it is possible to realize a long life of the organic electroluminescence element.
  • Organic electroluminescence element may have a structure as shown in FIG. 1, for example, but is not limited thereto.
  • An organic electroluminescent device 100 shown in FIG. 1 is a schematic cross-sectional view of an embodiment in which the amine derivative of the present invention is used as a material for an organic electroluminescent device, and is disposed on a glass substrate 102 and a glass substrate 102.
  • the hole injection layer 106 disposed on the anode 104, the hole transport layer 108 disposed on the hole injection layer 106, the light emitting layer 110 disposed on the hole transport layer 108, and the light emitting layer 110 And an electron transport layer 112 disposed on the electron transport layer 112 and a cathode 114 disposed on the electron transport layer 112.
  • the electron transport layer 112 also functions as an electron injection layer.
  • the anode 104 may be formed using indium tin oxide (ITO), indium zinc oxide (IZO), or the like.
  • the hole-injection layer 106 includes 4,4 ', 4 "-Tris (N-1-naphtyl-N-phenylamino) triphenylamine (1-TNATA), or 4,4', 4 ''-tris (N- (2 -naphthyl) -N-phenylamino) -triphenylamine (2-TNATA), 4,4-Bis (N, N-di (3-tolyl) amino) -3,3-dimethylbiphenyl (HMTPD), etc.
  • the compounds shown below may be included.
  • the hole transport layer 108 can be formed using the amine derivative having a silyl group of the present invention represented by the general formula (1).
  • the light emitting layer 110 may contain, for example, the following compound as a host material.
  • the compound contained as a host material in the light emitting layer 110 is not limited to the above-mentioned compound, and a known material may be used as the host material.
  • the light emitting layer 110 may include, for example, the following compounds as dopants.
  • the compound doped as a dopant in the light emitting layer 110 is not limited to the above-mentioned compound, and a known material may be used as a dopant according to a desired color region.
  • the dopant is preferably doped by 0.1% to 50% to the material constituting the light emitting layer 110.
  • the electron transport layer 112 may include, for example, Tris (8-hydroxyquinolinato) aluminum (Alq3). Moreover, you may include the compound shown below.
  • the cathode 114 is formed of a metal such as Al, Ag, or Ca, or a transparent material such as indium tin oxide (ITO) or indium zinc oxide (IZO).
  • a metal such as Al, Ag, or Ca
  • a transparent material such as indium tin oxide (ITO) or indium zinc oxide (IZO).
  • the organic electroluminescent element 100 may include an electron injection layer between the cathode 114 and the electron transport 112.
  • the electron injection layer may include, for example, lithium fluoride (LiF), lithium 8-quinolinate, and the like.
  • the amine derivative having a silyl group of the present invention represented by the general formula (1) can be used as a material for a hole transport layer of an organic electroluminescence element.
  • the use of the amine derivative having a silyl group of the present invention is not limited to the hole transport material of the organic electroluminescence device, and may be included in the hole injection layer as a hole injection material.
  • the amine derivative of the present invention for at least one of the hole injection layer material and the hole transport layer material constituting the organic electroluminescence element such as the hole injection layer 106 and the hole transport layer 108.
  • the lifetime of the organic electroluminescence element can be increased.
  • the amine derivative having a silyl group of the present invention is preferable as a hole transport layer material or a hole injection layer material of an organic electroluminescence device because it has electron resistance, but is not limited thereto. .
  • Example I With respect to the amine derivative having the silyl group of the present invention represented by the general formula (1), examples of the synthesis method of the compounds 1, 3, 61, 63 will be described below. However, the synthesis method described below is an example and does not limit the present invention.
  • Compound 1 of the present invention was synthesized as follows.
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: dichloromethane / hexane), and the obtained solid was recrystallized from toluene / hexane. As a result, a white powdered solid as the target compound 1 was obtained. Obtained 2.26 g, yield 90% (FAB-MS: C51H41NSi, measured value 695).
  • Compound 3 of the present invention was synthesized as follows.
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: dichloromethane / hexane), and the obtained solid was recrystallized from toluene / hexane. As a result, a white powdered solid as the target compound 3 was obtained. 1.00 g, 40% yield was obtained (FAB-MS: C48H35NSSi, measured value 685).
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: toluene / hexane), and the obtained solid was recrystallized from dichloromethane / hexane. As a result, a white powdered solid as the target compound 61 was obtained. 1.15 g, yield 89% (FAB-MS: C66H48N2Si, measured value 897).
  • the compound 63 of the present invention was synthesized as follows.
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: toluene / hexane), and the obtained solid was recrystallized from dichloromethane / hexane. As a result, a white powdered solid as the target compound 63 was obtained. 1.59 g was obtained with a yield of 94% (FAB-MS: C60H44N2Si, measured value 821).
  • Example 1 of an organic electroluminescence element using the above-described compound 1 as a hole transport layer as the organic electroluminescence element material of the present invention will be described.
  • the production of the organic electroluminescence element of Example 1 of the present invention was performed by vacuum deposition, and the following procedure was performed.
  • the ITO film has a thickness of 150 nm.
  • 4,4 ′, 4 ′′ -tris (N, N- (2-naphthyl) phenylamino) triphenylamine (2-TNATA, film thickness 60 nm) was used as the hole injection material.
  • a film was formed on top.
  • the compound 1 of the present invention was formed as a hole transporting material (30 nm), and then 2,5,8,11-tetra-t-butylperylene (TBP) was used as the light emitting material.
  • TBP 2,5,8,11-tetra-t-butylperylene
  • Example 2 an organic electroluminescence device was produced in the same manner as in Example 1 except that Compound 3 was used instead of Compound 1 used in Example 1.
  • Example 3 an organic electroluminescence device was produced in the same manner as in Example 1 except that Compound 61 was used instead of Compound 1 used in Example 1.
  • Example 4 an organic electroluminescence device was produced in the same manner as in Example 1 except that Compound 63 was used instead of Compound 1 used in Example 1.
  • Comparative Example 1 and Comparative Example 2 an organic electroluminescent device was prepared in the same manner as in Example 1, using Comparative Compound 1 and Comparative Compound 2 shown below as compounds constituting the material of the hole transport layer of the organic electroluminescent device. Produced.
  • the compound used in Comparative Example 1 and Comparative Example 2 is different from the amine derivative of the present invention in that it has a structure having no silyl group.
  • FIG. 2 shows a schematic diagram of Examples 1 to 4, Comparative Example 1, and Comparative Example 2 of the produced organic electroluminescence element 200.
  • the produced organic electroluminescence device 200 is disposed on the anode 204, the hole injection layer 206 disposed on the anode 204, the hole transport layer 208 disposed on the hole injection layer 206, and the hole transport layer 208.
  • Table 1 shows the element performance of the organic electroluminescent elements 200 of Examples 1 to 4 and Comparative Examples 1 and 2 that were produced.
  • the current efficiency is a value at 10 mA / cm 2
  • the half life is a luminance half time from an initial luminance of 1,000 cd / m 2 .
  • the amine derivative having a silyl group of the present invention represented by the general formula (1) includes a silyl group having electron resistance, and is a material capable of performing stable hole transport with respect to electrons. Therefore, by using the amine derivative having a silyl group of the present invention, it is possible to suppress the deterioration of the device caused by the electrons that have entered the hole transport layer, and to realize a long lifetime of the device.
  • Examples 1 to 4 described above examples in which the amine derivative having a silyl group of the present invention represented by the general formula (1) is used as a hole transport material of an organic electroluminescence element have been described.
  • Use of the amine derivative having a silyl group is not limited to the organic electroluminescence element, and may be used for other light-emitting elements or light-emitting devices.
  • 1 and 2 is used for a passive matrix driving type organic electroluminescence display, it can also be used for an active matrix driving type organic electroluminescence display.
  • the inventors of the present application particularly arrange an amine derivative having the structure described below as an organic electroluminescent material between the light emitting layer and the anode, thereby It was confirmed that a remarkable improvement was obtained in the luminous efficiency, driving voltage and lifetime of the electroluminescence element.
  • a preferred structure of the amine derivative represented by the general formula (1) is that, in the general formula (1), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. And at least one of Ar 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted dibenzofuryl group, and L is a divalent group containing no single bond.
  • Phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, triphenylene group, dibenzothiophenyl group, dibenzofuryl group, and N-phenylcarbazolyl group are preferable, and phenyl group, biphenyl group, fluorenyl group are particularly preferable.
  • Group, triphenylene group, dibenzothiophenyl group, dibenzofuryl group and N-phenylcarbazolyl group are preferable.
  • the aryl group of Ar 1 and Ar 2 is preferably an aryl group having 6 to 18 ring carbon atoms, and the heteroaryl group of Ar 1 and Ar 2 is a heteroaryl group having 5 to 18 ring atoms. preferable.
  • Examples of the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group.
  • Illustrative examples of the aryl group and heteroaryl group are the same as the aryl group and heteroaryl group mentioned as the specific groups of Ar 1 and Ar 2 described above.
  • Ar 3 in the general formula (1) is a substituted or unsubstituted dibenzofuryl group.
  • Each of the substituents substituted on the dibenzofuryl group is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl having 5 to 20 ring carbon atoms.
  • L in the general formula (1) is a divalent linking group, and may be a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, specifically May be a divalent group of the groups listed as Ar 1 and Ar 2 described above.
  • L is preferably an arylene group having 6 to 18 ring carbon atoms, and particularly preferably a phenylene group.
  • L does not include a single bond.
  • Examples of the substituent substituted with the arylene group or heteroarylene group of L include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Specifically, it may be the same as the alkyl group, alkoxy group, aryl group, and heteroaryl group described as the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 .
