WO2007099872A1

WO2007099872A1 - Organic electroluminescent device

Info

Publication number: WO2007099872A1
Application number: PCT/JP2007/053377
Authority: WO
Inventors: Kiyoshi Ikeda; Mitsunori Ito
Original assignee: Idemitsu Kosan Co., Ltd.
Priority date: 2006-02-23
Filing date: 2007-02-23
Publication date: 2007-09-07

Abstract

Disclosed is an organic electroluminescent device comprising a cathode, an anode, and an organic thin film which is interposed between the cathode and the anode and composed of one or more layers including a light-emitting layer. At least one layer of the organic thin film contains an indenoperylene compound represented by the formula (1) or (2) below and a compound having a fused aromatic ring having 10-50 nuclear carbon atoms.

Description

Organic electoluminescence device

Technical field

[0001] The present invention relates to an organic electoluminescence device (hereinafter abbreviated as an organic EL device).

Background art

An organic EL element is a self-luminous element that utilizes the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode when an electric field is applied.

[0003] Since Eastman 'Kodak's CW Tang et al. Reported a low-voltage driven organic EL device using a stacked device (see Non-Patent Document 1), research on organic EL devices composed of organic materials Is actively performed.

[0004] Tang et al. Employ a laminated structure in which tris (8-quinolinol) aluminum is used for the light-emitting layer and triphenyldiamine derivative is used for the hole-transporting layer. The advantages of the stacked structure are that the efficiency of hole injection into the light-emitting layer can be increased, the efficiency of excitons generated by recombination by blocking electrons injected into the cathode can be increased, and light emission For example, excitons generated in the layer can be confined. As shown in this example, the organic EL device has an element structure of a hole transport (injection) layer, a two-layer type of an electron transport light-emitting layer, or a hole transport (injection) layer, a light-emitting layer, an electron transport (injection). The three-layer structure of the) layer is well known. In such a multilayer structure element, various improvements have been made to the element structure and the formation method in order to increase the recombination efficiency of injected holes and electrons.

[0005] Patent Document 1 discloses an element using a dicyananthracene derivative and an indenoperylene derivative as a light emitting layer and a metal complex as an electron transporting layer. However, since the CIE chromaticity was (0. 63, 0.37), the emission color was reddish orange rather than pure red. In this element, holes penetrating the light emitting layer are injected into the electron transport layer, and as a result, even if the! There was a bad chromaticity caused by the slight emission of light. In addition, the electron transport layer with low hole durability deteriorates. As a result, the lifetime was significantly shortened.

Patent Document 2 discloses a red device using a naphthacene derivative and an indenoperylene derivative as a light emitting layer and a naphthacene derivative as an electron transport layer. This device also has a practical life with high color purity. However, this device requires two organic layers (an electron transport layer and an electron injection layer) that have a separate function between the light emitting layer and the cathode in order to improve color purity and extend the life, and the device structure is complicated. there were.

Patent Document 3 proposes a light emission preventing layer having a band gap larger than that of the light emitting layer and the electron transport layer in order to suppress light emission of the electron transport layer. However, this light emitting device has insufficient luminous efficiency of about lcdZA.

Patent Document 1: Japanese Patent Laid-Open No. 2001-307885

Patent Document 2: Japanese Patent Laid-Open No. 2003-338377

Patent Document 3: Japanese Patent Laid-Open No. 2005-235564

Non-Patent Document 1: C. W. Tang, S. A. Vanslyke, Applied Physics Letters, 51 卷, 913, 1987

[0008] The present invention has been made in view of the above-described problems, and an object thereof is to provide an organic EL device having good color purity and practical luminous efficiency and lifetime.

Disclosure of the invention

As a result of diligent research to solve the above-mentioned problems, the present inventors have obtained light emission by forming an organic thin film layer by combining a specific indenoperylene compound and a compound having a specific condensed aromatic ring. The present invention has been completed by finding that the efficiency and lifetime are improved.

[0010] According to the present invention, the following organic EL device is provided.

1. Cathode and anode,

An organic thin film layer having a single layer or multiple layer strength including a light emitting layer between them, and at least one of the organic thin film layers is an indenoperylene compound represented by the following formula (1) or formula (2), and An organic electoluminescence device containing a compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms.

[Chemical 1]

[Where

Ar ² and Ar ³ are each independently a substituted or unsubstituted aromatic group or aromatic heterocyclic group, χ′-χ ¹⁸ », each independently hydrogen, halogen, alkyl group, alkoxy group, alkylthio group, Alkenyl group, alkoxy group, alkenyl group, aromatic ring-containing alkyl group, aromatic ring-containing alkyloxy group, aromatic ring-containing alkylthio group, aromatic ring group, aromatic heterocyclic group, aromatic ring oxy group, Aromatic ring thio group, aromatic alkenyl group, alkenyl aromatic ring group, amino group, carbazolyl group, cyano group, hydroxyl group, CO OR ¹ ′ (R ¹ ′ is hydrogen, alkyl group, alkenyl group, aromatic ring-containing alkyl Or —COR ² ′ (R ² ′ is hydrogen, an alkyl group, an alkenyl group, an aromatic ring-containing alkyl group, an aromatic ring group or an amino group), or —OCOR ³ (R ³ ′ includes alkyl, alkenyl, and aromatic rings. An alkyl group or an aromatic ring group). Adjacent groups of ^1-8 may be bonded to each other to form a ring together with the carbon atom substituted. At least one of ~ ⁸ is not hydrogen. )

2. The organic electroluminescent device according to 1, wherein the indenoperylene compound is a dibenzotetraphenylperifuranthene derivative.

3. The organic electroluminescent device according to 1 or 2, wherein the compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms is a naphthacene derivative represented by the following formula (I).

[Chemical 2]

Each independently represents a hydrogen atom, a substituted or unsubstituted carbon number] 20 alkyl groups, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 50 carbon atoms, amino groups, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms 1 to 20 alkylthio groups, substituted or unsubstituted aryloxy groups having 6-20 carbon atoms, substituted or unsubstituted aryloxy groups having 6-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms A substituted or unsubstituted aralkyl group having 7 to 20 nuclear carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms, which may be the same or different, and adjacent to each other May form a saturated or unsaturated cyclic structure. ]

4. In the formula ^{(I), Q \ Q 2} , Q 3 and at least one organic elect port device as claimed in 3 is an aromatic hydrocarbon group Q ^4.

5. The organic electoluminescence device according to 3 or 4, wherein the naphthacene derivative represented by the formula (I) has a structure represented by the following formula (Π).

[Chemical 3]

[Wherein Q ^{3 to} Q ¹² , QQ ¹⁰⁵ and Q ^{2C> 1 to} Q ⁵ each independently represent the same group as Q ^ Q ¹² and adjacent to each other, which may be the same or different. And may form a saturated or unsaturated cyclic structure. ] 6. In the formula (Π), at least one of Q ¹⁰¹ , Q ¹⁰⁵ , Q ²⁰¹ and Q ²⁰⁵ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted nuclear carbon number of 6 to 50. Aromatic hydrocarbon groups, amino groups, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio groups having 1 to 20 carbon atoms, substituted or unsubstituted nuclear carbon numbers 6 to 20 aryloxy groups, substituted or unsubstituted aryloxy groups having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 20 carbon atoms, 6. The organic electroluminescent device according to 5, which is a substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms.

