JP4677221B2 - Organic light emitting device - Google Patents

Description

The present invention relates to an organic light emitting device using aminoanthryl derivative substitution compound.

  An organic light-emitting element generates an exciton of a fluorescent compound by sandwiching a thin film containing a fluorescent organic compound between an anode and a cathode and injecting electrons and holes from each electrode. It is an element that utilizes light emitted when the child returns to the ground state.

In 1987, Kodak Research (Non-patent Document 1) used ITO for the anode and magnesium silver alloy for the cathode, an aluminum quinolinol complex for the electron transport material and the light emitting material, and a triphenylamine derivative for the hole transport material. In the device having the function separation type two-layer structure, light emission of about 1000 cd / m ² has been reported at an applied voltage of about 10 V (Patent Documents 1 to 3).

  In addition, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared is possible, and recently, various compounds have been actively studied (Patent Documents 4 to 11).

  Furthermore, in addition to the organic light emitting device using the low molecular material as described above, an organic light emitting device using a conjugated polymer has been reported by a group of Cambridge University (Non-Patent Document 2). In this report, light emission was confirmed in a single layer by forming a film of polyphenylene vinylene (PPV) in a coating system. Patent documents 12-16 are mentioned as a related patent of the organic light emitting element using a conjugated polymer.

Recently, a phosphorescent organic light-emitting device using an iridium complex such as Ir (ppy) ₃ as a light-emitting material has attracted attention, and high luminous efficiency has been reported (Non-patent Document 3).

  Recent advances in organic light-emitting devices are remarkable, and their features are high brightness, variety of emission wavelengths, high-speed response, low-profile, and lightweight light-emitting devices with low applied voltage, enabling wide-ranging applications Suggests sex. However, there are still many problems in terms of durability, such as changes over time due to long-term use and deterioration due to atmospheric gas containing oxygen or moisture. When considering application to a full color display or the like, under the present circumstances, blue, green, and red light emission having a longer life, high conversion efficiency, and high color purity is necessary, and various proposals have been made.

  As an example of a material containing an anthracene ring and an organic light emitting device, Patent Document 17 discloses a phenylanthracene derivative. In particular, when it is used as a blue light emitting material or an electron injecting and transporting material, it is said that a good organic film can be formed because of low crystallinity, but the luminous efficiency and durability are not sufficient in practice.

  Patent Documents 18 and 19 disclose aminoanthracene derivatives and diaminoanthracene derivatives, respectively. Although it is said that green light emission can be obtained by using it as a light emitting material, the light emitting efficiency of the device is low, and the durability life is not sufficient in practice.

  Patent Document 20 discloses an element using a specific bianthryl compound as a light emitting material, and it is said that high luminance light emission can be obtained. However, there is no description regarding light emission efficiency and durability life.

  Patent Document 21 discloses a device using a specific anthracene compound containing an olefin moiety as a light emitting material, and it is said that yellow to red light emission can be obtained, but the light emission efficiency is not practically sufficient.

  Patent Document 22 discloses a device in which a light emitting medium layer includes an anthracene derivative having a specific structure, an electron transporting compound, and another fluorescent compound. Although it is said that a red light emitting device with improved reliability can be obtained, the light emission efficiency is not practically sufficient, and it is difficult to obtain blue light emission due to the device structure.

US Pat. No. 4,539,507 US Pat. No. 4,720,432 US Pat. No. 4,885,211 US Pat. No. 5,151,629 US Pat. No. 5,409,783 US Pat. No. 5,382,477 JP-A-2-247278 JP-A-3-255190 JP-A-5-202356 JP-A-9-202878 JP-A-9-227576 US Pat. No. 5,247,190 US Pat. No. 5,514,878 US Pat. No. 5,672,678 JP-A-4-145192 Japanese Patent Application Laid-Open No. 5-247460 JP-A-8-12600 Japanese Patent Laid-Open No. 9-157463 Japanese Patent Laid-Open No. 10-72579 Japanese Patent No. 3008897 Japanese Patent Laid-Open No. 11-8068 JP 2001-284050 A Appl. Phys. Lett. 51,913 (1987) Nature, 347, 539 (1990) Appl. Phys. Lett. 75, 4 (1999)

  The present invention has been made to solve such problems of the prior art, and has a light emission hue with extremely high purity, a material for an organic light emitting device having a light output with high efficiency, high luminance, and long life. Is to provide. It is another object of the present invention to provide an organic light emitting device that is easy to manufacture and can be produced at a relatively low cost.

  As a result of intensive investigations to solve the above-mentioned problems, the present inventors have completed the present invention.

（Ａｒ ₂ とＡｒ ₃ はそれぞれ独立に、フェニル基、ナフチル基のいずれかであり、前記フェニル基はアルキル基を有してもよい。Ｒ ₈ は水素原子、重水素原子のいずれかである。）

（Ａｒ ₈ とＡｒ ₉ はそれぞれ独立に、フェニル基、ナフチル基のいずれかであり、前記フェニル基はアルキル基を有してもよい。Ｒ ₄ は水素原子、重水素原子のいずれかである。Ｙ ₁ は水素原子あるいはアルキル基である。Ｒ ₆ は水素原子、重水素原子のいずれかである。） That is , the organic light-emitting device of the present invention is an organic light-emitting device composed of one or more layers including an organic compound sandwiched between a pair of electrodes, at least one of which is a transparent or translucent anode and cathode. At least one layer containing an organic compound contains at least one aminoanthryl derivative-substituted compound represented by any one of the following general formulas .

(Ar ₂ and Ar ₃ are each independently a phenyl group or a naphthyl group, and the phenyl group may have an alkyl group. R ₈ is either a hydrogen atom or a deuterium atom. )

(Ar ₈ and Ar ₉ are each independently a phenyl group or a naphthyl group, and the phenyl group may have an alkyl group. R ₄ is either a hydrogen atom or a deuterium atom. Y ₁ represents a hydrogen atom or an alkyl group, and R ₆ represents either a hydrogen atom or a deuterium atom.)