  • Examples of the substituent of the silyl group that is substituted with at least one of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Specifically, it is the same as the alkyl group, alkoxy group, aryl group, and heteroaryl group described as the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 , and a phenyl group is particularly preferable.
  • the silyl group substituted with at least one of Ar 1 and Ar 2 is preferably a triarylsilyl group in which the number of carbon atoms in the aryl group substituted with the silyl group is 6 or more and 18 or less. .
  • Examples of the amine derivative in which Ar 3 which is a dibenzofuryl group in General Formula (1) is bonded to a divalent linking group L include the compounds exemplified below, but are not limited thereto.
  • the preferred amine derivative of the present invention is that, in the general formula (1), Ar 3 is a substituted or unsubstituted dibenzofuryl group, and this dibenzofuryl group is bonded to the divalent linking group L. .
  • the dibenzofuryl group has strong electron resistance. Therefore, by using an amine derivative in which Ar 3 is a substituted or unsubstituted dibenzofuryl group in the general formula (1) as the hole transport layer material, the electron resistance of the hole transport layer can be improved. It is possible to suppress the deterioration of the hole transport material caused by the electrons that have entered the hole transport layer. Further, by introducing a dibenzofuryl group, the planarity of the amine derivative is increased and the glass transition temperature is increased.
  • the improvement of the light emission efficiency of an organic electroluminescent element, low drive voltage, and lifetime improvement are realizable. Furthermore, as described above, when the dibenzofuryl group and the amine moiety are bonded via the divalent linking group L, the conjugated system of ⁇ electrons in the entire molecule is expanded. Therefore, the hole transport property is improved and the stability of the molecule is also improved, so that the drive voltage, the lifetime, and the light emission efficiency of the organic electroluminescence element can be realized.
  • the preferred amine derivative of the present invention can realize improvement in light emission efficiency, low drive voltage, and long life of the organic electroluminescence device, particularly in the blue to blue-green region.
  • the substituted or unsubstituted dibenzofuryl group that is Ar 3 may be bonded to L at the 2-position, 3-position or 4-position. It is preferably bonded to the linking group L at the 3-position.
  • the substituted or unsubstituted dibenzofuryl group which is Ar 3 is preferably bonded to the para position of the divalent linking group with respect to the nitrogen atom (N) of the amine moiety.
  • the configuration of the organic electroluminescence element 100 shown in FIG. 1 is an embodiment of the organic electroluminescence element of the present invention, and is not limited to this, and various modifications are possible.
  • the use of the amine derivative of the present invention represented by the general formula (1), in which Ar 3 which is a dibenzofuryl group is bonded to a divalent linking group L, is intended for use in an organic electroluminescence device.
  • It is not limited to the hole transport material, and can be used as a material for a hole injection layer or a light emitting layer, and can be used as a material for a hole injection layer or a light emitting layer.
  • Example II Regarding the amine derivative of the present invention represented by the general formula (1), wherein Ar 3 which is a dibenzofuryl group is bonded to a divalent linking group L, the compounds A-10, A-18, Examples of synthesis methods of A-25, A-35 and A-41 are described below. However, the synthesis method described below is an example and does not limit the present invention.
  • the obtained crude product was purified by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) and then recrystallized with a mixed solvent of toluene / hexane to obtain 1.86 g of a white solid compound A-10 (yield 86 %)Obtained.
  • the chemical shift value of Compound A-10 measured by 1 H NMR measurement is 8.00 (d, 1H), 7.96 (d, 1H), 7.78 (d, 1H), 7.64-7.53 (m, 20 H), 7.48 -7.33 (m, 14H), 7.29-7.25 (m, 6H). Further, the molecular weight of Compound A-10 measured by FAB-MS measurement was 822.
  • the obtained crude product was purified by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) and then recrystallized with a mixed solvent of toluene / hexane to obtain 0.95 g of a white solid compound A-35 (yield 80 %)Obtained.
  • the chemical shift values of Compound A-35 measured by 1 H NMR measurement are 7.99 (d, 1H), 7.91 (d, 1H), 7.87 (d, 2H), 7.62-7.28 (m, 33H), 7.20 (d , 2H).
  • the molecular weight of Compound A-35 measured by FAB-MS measurement was 745.
  • the obtained crude product was purified by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) and then recrystallized with a mixed solvent of toluene / hexane to obtain 1.86 g of a white solid compound A-41 (yield 89 %)Obtained.
  • the chemical shift value of Compound A-41 measured by 1 H NMR measurement is 8.00 (d, 1H), 7.93-7.87 (m, 3H), 7.66-7.53 (m, 17H), 7.50-7.28 (m, 22H ) Met.
  • the molecular weight of compound A-41 measured by FAB-MS measurement was 822.
  • Example 5 shows an organic electroluminescence device using Compound A-10 for the hole transport layer
  • Example 6 shows an organic electroluminescence device using Compound A-18 for the hole transport layer
  • Example 7 is an organic electroluminescence device used for the layer
  • Example 8 is an organic electroluminescence device using Compound A-35 for the hole transport layer
  • Preparation of the organic electroluminescence element of Example 5 of the present invention was performed by vacuum deposition in the same manner as the organic electroluminescence element of Example 1 described above, and was performed according to the following procedure.
  • surface treatment with ozone was performed on an ITO-glass substrate that had been patterned and cleaned in advance.
  • the ITO film has a thickness of 150 nm.
  • 4,4 ′, 4 ′′ -tris (N, N- (2-naphthyl) phenylamino) triphenylamine (2-TNATA, film thickness 60 nm) was used as the hole injection material.
  • a film was formed on top.
  • the compound A-10 of the present invention was formed into a film (30 nm) as a hole transport material, and then 2,5,8,11-tetra-t-butylperylene (TBP) as a light-emitting material was 9,9.
  • TBP 2,5,8,11-tetra-t-butylperylene
  • a film doped with 3% of 10-di (2-naphthyl) anthracene (ADN) was formed by co-evaporation (25 nm).
  • the organic electroluminescent devices of Examples 6, 7, 8 and 9 were prepared by using Compound A-18, Compound A-25, Compound A-35 and Compound A-41 instead of Compound A-10 used in Example 5.
  • An organic electroluminescence element was produced in the same manner as in Example 5 except that it was used.
  • Example 5 was used using Comparative Compound 3, Comparative Compound 4 and Comparative Compound 5 shown below as the compounds constituting the material of the hole transport layer of the organic electroluminescence device.
  • An organic electroluminescence device was produced in the same manner as described above.
  • the driving voltage, the light emission efficiency, and the half life were evaluated.
  • the light emission efficiency indicates a value at 10 mA / cm 2
  • the half-life shows a luminance half-life from the initial luminance 1,000 cd / m 2.
  • the evaluation results are shown in Table 2.
  • the organic electroluminescence elements of Examples 5 to 9 of the present invention have improved luminous efficiency and longer life than the organic electroluminescence elements of Comparative Examples 3 to 5.
  • the compound A-10 having a structure in which the dibenzofuryl group as Ar 3 is bonded to the divalent linking group L at the 3-position is transported by holes.
  • Example 5 used as the material it can be seen that the luminous efficiency and the lifetime are remarkably improved.
  • Ar 3 in the general formula (1) is a substituted or unsubstituted dibenzofuryl group, and L is not a single bond.
  • an organic electroluminescence device using a preferred amine derivative of the present invention in which Ar 3 is a substituted or unsubstituted dibenzofuryl group and L is a divalent linking group
  • the present invention may be used for a matrix driving type organic electroluminescence display, or may be used for an active matrix driving type organic electroluminescence display.
  • the inventors of the present application particularly arrange an amine derivative having the structure described below as an organic electroluminescent material between the light emitting layer and the anode, thereby It was confirmed that a remarkable improvement was obtained in the luminous efficiency, driving voltage and lifetime of the electroluminescence element.
  • a preferred structure of the amine derivative represented by the general formula (1) is that, in the general formula (1), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. And at least one of Ar 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted dibenzofuryl group, and L is a single bond.
  • Gerare phenyl, naphthyl, biphenyl, a terphenyl group, a a fluorenyl group, a triphenylene group, dibenzothiophenyl group, dibenzofuryl group, N- phenylcarbazolyl group.
  • the aryl group preferably has 6 to 18 ring carbon atoms, and the heteroaryl group preferably has 5 to 18 ring atoms.
  • Examples of the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group.
  • Illustrative examples of the aryl group and heteroaryl group are the same as the aryl group and heteroaryl group mentioned as the specific groups of Ar 1 and Ar 2 described above.
  • Examples of the substituent of the silyl group that is substituted with at least one of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Specifically, it is the same as the alkyl group, alkoxy group, aryl group, and heteroaryl group described as the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 , and a phenyl group is particularly preferable.
  • the silyl group substituted with at least one of Ar 1 and Ar 2 is preferably a triarylsilyl group in which the number of carbon atoms in the aryl group substituted with the silyl group is 6 or more and 18 or less. .
  • only one of Ar 1 and Ar 2 may be substituted with a substituted or unsubstituted silyl group.
  • the silyl group exhibits strong electron resistance
  • the amine derivative into which the silyl group is introduced can be used as a hole transport material, thereby improving the electron resistance of the hole transport layer.
  • Ar 3 is a substituted or unsubstituted dibenzofuryl group.
  • the substituents substituted on the dibenzofuryl group are independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
  • the substituents substituted on the dibenzofuryl group may be bonded to each other to form a saturated or unsaturated ring. However, substituents substituted at the 1-position and 9-position of the dibenzofuryl group are not bonded to each other.
  • L is a single bond.