7. The compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms is represented by an anthracene derivative represented by the following formula (3), an asymmetric anthracene derivative represented by the following formula (4), or the following formula (5): 3. The organic electoluminescence device according to 1 or 2, which is an asymmetric pyrene derivative, an asymmetric diphenylanthracene derivative represented by the following formula (6), or a bispyrene derivative represented by the following formula (7).

[Chemical 4]

[In the formula (3), X ^{19 to} X ²¹ are each a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 5 to 50 nuclear carbon atoms. Group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or Unsubstituted aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms 1 to 50 alkoxycarbonyl groups, substituted or unsubstituted silyl groups, force carboxyl groups, halogen atoms, cyano groups, nitro groups or hydroxyl groups. Ar ⁴ and Ar ⁵ is each independently a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms, and at least one of Ar ^{4 and} Ar ⁵ is a 1 naphthyl derivative represented by the following formula (3a) or It is a 2-naphthyl derivative represented by the following formula (3b).

[Chemical 5]

1 ~! ^ ⁷ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms! At least one pair of ^ ˜ adjacent to each other may be bonded to each other to form a ring structure. )

a, b and c are each an integer of 0 to 4, and d is an integer of 1 to 3. When d is 2 or more, the numbers in [] may be the same or different. ]

[Chemical 6]

X

Y (4)

[In Formula (4), A ¹ and A ² are each independently a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 20 nuclear carbon atoms, Ar ⁶ and Ar ⁷ are each independently , A hydrogen atom, or a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and R ^{8 to} R ¹⁵ each independently represent a hydrogen atom, a substituted or unsubstituted nuclear carbon number of 6 to 50 aromatic charcoal Hydrogenated cyclic group, substituted or unsubstituted aromatic heterocyclic group having 5 to 50 carbon atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted carbon group having 3 to 50 carbon atoms A cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or An unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbon group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a force carboxyl group, a halogen atom, a cyano group, a nitro group, or R ¹⁶ and R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted nuclear carbon group having 5 to 50 carbon atoms. Aromatic heterocyclic group, substituted Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted group. Aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted 1 to 50 carbon atoms An alkoxycarbo group, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group. Ar R ¹⁶ and R ¹⁷ may be bonded to a plurality of Α ¹ or Α ² or adjacent to each other to form a saturated or unsaturated cyclic structure. However, there is no case where a group which is symmetrical with respect to the Χ-Υ axis shown on the anthracene is bonded to the 9th and 10th positions of the central anthracene. ]

[Chemical 7]

[In formula (5), Ar ⁸ and Ar ⁹ are each a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms. L ¹ and L ² are each a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzosilolylene group. It is. m is an integer from 0 to 2, n is an integer from 1 to 4, s is an integer from 0 to 2, and t is an integer from 0 to 4. L ¹ or Ar ⁸ is bonded to any of the 1-5 positions of pyrene, and L ² or Ar ⁹ is bonded to any of the 6-10 positions of pyrene.

However, when n + t is an even number, Ar ⁸ , Ar ⁹ and L \ L ² satisfy the following (1) or (2).

(1) Ar ⁸ ≠ Ar ⁹ and / or LL ² (where ≠ indicates a group having a different structure)

(2) When Ar ⁸ = Ar ⁹ and L ¹ = L ²

(2—l) m ≠ s and / or n ≠ t, or

(2-2) When m = s and n = t,

(2-2—DL ¹ and L ² or pyrene are bonded to different bonding positions on Ar ⁸ and Ar ⁹ respectively,

(2-2-2) 1 ^ and 1, or pyrene is, if bonded to the same position of Ar ⁸ and Ar ^9, L ¹ and L ^2, or substitution position of pyrene Ar ⁸ and Ar ⁹ Are never symmetric. ]

[Chemical 8]

[In the formula (6), Ar ¹ "and Ar ¹¹ are each independently a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and m 'and n are each 1 to It is an integer of 4. However, if m, = n, = 1, and the bonding position of Ar ^1G and Ar ^{11 to} the benzene ring is symmetrical, Ar ^1G and Ar ¹¹ are not the same m, or When n 'is an integer from 2 to 4, m and n' are different integers. R ^{18 to} R ²⁵ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear carbon atoms. Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted Aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted alkoxy having 1 to 50 carbon atoms A carbonyl group, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group.

R ²⁶ and R ²⁷ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or An unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 to 50 aryloxy group, substituted or unsubstituted aryloxy group having 50 to 50 carbon atoms, substituted or unsubstituted alkoxycarbon group having 1 to 50 carbon atoms, substituted or unsubstituted silyl group, carboxyl group, A halogen atom, a cyano group, a nitro group or a hydroxyl group; ]

(A ³ ) ― (X ²² ) ― (Ar ¹² ) ― (Y ¹ ) ― (B ¹ ) (7)

e f g h l

[In Formula (7), X ²² each independently represents a substituted or unsubstituted pyrene residue, and A ³ and B ¹ each independently represent a hydrogen atom, a substituted or unsubstituted nuclear carbon number of 3 -50 aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group having 1 to 50 carbon atoms, substituted or unsubstituted alkyl group or alkylene group having 1 to 50 carbon atoms, substituted or unsubstituted Ar ¹² is a substituted or unsubstituted alkenyl group or alkellene group having 1 to 50 carbon atoms, each independently substituted or unsubstituted aromatic hydrocarbon group having 3 to 50 nuclear carbon atoms, or substituted. Is an unsubstituted aromatic heterocyclic group having 1 to 50 nuclear carbon atoms, and Y ¹ is independently a substituted or unsubstituted aryl group. f is an integer of 1 to 3, e and i are each independently an integer of 0 to 4, h is an integer of 0 to 3, and g is an integer of 1 to 5. ]

8. The compound having a condensed aromatic ring having 10-50 nuclear carbon atoms is represented by the following formula (8): The organic electoluminescence device according to 1 or 2, wherein the compound is a compound.

X ^23- (Y ² ) (8)

j

[Wherein X ²³ is a condensed aromatic ring group having 2 or more carbon rings, and Y ² is independently a substituted or unsubstituted aryl group, a substituted or unsubstituted dialyl amino group, a substituted or unsubstituted alkyl group, A reel alkyl group or a substituted or unsubstituted alkyl group. j is 1 ~

It is an integer of 6. When j is 2 or more, Y ² may be the same or different. ]

X ²³ 9. Formula (8) is, naphthacene, pyrene, benzo-anthracene, pentacene, self - supplied zo anthracene, benzopyrene, Benzofunore old Ren, Funore old Ranten, Benzofunore old run Teng, naphthyl fluoranthene, dibenzo fluorene, dibenzopyrene 9. The organic electroluminescent device according to 8, wherein a compound having a carbocyclic force selected from the group consisting of dibenzofluoranthene and acenaphthylfluoranthene is used.

10. Compound power represented by the above formula (8) Naphthacene derivative, anthracene derivative, benzoanthracene derivative, dibenzoanthracene derivative, pentacene derivative, bisanthracene derivative, pyrene derivative, bispyrene derivative, benzopyrene derivative, dibenzopyrene derivative, fluorene derivative , Benzofluorene derivatives, dibenzofluorene derivatives, fluoranthene derivatives, benzofluoranthene derivatives, dibenzofluoranthene derivatives, naphthylfluoranthene derivatives, acenaphthylfluoranthene derivatives, diaminoanthracene derivatives, naphthofluoranthene derivatives, Selected from the group consisting of diaminobilene derivatives, diaminoperylene derivatives, dibenzidine derivatives, aminoanthracene derivatives, aminobilene derivatives and dibenzochrysene derivatives. 9. The organic electroluminescent device according to 8, which is one or more compounds.