  The aminoanthryl-derived group-substituted compound of the present invention is a material for an organic light-emitting device having multifunctionality within the same molecule such as high-efficiency light emission and efficient electron and hole transport. The organic light emitting device using the aminoanthryl derivative-substituted compound of the present invention provides highly efficient light emission at a low applied voltage. In addition, various emission colors can be easily obtained by converting the substituents of the aminoanthryl derivative-substituted compound, and excellent durability can be obtained.

  Hereinafter, the present invention will be described in detail.

（Ｚ ₁ は、直接単結合、置換あるいは未置換のアルキレン基、アルケニレン基、アルキニレン基、アラルキレン基、アリーレン基及び二価の複素環基からなる群より選ばれた基であり、連結基で結合された基でもよい。
Ａｒ ₁ は、置換あるいは未置換のフェナントレン、アセナフチレン、アセフェナントリレン、アセアントリレン、トリフェニレン、クリセン、ベンゾ［ｃ］フェナントレン、ナフタセン、ジベンゾ［ａ，ｃ］アントラセン、ジベンゾ［ａ，ｈ］アントラセン、ジベンゾ［ｂ，ｄｅｆ］クリセン、ピセン、ペリレン、ペンタセンから選ばれる芳香族縮合多環ユニットからなる置換基、または置換あるいは未置換の複素環基であり、同じであっても異なっていてもよい。
Ａｒ ₂ 、Ａｒ ₃ は、置換あるいは未置換のアルキル基、アラルキル基、アリール基及び複素環基からなる群より選ばれた基であり、連結基で結合された基でもよく、同じであっても異なっていてもよい。
Ｘ ₁ は、直接単結合、置換あるいは未置換のアリーレン基及び二価の複素環基からなる群より選ばれた基であり、連結基で結合された基でもよい。
Ｒ ₁ は、水素原子、重水素原子、ハロゲン原子、置換あるいは未置換のアルキル基、アリール基、アルコキシ基、アミノ基からなる群より選ばれた基であり、同じであっても異なっていてもよい。Ｒ ₂ は、重水素原子、ハロゲン原子、置換あるいは未置換のアルキル基、アリール基、アルコキシ基、アミノ基からなる群より選ばれた基であり、同じであっても異なっていてもよい。
ａは１〜８の整数、ｂは１〜３の整数、ｃは０〜４の整数。）
また、本発明の他のアミノアントリル誘導基置換化合物は、下記一般式［１５］で示されることを特徴とする。

（Ａｒ ₇ は、置換あるいは未置換のナフタレン、フェナントレン、アセナフチレン、アセフェナントリレン、アセアントリレン、トリフェニレン、クリセン、ベンゾ［ｃ］フェナントレン、ナフタセン、ジベンゾ［ａ，ｃ］アントラセン、ジベンゾ［ａ，ｈ］アントラセン、ジベンゾ［ｂ，ｄｅｆ］クリセン、ピセン、ペリレン、ペンタセンから選ばれる芳香族多環縮環ユニット、または置換あるいは未置換の複素環基である。
Ａｒ ₈ 、Ａｒ ₉ は、置換あるいは未置換のアルキル基、アラルキル基、アリール基及び複素環基からなる群より選ばれた基であり、連結基で結合された基でもよく、同じであっても異なっていてもよい。
Ｘ ₄ は、直接単結合、置換あるいは未置換のアリーレン基及び二価の複素環基からなる群より選ばれた基であり、連結基で結合された基でもよい。
Ｒ ₄ は、水素原子、重水素原子、ハロゲン原子、置換あるいは未置換のアルキル基、アリール基、アルコキシ基、アミノ基からなる群より選ばれた基であり、同じであっても異なっていてもよい。
Ｙ ₁ は、水素原子、置換あるいは未置換のアルキル基からなる群より選ばれた基である。
ｅは１〜８の整数。） First, the aminoanthryl derivative-substituted compound of the present invention will be described.
The aminoanthryl derivative-substituted compound of the present invention is represented by the following general formula [1].

(Z ₁ is a group selected from the group consisting of a direct single bond, a substituted or unsubstituted alkylene group, an alkenylene group, an alkynylene group, an aralkylene group, an arylene group and a divalent heterocyclic group, and is bonded by a linking group. It may also be a group.
Ar ₁ represents substituted or unsubstituted phenanthrene, acenaphthylene, acephenanthrylene, acanthrylene, triphenylene, chrysene, benzo [c] phenanthrene, naphthacene, dibenzo [a, c] anthracene, dibenzo [a, h] anthracene, A substituent composed of an aromatic condensed polycyclic unit selected from dibenzo [b, def] chrysene, picene, perylene, and pentacene, or a substituted or unsubstituted heterocyclic group, which may be the same or different.
Ar ₂ and Ar ₃ are groups selected from the group consisting of a substituted or unsubstituted alkyl group, an aralkyl group, an aryl group and a heterocyclic group, and may be a group bonded by a linking group or the same. May be different.
X ₁ is a group selected from the group consisting of a direct single bond, a substituted or unsubstituted arylene group and a divalent heterocyclic group, and may be a group bonded by a linking group.
R ₁ is a group selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, an aryl group, an alkoxy group, and an amino group, and may be the same or different. Good. R ₂ is a group selected from the group consisting of a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, an aryl group, an alkoxy group, and an amino group, and may be the same or different.
a is an integer of 1 to 8, b is an integer of 1 to 3, and c is an integer of 0 to 4. )
Another aminoanthryl derivative-substituted compound of the present invention is represented by the following general formula [15].

(Ar ₇ is substituted or unsubstituted naphthalene, phenanthrene, acenaphthylene, acephenanthrylene, acanthrylene, triphenylene, chrysene, benzo [c] phenanthrene, naphthacene, dibenzo [a, c] anthracene, dibenzo [a, h ] An aromatic polycyclic fused ring unit selected from anthracene, dibenzo [b, def] chrysene, picene, perylene, and pentacene, or a substituted or unsubstituted heterocyclic group.
Ar ₈ and Ar ₉ are groups selected from the group consisting of a substituted or unsubstituted alkyl group, an aralkyl group, an aryl group and a heterocyclic group, and may be a group bonded by a linking group or the same. May be different.
X ₄ is a group selected from the group consisting of a direct single bond, a substituted or unsubstituted arylene group and a divalent heterocyclic group, and may be a group bonded by a linking group.
R ₄ is a group selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, an aryl group, an alkoxy group, and an amino group, and may be the same or different. Good.
Y ₁ is a group selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group.
e is an integer of 1-8. )

  The aminoanthryl derivative-substituted compound of the present invention can be used mainly as a material for an organic light emitting device. Among them, when used for a light emitting layer, it can be used alone in the light emitting layer, and can be used for the purpose of a dopant (guest) material and a host material, and can obtain a high color purity, high light emission efficiency, and a long life element. it can.