  • the position of bonding with L of the substituted or unsubstituted dibenzofuryl group which is Ar 3 is not particularly limited, but is preferably the 2-position, 3-position or 4-position, particularly the 3-position. It is preferable that That is, as described above, since L is a single bond in the preferred structure of the amine derivative of the present invention, the substituted or unsubstituted dibenzofuryl group which is Ar 3 is an amine at the 2-position, 3-position or 4-position. It is preferable to combine with the nitrogen atom (N) of the amine site in the derivative, and particularly preferable to bond with the nitrogen atom (N) at the 3-position.
  • the dibenzofuryl group When the dibenzofuryl group is bonded to the nitrogen atom (N) of the amine site at the 3-position, the conjugated system of ⁇ electrons of the whole molecule is expanded, so that the hole transporting property is expected to be improved, and the organic electroluminescence device Further improvement in luminous efficiency and longer life can be expected. Further, since L is a single bond, it is possible to prevent deterioration of film forming property due to an increase in molecular weight.
  • the dibenzofuryl group which is Ar 3 in the preferred structure of the amine derivative of the present invention exhibits strong electron resistance, like the silyl group substituted on at least one of Ar 1 or Ar 2 . Therefore, the amine derivative of the present invention having a dibenzofuryl group is more stable with respect to electrons, and is used as a material for an organic electroluminescent element, in particular, a laminated film between a light emitting layer and an anode. Suppresses deterioration of materials caused by electrons entering the film.
  • the dibenzofuryl group exhibits a high glass transition point due to its high planarity.
  • the amine derivative in which the dibenzofuryl group which is Ar 3 in the general formula (1), which is a preferred amine derivative of the present invention, is bonded to L which is a single bond is an organic electroluminescence device in a blue to blue-green region.
  • the light emission efficiency can be improved, and further, the drive voltage can be lowered and the life can be extended.
  • Examples of the amine derivative that is a preferable amine derivative of the present invention, in which the dibenzofuryl group that is Ar 3 in the general formula (1) is bonded to L that is a single bond, include the compounds exemplified below. It is not limited to these.
  • the amine derivative in which the dibenzofuryl group which is Ar 3 in the general formula (1), which is a preferred amine derivative of the present invention, is bonded to L which is a single bond, is the organic electroluminescence represented in FIG. 1 as described above. It can be used as a material for the hole transport layer of the element 100.
  • the configuration of the organic electroluminescence element 100 shown in FIG. 1 is an embodiment of the organic electroluminescence element of the present invention, and is not limited to this, and various modifications are possible.
  • the use of the amine derivative which is a preferable amine derivative of the present invention in which the dibenzofuryl group which is Ar 3 in the general formula (1) is bonded to L which is a single bond is used as a hole transport material of an organic electroluminescence device
  • the present invention can be used as a material for a hole injection layer or a light emitting layer, and can also be used as a material for a hole injection layer or a light emitting layer. As in the case of using as, it is possible to improve the light emission efficiency of the organic electroluminescence element and to extend the life of the organic electroluminescence element.
  • Example III The amine derivatives in which the dibenzofuryl group, which is Ar 3 in the general formula (1), which is a preferred amine derivative of the present invention is bonded to L which is a single bond, are the compounds B-1, B-16, B-21. Examples of synthesis methods of B-34 and B-39 are described below. However, the synthesis method described below is an example and does not limit the present invention.
  • the chemical shift values of Compound B-1 measured by 1 H NMR measurement are 7.89 (d, 2H), 7.80 (d, 2H), 7.66-7.51 (m, 14H), 7.50-7.31 (m, 13H), 7.22 (d, 2H), 7.19 (d, 2H). Further, the molecular weight of Compound B-1 measured by FAB-MS measurement was 669.
  • the chemical shift values of Compound B-16 measured by 1 H NMR measurement are 7.88 (d, 1H), 7.80 (d, 1H), 7.67-7.59 (m, 12H), 7.58-7.51 (m, 6H), 7.50-7.39 (m, 11H), 7.39-7.31 (m, 4H), 7.22-7.19 (m, 4H).
  • the molecular weight of compound B-16 measured by FAB-MS measurement was 745.
  • the chemical shift values of Compound B-21 measured by 1 H NMR measurement are 7.88-7.81 (m, 2H), 7.61-7.52 (m, 12H), 7.58-7.51 (m, 6H), 7.50-7.39 (m 11H), 7.39-7.31 (m, 4H), 7.22-7.19 (m, 4H).
  • the molecular weight of Compound B-21 measured by FAB-MS measurement was 745.
  • the chemical shift values of Compound B-34 measured by 1 H NMR measurement are 7.88-7.81 (m, 2H), 7.61-7.52 (m, 12H), 7.58-7.51 (m, 6H), 7.50-7.39 (m 11H), 7.39-7.31 (m, 4H), 7.22-7.19 (m, 4H).
  • the molecular weight of compound B-34 measured by FAB-MS measurement was 745.
  • the chemical shift value of Compound B-39 measured by 1 H NMR measurement is 8.49 (d, 2H), 8.16 (d, 2H), 7.81 (d, 2H), 7.78-7.55 (m, 12H), 749- 7.33 (m, 16H), 7.32-7.25 (m,, 5H), 7.13 (d, 2H).
  • the molecular weight of compound B-39 measured by FAB-MS measurement was 795.
  • Example 10 shows an organic electroluminescence device using Compound B-1 as a hole transport layer
  • Example 11 shows an organic electroluminescence device using Compound B-16 as a hole transport layer
  • Example 12 was an organic electroluminescence device used for the layer
  • Example 13 was an organic electroluminescence device using Compound B-34 for the hole transport layer
  • Organic Electroluminescence device using Compound B-39 for the hole transport layer This is referred to as Example 14.
  • Preparation of the organic electroluminescence element of Example 10 of the present invention was performed by vacuum deposition in the same manner as the organic electroluminescence element of Example 1 described above, and was performed in the following procedure.
  • surface treatment with ozone was performed on an ITO-glass substrate that had been patterned and cleaned in advance.
  • the ITO film has a thickness of 150 nm.
  • 4,4 ′, 4 ′′ -tris (N, N- (2-naphthyl) phenylamino) triphenylamine (2-TNATA, film thickness 60 nm) was used as the hole injection material.
  • a film was formed on top.
  • the compound B-1 of the present invention was formed as a hole transporting material (30 nm), and then 2,5,8,11-tetra-t-butyl-perylene (TBP) as a light-emitting material was used.
  • TBP 2,5,8,11-tetra-t-butyl-perylene
  • ADN 10-di (2-naphthyl) anthracene
  • the organic electroluminescence devices of Examples 11, 12, 13, and 14 were prepared by using Compound B-16, Compound B-21, Compound B-34, and Compound B-39 instead of Compound B-1 used in Example 10.
  • An organic electroluminescence element was produced in the same manner as in Example 10 except that it was used.
  • Comparative Example 6 and Comparative Example 7 an organic electroluminescent device was prepared in the same manner as in Example 10 by using Comparative Compound 6 and Comparative Compound 7 shown below as compounds constituting the material of the hole transport layer of the organic electroluminescent device. Produced.
  • the driving voltage, current efficiency, and half life were evaluated.
  • the light emission efficiency indicates a value at 10 mA / cm 2
  • the half-life shows a luminance half-life from the initial luminance 1,000 cd / m 2.
  • the evaluation results are shown in Table 3.
  • the organic electroluminescent elements of Examples 10 to 14 of the present invention have a lower driving voltage and improved luminous efficiency than the organic electroluminescent elements of Comparative Examples 6 and 7. And it can be seen that the life is extended.
  • a compound B-21 in which a substituted or unsubstituted dibenzofuryl group as Ar 3 is bonded to the nitrogen atom (N) of the amine moiety at the 3-position is used.
  • N nitrogen atom
  • an amine derivative in which the dibenzofuryl group which is Ar 3 in General Formula (1) is bonded to L which is a single bond which is a preferred amine derivative of the present invention
  • the example utilized for the hole transport material of a luminescent element was demonstrated, utilization of the amine derivative of this invention is not limited to an organic electroluminescent element, You may utilize for another light emitting element or light-emitting device.
  • an organic electroluminescence device using an amine derivative in which the dibenzofuryl group that is Ar 3 in General Formula (1), which is a preferred amine derivative of the present invention, is bonded to L that is a single bond is a passive matrix drive.
  • the present invention may be used for an organic electroluminescence display of a type, and may be used for an organic electroluminescence display of an active matrix driving type.
  • the inventors of the present application particularly arrange an amine derivative having the structure described below as an organic electroluminescent material between the light emitting layer and the anode, thereby It was confirmed that a remarkable improvement was obtained in the luminous efficiency, driving voltage and lifetime of the electroluminescence element.
  • a preferred structure of the amine derivative represented by the general formula (1) is that, in the general formula (1), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. At least one of Ar 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted fluorenyl group, and L is a substituted or unsubstituted arylene group Or a substituted or unsubstituted heteroarylene group.
  • Gerare phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, a triphenylene group, dibenzothiophenyl group, dibenzofuryl group, N- phenylcarbazolyl group.
  • the aryl group preferably has 6 to 18 ring carbon atoms, and the heteroaryl group preferably has 5 to 18 ring atoms.
  • Examples of the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group.
  • Illustrative examples of the aryl group and heteroaryl group are the same as the aryl group and heteroaryl group of Ar 1 and Ar 2 described above.
  • the alkyl group of the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 is not particularly limited, but is methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl group, isobutyl group, t -Butyl group, cyclobutyl group, pentyl group, isopentyl group, neopentyl group, cyclopentyl group, hexyl group, cyclohexyl group, heptyl group, cycloheptyl group, octyl group, nonyl group, decyl group and the like can be exemplified.