11. The organic electroluminescent device according to any one of 1 to 10, wherein the light-emitting layer contains the indenoperylene compound and a compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms.

12. The organic electroluminescent device according to any one of 1 to 11, wherein the organic thin film layer includes an electron transport layer, and the electron transport layer contains an aromatic hydrocarbon compound represented by the following formula (9): .

A ⁴ -B ² (9) [In the formula (9), A ⁴ is an aromatic hydrocarbon group having 2 or more carbon rings, and B ² is a substituted or unsubstituted heterocyclic group. )

A ⁴ force anthracene 13. Formula (9), Fuenantoren, naphthacene, pyrene, Tarisen, benzanthracene, pentacene, dibenzoanthracene, benzopyrene, fluorene, Baie Nzofuruoren, fluoranthene, benzofluoranthene, naphthoquinone source fluoranthene, Jibe 13. The organic electroreductive element according to 12, which is a heterocyclic compound having in its molecule one or more skeletons selected from the group consisting of nzofluorene, dibenzopyrene and dibenzofluoranthene.

14. The compound power represented by the above formula (9) The organic electoluminescence device according to 12 or 13, which is a nitrogen-containing heterocyclic compound.

15. The organic electroluminescent device according to 14, wherein the nitrogen-containing heterocyclic compound is a compound represented by the following formula (10) or formula (11).

[Chemical 9]

[In the formula, each R is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted carbon. An alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, k is an integer of 0 to 4, and R ²⁷ is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. R ²⁸ is a hydrogen atom, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms. Atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, A substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, L ³ Is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted quinolylene group or a substituted or unsubstituted fluorenylene group, Ar ¹³ Is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted quinolinylene group. ]

16. A compound having one or more skeletons in which the nitrogen-containing heterocyclic compound is selected from the group power of pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinoxaline, atalidine, imidazopyridine, imidazopyrimidine and phenanthrolinca 14. The organic electoluminescence device according to 14.

17. The organic electroluminescence device according to any one of 1 to 16, wherein the emission color is orange to red.

18. The light emitting layer contains a dopant material, the concentration of the dopant material occupied in the luminescent layer is 0.5 1 to 10 weight ^_0/0 1 17!, Organic elect port device as claimed in one shift.

19. The organic elect opening device as described in the concentration from 0.5 to 2 weight of the dopant material ^_0/0, which is 18.

According to the present invention, an organic EL device having excellent color purity and luminous efficiency and having a long lifetime can be provided.

Brief Description of Drawings

FIG. 1 is a diagram showing an embodiment according to an organic EL element of the present invention.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the organic EL device of the present invention will be specifically described.

The organic EL device of the present invention includes a cathode and an anode, and an organic thin film layer composed of one or more layers including a light emitting layer between these electrodes.

FIG. 1 is a cross-sectional view showing an example of the organic EL device of the present invention.

The organic EL element 1 has an anode 20, a hole injection layer 30, a hole transport layer 40, a light emitting layer on a substrate 10. 50, an electron transport layer 60, an electron injection layer 70, and a cathode 80 are stacked in this order. In this element, the organic thin film layers are a hole injection layer 30, a hole transport layer 40, a light emitting layer 50, an electron transport layer 60 and an electron injection layer 70.

In the present invention, at least one of the organic thin film layers comprises an indenoperylene compound (compound A) represented by the following formula (1) or (2) and a condensed aromatic ring having 10 to 50 nuclear carbon atoms. A compound (compound B) having By using these compounds in combination, a highly efficient red light-emitting organic EL device with excellent color purity can be obtained.

[0015] [Chemical 10]

[Where

Ar ² and Ar ³ are each independently a substituted or unsubstituted aromatic group or aromatic heterocyclic group, χ′-χ ¹⁸ », each independently hydrogen, halogen, alkyl group, alkoxy group, alkylthio group, Alkenyl group, alkoxy group, alkenyl group, aromatic ring-containing alkyl group, aromatic ring-containing alkyloxy group, aromatic ring-containing alkylthio group, aromatic ring group, aromatic heterocyclic group, aromatic ring oxy group, Aromatic ring thio group, aromatic alkenyl group, alkenyl aromatic ring group, amino group, carbazolyl group, cyano group, hydroxyl group, CO OR ¹ ′ (R ¹ ′ is hydrogen, alkyl group, alkenyl group, aromatic ring-containing alkyl Or —COR ² ′ (R ² ′ is hydrogen, an alkyl group, an alkenyl group, an aromatic ring-containing alkyl group, an aromatic ring group or an amino group), or OCOR ³ ′. (R ³ 'is an alkyl group, Aruke - group, aromatic ring-containing An alkyl group or an aromatic ring group). Adjacent groups of to ¹⁸ may be bonded to each other to form a ring together with the carbon atom substituted. At least 1 to ¹ ⁸ is not hydrogen. )

Preferable examples of 8 to 8 are a substituted or unsubstituted phenyl group, naphthyl group, anthral group, and phenanthryl group.

Preferred examples of (1) to ( ¹⁸ ) include substituted or unsubstituted phenyl group, biphenyl group, Examples include a phenyl group, a methyl group, an ethyl group, a propyl group, a butyl group, and a cyclohexyl group.

[0017] As the compound A, a dibenzotetraphenylperifuranthene derivative is particularly preferable.

The number of carbon atoms in the basic skeleton of compound A is preferably 45 to: L00. If it is less than 45, the heat resistance may be inferior, and if it is greater than 100, the vapor pressure will be insufficient when the device is fabricated, so it may not be possible to form a film by vapor deposition, or it may be difficult to adjust the solution. Therefore, there is a possibility that the film formation by this becomes difficult.

Specific examples of Compound A are shown below. These compounds can be synthesized with reference to, for example, JP-A-10 330295.

[0018] [Chemical 11]

[0019] [Chemical 12]

91 ·

LL £ ^ 0 / LOOZd / lDd Z.8660 / .00Z OAV

Li

LL £ iSO / LOOZdtll d Z.8660 / .00Z ΟΛ

81 ·

.. £ CS0 / L00ldf / X3d 8660 / Δ00Ζ OAV

61 ·

LL £ tS0 / L00ZdT / 13d [0020] In the compound (compound B) having a condensed aromatic ring having 10 to 50 nuclear carbon atoms, examples of the condensed aromatic ring having 10 to 50 nuclear carbon atoms include anthracene, phenanthrene, pyrene and talisene. , Triphenylene, perylene and the like, and anthracene and pyrene are preferable.

[0021] The compound B is preferably a naphthacene derivative represented by the following formula (I).

[Chemical 13]

[0022] [In Formula (I), Q ^ Q ¹² ^, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms. Group hydrocarbon group, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted nucleus group having 6 to 20 carbon atoms A reeloxy group, a substituted or unsubstituted aryloxy group having 6 to 20 nuclear carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 nuclear carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms, which may be the same or different, and those in contact with each other may form a saturated or unsaturated cyclic structure. ]

In the formula (I), examples of the groups (^ to ² ) include the same examples as those mentioned for Xi X ¹⁸ in the formulas (1) and (2).

Examples of saturated or unsaturated cyclic structures formed by adjacent ones include the following examples.

[0023] [Chemical 14]

In the formula (I), it is preferable that at least one of Q \ QQ ³ and Q ⁴ is an aromatic hydrocarbon group.