  The aminoanthryl derivative-substituted compound of the present invention is an aminoanthryl derivative group and an aromatic polycyclic fused ring in consideration of formation of multifunctionality in the same molecule such as high-efficiency light emission and efficient electron and hole transport. The molecular design to arrange the group was performed. By introducing a substituted amino group into an anthryl group that is expected to have high efficiency light emission and hole transportability, the HOMO / LUMO level of the material is adjusted by conversion of the substituent on the amino group, and the blue, green, and even longer wavelength side It can be converted into a luminescent color. By predicting the HOMO / LUMO level by calculation, it is easy to design a molecule in consideration of the energy level difference between the host material, the hole transport layer, and the electron transport layer. The aromatic polycyclic fused ring group generally shows a high quantum yield, and an improvement in the carrier transport property due to the overlap of the aromatic polycyclic fused ring group can also be expected. Furthermore, an amino group on the anthryl group can provide a material having a high Tg and a high thermal stability. In addition to the above considerations, the aminoanthryl derivative-substituted compound of the present invention also considered introduction of deuterium atom-containing molecular units in consideration of suppressing molecular vibrations and suppressing thermal deactivation due to isotope effects. The aminoanthryl derivative-substituted compound of the present invention has been invented by molecular design based on the above consideration.

  When the aminoanthryl derivative-substituted compound of the present invention is used as a dopant material, the dopant concentration relative to the host material is 0.01 wt% to 80 wt%, preferably 1 wt% to 40 wt%. The dopant material may be included in the entire layer of the host material with a uniform or concentration gradient, or there may be a region of the host material layer that is partially included in a region and does not include the dopant material.

In the above general formula [1] [15] , the substituted or unsubstituted alkyl group includes a methyl group, a methyl-d1 group, a methyl-d3 group, an ethyl group, an ethyl-d5 group, an n-propyl group, and an n-butyl group. Group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-decyl group, iso-propyl group, iso-propyl-d7 group, iso-butyl group, sec-butyl group, tert -Butyl, tert-butyl-d9, iso-pentyl, neopentyl, tert-octyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2,2-tri Fluoroethyl group, perfluoroethyl group, 3-fluoropropyl group, perfluoropropyl group, 4-fluorobutyl group, perfluorobutyl group, 5-fluoropentyl group, 6-fluorohexyl group, chloromethyl group, trichloromethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 4-chlorobutyl group, 5-chloropentyl group, 6-chlorohexyl Group, bromomethyl group, 2-bromoethyl group, iodomethyl group, 2-iodoethyl group, hydroxymethyl group, hydroxyethyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentylmethyl group, cyclohexylmethyl group, cyclohexylethyl group , 4-fluorocyclohexyl group, norbornyl group, adamantyl group and the like, but are not limited thereto.

  Examples of the substituted or unsubstituted aralkyl group include benzyl group, 2-phenylethyl group, 2-phenylisopropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, 2- (1-naphthyl) ethyl group, 2- ( 2-naphthyl) ethyl group, 9-anthrylmethyl group, 2- (9-anthryl) ethyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3- A chlorobenzyl group, a 4-chlorobenzyl group, a 2-bromobenzyl group, a 3-bromobenzyl group, a 4-bromobenzyl group, and the like can be mentioned, but the present invention is not limited to these.

  Examples of the substituted or unsubstituted alkenyl group include a vinyl group, an allyl group (2-propenyl group), a 1-propenyl group, an iso-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, and a styryl group. Of course, it is not limited to these.

  Examples of the substituted or unsubstituted alkynyl group include, but are not limited to, an acetylenyl group, a phenylacetylenyl group, and a 1-propynyl group.

  Examples of the substituted or unsubstituted aryl group include phenyl group, phenyl-d5 group, 4-methylphenyl group, 4-methoxyphenyl group, 4-ethylphenyl group, 4-fluorophenyl group, 4-trifluorophenyl group, 3 , 5-dimethylphenyl group, 2,6-diethylphenyl group, mesityl group, 4-tert-butylphenyl group, ditolylaminophenyl group, biphenyl group, terphenyl group, naphthyl group, naphthyl-d7 group, acenaphthylenyl group, Anthryl, anthryl-d9, phenanthryl, phenanthryl-d9, pyrenyl, pyrenyl-d9, acephenanthrenyl, aceanthrylenyl, chrysenyl, dibenzochrysenyl, benzoanthryl, Benzoanthryl-d11 group, dibenzoanthryl group, naphthaceni Group, a picenyl group, a pentacenyl group, a fluorenyl group, triphenylenyl group, but perylenyl group, perylenyl -d-11 and the like, but the present invention is of course not limited thereto.

  Examples of substituted or unsubstituted heterocyclic groups include pyrrolyl, pyridyl, pyridyl-d5, bipyridyl, methylpyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, terpyrrolyl, thienyl, thienyl-d4, and tertenyl. Group, propylthienyl group, benzothienyl group, dibenzothienyl group, dibenzothienyl-d7 group, furyl group, furyl-d4 group, benzofuryl group, isobenzofuryl group, dibenzofuryl group, dibenzofuryl-d7 group, quinolyl group, quinolyl -D6 group, isoquinolyl group, quinoxalinyl group, naphthyridinyl group, quinazolinyl group, phenanthridinyl group, indolizinyl group, phenazinyl group, carbazolyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, acridinyl group, phenidinyl group Jiniru group, and the like, but the invention is of course not limited thereto.