  • the alkoxy group of the substituent substituted by the aryl group or heteroaryl group of Ar 1 and Ar 2 is not particularly limited, but a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, Isobutoxy group, t-butoxy group, n-pentyloxy group, neopentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3 , 7-dimethyloctyloxy group and the like can be exemplified.
  • Examples of the substituent of the silyl group that is substituted with at least one of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Specifically, it is the same as the alkyl group, alkoxy group, aryl group, and heteroaryl group described as the substituent substituted by the aryl group or heteroaryl group of Ar 1 and Ar 2 , and in particular, a phenyl group and a methyl group Is preferred.
  • the silyl group substituted with at least one of Ar 1 and Ar 2 is a triarylsilyl group having 6 to 18 ring carbon atoms of the aryl group substituted with the silyl group or the silyl group.
  • the substituted alkyl group is preferably a trialkylsilyl group having 1 to 6 carbon atoms.
  • only one of Ar 1 and Ar 2 may be substituted with a substituted or unsubstituted silyl group.
  • LUMO is prevented from being localized around the amine site, and the energy gap is reduced. Can be prevented.
  • Ar 3 is a substituted or unsubstituted fluorenyl group.
  • the substituents substituted on the fluorenyl group are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.
  • the substituent substituted on the fluorenyl group is preferably a substituted or unsubstituted aryl group, and particularly preferably a phenyl group is substituted at the 9-position.
  • L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • aryl group and heteroarylene group of the “substituted or unsubstituted arylene group” and “substituted or unsubstituted heteroarylene group” which are L the “substituted or unsubstituted group” mentioned in Ar 1 and Ar 2
  • arylene group and heteroarylene group of the “substituted or unsubstituted arylene group” and “substituted or unsubstituted heteroarylene group” of L an aryl group having 6 to 18 ring carbon atoms and 5 or more ring atoms.
  • a heteroarylene group of 18 or less is preferable, and a phenylene group and a biphenylylene group are particularly preferable.
  • a substituted or unsubstituted fluorenyl group is Ar 3 is a position of the 2-position, it is preferable to bind to L in para-position to the nitrogen atom of the amine moiety (N). When the fluorenyl group is bonded to L at the 2-position, appropriate HOMO and LUMO levels can be realized.
  • Ar 3 is a substituted or unsubstituted fluorenyl group
  • L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • Ar 1 and Ar 2 in which at least one silyl group is substituted via L, which is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, wherein Ar 3 is a substituted or unsubstituted fluorenyl group;
  • the use of the amine derivative of the present invention as a material for the hole transport layer disposed between the light emitting layer and the anode improves the light emission efficiency of the organic electroluminescence device, and further reduces the driving voltage and length. It is possible to achieve a long life. In particular, in the blue to blue-green region, it is possible to improve the light emission efficiency of the organic electroluminescence element, and to realize a lower driving voltage and longer life.
  • the derivatives include, but are not limited to, compounds exemplified below.
  • the amine derivative can be used as a material for the hole transport layer of the organic electroluminescence device 100 shown in FIG. 1 as described above.
  • the configuration of the organic electroluminescence element 100 shown in FIG. 1 is an embodiment of the organic electroluminescence element of the present invention, and is not limited to this, and various modifications are possible.
  • an amine derivative which is a preferred amine derivative of the present invention in which the fluorenyl group which is Ar 3 in the general formula (1) is bonded to L which is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group
  • L which is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group
  • the use of is not limited to the hole transport material of the organic electroluminescence device, but can also be used as the material of the hole injection layer or the light emitting layer. Also when used as a material for the organic electroluminescence element, it is possible to improve the light emission efficiency of the organic electroluminescence element and to extend the life of the organic electroluminescence element, as in the case of using as the material for the hole transport layer.
  • Example IV Regarding the amine derivative which is a preferred amine derivative of the present invention, the fluorenyl group which is Ar 3 in the general formula (1) is bonded to L which is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group. Examples of methods for synthesizing Compound C-1, Compound C-2, Compound C-4, and Compound C-6 are described below. However, the synthesis method described below is an example and does not limit the present invention.
  • Example 15 shows an organic electroluminescence device using Compound C-1 as a hole transport layer
  • Example 16 shows an organic electroluminescence device using Compound C-2 as a hole transport layer
  • the organic electroluminescence device used for the layer is Example 17, and the organic electroluminescence device using Compound C-6 for the hole transport layer is Example 18.
  • Preparation of the organic electroluminescence element of Example 15 of the present invention was performed by vacuum evaporation in the same manner as the organic electroluminescence element of Example 1 described above, and was performed according to the following procedure.
  • surface treatment with ozone was performed on an ITO-glass substrate that had been patterned and cleaned in advance.
  • the ITO film has a thickness of 150 nm.
  • 4,4 ′, 4 ′′ -tris (N, N- (2-naphthyl) phenylamino) triphenylamine (2-TNATA, film thickness 60 nm) was used as the hole injection material.
  • a film was formed on top.
  • the compound C-1 of the present invention was formed as a hole transporting material (30 nm), and then 2,5,8,11-tetra-t-butyl-perylene (TBP) as a light emitting material was used.
  • TBP 2,5,8,11-tetra-t-butyl-perylene
  • ADN 10-di (2-naphthyl) anthracene
  • the organic electroluminescence devices of Examples 16, 17 and 18 were prepared except that Compound C-2, Compound C-4 and Compound C-6 were used instead of Compound C-1 used in Example 15.
  • An organic electroluminescence device was produced in the same manner as in Example 15.
  • Comparative Example 8 an organic electroluminescence element was produced in the same manner as in Example 15 using Comparative Compound 8 shown below as a compound constituting the material of the hole transport layer of the organic electroluminescence element.
  • the driving voltage, current efficiency, and half-life were evaluated for the organic electroluminescence elements 200 produced in Examples 15 to 18 and Comparative Example 8.
  • the light emission efficiency indicates a value at 10 mA / cm 2
  • the half-life shows a luminance half-life from the initial luminance 1,000 cd / m 2.
  • the evaluation results are shown in Table 4.
  • the organic electroluminescent elements of Examples 15 to 18 of the present invention have a lower driving voltage, improved luminous efficiency, and longer life compared to the organic electroluminescent elements of Comparative Example 8.
  • the driving voltage of The decrease, the improvement of the luminous efficiency, and the improvement of the luminous lifetime were remarkable.
  • the substituted or unsubstituted fluorenyl group which is Ar 3 in the general formula (1), which is a preferred amine derivative of the present invention is substituted or unsubstituted arylene group, or substituted or
  • an amine derivative bonded to L, which is an unsubstituted heteroarylene group is used as a hole transport material of an organic electroluminescence device.
  • the use of the amine derivative of the present invention is limited to an organic electroluminescence device. Instead, it may be used for other light emitting elements or light emitting devices.
  • the organic electroluminescence device using the preferred amine derivative of the present invention may be used for a passive matrix driving type organic electroluminescence display or an active matrix driving type organic electroluminescence display. .
  • the inventors of the present application particularly arrange an amine derivative having the structure described below as an organic electroluminescent material between the light emitting layer and the anode, thereby It was confirmed that a remarkable improvement was obtained in the luminous efficiency, driving voltage and lifetime of the electroluminescence element.
  • a preferred structure of the amine derivative represented by the general formula (1) is that, in the general formula (1), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. And at least one of Ar 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted fluorenyl group, and L is a single bond.
  • a preferred structure of the amine derivative represented by the general formula (1) is represented by the following general formula (3).
  • Gerare phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, a triphenylene group, dibenzothiophenyl group, dibenzofuryl group, N- phenylcarbazolyl group.
  • the aryl group an aryl group having 6 to 18 ring carbon atoms is preferable, and a phenyl group, a biphenyl group, and a triphenylene group are particularly preferable.
  • the heteroaryl group is preferably a heteroaryl group having 5 to 18 ring atoms, and particularly preferably a dibenzofuryl group or an N-phenylcarbazolyl group.
  • Ar 1 and Ar 2 may each independently be a substituted or unsubstituted aryl group.
  • Ar 1 may be a substituted or unsubstituted aryl group, and
  • Ar 2 may be a substituted or unsubstituted dibenzoheterol group.
  • Examples of the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 include a halogen atom, an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group.
  • Illustrative examples of the aryl group and heteroaryl group are the same as the aryl group and heteroaryl group mentioned as the specific groups of Ar 1 and Ar 2 described above.
  • a fluorine atom may be sufficient.
  • the alkyl group is not particularly limited, but is methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl group, isobutyl group, t-butyl group, cyclobutyl group, pentyl group, isopentyl group, neopentyl group, cyclopentyl group.
  • alkoxy group examples include, but are not limited to, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, t-butoxy group, n-pentyloxy group, neopentyloxy group, n It may be a -hexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group or the like.
  • Ar 3 in the general formula (1) is a substituted or unsubstituted fluorenyl group.
  • the hole transport property of the amine derivative of the present invention is improved. Therefore, by using the preferred amine derivative of the present invention in which a fluorenyl group is introduced as a material for the hole transport layer disposed between the anode and the light emitting layer, the luminous efficiency of the organic electroluminescence device can be further improved and increased. Life expectancy can be realized.
  • the substituents of the fluorenyl group are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • the alkyl group substituted for the fluorenyl group of Ar 3 an alkyl group having 1 to 10 carbon atoms is preferable, and examples thereof include a methyl group.
  • the aryl group substituted on the Ar 3 fluorenyl group is preferably an aryl group having 6 to 12 ring carbon atoms, and examples thereof include a phenyl group and a naphthyl group.