[0025] The naphthacene derivative represented by the formula (I) preferably has a structure represented by the following formula (I).

[Chemical 15]

[In the formula (Π), Q ^{3 to} Q ¹² , Q ^ Q ¹⁰⁵ and Q ^{201 to} Q ² . ⁵ each independently represents the same group as Q ¹ ^ ² described above, and may be saturated with adjacent ones that may be the same or different. Alternatively, an unsaturated cyclic structure may be formed. ]

In the formula (式), Q ^{3 to} Q ¹² , Q ^{101 to} Q ¹⁰⁵ and Q ^{201 to} Q ² . Examples of each group of ⁵ include the same examples as those described in the formulas (1) and ( ¹⁸ ) to ¹⁸ above. Examples of the cyclic structure include the same examples as in formula (I).

In the formula (Π), at least one of Q ¹⁰ \ Q ¹⁰⁵ , Q ²⁰¹ and Q ² ° ⁵ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted nuclear carbon number of 6 to 50 Aromatic hydrocarbon group, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted nuclear carbon number 6 to 20 aryloxy group, substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms is preferred.

[0027] Further, Compound B includes an anthracene derivative represented by the following formula (3), an asymmetric anthracene derivative represented by the following formula (4), an asymmetric pyrene derivative represented by the following formula (5), An asymmetric diphenylanthracene derivative represented by 6) or a bispyrene derivative represented by the following formula (7) is preferred.

[0028] [Chemical 16]

[In the formula (3), X ^{19 to} X ²¹ are each a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 5 to 50 nuclear carbon atoms. Group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or Unsubstituted aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms Roxy group, substituted or unsubstituted arylenethio group having 5 to 50 carbon atoms, substituted or unsubstituted alkoxycarbon group having 1 to 50 carbon atoms, substituted or unsubstituted silyl group, force ruxyl group, halogen atom, cyano A group, a nitro group or a hydroxyl group. Ar ⁴ and Ar ⁵ are each independently a condensed aromatic group substituted or unsubstituted aromatic ring group having 10 to 50, at least one of Ar ⁴ and Ar ^5, represented by the following formula (3a) 1 A naphthyl derivative or a 2-naphthyl derivative represented by the following formula (3b).

[Chemical 17]

1 to! ^ ⁷ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one adjacent pair of R ¹ ! ^ Is bonded to each other to form a cyclic structure. May be formed. )

Examples of the aromatic hydrocarbon group represented by X ^{19 to} X ²¹ include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2 anthryl group, 9 anthryl group, 9- (10 phenol). Anthryl group, 9- (10-naphthyl-1-yl) anthryl group, 9 (10-naphthyl-2-yl) anthryl group, 1-phenanthryl group, 2 phenanthryl group, 3 phenanthryl group, 4 phenanthryl group, 9 thiol group Nantryl group, 6 chrysyl group, 1 naphthasel group, 2 naphthasel group, 9 naphthasel group, 1-pyrole group, 2 pyrel group, 4-pyrole group, 2 biphenyl group , 3 biphenyl group, 4-biphenyl group, p terferu 4-l group, p terferu group 3 — yl group, p terferu group 2 — yl group, m-terferu group 4— Myl, m-Turfer-Leu 3—Yel, m-Turfer-Lu 2— Group, o-tolyl group, m-tolyl group, ρ-tolyl group, p-t-butylphenyl group, 3-methyl-2-naphthyl group, 4-methyl-1 naphthyl group, 4-methyl-1 anthryl group and the like. Examples of the aromatic heterocyclic group include 1 pyrrolyl group, 2 pyrrolyl group, 3 pyrrolyl group, pyradyl group, 2-pyridinyl group, 1 imidazolyl group, 2-imidazolyl group, 1 virazolyl group, 1-indolidyl group. , 2—Indosyl group, 3—Indosyl group, 5—Indosyl group, 6 Indosyl group, 7 Indosyl group, 8 Indosyl group, 2 Imidazopyridyl group, 3— Imidazopyridyl group, 5-Imidazopyridyl group, 6-Imidazopyridyl group, 7-Imidazopyridyl group, 8-Imidazopyridyl group, 3-Pyridyl group, 4 Pyridyl group, 1 Indolyl group , 2 indolyl group, 3 indolyl group, 4 indolyl group, 5—indolyl group, 6—indolyl group, 7—indolyl group, 1—isoindolyl group, 2—isoindolyl group, 3—isoindolyl group, 4 isoindole group Group, 5—isoindolyl group, 6—isoindolyl group, 7 isoindolyl group, 2 furyl group, 3 furyl group, 2 benzofural group, 3—benzofural group, 4 benzofural group, 5— Benzofuller group, 6-Benzofuller group, 7 Benzofuller group, 1 Isobenzofural group, 3 Isobenzofural group, 4 Isobenzofural group, 5-Isobenzolfuran -Lole group, 6-isobenzofural group, 7-isobenzofural group, 2 quinolyl group, 3 quinolyl group, 4 quinolyl group, 5 quinolyl group, 6 quinolyl group, 7 quinolyl group, 8 quinolyl group, 1 isoquinolyl group, 3 isoquinolyl group, 4 isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8 isoquinolyl group, 2 quinoxalinyl group, 5 quinoxalinyl group, 6 quinoxalyl group, 1 Rubazolyl group, 2—force Basolyl group, 3—force rubazolyl group, 4 1 force rubazolyl group, 9 1 force rubazolyl group, j8—carboline 1 yl, j8—carboline 3 yl, j8—carboline—4 yl, j8—carboline— 5 —Yl, j8—carboline— 6—yl, 13 carboline—7 jyl, j8—carboline, 6 jyl, j8—carboline, 9 yyl, 1 phenanthridyl group, 2 phenanthridyl group, 3 phenanthridyl group 4 Phenyl rigid group, 6-Phenandyl group, 7-Phenandyl group, 8-Phenandyl group, 9 Phenidyl group, 10 Phenidyl group, 1-Attalidyl group, 2 Ataridyl group, 3 Ataridyl group, 4 Ataridyl group, 9 Ataridyl group, 1, 7 Phenylthroline— 2-yl group, 1, 7 Phenylanthrolin— 3-yl group, 1, 7 — Phenylthroline 1 4-yl group, 1, 7 Surorin one 5-I group, 1, 7 Fuena Nsurorin one 6-I group, 1, 7 Fuenansurorin one 8-I group, 1, 7 Fuenansurorin —9—yl group, 1,7 phenanthroline—10—yl group, 1,8 phenanthroline—2—yl group, 1,8 phenanthroline—3—yl group, 1,8 phenanthroline—4-yl group 1, 8 phenanthroline 5-yl group, 1, 8 phenanthroline 6-yl group, 1, 8 phenanthroline 7-yl group, 1, 8 phenanthroline 9-yl group, 1, 8 phenanthrene Mouth phosphorus—10—yl group, 1,9 phenanthroline—2-yl group, 1,9 phenanthroline—3—yl group, 1,9 phenanthroline—4-yl group, 1,9 phenanthroline—5-— 1, 9 phenanthroline-6-yl group, 1,9 phenanthroline-7-yl group, 1,9-phenanthroline 1-8-yl group, 1,9 phenanthroline 1-10-yl group, 1, 10 Phenanthroline—2-yl group, 1, 10 Phenanthroline—3-yl group, 1, 10 Phenol Scan port Phosphorus - 4-I group, 1, 10 Fuenansurorin - 5-I group, 2, 9 Fuenansurorin -