  Examples of the substituted or unsubstituted alkylene group include methylene group, methylene-d2 group, difluoromethylene group, ethylene group, ethylene-d4 group, perfluoroethylene group, propylene group, iso-propylene group, butylene group, 2,2- Examples thereof include, but are not limited to, a dimethylpropylene group.

  Examples of the substituted or unsubstituted aralkylene group include benzylene group, 2-phenylethylene group, 2-phenylisopropylene group, 1-naphthylmethylene group, 2-naphthylmethylene group, 9-anthrylmethylene group, and 2-fluorobenzylene. Group, 3-fluorobenzylene group, 4-fluorobenzylene group, 4-chlorobenzyl group, 4-bromobenzylene group and the like, but are not limited thereto.

  Examples of the substituted or unsubstituted alkenylene group include, but are not limited to, a vinylene group, an iso-propenylene group, a styrylene group, and a 1,2-diphenylvinylene group.

  Examples of the substituted or unsubstituted alkynylene group include an acetylenylene group and a phenylacetylenylene group, but are not limited thereto.

  Examples of the substituted or unsubstituted arylene group include a phenylene group, a biphenylene group, a tetrafluorophenylene group, a dimethylphenylene group, a naphthylene group, a phenanthrylene group, a pyrenylene group, a naphthacenylene group, a pentasenylene group, and a peryleneylene group. It is not limited to.

  Examples of the substituted or unsubstituted divalent heterocyclic group include a furylene group, a pyrrolylene group, a pyridylene group, a terpyridylene group, a thienylene group, a tertienylene group, an oxazolylene group, a thiazolylene group, a carbazolylene group, a dibenzothienylene group, and a dibenzofurylene group. Of course, it is not limited to these.

  As a substituted or unsubstituted amino group (—NR′R ″), R ′ and R ″ are hydrogen atom, deuterium atom, substituted or unsubstituted alkyl group, aralkyl group, aryl group, An alkyl group, an alkenyl group, an alkynyl group, an aralkyl group and an amino group linked by a cyclic group, a substituted or unsubstituted arylene group or a divalent heterocyclic group, a substituted silyl group, an ether group, a thioether group, or a carbonyl group. For example, an amino group, N-methylamino group, N-ethylamino group, N, N-dimethylamino group, N, N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N, N-dibenzylamino group, anilino group, N, N-diphenylamino group, N-phenyl-N-tolylamino group, , N-ditolylamino group, N-methyl-N-phenylamino group, N, N-dianisolylamino group, N-mesityl-N-phenylamino group, N, N-dimesitylamino group, N-phenyl-N- ( 4-tert-Butylphenyl) amino group, N-phenyl-N- (4-trifluoromethylphenyl) amino group and the like can be mentioned, but of course not limited thereto.

  Examples of the substituted or unsubstituted alkoxy group include the above-described substituted or unsubstituted alkyl group, the alkyloxy group having an aralkyl group, the aralkyloxy group, the above-described substituted or unsubstituted aryl group, and an aryl having a heterocyclic group. Examples include methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, phenoxy group, 4-tert-butylphenoxy group, benzyloxy group, thienyloxy group, etc. It is not limited to.

  The substituted or unsubstituted sulfide group includes the above-described substituted or unsubstituted alkyl group, the alkylsulfide group having an aralkyl group, the aralkyl sulfide group, the above-described substituted or unsubstituted aryl group, and an aryl having a heterocyclic group. Examples thereof include, but are not limited to, a methyl sulfide group, an ethyl sulfide group, a phenyl sulfide group, a 4-methylphenyl sulfide group, and the like.

  As the linking group for bonding the substituent, the substituted or unsubstituted arylene group, divalent heterocyclic group, alkylene group, alkenylene group, alkynylene group and aralkylene group, substituted silyl group, ether group, thioether group, Examples thereof include, but are not limited to, a carbonyl group and the like.

  Examples of the substituent that the substituent and the linking group may further include a deuterium atom, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n- Heptyl group, n-octyl group, n-decyl group, iso-propyl group, iso-butyl group, sec-butyl group, tert-butyl group, iso-pentyl group, neopentyl group, tert-octyl group, benzyl group, 2 -Alkyl group such as phenylethyl group, aralkyl group, methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, phenoxy group, 4-tert-butylphenoxy group, alkoxy group such as benzyloxy group, phenyl group 4-methylphenyl group, 4-ethylphenyl group, 3-chlorophenyl group, 3,5-dimethylphenyl group, triphenylamino Group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group and other aryl groups, pyridyl group, bipyridyl group, methylpyridyl group, thienyl group, terthienyl group, propylthienyl group, furyl group, quinolyl group , A carbazolyl group, a heterocyclic group such as N-ethylcarbazolyl group, a halogen group, a hydroxyl group, a cyano group, and a nitro group, but of course not limited thereto.

Preferred as the aminoanthryl derivative-substituted compound represented by the general formula [1] of the present invention is a compound in which Z ₁ is a direct single bond and b = 1, that is, a compound represented by the following general formula [2] More preferred is a compound represented by the following general formula [3].

Further, Ar ₁ is comprised of a heterocyclic unit chosen from substituted or unsubstituted pyridine, thiophene, quinoline, isoquinoline, quinoxaline, naphthyridine, quinazoline, Fenantoriji down, Baie Nzochiofen, benzofuran, dibenzothiophene, dibenzofuran, acridine, phenazine substituted It is preferably a group.

Ar ₁ is preferably any substituent represented by the following general formula [4] [5] [7] [8], and the following general formula [9] [10] [12] [13] It is more preferable that the substituent is any one of the following.

(R ₅ , R ₆ , R ₈ and R ₉ are groups selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, aryl groups, alkoxy groups and amino groups. , May be the same or different.

f is an integer from 1 to 9, g is an integer of 1 to 7, i is 1 to 11 integer, j is 1 to 11 integer. )

On the other hand, preferred as aminoanthryl derivative substitution compound represented by the general formula [15] of the present invention, Ar ₇ is a substituted or unsubstituted pyridine, thiophene, quinoline, isoquinoline, quinoxaline, naphthyridine, quinazoline, Fenantoriji down , base Nzochiofen, benzofuran, dibenzothiophene, dibenzofuran, acridine, be a substituent consisting of heterocyclic units selected from phenazine preferred.