  • the heteroaryl group substituted on the fluorenyl group of Ar 3 is preferably a heteroaryl group having 4 to 12 ring carbon atoms, and examples thereof include a dibenzofuryl group.
  • Examples of the substituent substituted with the alkyl group, aryl group, or heteroaryl group substituted with the fluorenyl group include an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, and a halogen atom.
  • Illustrative specific examples of the aryl group and heteroaryl group may be the same as the aryl group and heteroaryl group listed as specific groups for Ar 1 and Ar 2 described above. Although it does not specifically limit as a halogen atom, A fluorine atom may be sufficient.
  • Specific examples of the alkyl group may be the same as the alkyl group described as the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 .
  • L is a single bond.
  • the bonding position with L in the substituted or unsubstituted fluorenyl group that is Ar 3, that is, the bonding position with the nitrogen atom (N) in the fluorenyl group is not particularly limited, but may be bonded at the 2-position. preferable.
  • a substituted or unsubstituted fluorenyl group which is Ar 3 is bonded to the nitrogen atom (N) of the amine moiety at the 2-position, whereby Since the conjugated system spreads, the hole transportability is improved, and the stability of the molecule is improved, the emission efficiency and the life of the organic electroluminescent element can be improved.
  • Examples of the substituent of the silyl group that is substituted with at least one of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Specifically, it is the same as the alkyl group, the alkoxy group, the aryl group, and the heteroaryl group described as the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 .
  • the substituted silyl group substituted with at least one of Ar 1 and Ar 2 is a triarylsilyl group having 6 to 18 ring carbon atoms in the aryl group substituted with the silyl group,
  • the alkyl group substituted with the silyl group is a trialkylsilyl group having 1 to 6 carbon atoms.
  • Examples of the amine derivative represented by the general formula (3), which is a preferred amine derivative of the present invention, include compounds exemplified below, but are not limited thereto.
  • Ar 3 in the general formula (1) is a substituted or unsubstituted fluorenyl group.
  • L which is a single bond
  • the substituted or unsubstituted fluorenyl group which is Ar 3 is bonded to the nitrogen atom (N) of the amine portion
  • hole transportability is improved. Therefore, by arranging this amine derivative as an organic electroluminescent material between the light emitting layer and the anode, it is possible to improve the light emission efficiency of the organic electroluminescent element and to achieve a long lifetime.
  • the amine derivative of the present invention can improve the light emission efficiency of the organic electroluminescence device and achieve a long lifetime in the blue to blue-green region.
  • the amine derivative of the present invention represented by the general formula (3) representing the preferred structure of the amine derivative of the present invention is used as a material for the hole transport layer of the organic electroluminescence device 100 represented in FIG. 1 as described above. be able to.
  • the configuration of the organic electroluminescence element 100 shown in FIG. 1 is an embodiment of the organic electroluminescence element of the present invention, and is not limited to this, and various modifications are possible.
  • the use of the amine derivative of the present invention represented by the general formula (3) representing the preferred structure of the amine derivative of the present invention is not limited to the hole transport material of the organic electroluminescence device, It can also be used as a layer material or a light emitting layer material, and when used as a hole injection layer material or a light emitting layer material, the organic electroluminescence is the same as when used as a hole transport layer material. It is possible to improve the light emission efficiency of the element and to extend the life of the organic electroluminescence element.
  • Example V With respect to the amine derivative of the present invention represented by the general formula (3), examples of methods for synthesizing the compounds D-1, D-3 and D-26 will be described below. However, the synthesis method described below is an example and does not limit the present invention.
  • Compound D-1 is the same as Compound 1 in Example 1 described above.
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: dichloromethane / hexane), and the obtained solid was recrystallized from toluene / hexane to give the target compound, D-1, as a white powder. 2.26 g of a solid was obtained with a yield of 90% (FAB-MS: C51H41NSi, measured value 695).
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: dichloromethane / hexane), and the obtained solid was recrystallized from toluene / hexane to give the target compound D-3 as a white powder. 1.38 g of a solid was obtained with a yield of 70% (FAB-MS: C61H45NSi, measured value 819).
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: dichloromethane / hexane), and the obtained solid was recrystallized from toluene / hexane to give the target compound, D-26, as a white powder. 1.06 g of a solid was obtained with a yield of 75% (FAB-MS: C57H45NSi, measured value 771).
  • Example 19 shows an organic electroluminescence device using Compound D-1 for the hole transport layer
  • Example 20 shows an organic electroluminescence device using Compound D-3 for the hole transport layer
  • the organic electroluminescence element used for the layer is referred to as Example 21.
  • Compound D-1 is the same as Compound 1 in Example 1 described above.
  • Preparation of the organic electroluminescent element of Example 19 of the present invention was performed by vacuum deposition in the same manner as the organic electroluminescent element of Example 1 described above, and was performed in the following procedure.
  • surface treatment with ozone was performed on an ITO-glass substrate that had been patterned and cleaned in advance.
  • the ITO film has a thickness of 150 nm.
  • 4,4 ′, 4 ′′ -tris (N, N- (2-naphthyl) phenylamino) triphenylamine (2-TNATA, film thickness 60 nm) was used as the hole injection material.
  • a film was formed on top.
  • the compound D-1 of the present invention was formed as a hole transporting material (30 nm), then 2,5,8,11-tetra-t-butylperylene (TBP) was used as the light emitting material.
  • TBP 2,5,8,11-tetra-t-butylperylene
  • the organic electroluminescence devices of Examples 20 and 21 were prepared in the same manner as in Example 19 except that Compound D-3 and Compound D-26 were used instead of Compound D-1 used in Example 19. A luminescence element was produced.
  • Comparative Example 9 and Comparative Example 10 as the compound constituting the material of the hole transport layer of the organic electroluminescence device, as in Example I described above, the following Comparative Compound 9 and Comparative Compound 10 were used. An organic electroluminescence element was produced in the same manner as in Example 19.
  • Comparative Example 9 and Comparative Example 10 With respect to the organic electroluminescence elements 200 prepared in Examples 19 to 21, Comparative Example 9 and Comparative Example 10, the driving voltage, current efficiency, and half life were evaluated.
  • the current efficiency indicates a value at 10 mA / cm 2
  • the half life indicates a luminance half time from an initial luminance of 1,000 cd / m 2 .
  • the evaluation results are shown in Table 5.
  • the organic electroluminescence elements of Examples 19 to 21 of the present invention have improved luminous efficiency and longer life than the organic electroluminescence elements of Comparative Example 9 and Comparative Example 10. I understand that. Moreover, it turns out that the organic electroluminescent element of Example 19 thru
  • the preferred amine derivative of the present invention represented by the general formula (3) is used as the hole transport material of the organic electroluminescence device.
  • the use of the derivative is not limited to the organic electroluminescence element, and may be used for other light emitting elements or light emitting devices.
  • the organic electroluminescence device using the amine derivative having a silyl group of the present invention represented by the general formula (3) may be used for a passive matrix driving type organic electroluminescence display, and an active matrix driving device may be used.
  • the present invention may be used for a type of organic electroluminescence display.
  • the inventors of the present application particularly arrange an amine derivative having the structure described below as an organic electroluminescent material between the light emitting layer and the anode, thereby It was confirmed that a remarkable improvement was obtained in the luminous efficiency, driving voltage and lifetime of the electroluminescence element.
  • a preferred structure of the amine derivative represented by the general formula (1) is that, in the general formula (1), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. And at least one of Ar 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted carbazolyl group, and L is a substituted or unsubstituted arylene group Or a substituted or unsubstituted heteroarylene group.
  • Gerare phenyl group, naphthyl group, biphenyl group, terphenyl group, fluorenyl group, a triphenylene group, dibenzothiophenyl group, dibenzofuryl group, N- phenylcarbazolyl group.
  • the aryl group preferably has 6 to 18 ring carbon atoms, and the heteroaryl group preferably has 5 to 18 ring atoms.
  • Examples of the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group.
  • Illustrative examples of the aryl group and heteroaryl group are the same as the aryl group and heteroaryl group of Ar 1 and Ar 2 described above.
  • the alkyl group of the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 is not particularly limited, but is methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl group, isobutyl group, t -Butyl group, cyclobutyl group, pentyl group, isopentyl group, neopentyl group, cyclopentyl group, hexyl group, cyclohexyl group, heptyl group, cycloheptyl group, octyl group, nonyl group, decyl group and the like can be exemplified.
  • the alkoxy group of the substituent substituted by the aryl group or heteroaryl group of Ar 1 and Ar 2 is not particularly limited, but a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, Isobutoxy group, t-butoxy group, n-pentyloxy group, neopentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3 , 7-dimethyloctyloxy group and the like can be exemplified.
  • Examples of the substituent of the silyl group that is substituted with at least one of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Specifically, it is the same as the alkyl group, alkoxy group, aryl group, and heteroaryl group described as the substituent substituted by the aryl group or heteroaryl group of Ar 1 and Ar 2 , and in particular, a phenyl group and a methyl group Is preferred.
  • the silyl group substituted with at least one of Ar 1 and Ar 2 is a triarylsilyl group having 6 to 18 ring carbon atoms of the aryl group substituted with the silyl group or the silyl group.
  • the substituted alkyl group is preferably a triarylmethyl group having 1 to 6 carbon atoms.
  • Ar 3 in the general formula (1) is a substituted or unsubstituted carbazolyl group.
  • the substituents substituted on the carbazolyl group are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.
  • the substituent substituted on the carbazolyl group is preferably a substituted or unsubstituted aryl group, and particularly preferably a phenyl group is substituted at the 9-position of the carbazolyl group.