1—yl group, 2, 9 phenanthroline— 3—yl group, 2, 9 phenanthroline—4—yl group, 2, 9 phenanthroline—5—yl group, 2, 9 phenanthroline—— Group, 2, 9 —phenanthroline 1—yl group, 2, 9 phenanthroline 1—yl group, 2, 9 phenanthroline 1—yl group, 2, 9 phenanthroline 1—yl group, 2,8 phenanthroline—3-yl group, 2,8 phenanthroline—4-yl group, 2,8 phenanthroline—5-yl group, 2,8 phenanthroline 6-yl group, 2,8 phenanthroline one 7-yl group, 2, 8 phenanthroline 9-yl group, 2, 8 phenanthroline 10-yl group, 2, 7- phenanthroline 1-yl group, 2, 7 phenanthroline 1-yl group , 2, 7-phenanthroline—4-yl group, 2, 7 phenanthroline—5-yl group, 2,7 phenanthrene Lorin-6-yl, 2, 7 phenanthroline-8-yl, 2,7 phenanthroline-9-yl, 2,7 phenanthroline 10-yl, 1 phenadyl, 2 phenadyl Group, 1 phenothiazyl group, 2 phenothiazyl group, 3 phenothiazyl group, 4-phenothiazyl group, 10-phenothiazyl group, 1 phenoxazyl group, 2-phenoxazyl group, 3 Phenoxazyl group, 4 Phenoxazyl group, 10 Phenoxazyl group, 2-Oxazolyl group, 4-Oxazolyl group, 5-Oxazolyl group, 2-Oxadiazolyl group, 5 Oxadiazolyl group, 3 Frazazal group, 2 Group, 3 chael group,

2-methyl pyrrole 1-yl group, 2-methyl pyrrole 3-yl group, 2-methyl pyrrole 4-yl group, 2-methyl pyrrole 5-yl group, 3-methyl pyrrole 1-yl group, 3 methyl pyrrole 2-yl group, 3 methyl pyrrole 4-yl group, 3 methyl pyrrole 5-yl group, 2-t-butyl pyrrole 4-yl group, 3— (2 propyl) pyrrole 1 -Yl group, 2-methyl-1 indolyl group, 4-methyl-1 indolyl group, 2-methyl-3 indolyl group, 4-methyl-3 indolyl group, 2 tbutyl 1 indolyl group, 4 tbutyl1 indolyl group, 2 tbutyl3 indolyl group, 4 t-butyl 3-indolyl group and the like can be mentioned.

[0031] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, and n. —Heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3 dihydroxyisopropyl group, 2,3 dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group,

2 Black mouth isobutyl group, 1, 2 dichloroethyl group, 1, 3 dichloroisopropyl group, 2,

3 Dichloro-t-butyl group, 1, 2, 3 Trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3 dibromoisopropyl group , 2, 3 Jib mouth tert-butyl group, 1, 2, 3 tribromopropyl group, odomethyl group, 1- odoethyl group, 2- odoethyl group, 2- odoisobutyl group, 1,2 jordoethyl group, 1,3 jordo Isopropyl group, 2, 3 Jododo t-butyl group, 1, 2, 3 Triodopropyl group, Aminomethyl group, 1-Aminoethyl group, 2 Aminoethyl group, 2 Aminoisobutyl group, 1, 2 Diamino Ethyl group, 1,3 diaminoisopropyl group, 2,3 diamino-tert-butyl group, 1,2,3 triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-si group Noisobutyl group, 1,2 dicyanethyl group, 1,3 dicyananoisopropyl group, 2,3 dicyanote t-butyl group, 1,2,3 tricyanopropyl group, nitromethyl group, 1--troethyl group, 2-troeth Examples include til group, 2-troisobutyl group, 1,2 di-troethyl group, 1,3 di-troisopropyl group, 2,3 dinitro-t-butyl group, 1,2,3 tri-tropropyl group, etc. Be

[0032] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, and a cyclopente. Examples include a til group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1 norbornyl group, and a 2-norbornyl group.

The substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms is a group represented by —OY, and examples of Y include the same examples as those described for the alkyl group.

[0033] Examples of the aralkyl group include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, and a phenyl-tert-butylene group. , A naphthinoremethinole group, 1-a naphthinoreethinole group, 2-a naphthinoreethyl group, 1 α naphthylisopropyl group, 2—a naphthylisopropyl group, β naphthylmethyl group, 1—β naphthylethyl group, 2- β-naphthylethyl, 1 β-naphthylisopropyl, 2-β-naphthylisopropyl, 1-pyrrolylmethyl, 2- (1 pyrrolyl) ethyl, ρ-methylbenzyl, m-methylbenzyl, o-methylbenzenole Group, p-chlorobenzene, m-chlorobenzene, o-chlorobenzene, p-bromobenzyl, m-bromobenzyl, o bromobenzyl P podobenzyl group, m-podobenzyl group, o podobenzyl group, p hydroxybenzyl group, m-hydroxybenzyl group, o hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-Nitrobenzyl group, m-Nitrobenzyl group, o-Nitrobenzyl group, p-Cyanobenzyl group, m-Cyanobenzyl group, o Cyanobenzyl group, 1-Hydroxy-2-phenylisopropyl group, 1-Chloro One example is 2-phenol isopropyl group.

[0034] The aryloxy group is represented as OY ', and examples of Y' include the same examples as the aromatic hydrocarbon group and aromatic heterocyclic group.

The arylthio group is represented by —SY ′, and examples of Y ′ include the same examples as the aromatic hydrocarbon group and aromatic heterocyclic group.

The alkoxycarbonyl group is a group represented by COOY, and examples of Y include the same examples as those described for the alkyl group.

Examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a butyldimethylsilyl group, and a propyldimethylsilyl group.

[0035] Examples of the condensed aromatic ring group of Ar ⁴ and Ar ⁵ include naphthalene, anthracene, and phena. And enanthene, pyrene, taricene, triphenylene and perylene.

Examples of the alkyl group of I ^ to R ⁷ include the same examples as those described for X ^{19 to} X ²¹ . Examples of the cyclic structure formed by R ^{1 to} R ⁷ include cycloalkanes having 4 to 12 carbon atoms such as cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, and the like.

X

Y (4)

[In Formula (4), A ¹ and A ² are each independently a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 20 nuclear carbon atoms, Ar ⁶ and Ar ⁷ are each independently , A hydrogen atom, or a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and R ^{8 to} R ¹⁵ each independently represent a hydrogen atom, a substituted or unsubstituted nuclear carbon number of 6 to 50 aromatic hydrocarbon ring group, substituted or unsubstituted aromatic heterocyclic group having 5 to 50 carbon atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted carbon A C3-C50 alkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms Roxy group, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted Prime 1-50 alkoxycarbonyl - group, a substituted or unsubstituted silyl group, a force carboxyl group, a halogen atom, Shiano group, a nitro group or a hydroxyl group, R ¹⁶ and R ¹⁷ each independently represent a hydrogen atom Substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted aromatic heterocyclic group group having 5 to 50 nuclear carbon atoms, substituted Or an unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon Aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted alkoxy having 1 to 50 carbon atoms A carbo group, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyan group, a nitro group or a hydroxyl group. Ar R ¹⁶ and R ¹⁷ may be bonded to a plurality of Α ¹ or Α ² or adjacent to each other to form a saturated or unsaturated cyclic structure. However, there is no case where a group which is symmetrical with respect to the Χ-Υ axis shown on the anthracene is bonded to the 9th and 10th positions of the central anthracene. ]

[0037] Examples of the condensed aromatic rings Α ¹ and Α ² include those in which the number of carbons is suitable among the examples given for Ar ⁴ and Ar ⁵ in the formula (3).