Ar ₇ is preferably any one of the substituents represented by the general formulas [4] [5] [7] [8], and the general formulas [9] [10] [12] [13] It is more preferable that the substituent is any one of the following.

Next, typical examples of the aminoanthryl derivative-substituted compound of the present invention (excluding Exemplified Compounds 29 to 38) are listed. However, it is not limited to these compounds.

  Next, the organic light emitting device of the present invention will be described in detail.

The organic light-emitting device of the present invention is a layer containing an organic compound in an organic light-emitting device having at least a pair of electrodes composed of an anode and a cathode, and a layer containing one or a plurality of organic compounds sandwiched between the pair of electrodes. At least one of the above, preferably the light emitting layer, contains at least one of the aminoanthryl derivative-substituted compounds of the present invention.

  1 to 5 show preferred examples of the organic light emitting device of the present invention.

  FIG. 1 is a cross-sectional view showing an example of the organic light emitting device of the present invention. FIG. 1 shows a structure in which an anode 2, a light emitting layer 3 and a cathode 4 are sequentially provided on a substrate 1. The light-emitting element used here is useful when the device itself has a hole transport ability, an electron transport ability, and a light-emitting performance, or when a compound having each characteristic is used in combination.

  FIG. 2 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 2 shows a configuration in which an anode 2, a hole transport layer 5, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. In this case, the light emitting material is either a hole transporting property or an electron transporting property, or a material having both functions is used for each layer, and it is combined with a simple hole transporting material or an electron transporting material having no light emitting property. This is useful when used. In this case, the light emitting layer is composed of either the hole transport layer 5 or the electron transport layer 6.

  FIG. 3 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 3 shows a structure in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. This is a function that separates the functions of carrier transport and light emission, and is used in combination with compounds having hole transport properties, electron transport properties, and light emission properties in a timely manner, and the degree of freedom of material selection is greatly increased. Since various compounds having different emission wavelengths can be used, the emission hue can be diversified. Further, it is possible to effectively confine each carrier or exciton in the central light emitting layer 3 to improve the light emission efficiency.

  FIG. 4 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 4 shows a configuration in which a hole injection layer 7 is inserted on the anode 2 side with respect to FIG. 3, and is effective in improving the adhesion between the anode 2 and the hole transport layer 5 or improving the hole injection property. It is effective.

  FIG. 5 is a cross-sectional view showing another example of the organic light-emitting device of the present invention. FIG. 5 shows a configuration in which a layer (hole / exciton blocking layer 8) that prevents holes or excitons (excitons) from escaping to the cathode 4 side is inserted between the light emitting layer 3 and the electron transport layer 6. It is. By using a compound having a very high ionization potential as the hole / exciton blocking layer 8, the structure is effective in improving the light emission efficiency.

  However, FIGS. 1 to 5 are very basic device configurations, and the configuration of the organic light emitting device using the aminoanthryl derivative-substituted compound of the present invention is not limited thereto. For example, various layer configurations such as providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or an interference layer, and the hole transport layer including two layers having different ionization potentials can be employed.

  The aminoanthryl derivative-substituted compound of the present invention can be used in any form of FIGS.

  In particular, an organic layer using the aminoanthryl derivative-substituted compound of the present invention is useful as a light-emitting layer, an electron transport layer, or a hole transport layer, and a layer formed by a vacuum deposition method or a solution coating method is crystallized. Is less likely to occur and has excellent stability over time.

  In the present invention, a light-emitting compound or an electron transporting compound can be used together.

  Examples of these compounds are given below.

  The hole injecting and transporting material preferably has excellent mobility for facilitating the injection of holes from the anode and transporting the injected holes to the light emitting layer. Low molecular and high molecular weight materials having hole injection and transport performance include triarylamine derivatives, phenylenediamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, pyrazoline derivatives, pyrazolone derivatives, oxazole derivatives, fluorenone derivatives, hydrazones. Derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, and poly (vinyl carbazole), poly (silylene), poly (thiophene), and other conductive polymers are, of course, not limited thereto. Some specific examples are shown below.

  Examples of materials that can be used in addition to the aminoanthryl-derived group-substituted compounds of the present invention and mainly related to the light emitting function include aromatic polycyclic condensed compounds (for example, naphthalene derivatives, phenanthrene derivatives, fluorene derivatives, pyrene derivatives, tetracene derivatives, coronene derivatives). , Chrysene derivatives, perylene derivatives, 9,10-diphenylanthracene derivatives, rubrene, etc.), quinacridone derivatives, acridone derivatives, coumarin derivatives, pyran derivatives, nile red, pyrazine derivatives, benzimidazole derivatives, benzothiazole derivatives, benzoxazole derivatives, stilbene Derivatives, organometallic complexes (eg, organoaluminum complexes such as tris (8-quinolinolato) aluminum, organoberyllium complexes) and poly (phenylene vinylene) derivatives, poly (fluoro Down) derivatives, poly (phenylene) derivatives, poly (thienylene vinylene) derivatives, poly (acetylene) derivatives, such as derivatives, but the present invention is of course not limited thereto. Some specific examples are shown below.

  The electron injecting and transporting material can be arbitrarily selected from those having the function of facilitating the injection of electrons from the cathode and transporting the injected electrons to the light emitting layer, and the balance with the carrier mobility of the hole transporting material. It is selected in consideration of etc. Materials having electron injection and transport performance include oxadiazole derivatives, oxazole derivatives, thiazole derivatives, thiadiazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, fluorenone derivatives, anthrone derivatives, phenanthroline derivatives. And organometallic complexes, but of course not limited to these. Some specific examples are shown below.

  In the organic light-emitting device of the present invention, the layer containing the aminoanthryl derivative-substituted compound of the present invention and the layer composed of other organic compounds are generally formed by vacuum deposition, ionization deposition, sputtering, plasma, or a suitable solvent. And a thin film is formed by a known coating method (for example, spin coating, dipping, casting method, LB method, ink jet method, etc.). In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.