  • a phenyl group is substituted at the 9-position of the carbazolyl group.
  • L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • aryl group and heteroarylene group of the “substituted or unsubstituted arylene group” and “substituted or unsubstituted heteroarylene group” which are L, the “substituted or unsubstituted group” mentioned in Ar 1 and Ar 2 And the aryl group and the heteroaryl group of the “substituted aryl group” or “substituted or unsubstituted heteroaryl group”.
  • arylene group and heteroarylene group of the “substituted or unsubstituted arylene group” and “substituted or unsubstituted heteroarylene group” of L an aryl group having 6 to 18 ring carbon atoms and 5 or more ring atoms.
  • a heteroarylene group of 18 or less is preferable, and a phenylene group is particularly preferable.
  • L is a phenylene group, an appropriate energy level can be realized.
  • a substituted or unsubstituted carbazolyl group that is Ar 3 is a linked or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group at the 1st to 4th positions. Bonded to the group L.
  • the substituted or unsubstituted carbazolyl group which is Ar 3 is bonded to L at the 2-position or 3-position, and more preferably is bonded to L at the 3-position.
  • HOMO is expanded and hole transportability is improved.
  • the bonding position with L is the 3-position of the carbazolyl group, LUMO does not ride on the carbazolyl group, which contributes to extending the lifetime of the organic electroluminescence device.
  • Ar 3 is a substituted or unsubstituted carbazolyl group in the general formula (1)
  • L is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • the conjugated system of ⁇ electrons is expanded, so that the hole transport property is improved and the HOMO level is adjusted to increase the luminous efficiency of the organic electroluminescence device.
  • N nitrogen atom
  • the conjugated system of ⁇ electrons is expanded, so that the hole transport property is improved and the HOMO level is adjusted to increase the luminous efficiency of the organic electroluminescence device.
  • in the blue to blue-green region it is possible to improve the light emission efficiency of the organic electroluminescence element, and to realize a lower driving voltage and longer life.
  • the derivatives include, but are not limited to, compounds exemplified below.
  • the amine derivative can be used as a material for the hole transport layer of the organic electroluminescence device 100 shown in FIG. 1 as described above.
  • the configuration of the organic electroluminescence element 100 shown in FIG. 1 is an embodiment of the organic electroluminescence element of the present invention, and is not limited to this, and various modifications are possible.
  • amines in the general formula (1) is a carbazolyl group is Ar 3 is bonded to L is substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group derivatives
  • the use of is not limited to the hole transport material of the organic electroluminescence device, but can also be used as the material of the hole injection layer or the light emitting layer. Also when used as a material for the organic electroluminescence element, it is possible to improve the light emission efficiency of the organic electroluminescence element and to extend the life of the organic electroluminescence element, as in the case of using as the material for the hole transport layer.
  • Example VI Regarding the amine derivative which is a preferred amine derivative of the present invention, the carbazolyl group which is Ar 3 in the general formula (1) is bonded to L which is a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, Examples of methods for synthesizing Compound E-1, Compound E-2 and Compound E-3 are described below. However, the synthesis method described below is an example and does not limit the present invention. Compound E-1 is the same as Compound 61 in Example 3 described above, and Compound E-2 is the same as Compound 63 in Example 4 described above.
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: toluene / hexane), and the obtained solid was recrystallized from dichloromethane / hexane to give a white powder represented by the target compound E-1.
  • a solid was obtained in a yield of 89% (FAB-MS: C66H48N2Si, measured value 897).
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: toluene / hexane), and the obtained solid was recrystallized from dichloromethane / hexane to obtain a white powder represented by the target compound E-2.
  • a solid solid was obtained in an amount of 1.59 g with a yield of 94% (FAB-MS: C60H44N2Si, measured value 821).
  • the obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary evaporator.
  • the obtained crude product was purified by silica gel column chromatography (developing solvent: toluene / hexane), and the resulting solid was recrystallized from dichloromethane / hexane to give a white powder represented by the target compound E-3. 2.00 g of a solid was obtained in a yield of 97% (FAB-MS: C60H44N2Si, measured value 821).
  • Example 22 shows an organic electroluminescence device using Compound E-1 for the hole transport layer
  • Example 23 shows an organic electroluminescence device using Compound E-2 for the hole transport layer
  • the organic electroluminescent element used for the layer is referred to as Example 24.
  • Compound E-1 is the same as Compound 61 in Example 3 described above
  • Compound E-2 is the same as Compound 63 in Example 4 described above.
  • the production of the organic electroluminescence element of Example 22 of the present invention was performed by vacuum vapor deposition in the same manner as the organic electroluminescence element of Example 1 described above, and was performed according to the following procedure.
  • surface treatment with ozone was performed on an ITO-glass substrate that had been patterned and cleaned in advance.
  • the ITO film has a thickness of 150 nm.
  • 4,4 ′, 4 ′′ -tris (N, N- (2-naphthyl) phenylamino) triphenylamine (2-TNATA, film thickness 60 nm) was used as the hole injection material.
  • a film was formed on top.
  • the compound E-1 of the present invention was formed as a hole transporting material (30 nm), and then 2,5,8,11-tetra-t-butyl-perylene (TBP) as a light emitting material , 10-di (2-naphthyl) anthracene (ADN) was doped at a rate of 3% by co-evaporation (25 nm).
  • TBP 2,5,8,11-tetra-t-butyl-perylene
  • ADN 2-naphthyl anthracene
  • the organic electroluminescent devices of Examples 23 and 24 were prepared in the same manner as in Example 22 except that Compound E-2 and Compound E-3 were used instead of Compound E-1 used in Example 22. A luminescence element was produced.
  • Example 22 was used using Comparative Compound 11, Comparative Compound 12, and Comparative Compound 13 shown below as the compounds constituting the material of the hole transport layer of the organic electroluminescence device.
  • An organic electroluminescence device was produced in the same manner as described above.
  • the driving voltage, current efficiency, and half life were evaluated.
  • the light emission efficiency indicates a value at 10 mA / cm 2
  • the half-life shows a luminance half-life from the initial luminance 1,000 cd / m 2.
  • the evaluation results are shown in Table 6.
  • the organic electroluminescent elements of Examples 22 to 24 of the present invention have a lower driving voltage than the organic electroluminescent elements of Comparative Example 11, Comparative Example 12, and Comparative Example 13, It can be seen that the luminous efficiency is improved and the life is extended.
  • the substituted or unsubstituted carbazolyl group which is Ar 3 in General Formula (1) which is a preferred amine derivative of the present invention, is a substituted or unsubstituted arylene group, or a substituted or unsubstituted arylene group.
  • an amine derivative bonded to L, which is an unsubstituted heteroarylene group is used as a hole transport material of an organic electroluminescence device.
  • the use of the amine derivative of the present invention is limited to an organic electroluminescence device. Instead, it may be used for other light emitting elements or light emitting devices.
  • the organic electroluminescence device using the preferred amine derivative of the present invention may be used for a passive matrix driving type organic electroluminescence display or an active matrix driving type organic electroluminescence display. .
  • the inventors of the present application particularly arrange an amine derivative having the structure described below as an organic electroluminescent material between the light emitting layer and the anode, thereby It was confirmed that a remarkable improvement was obtained in the luminous efficiency, driving voltage and lifetime of the electroluminescence element.
  • a preferred structure of the amine derivative represented by the general formula (1) is that, in the general formula (1), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. At least one of Ar 1 and Ar 2 is substituted with a substituted or unsubstituted silyl group, Ar 3 is a substituted or unsubstituted carbazolyl group, and L is a substituted or unsubstituted arylene group, Or a divalent linking group containing a substituted or unsubstituted heteroarylene group.
  • a preferred structure of the amine derivative represented by the general formula (1) is represented by the following general formula (4).
  • Gerare phenyl, naphthyl, biphenyl, a terphenyl group, a a fluorenyl group, a triphenylene group, dibenzothiophenyl group, dibenzofuryl group, N- phenylcarbazolyl group.
  • the aryl group preferably has 6 to 18 ring carbon atoms, and the heteroaryl group preferably has 5 to 18 ring atoms.
  • Examples of the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 include a halogen atom, an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group.
  • Illustrative examples of the aryl group and heteroaryl group are the same as the aryl group and heteroaryl group mentioned as the specific groups of Ar 1 and Ar 2 described above.
  • a fluorine atom may be sufficient.
  • the alkyl group is not particularly limited, but is methyl group, ethyl group, propyl group, isopropyl group, cyclopropyl group, butyl group, isobutyl group, t-butyl group, cyclobutyl group, pentyl group, isopentyl group, neopentyl group, cyclopentyl group.
  • alkoxy group examples include, but are not limited to, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, t-butoxy group, n-pentyloxy group, neopentyloxy group, n It may be a -hexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group or the like.
  • Ar 3 is a substituted or unsubstituted carbazolyl group, and the carbazolyl group is bonded to L at the 9-position.
  • R 1 to R 8 in the general formula (4) are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 30 ring atoms.
  • the aryl group or heteroaryl group substituted by R 1 to R 8 of the carbazolyl group may be the same as the substituted or unsubstituted aryl group and heteroaryl group of Ar 1 and Ar 2 described above.
  • the alkyl group substituted by R 1 to R 8 of the carbazolyl group may be the same as the alkyl group substituted by the aryl group and heteroaryl group of Ar 1 and Ar 2 described above.
  • the substituent substituted with R 1 to R 8 of the carbazolyl group described above may be the same as the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 described above, for example. .
  • R 1 to R 8 in the general formula (4) may be bonded to each other to form a saturated or unsaturated ring.