Examples of groups of Ar ⁶ , Ar ⁷ and R ^{8 to} R ¹⁷ , Ar ⁶ ,

Examples of the cyclic structure that R ¹⁶ and R ¹⁷ may form include cycloalkanes having 4 to 12 carbon atoms such as cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, cyclobutene, cyclopentene, and cyclohexane. C4-C12 cycloalkene such as hexene, cycloheptene, cyclootaten, etc., cyclohexacene, cyclohexadiene, cyclooctagen, etc.C6-C12 cyclorecadien, benzene, naphthalene, phenanthrene, anthracene, pyrene And aromatic rings having 6 to 50 carbon atoms such as talisene and acenaphthylene, and heterocyclic rings having 5 to 50 carbon atoms such as imidazole, pyrrole, furan, thiophene and pyridine.

[0038] [Chemical 19]

(() _n

10 1 I [In Formula (5), Ar ⁸ and Ar ⁹ are each a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, and L ¹ and L ² are each a substituted or unsubstituted phenylene group. A substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorenylene group, and a substituted or unsubstituted dibenzosilolylene group. m is an integer from 0 to 2, n is an integer from 1 to 4, s is an integer from 0 to 2, and t is an integer from 0 to 4. L ¹ or Ar ⁸ is bonded to any of the 1-5 positions of pyrene, and L ² or Ar ⁹ is bonded to any of the 6-10 positions of pyrene.

However, when n + t is an even number, Ar ⁸ , Ar ⁹ ,

L ² satisfies the following (1) or (2).

(2) When Ar ⁸ = Ar ⁹ and L ¹ = L ²

(2—l) m ≠ s and / or n ≠ t, or

(2-2) When m = s and n = t,

[0039] aromatic hydrocarbon group Ar ⁸ and Ar ^9, examples of the aromatic heterocyclic group include those exemplified the same groups in formula (3).

[0040] [Chemical 20]

[In the formula (6), Ar ¹ "and Ar ¹¹ are each independently a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and m 'and n are each 1 to An integer of 4 provided that , M, = n, = 1 and when Ar ^lu and Ar ¹¹ bond to the benzene ring is symmetrical, Ar ^1G and Ar ¹¹ are not the same m, or n 'is 2-4 In the case of integers, m and n 'are different integers.

R ^{18 to} R ²⁵ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear carbon atoms. Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted Aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted alkoxy having 1 to 50 carbon atoms A carbonyl group, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group.

[0041] Examples of each group of Ar ^1G , Ar ¹¹ and R ^{18 to} R ²⁷ include the same examples as those given in formula (3).

[0042] (A ³ )-(X ²² )-(Ar ¹² )-(Y ¹ )-(B ¹ ) (7)

e f g h i

[In Formula (7), X ²² each independently represents a substituted or unsubstituted pyrene residue, and A ³ and B ¹ each independently represent a hydrogen atom, a substituted or unsubstituted nuclear carbon number of 3 -50 aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group having 1 to 50 carbon atoms, substituted or unsubstituted alkyl group or alkylene group having 1 to 50 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C 1-50 alkyl group or alkylene group, and Ar ¹² is Each independently a substituted or unsubstituted aromatic hydrocarbon group having 3 to 50 nuclear carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 1 to 50 nuclear carbon atoms, and Y ¹ is independently It is a substituted or unsubstituted aryl group. f is an integer of 1 to 3, e and i are each independently an integer of 0 to 4, h is an integer of 0 to 3, and g is an integer of 1 to 5. ]

[0043] Examples of each group of A ³ , B ¹ and Ar ¹² include the same examples as those given in formula (3). Note that a substituted or unsubstituted alkenyl having 1 to 50 carbon atoms. Examples of the group or the alkene group include a styryl group.

Examples of the condensed ring group or condensed heterocyclic group having 5 to 50 nuclear carbon atoms of Y ¹ include a naphthyl group, an anthryl group, a phenanthryl group, and a chrysenyl group.

[0044] In addition, as the substituent of each group of the above formulas (I), (II), (3) to (7), a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, substituted Or an unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 nuclear carbon atoms, substituted or Unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted nuclear atoms 5 Examples include ˜50 arylothio groups, substituted or unsubstituted alkoxycarbon groups having 1 to 50 carbon atoms, substituted or unsubstituted silyl groups, carboxyl groups, halogen atoms, cyano groups, nitro groups, and hydroxyl groups.

[0045] As the compound B, a compound represented by the following formula (8) can also be preferably used.

X ^23- (Y ² ) (8)

j

[0046] In Formula (8)! /, X ²³ is naphthacene, pyrene, benzoanthracene, pentacene, dibenzoanthracene, benzopyrene, benzofunole ren, funole lanten, benzofunole lanten, naphthyl fluoranthene, Dibenzofluorene, dibenzopyrene, dibenzofluorene It is preferable to contain one or more skeletons selected from the group force of lanthanum and acenaphthyl fluoranthene.

Y ² is preferably an aryl group or a diarylamino group having 12 to 60 carbon atoms, and more preferably an aryl group having 12 to 20 carbon atoms or a diarylamino group having 12 to 40 carbon atoms. n is preferably 2.

[0047] Further, as compound B, naphthacene derivative, anthracene derivative, bisanthracene derivative, pyrene derivative, bispyrene derivative, diaminoanthracene derivative, naphthofluoranthene derivative, diaminobilene derivative, diaminoperylene derivative, dibenzidine derivative, aminoanthracene derivative, aminobilene Also preferred are one or more compounds selected from the group consisting of derivatives and dibenzochrysene derivatives.

In the present invention, it is preferable that the light emitting layer of the organic thin film layer contains the compound A and the compound B. Since the compound A functions as a host material and the compound B functions as a dopant material, the light emission efficiency is improved by using it in the light emitting layer. In addition, in the organic EL device of the present invention, both the electron transport property and the hole transport property of the light emitting layer are improved depending on the use ratio of the compound A and the compound B, and the hole injection layer, the hole transport layer, An intermediate layer such as an electron injection layer can be omitted.

In the organic EL device of the present invention, by combining Compound A and Compound B, red light emission with high color purity can be obtained without impairing the effect of emitting long wavelengths. Further, a compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms and having an asymmetric structure, such as compound B, particularly a compound having a specific terminal substituent as described above, has steric hindrance between the compounds. The concentration becomes higher and concentration quenching due to molecular association can be prevented, and the lifetime can be further extended. Therefore, red emission with high color purity can be obtained while having high luminous efficiency and long lifetime.

The red emission color of the organic EL element can be divided by the maximum emission wavelength of the emission spectrum: orange (585 to 595 nm), red (maximum emission wavelength: 595 to 620 nm), pure red (maximum emission wavelength: 620). ~ 700nm).

In red light-emitting elements showing yellow to orange or red, red light emission means that CIEx value in CIE chromaticity coordinates is 0.62 or more (preferably 0.62 or more and less than 0.73), orange Luminescence is a CIEx value between 0.54 and less than 0.62.

[0050] In the organic EL device of the present invention, an electron transport layer is preferably formed. As a material for forming the electron transport layer, a compound represented by the following formula (9) is preferable.