  The binder resin can be selected from a wide range of binder resins, such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, ABS resin, polybutadiene resin, polyurethane resin, acrylic resin, methacrylic resin. , Butyral resin, polyvinyl acetal resin, polyamide resin, polyimide resin, polyethylene resin, polyethersulfone resin, diallyl phthalate resin, phenol resin, epoxy resin, silicone resin, polysulfone resin, urea resin, etc. It is not something. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer. Furthermore, you may use together additives, such as a well-known plasticizer, antioxidant, and an ultraviolet absorber, as needed.

  As the anode material, a material having a work function as large as possible is good. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, or alloys thereof, tin oxide, zinc oxide, Metal oxides such as indium oxide, indium tin oxide (ITO), and indium zinc oxide can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode materials can be used alone or in combination. Further, the anode may have a single layer structure or a multilayer structure.

  On the other hand, the cathode material preferably has a small work function, for example, simple metals such as lithium, sodium, potassium, calcium, magnesium, aluminum, indium, ruthenium, titanium, manganese, yttrium, silver, lead, tin, and chromium. Alternatively, lithium-indium, sodium-potassium, magnesium-silver, aluminum-lithium, aluminum-magnesium, magnesium-indium and the like can be used. A metal oxide such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination. Further, the cathode may have a single layer structure or a multilayer structure.

  Although it does not specifically limit as a board | substrate used by this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film, or the like on the substrate.

  Note that a protective layer or a sealing layer can be provided on the prepared element for the purpose of preventing contact with oxygen or moisture. Examples of protective layers include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluororesins, polyparaxylene, polyethylene, silicone resins, and polystyrene resins, and photocurable resins. Can be mentioned. Further, it is possible to cover glass, a gas impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.

  In the device of the present invention, a thin film transistor (TFT) is formed on a substrate, and the device can be formed by connecting to the thin film transistor.

  Further, regarding the light extraction direction of the element, either a bottom emission configuration (configuration in which light is extracted from the substrate side) or a top emission (configuration in which light is extracted from the opposite side of the substrate) is possible.

Hereinafter, the present invention will be described more specifically by way of examples (excluding Examples 9, 20, 31, and 40), but the present invention is not limited thereto.

<Example 1> [Exemplary Compound No. 1] Manufacturing method 1]
(1) Synthesis of intermediate (9-bromo-10- (9-phenanthryl) anthracene) Under a nitrogen stream, 16.8 g (50 mmol) of 9,10-dibromoanthracene was mixed with 300 ml of degassed toluene and 200 ml of ethanol. The mixture was stirred and dissolved, and an aqueous sodium carbonate solution prepared by dissolving 10.6 g of anhydrous sodium carbonate in 100 ml of water was added thereto, and 5.78 g (5 mmol) of tetrakis (triphenylphosphine) palladium was further added. The solution was stirred on an oil bath heated to 50 ° C., and 15.3 g (50 mmol) of 9- [4,4,5,5-tetramethyl-1,3,2-dioxaboranyl] phenanthrene dissolved in 100 ml of toluene was added. It was slowly dropped in divided portions. The mixture was heated and stirred for about 4 hours on an oil bath heated to 80 ° C. in a nitrogen stream. The reaction solution was returned to room temperature, toluene, ethyl acetate and water were added to separate the organic layer, dried over magnesium sulfate, and the solvent was distilled off. Purification by silica gel column chromatography (toluene: heptane = 1: 3) gave 9.3 g of 9-bromo-10- (9-phenanthryl) anthracene.

(2) Exemplified Compound No. Synthesis of 1 Under a nitrogen atmosphere, 516 mg (2.30 mmol) of palladium acetate and 2.79 g (9.18 mmol) of tri-o-tolylphosphine were dissolved in 50 ml of xylene and stirred at room temperature for 15 minutes. 130 ml of xylene was added, 10.1 g (32.9 mmol) of 9-bromo-10- (9-phenanthryl) anthracene was added, and the mixture was stirred for 5 minutes on an oil bath heated to 50 ° C. 6.59 g (39 mmol) of N, N-diphenylamine was dissolved in 30 ml of xylene and added dropwise, followed by 6.95 g (72.3 mmol) of sodium tert-butoxide. The mixture was heated and stirred for about 5 hours on an oil bath heated to 130 ° C. After returning the reaction solution to room temperature, 100 ml of water was added, the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with toluene and ethyl acetate, and combined with the previous organic layer and dried over sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene: heptane = 1: 3). 12.4g of 1 was obtained.

<Examples 2 to 6> [Exemplary Compound No. Manufacturing method of 2-5, 7]
Instead of N, N-diphenylamine, N- (1-naphthyl) -N-phenylamine, N- (2-naphthyl) -N-phenylamine, N, N-bis (4-methylphenyl) amine, N- The reaction was conducted in the same manner as in Example 1 except that (9-phenanthryl) -N-phenylamine and N- (1-pyrenyl) -N-phenylamine were used. 2 to 5 and 7 were produced.

<Example 7> [Exemplary Compound No. 18 Manufacturing Method]
(1) Synthesis of intermediate (3-bromo-5- [9- (N, N-bis (4-methylphenyl) amino) -10-anthryl] toluene) 3,5-dibromotoluene 12. 5 g (50 mmol) was dissolved and stirred in a mixed solvent of 300 ml of degassed toluene and 200 ml of ethanol, and an aqueous sodium carbonate solution prepared by dissolving 10.6 g of anhydrous sodium carbonate in 100 ml of water was added thereto. Phenylphosphine) palladium 5.78 g (5 mmol) was added. The solution was stirred on an oil bath heated to 50 ° C., and 20.9 g (50 mmol) of 9- (N, N-bis (4-methylphenyl) amino) anthryl-10-boronic acid dissolved in 100 ml of toluene was slowly added. It was dripped. The mixture was heated and stirred for about 4 hours on an oil bath heated to 80 ° C. in a nitrogen stream. The reaction solution was returned to room temperature, toluene, ethyl acetate and water were added to separate the organic layer, dried over magnesium sulfate, and the solvent was distilled off. Purification by silica gel column chromatography (toluene: heptane = 1: 3) and 16.8 g of 3-bromo-5- [9- (N, N-bis (4-methylphenyl) amino) -10-anthryl] toluene Obtained.