  • L is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • the substituted or unsubstituted arylene group of L preferably has 6 to 18 ring carbon atoms.
  • the substituted or unsubstituted heteroarylene group for L preferably has 5 to 18 ring-forming atoms.
  • Examples of the arylene group and heteroarylene group of the “substituted or unsubstituted arylene group” or “substituted or unsubstituted heteroarylene group” of L include a phenylene group, a naphthylene group, a biphenylylene group, an anthracenylene group, a triphenylene group, a fluorenylene group, and the like. And a phenylene group, a biphenylene group, and a fluorenylene group are preferable.
  • Ar 1 and Ar 2 in the general formula (4) may be an aryl group having 6 to 12 ring carbon atoms.
  • Examples of the substituent of the silyl group that is substituted with at least one of Ar 1 and Ar 2 include an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group. Specifically, it is the same as the alkyl group, the alkoxy group, the aryl group, and the heteroaryl group described as the substituent substituted with the aryl group or heteroaryl group of Ar 1 and Ar 2 .
  • the substituted silyl group substituted with at least one of Ar 1 and Ar 2 is a triarylsilyl group having 6 to 18 ring carbon atoms in the aryl group substituted with the silyl group,
  • the alkyl group substituted with the silyl group is a trialkylsilyl group having 1 to 6 carbon atoms.
  • Examples of the amine derivative represented by the general formula (4), which is a preferred amine derivative of the present invention, include compounds exemplified below, but are not limited thereto.
  • Ar 3 in the general formula (1) is a substituted or unsubstituted carbazolyl group.
  • a carbazolyl group into the amine derivative of the present invention, hole transportability is improved.
  • a more appropriate HOMO level can be realized by introducing a carbazolyl group. Further, when the carbazolyl group is bonded to the amine moiety via the linking group L, the HOMO level is further adjusted.
  • the amine derivative of the present invention can improve the light emission efficiency of the organic electroluminescence device in the blue to blue-green region, and can realize a low driving voltage and a long life.
  • the amine derivative of the present invention represented by the general formula (4) representing the preferred structure of the amine derivative of the present invention is used as a material for the hole transport layer of the organic electroluminescence device 100 represented in FIG. 1 as described above. be able to.
  • the configuration of the organic electroluminescence element 100 shown in FIG. 1 is an embodiment of the organic electroluminescence element of the present invention, and is not limited to this, and various modifications are possible.
  • the use of the amine derivative of the present invention represented by the general formula (4) representing the preferred structure of the amine derivative of the present invention is not limited to the hole transport material of the organic electroluminescence device, and hole injection It can also be used as a layer material or a light emitting layer material, and when used as a hole injection layer material or a light emitting layer material, the organic electroluminescence is the same as when used as a hole transport layer material. It is possible to improve the light emission efficiency of the element and to extend the life of the organic electroluminescence element.
  • Example VII Examples of methods for synthesizing the compounds F-10, F-26, F-38 and F-39 for the amine derivative of the present invention represented by the general formula (4) will be described below. However, the synthesis method described below is an example and does not limit the present invention.
  • the obtained crude product was purified by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane) and then recrystallized with a mixed solvent of toluene / hexane to obtain 2.50 g of a white solid compound F-1 (yield 81 %)Obtained.
  • the chemical shift value of Compound F-1 measured by 1 H NMR measurement is 8.15 (d, 2H), 7.81 (d, 2H), 7.66-7.51 (m, 14H), 7.51-7.34 (m, 18H), 7.34-7.26 (m, 6H), 7.17 (d, 2H).
  • the molecular weight of Compound F-1 measured by FAB-MS measurement was 821.
  • the chemical shift value of Compound F-23 measured by 1 H NMR measurement is 8.30 (d, 2H), 7.98 (d, 2H), 7.82 (d, 1H), 7.75-7.18 (m, 39H), 7.37- 7.23 (m, 6H) and 7.15 (d, 2H).
  • the molecular weight of compound F-23 measured by FAB-MS measurement was 984.
  • the chemical shift value of Compound F-26 measured by 1 H NMR measurement is 8.07 (d, 2H), 7.75 (d, 2H), 7.67-7.52 (m, 12H), 7.51-7.33 (m, 18H), 7.33-7.20 (m, 8H), 7.16 (d, 2H).
  • the molecular weight of compound F-26 measured by FAB-MS measurement was 821.
  • the chemical shift value of compound F-38 measured by 1 H NMR measurement is 8.09 (d, 2H), 7.76 (d, 2H), 7.65-7.51 (m, 10H), 7.51-7.35 (m, 18H), 7.32-7.21 (m, 6H), 7.18 (d, 2H).
  • the molecular weight of Compound F-38 measured by FAB-MS measurement was 744.
  • the chemical shift value of Compound F-39 measured by 1 H NMR measurement is 8.18 (d, 2H), 7.82 (d, 2H), 7.68-7.51 (m, 14H), 7.51-7.35 (m, 20H), 7.35-7.28 (m, 8H), 7.16 (d, 2H). Further, the molecular weight of the compound F-39 measured by FAB-MS measurement was 896.
  • an organic electroluminescence device material of the present invention an organic electroluminescence device using the compound F-1, the compound F-23, the compound F-26, the compound F-38, and the compound F-39 described above for the hole transport layer.
  • An organic electroluminescence device using Compound F-1 as a hole transport layer is Example 25
  • an organic electroluminescence device using Compound F-23 as a hole transport layer is Example 26, and a compound F-26 is transported as a hole.
  • Example 27 was an organic electroluminescence device used for the layer
  • Example 28 was an organic electroluminescence device using Compound F-38 for the hole transport layer
  • Organic Electroluminescence device was a compound F-39 used for the hole transport layer This is referred to as Example 29.
  • Preparation of the organic electroluminescence element of Example 25 of the present invention was performed by vacuum deposition in the same manner as the organic electroluminescence element of Example 1 described above, and was performed according to the following procedure.
  • surface treatment with ozone was performed on an ITO-glass substrate that had been patterned and cleaned in advance.
  • the ITO film has a thickness of 150 nm.
  • 4,4 ′, 4 ′′ -tris (N, N- (2-naphthyl) phenylamino) triphenylamine (2-TNATA, film thickness 60 nm) was used as the hole injection material.
  • a film was formed on top.
  • the compound F-1 of the present invention was formed as a hole transporting material (30 nm), then 2,5,8,11-tetra-t-butyl-perylene (TBP) was used as the light emitting material.
  • TBP 2,5,8,11-tetra-t-butyl-perylene
  • ADN 10-di (2-naphthyl) anthracene
  • the organic electroluminescence devices of Examples 26, 27, 28 and 29 were prepared by using Compound F-23, Compound F-26, Compound F-38 and Compound F-39 instead of Compound F-1 used in Example 25.
  • An organic electroluminescence element was produced in the same manner as in Example 25 except that it was used.
  • Comparative Example 14 and Comparative Example 15 an organic electroluminescent device was prepared in the same manner as in Example 25, using Comparative Compound 14 and Comparative Compound 15 shown below as the compounds constituting the material of the hole transport layer of the organic electroluminescent device. Produced.
  • the driving voltage, current efficiency, and half life were evaluated.
  • the light emission efficiency indicates a value at 10 mA / cm 2
  • the half-life shows a luminance half-life from the initial luminance 1,000 cd / m 2.
  • Table 7 shows the evaluation results.
  • the organic electroluminescence elements of Examples 25 to 29 of the present invention have improved luminous efficiency and longer life than the organic electroluminescence elements of Comparative Example 14 and Comparative Example 15. I understand that. In addition, it can be seen that the driving voltages of the organic electroluminescence elements of Examples 25 to 29 of the present invention are lower than those of the organic electroluminescence elements of Comparative Examples 14 and 15.
  • Examples 25 to 29 described above examples in which the preferred amine derivative of the present invention represented by the general formula (4) is used as a hole transport material of an organic electroluminescence device have been described.
  • the use of the derivative is not limited to the organic electroluminescence element, and may be used for other light emitting elements or light emitting devices.
  • the organic electroluminescence device using the amine derivative having a silyl group of the present invention represented by the general formula (4) may be used for a passive matrix driving type organic electroluminescence display, and is active matrix driving.
  • the present invention may be used for a type of organic electroluminescence display.
  • the inventors of the present invention arrange an amine derivative having the structure described below among the amine derivatives having the silyl group represented by the general formula (1) as an organic electroluminescent material between the light emitting layer and the anode. As a result, it was confirmed that a remarkable improvement was obtained in the luminous efficiency and lifetime of the organic electroluminescence device.
  • a preferred structure of the amine derivative having a silyl group represented by the general formula (1) is represented by the following general formula (8).
  • Ar 1 is an aryl group represented by the following general formula (5) substituted with a silyl group.
  • o is an integer that satisfies 0 ⁇ o ⁇ 2
  • R 11 , R 12 , and R 13 are each independently an alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted ring formation.
  • R 11 , R 12 and R 13 may be connected to each other to form a ring.
  • o is preferably 0 or 1.
  • R 11 , R 12 and R 13 are each a methyl group, a normal alkyl group having 6 or less carbon atoms, a phenyl group, a biphenylyl group, a terphenyl group, a quaterphenyl group, and a naphthyl group.
  • Tg glass transition temperature
  • a preferred amine derivative having a silyl group of the present invention represented by the general formula (8) is represented by the above general formula (1), wherein Ar 2 in the amine derivative has 6 to 30 ring carbon atoms. A substituted or unsubstituted aryl group.
  • Ar 2 in the amine derivative is also represented by Ar 2 in the amine derivative represented by the general formula (8).
  • Examples of the aryl group of Ar 2 include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, and a quaterphenyl group.