A ⁴ -B ² (9)

(In the formula, A ⁴ is an aromatic hydrocarbon residue having 3 or more carbon rings, and B ² is a substituted or unsubstituted bicyclic group.)

[0051] The compound of the formula (9) is preferably anthracene, phenanthrene, naphthacene, pyrene, chrysene, benzoanthracene, pentacene, dibenzoanthracene, benzopyrene, fluorene, benzofluorene, fluoranthene, benzofluoranthene, naphthofluorene It is a heterocyclic compound having in its molecule one or more skeletons selected from lanthanum, dibenzofluorene, dibenzopyrene and dibenzofluoranthene.

More preferably, it is a nitrogen-containing heterocyclic compound.

[0052] The nitrogen-containing heterocyclic compound is more preferably a pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinoxaline, atalidine, imidazopyridine, imidazopyrimidine and phenantine linker. Contains one or more nitrogen-containing heterocyclic compounds.

Examples of the nitrogen-containing heterocyclic compound include benzimidazole derivatives represented by the following formula (10) or (11).

[Chemical 21]

[Wherein R ²⁶ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, Or an unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and k is 0 to R ²⁷ is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted carbon number 1 to 20 R ²⁸ is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted group. A quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and L 3 is a substituted or unsubstituted arylene having 6 to 60 carbon atoms. Group, substitution or Is an unsubstituted pyridylene group, a substituted or unsubstituted quinolylene group or a substituted or unsubstituted fluorylene group, Ar ¹³ is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, It is a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted quinolylene group. [0053] The benzimidazole derivatives represented by the formulas (10) and (11) are preferably such that k is 0, R ^{28 is an} aryl group, L ³ has 6 to 30 carbon atoms (more preferably 6 carbon atoms). ~ 20) aryl group and Ar ¹³ is an aryl group having 6 to 30 carbon atoms.

It is particularly preferable to form an electron transport layer containing such a compound because electron injection properties are improved.

[0054] In the organic EL device of the present invention, as described above, a conventionally known configuration may be used as long as at least one of the organic thin film layers contains the compound A and the compound B. Can be adopted. This will be described below.

[0055] [Configuration of organic EL element]

The typical structural example of the organic EL element used for this invention is shown. The present invention is not limited to this.

(1) Anode Z hole transport layer Z light emitting layer Z electron transport layer Z cathode

(2) Anode Z hole injection layer Z hole transport layer Z light emitting layer Z electron transport layer Z cathode

(3) Anode Z hole transport layer Z light emitting layer Z electron transport layer Z electron injection layer Z cathode

(4) Anode Z hole injection layer Z hole transport layer Z light emitting layer Z electron transport layer Z electron injection layer Z negative electrode (5) Anode z Insulating layer z Hole transport layer z Light emitting layer z Electron transport layer z Cathode

(6) Anode Z hole transport layer Z light emitting layer Z electron transport layer Z insulating layer Z cathode

(7) Anode z Insulating layer Z Hole transport layer Z Light emitting layer Z Electron transport layer Z Insulating layer Z Cathode

(8) Anode Z hole injection layer Z hole transport layer Z light emitting layer Z electron transport layer Z insulating layer Z cathode

(9) Anode Z insulating layer Z hole injection layer Z hole transport layer Z light emitting layer Z electron transport layer Z electron injection layer Z cathode

do) Anode Z insulation layer Z hole injection layer Z hole transport layer Z light emitting layer Z electron transport layer Z electron injection layer Z insulation layer Z cathode

And the like.

Of these, the configurations of (1) (2) (3) (4) (7) (8) (10) are preferably used.

In the present invention, the electron transport layer and the electron injection layer may be formed as in the above configurations (3), (4), (9) and (10), respectively, but the electron transport is performed as in other configurations. Even when only the layer is formed, the lifetime can be improved as compared with the conventional device.

[0056] [Translucent substrate]

The organic EL device of the present invention is manufactured on a light-transmitting substrate. Here, the transparent substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 to 700 nm of 50% or more.

Specifically, a glass plate, a polymer plate, etc. are mentioned. Examples of the glass plate include soda-lime glass, norlium strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, norium borosilicate glass, and quartz. Examples of the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyethersulfide, and polysulfone.

It should be noted that the substrate does not necessarily have to be transparent in a form in which the substrate power on which the element is formed does not extract light (for example, a top emission type element).

[0057] [Anode]

The anode of the organic thin film EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to have a work function of 4.5 eV or more. Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), acid tin tin (NESA), Indium zinc oxide alloy (IZO), gold, silver, platinum, copper, etc. can be applied.

These materials can be used alone. An alloy of these materials or a material to which other elements are added can be appropriately selected and used.

The anode can be produced by forming a thin film from these electrode materials by a method such as vapor deposition or sputtering.

When light emitted from the light-emitting layer is taken out from the anode, the transmittance of the anode for light emission is preferably greater than 10%. Further, the sheet resistance of the anode is preferably several hundred Ω or less. The film thickness of the anode is a force depending on the material, and is usually selected in the range of 10 nm to l μm, preferably 10 to 200 nm.

[0058] [Hole Injection Layer / Hole Transport Layer]

The hole injection / transport layer is a layer that assists the injection of holes into the light emitting layer and transports it to the light emitting region, and has a high ion mobility with a high hole mobility, usually as low as 5.5 eV or less. For such a hole injection / transport layer, a material that transports holes to the light emitting layer with a lower electric field strength is preferred. Further, the mobility force of holes, for example, at least when an electric field of 10 ⁴ to 10 ⁶ VZcm is applied. what is 10- ⁶ cm ² ZV 'seconds is preferred. As such a material, those conventionally used as a hole transport material in an optical material, and any of the known materials used for a hole injection layer of an organic EL element are used. It can be selected and used. In order to form this hole injection 'transport layer, the hole injection' transport material may be thinned by a known method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method. . In this case, the thickness of the hole injection / transport layer is not particularly limited, but is usually 5ηπ! ~) At 5 μm.

[0059] [Light emitting layer]

The light emitting layer of the organic EL device has the following functions. That is,

(i) Injection function: A function capable of injecting holes from the anode or hole injection 'transport layer when an electric field is applied, and an electron from the cathode or electron injection / transport layer.

(ii) Transport function: Function to move injected charges (electrons and holes) by the force of electric field

(iii) Luminescent function: Provides a field for recombination of electrons and holes and connects it to light emission. However, there may be a difference between the ease of hole injection and the ease of electron injection, and the transport ability represented by the mobility of holes and electrons may be large or small. It is preferable to move the charge.

[0060] As a method of forming the light emitting layer, for example, a known method such as a vapor deposition method, a spin coating method, or an LB method can be applied. The light emitting layer is particularly preferably a molecular deposited film. Here, the molecular deposited film is a thin film formed by deposition from a material compound in a gas phase state or a solidified from a material compound in a solution state or a liquid phase state. Usually, this molecular deposited film is distinguished from the thin film (molecular accumulation film) formed by the LB method by the difference in aggregated structure, higher order structure, and functional difference resulting from it. be able to.

In addition, as disclosed in JP-A-57-51781, a binder such as rosin and a material compound are dissolved in a solvent to form a solution, which is then thin-filmed by spin coating or the like. The light emitting layer can also be formed by twisting.

[0061] The light emitting layer mainly has a host material and a dopant material strength. The doping concentration of the dopant material contained in the light emitting layer is preferably 0.1 to: LO wt%, more preferably 0.5 to 2 wt%. In the present invention, as described above, it is preferable to use Compound B as a dopant material and Compound A as a host material.