(2) Exemplified Compound No. Synthesis of 18 Under nitrogen stream 3-bromo-5- [9- (N, N-bis (4-methylphenyl) amino) -10-anthryl] toluene 2.5 g (4.61 mmol), 9- (4 (4,5,5-tetramethyl-1,3,2-dioxaboranyl) phenanthrene (1.76 g, 5.76 mmol) was dissolved in 80 ml of degassed toluene and 40 ml of ethanol and stirred. A sodium carbonate aqueous solution prepared by dissolving 916 mg in 20 ml of water was added dropwise. After stirring for 1 hour on an oil bath heated to 50 ° C. in a nitrogen stream, 533 mg (0.461 mmol) of tetrakis (triphenylphosphine) palladium was added. The mixture was heated and stirred for about 4 hours on an oil bath heated to 80 ° C. The reaction solution was returned to room temperature, toluene, ethyl acetate and water were added, the organic layer was separated, dried over magnesium sulfate, and the solvent was distilled off. The product was purified by silica gel column chromatography (toluene: heptane = 1: 4). 2.51 g of 18 was obtained.

<Examples 8 to 16> [Exemplary Compound No. Method for producing 20, 34, 43, 53, 58, 64, 90, 93, 96]
In the same manner and under the same synthesis conditions as in Example 7, instead of 9- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) phenanthrene, 3- (4,4,5,5- Tetramethyl-1,3,2-dioxaboranyl) phenanthrene, 8- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) fluoranthene, 1- (4,4,5,5-tetramethyl -1,3,2-dioxaboranyl) acenaphthylene, 2- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) triphenylene, 6- (4,4,5,5-tetramethyl-1 , 3,2-dioxaboranyl) chrysene, 7- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) benz [a] anthracene, 9- (4,4,5,5-tetramethyl -1,3,2 Jiokisaboraniru) acridine, 2-benzofuran, 2 except for the use of benzothiophene -d7 A reaction was conducted in the same manner as in Example 7, Exemplary Compound No. 20, 34, 43, 53, 58, 64, 90, 93, 96 were produced.

<Example 17> [Exemplary Compound No. 19 Manufacturing Method]
3,5-Dibromo-tert-butylbenzene was synthesized from 4-tert-butylaniline according to the literature (J. Am. Chem. Soc. (1991), 113, 4238.).

(1) Synthesis of intermediate (3-bromo-5- {9- [N- (4-tert-butylphenyl) -N- (4-methylphenyl) amino] -10-anthryl} toluene) 3,5- Instead of dibromotoluene and 9- (N, N-bis (4-methylphenyl) amino) anthryl-10-boronic acid, 3,5-dibromo-tert-butylbenzene and 9- [N- (4-tert-butyl) (Phenyl) -N- (4-methylphenyl) amino] anthracene-10-boronic acid was used and synthesized in the same manner and scale as the intermediate synthesis of Example 7 to obtain 12.5 g of intermediate.

(2) Exemplified Compound No. Synthesis of 19 3-bromo-5- [9- (N, N-bis (4-methylphenyl) amino) -10-anthryl] toluene 3-bromo-5- {9- [N- (4-tert -Butylphenyl) -N- (4-methylphenyl) amino] -10-anthryl} toluene was synthesized by the same method and scale as the synthesis of Exemplified Compound 18 of Example 7, and silica gel column chromatography (toluene) : Heptane = 1: 3), and the exemplified compound No. 2.83 g of 19 was obtained.

<Example 18> [Exemplary Compound No. 92 manufacturing method]
In the same method and scale as in Example 17, instead of 9- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) phenanthrene , 3- (4,4,5,5-tetra using methyl-1,3,2 Jiokisaboraniru) -1-benzothiophene, silica gel column chromatography (toluene: heptane = 1: 3) to give example shows compound No. 2.13 g of 92 was obtained.

<Example 19> [Exemplary Compound No. 74 Manufacturing Method]
Under a nitrogen stream, 3-bromo-5- [9- (N, N-bis (4-methylphenyl) amino) -10-anthryl] toluene 2.71 g (6 mmol), 6- (4,4,5,5 -Tetramethyl-1,3,2-dioxaboranyl) quinoline 1.91 g (7.5 mmol) was dissolved and stirred in a mixed solvent of 80 ml of degassed toluene and 40 ml of ethanol, and 1.2 g of anhydrous sodium carbonate was added thereto. A sodium carbonate aqueous solution prepared by dissolving in 30 ml was added dropwise. After stirring for 1 hour on an oil bath heated to 50 ° C. in a nitrogen stream, 694 mg (0.6 mmol) of tetrakis (triphenylphosphine) palladium was added. The mixture was heated and stirred for about 6 hours on an oil bath heated to 80 ° C. The reaction solution was returned to room temperature, toluene, ethyl acetate and water were added, the organic layer was separated, dried over magnesium sulfate, and the solvent was distilled off. Purification by silica gel column chromatography (toluene: heptane = 1: 2) gave Exemplified Compound No. As a result, 2.31 g of 74 was obtained.

<Examples 20 to 26> [Exemplary Compound No. Method for producing 30, 40, 50, 77, 79, 80, 85]
Instead of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) quinoline, 8- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) fluoranthene 1- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) acenaphthylene, 2- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) triphenylene, 8 -(4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) -1,6-naphthyridine, 6- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) Except for using phenanthridine and 9- (4,4,5,5-tetramethyl-1,3,2-dioxaboranyl) phenanthridine, the synthesis was carried out by the same method and scale as in Example 19 and exemplified. Compound No. 30, 40, 50, 77, 79, 80, 85 were obtained.

<Example 27>
An organic light emitting device having the structure shown in FIG. 3 was prepared by the following method.

  What formed indium tin oxide (ITO) as an anode 2 with a film thickness of 120 nm on a glass substrate as a substrate 1 by a sputtering method was used as a transparent conductive support substrate. This was ultrasonically washed successively with acetone and isopropyl alcohol (IPA), then boiled and washed with IPA and then dried. Furthermore, what was UV / ozone cleaned was used as a transparent conductive support substrate.