  • a preferred amine derivative having a silyl group of the present invention represented by the general formula (8) is represented by the above general formula (1), and Ar 3 in the amine derivative is represented by the following general formula (6).
  • each R 9 is independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, m Is an integer satisfying 0 ⁇ m ⁇ 5.
  • each R 10 is independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • l is 0 ⁇ m ⁇ 4
  • n is an integer that satisfies 2 ⁇ n ⁇ 5.
  • n is preferably 2 or 3.
  • n is 2 or 3
  • the electron resistance of the amine derivative can be further improved.
  • Examples of the amine derivative having a silyl group of the present invention represented by the general formula (8) include compounds exemplified below, but are not limited thereto.
  • Ph represents a phenyl group
  • Me represents a methyl group.
  • the amine derivative having a silyl group of the present invention represented by the general formula (8) is an aryl in which Ar 1 in the amine derivative of the present invention represented by the general formula (1) is substituted with a silyl group exhibiting strong electron resistance. It is a group. Therefore, the amine derivative having a silyl group of the present invention represented by the general formula (8) is stable to electrons and is used as a material for an organic electroluminescence element, particularly as a hole transport layer material adjacent to a light emitting layer. When used, the electron resistance of the hole transport layer can be improved, the deterioration of the hole transport material caused by the electrons entering the hole transport layer is suppressed, and the lifetime of the organic electroluminescent element is extended. It becomes possible.
  • the amine derivative having a silyl group of the present invention represented by the general formula (8) has an arylene group in which n is 2 or more in the general formula (7).
  • the amine derivative having a silyl group of the present invention represented by the general formula (8) has an arylene group in which n is 2 or more in the general formula (7), thereby increasing the glass transition temperature (Tg).
  • Tg glass transition temperature
  • the film forming property is improved.
  • the amine derivative having a silyl group of the present invention represented by the general formula (8) in the case of an arylene group in which n is 2 in the general formula (7), an aryl group represented by the general formula (6) In addition, at least one terphenyl group is bonded to the N atom of the amine.
  • a compound having a terphenylamine skeleton has very high hole resistance and electron resistance. Therefore, when n in the general formula (7) is 2, the amine derivative having a silyl group of the present invention represented by the general formula (8) is an organic electroluminescent element material, particularly a positive electrode adjacent to the light emitting layer.
  • the resistance to electrons flowing from the light emitting layer to the hole transport layer side is further improved, the luminous efficiency of the organic electroluminescent device is improved, and the lifetime of the organic electroluminescent device is further increased. Life can be extended.
  • the amine derivative having a silyl group of the present invention represented by the general formula (8) can be used as a material for the hole transport layer of the organic electroluminescence device 100 represented in FIG. 1 as described above.
  • the configuration of the organic electroluminescence element 100 shown in FIG. 1 is an embodiment of the organic electroluminescence element of the present invention, and is not limited to this, and various modifications are possible.
  • the use of the amine derivative having a silyl group of the present invention represented by the general formula (8) is the same as that of the amine derivative having a silyl group represented by the general formula (1).
  • the material is not limited to a transport material, and can also be used as a material for a hole injection layer.
  • the amine derivative having a silyl group represented by the general formula (8) is used as the material for the hole injection layer, the luminous efficiency of the organic electroluminescence device is improved in the same manner as when the amine derivative is used as the material for the hole transport layer. Thus, the lifetime of the organic electroluminescence element can be extended.
  • Example VIII With respect to the amine derivative having the silyl group of the present invention represented by the general formula (8), examples of synthesis methods of the compound G-8, the compound G-9, the compound G-13, and the compound G-18 will be described below. However, the synthesis method described below is an example and does not limit the present invention.
  • Example 30 of the organic electroluminescence device using the above-mentioned compound G-8 for the hole transport layer as the organic electroluminescence device material of the present invention will be described.
  • Preparation of the organic electroluminescent element of Example 30 of the present invention was performed by vacuum deposition in the same manner as the organic electroluminescent element of Example 1 described above, and was performed in the following procedure.
  • surface treatment with ozone was performed on an ITO-glass substrate that had been patterned and cleaned in advance.
  • the ITO film has a thickness of 150 nm.
  • 4,4 ′, 4 ′′ -tris (N, N- (2-naphthyl) phenylamino) triphenylamine (2-TNATA, film thickness 60 nm) was used as the hole injection material.
  • a film was formed on top.
  • the compound G-8 of the present invention was formed as a hole transporting material (30 nm), and then 2,5,8,11-tetra-t-butyl-perylene (TBP) was used as the light emitting material.
  • TBP 2,5,8,11-tetra-t-butyl-perylene
  • ADN 10-di (2-naphthyl) anthracene
  • Example 31 an organic electroluminescence device was produced in the same manner as in Example 30, except that Compound G-9 was used instead of Compound G-8 used in Example 30.
  • Example 32 an organic electroluminescence device was produced in the same manner as in Example 30, except that Compound G-13 was used instead of Compound G-8 used in Example 30.
  • Example 33 an organic electroluminescence device was produced in the same manner as in Example 30, except that Compound G-18 was used instead of Compound G-8 used in Example 30.
  • Example 30 was performed using the following Comparative Compound 16, Comparative Compound 17, and Comparative Compound 18 as the compounds constituting the material of the hole transport layer of the organic electroluminescence device.
  • An organic electroluminescence device was produced in the same manner as described above.
  • the driving voltage, luminous efficiency, half life, and glass transition temperature (Tg) were evaluated.
  • the light emission efficiency indicates a value at 10 mA / cm 2
  • the half-life shows a luminance half-life from the initial luminance 1,000 cd / m 2.
  • the evaluation results are shown in Table 8.
  • the organic electroluminescence elements of Examples 30 to 33 of the present invention have improved luminous efficiency as compared with the organic electroluminescence elements of Comparative Example 16, Comparative Example 17, and Comparative Example 18, It can be seen that the life has been extended.
  • the amine derivative having a silyl group of the present invention represented by the general formula (8) has strong electron resistance due to the presence of the silyl group having electron resistance. Further, in the general formula (7), n is 2
  • the electron resistance is improved and the hole transport property is improved, so that the light emission efficiency and the life of the organic electroluminescent element can be improved.
  • the hole transportability is improved while suppressing the deterioration of the device caused by the electrons entering the hole transport layer. Therefore, it is possible to improve the light emission efficiency and extend the life of the organic electroluminescence element.
  • Examples 30 to 33 described above examples in which the amine derivative having a silyl group of the present invention represented by the general formula (8) is used as a hole transport material of an organic electroluminescence device have been described.
  • the use of the amine derivative having a silyl group of the invention is not limited to an organic electroluminescence element, and may be used for other light emitting elements or light emitting devices.
  • the organic electroluminescence device using the amine derivative having a silyl group of the present invention represented by the general formula (8) may be used for a passive matrix driving type organic electroluminescence display, and is active matrix driving.
  • the present invention may be used for a type of organic electroluminescence display.
  • the amine derivative of the present invention can improve the light emission efficiency and extend the life of an organic electroluminescence device, and can be used for various applications such as an organic electroluminescence display and illumination.

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Abstract

La présente invention concerne un dérivé d'amine représenté par la formule générale (1). Dans la formule générale (1), Ar1, Ar2 et Ar3 représentent chacun indépendamment un groupe aryle substitué ou non substitué ou un groupe hétéroaryle substitué ou non substitué, au moins l'un des Ar1, Ar2 et Ar3 étant substitué par un groupe silyle substitué ou non substitué, et L représente un groupe de liaison, un groupe arylène substitué ou non substitué, ou un groupe hétéroarylène substitué ou non substitué.
PCT/JP2013/082647 2012-12-05 2013-12-04 Dérivé d'amine, matériau électroluminescent organique et élément électroluminescent organique l'utilisant Ceased WO2014088047A1 (fr)

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KR1020177018061A KR20170081718A (ko) 2012-12-05 2013-12-04 아민 유도체, 유기 발광 재료 및 그것을 사용한 유기 일렉트로루미네센스 소자
KR1020157002270A KR20150090021A (ko) 2012-12-05 2013-12-04 아민 유도체, 유기 발광 재료 및 그것을 사용한 유기 일렉트로루미네센스 소자
US14/731,180 US9780317B2 (en) 2012-12-05 2015-06-04 Amine derivative, organic luminescent material and organic electroluminescent device using the amine derivative or the organic luminescent material
US15/716,613 US10629830B2 (en) 2012-12-05 2017-09-27 Organic electroluminescent device

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CN112745231A (zh) * 2019-10-29 2021-05-04 东进世美肯株式会社 新型化合物以及包含上述新型化合物的有机发光元件
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JP2024138256A (ja) * 2017-12-15 2024-10-08 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセントデバイスに使用するための置換芳香族アミン
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JP2021503502A (ja) * 2018-08-24 2021-02-12 エルジー・ケム・リミテッド 化合物、これを含むコーティング組成物、これを用いた有機発光素子およびその製造方法
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CN112745231A (zh) * 2019-10-29 2021-05-04 东进世美肯株式会社 新型化合物以及包含上述新型化合物的有机发光元件
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CN114456204A (zh) * 2020-11-10 2022-05-10 三星显示有限公司 发光二极管和用于其的胺化合物
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CN114975839A (zh) * 2022-07-26 2022-08-30 吉林奥来德光电材料股份有限公司 一种有机电致发光器件、有机电致发光装置及光电设备
CN114975839B (zh) * 2022-07-26 2022-10-28 吉林奥来德光电材料股份有限公司 一种有机电致发光器件、有机电致发光装置及光电设备

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