  Using a compound represented by the following structural formula as a hole transport material, a chloroform solution was prepared so that the concentration was 0.2 wt%.

  This solution was dropped on the ITO electrode, and a film was formed by spin coating first at a rotation of 500 RPM for 10 seconds and then at a rotation of 1000 RPM for 1 minute. Thereafter, the film was dried in a vacuum oven at 80 ° C. for 10 minutes to completely remove the solvent in the thin film. The formed hole transport layer 5 had a thickness of 25 nm.

Next, as the light emitting layer 3 on the hole transport layer 5, the exemplified compound Nos. 5 was deposited to provide a 20 nm light emitting layer 3. The degree of vacuum at the time of vapor deposition was 1.0 × 10 ⁻⁴ Pa, and the film formation rate was 0.2 to 0.3 nm / sec.

Further, bathophenanthroline (BPhen) was formed as an electron transport layer 6 to a film thickness of 50 nm by vacuum deposition. The degree of vacuum during vapor deposition was 1.0 × 10 ⁻⁴ Pa, and the film formation rate was 0.2 to 0.3 nm / sec.

Next, using a vapor deposition material made of lithium fluoride (LiF) (lithium concentration 1 atomic%), a metal layer film having a thickness of 0.5 nm is formed on the organic layer by vacuum deposition, An aluminum light-emitting element having an aluminum film having a thickness of 150 nm formed by a vacuum deposition method and using an aluminum-lithium alloy film as an electron injection electrode (cathode 4) was produced. The degree of vacuum during vapor deposition is 1.0 × 10 ⁻⁴ Pa, and the film formation rate. Lithium fluoride was formed at 0.05 nm / sec, and aluminum was formed at 1.0 to 1.2 nm / sec.

  The obtained organic EL device was covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive so that the device did not deteriorate due to moisture adsorption.

In the thus obtained device, with an ITO electrode (anode 2) as a positive electrode and aluminum (cathode 4) as a negative electrode, an emission luminance of 770 cd / m ² and an emission efficiency of 7.6 lm / m ² at an applied voltage of 4.0 V. A green emission of W was observed.

Furthermore, when a voltage was applied for 100 hours while keeping the current density at 3.0 mA / cm ² in a nitrogen atmosphere, the luminance deterioration was small, 270 cd / m ² after 100 hours from the initial luminance 290 cd / m ² .

<Comparative Example 1>
Exemplified Compound No. A device was prepared in the same manner as in Example 27 except that the comparative compound shown below was used in place of 5, and the same evaluation was performed.

At an applied voltage of 4 V, green light emission with an emission luminance of 190 cd / m ² and an emission efficiency of ² lm / W was observed. Furthermore, when a voltage was applied for 100 hours while keeping the current density at 3.0 mA / cm ² in a nitrogen atmosphere, the luminance was greatly deteriorated to 26 cd / m ² after 100 hours from the initial luminance of 52 cd / m ² .

<Examples 28 to 34>
Exemplified Compound No. A device was prepared in the same manner as in Example 27 except that the compounds shown in Table 1 were used in place of 5, and the same evaluation was performed. The results are shown in Table 1.

<Example 35>
2,9-bis [2- (9,9-dimethylfluorenyl)] phenanthroline was used for the electron transport layer 6, and exemplary compound No. An organic light emitting device was prepared in the same manner as in Example 27 except that 2 was deposited.

In the thus obtained device, with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, with an applied voltage of 4 V, the emission luminance was 730 cd / m ² , and the emission efficiency was 7.1 lm. A green emission of / W was observed.

<Examples 36 to 50>
Exemplified Compound No. A device was prepared in the same manner as in Example 35 except that the compounds shown in Table 2 were used in place of 2, and the same evaluation was performed. The results are shown in Table 2.

In addition, when a voltage was applied to the devices prepared in Examples 35 and 49 for 100 hours under a nitrogen atmosphere while keeping the current density at 3.0 mA / cm ² , in Example 35, after 100 hours from the initial luminance of 270 cd / m ^2. At 260 cd / m ² , in Example 49, the luminance deterioration was small at 330 cd / m ² after 100 hours from the initial luminance of 350 cd / m ² .

It is sectional drawing which shows an example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention. It is sectional drawing which shows the other example of the organic light emitting element in this invention.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Substrate 2 Anode 3 Light emitting layer 4 Cathode 5 Hole transport layer 6 Electron transport layer 7 Hole injection layer 8 Hole / exciton blocking layer

Claims (5)

In an organic light-emitting device composed of one or more layers including an organic compound sandwiched between a pair of electrodes, each of which is a transparent or translucent anode and cathode, at least one of the layers including the organic compound is An organic light emitting device comprising at least one aminoanthryl derivative-substituted compound represented by any one of the following general formulas :

(Ar ₂ and Ar ₃ are each independently a phenyl group or a naphthyl group, and the phenyl group may have an alkyl group. R ₈ is either a hydrogen atom or a deuterium atom. ) The organic light-emitting device according to claim 1, wherein the aminoanthryl derivative-substituted compound is represented by any of the following structural formulas.

In an organic light-emitting device composed of one or more layers including an organic compound sandwiched between a pair of electrodes, each of which is a transparent or translucent anode and cathode, at least one of the layers including the organic compound is An organic light emitting device comprising at least one aminoanthryl derivative-substituted compound represented by the following general formula :

(Ar ₈ and Ar ₉ are each independently a phenyl group or a naphthyl group, and the phenyl group may have an alkyl group. R ₄ is either a hydrogen atom or a deuterium atom. Y ₁ represents a hydrogen atom or an alkyl group, and R ₆ represents either a hydrogen atom or a deuterium atom.) The organic light-emitting device according to claim 3 , wherein the aminoanthryl derivative-substituted compound is represented by any of the following structural formulas.

The organic light-emitting device according to any one of claims 1 to 4, wherein the layer containing at least one aminoanthryl derivative-substituted compound is a light-emitting layer.

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