[0062] [Electron injection layer 'electron transport layer]

The electron injection layer 'transport layer assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a high electron mobility. In the present invention, the compounds of the above formulas (9) to (11) are preferable.

In addition, an adhesion improving layer which is an electron injection / transport layer and is particularly a material with good adhesion to the cathode may be formed.

[0063] A preferred embodiment of the present invention is an element containing a reducing dopant in an electron transporting region or an interface region between a cathode and an organic layer. Here, the reducing dopant is defined as a substance capable of reducing an electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals. Oxide, Alkaline earth metal halide, rare earth metal oxide or rare earth metal halide, alkali metal organic complex, alkaline earth metal organic complex, rare earth metal organic complex power One substance can be preferably used.

[0064] More specifically, preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), and Cs (work Function: 1. 95eV) Force The group force at least one selected alkali metal, Ca (work function: 2.9eV), Sr (work function: 2.0 to 2.5eV), and Ba (work function: 2. 52 eV) Forces Group Forces It is particularly preferred that the work function in which at least one selected alkaline earth metal is mentioned is 2.9 eV or less. Among these, a more preferable reducing dopant is at least one alkali metal selected from the group power consisting of K, Rb and Cs, more preferably Rb or Cs, and most preferably Cs. It is. These alkali metals can improve emission brightness and extend the life of organic EL devices by adding a relatively small amount to the electron injection region, which has a particularly high reducing ability. In addition, as a reducing dopant having a work function of 2.9 eV or less, a combination of two or more alkali metals is also preferred. A combination of Cs and Rb or Cs, Na and Na is preferred. By including Cs in combination, the reducing ability can be efficiently demonstrated, and by adding to the electron injection region, the emission luminance of the organic EL element can be improved and the lifetime can be extended.

In the present invention, an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer. At this time, current leakage can be effectively prevented, and the electron injection property can be improved. As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides. Good. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved. Specifically, preferred alkali metal chalcogenides include, for example, Li 0, LiO, Na S, Na Se and NaO.

2 2 2

Preferred alkaline earth metal chalcogenides include, for example, CaO, BaO, SrO, Be 0, BaS, and CaSe. Also, as a preferred alkali metal halide Examples include LiF, NaF, KF, LiCl, KC1, and NaCl. Preferred alkaline earth metal halides include, for example, CaF, BaF, SrF, MgF, and

2 2 2 2

Examples include fluorides such as BeF and halides other than fluorides.

2

[0066] As a semiconductor constituting the electron injection layer, at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn is used. One kind or a combination of two or more kinds of oxides, nitrides, or oxynitrides are included. In addition, the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such an inorganic compound include the above-mentioned alkali metal chalcogenides, alkaline earth metal lucogenides, alkali metal halides, and alkaline earth metal halides.

[0067] [Cathode]

As the cathode, a material having a low work function (for example, 4 eV or less) metal, an alloy, an electrically conductive compound, or a mixture thereof is used. Specific examples of such electrode materials include sodium, sodium monopotassium alloy, magnesium, lithium, magnesium silver alloy, aluminum Z aluminum oxide, aluminum lithium alloy, indium, and rare earth metals.

[0068] This cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.

Here, when the light emission from the light emitting layer is taken out by the cathode power, the transmittance for the light emission of the cathode is preferably larger than 10%.

In addition, the sheet resistance as a cathode is several hundred Ω or less. The preferred film thickness is usually ΙΟηπ! To 1 m, preferably 50 to 200 nm.

[0069] [Insulating layer]

Since organic EL applies an electric field to an ultra-thin film, pixel defects are likely to occur due to leaks and shorts. In order to prevent this, it is preferable to insert an insulating thin film layer between the pair of electrodes. [0070] Examples of the material used for the insulating layer include acid aluminum, lithium fluoride, lithium oxide, fluoresceium, acid cesium, acid magnesium, fluoric magnesium, acid calcium, and fluoride. Examples include calcium, cesium fluoride, cesium carbonate, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, yttrium oxide, and vanadium oxide.

Use a mixture or laminate of these.

[0071] [Example of manufacturing organic EL device]

An anode, a hole transport layer, a light emitting layer, an electron transport layer, a hole injection layer if necessary, and an electron injection layer as necessary are formed by the materials and methods exemplified above, and a cathode is further formed. This makes it possible to fabricate organic EL devices. In addition, organic EL elements can be fabricated from the cathode to the anode in the reverse order.

[0072] Hereinafter, an example of manufacturing an organic EL device having a structure in which an anode, a hole transport layer, a light emitting layer, a electron transport layer, and a cathode are sequentially provided on a light transmitting substrate will be described.

First, a thin film made of an anode material is formed on a suitable translucent substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably in the range of 10 to 200 nm, to produce an anode. Next, a hole transport layer is provided on the anode. As described above, the hole transport layer can be formed by a vacuum deposition method, a spin coat method, a cast method, an LB method, or the like, but a homogeneous film can be obtained immediately and pinholes are generated. It is preferable to form a point force that is difficult to form by vacuum deposition. When a hole transport layer is formed by vacuum deposition, the deposition conditions vary depending on the compound used, the crystal structure and recombination structure of the target hole transport layer, etc., but generally the deposition source temperature is 50 to 450 ° C. The degree of vacuum is preferably 10 to ⁷ to 10 ^_3 torr, the deposition rate is 0.01 to 50 nm Z seconds, the substrate temperature is 50 to 300 ° C., and the film thickness is preferably 5 nm to 5 μm.

[0073] Next, the formation of a light-emitting layer in which a light-emitting layer is provided on a hole transport layer is also performed using a desired organic light-emitting material by a method such as vacuum deposition, sputtering, spin coating, or casting. However, it is preferable to form the film by a vacuum evaporation method from the viewpoint that a homogeneous film can be obtained immediately and pinholes are not easily generated. When forming a light-emitting layer by vacuum deposition, the deposition conditions vary depending on the compound used. Generally, it can be selected from the same condition range as that of the hole transport layer.

Next, an electron transport layer is provided on the light emitting layer. As with the hole transport layer and the light emitting layer, it is preferable to form by a vacuum evaporation method because it is necessary to obtain a homogeneous film. The vapor deposition conditions can be selected from the same condition ranges as those for the hole transport layer and the light emitting layer.

Finally, a cathode can be stacked to obtain an organic EL device.

[0075] The cathode also has a metallic force, and vapor deposition or sputtering can be used. However, vacuum deposition is preferred to protect the underlying organic layer from damage during film formation. The organic EL devices described so far are preferably produced from the anode to the cathode in a single vacuum.

[0076] The method of forming each layer of the organic EL device of the present invention is not particularly limited. Conventionally known vacuum deposition methods, molecular beam deposition methods, spin coating methods, dating methods, casting methods, bar coating methods, roll coating methods and the like can be used.

[0077] The thickness of each organic layer of the organic EL device of the present invention is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes occur, and conversely, if it is too thick, a high applied voltage is required. Usually, the range of several nm to 1 μm is preferable.

[Example]

[0078] Example 1

25 mm X 75 mm X O. A transparent electrode having a thickness of 120 nm and having a physical strength of indium oxide oxide was provided on a 7 mm size glass substrate. This glass substrate was ultrasonically cleaned in isopropyl alcohol for 5 minutes, then UV ozone cleaned for 30 minutes, and this substrate was placed in a vacuum evaporation system.

First, N, N, bis [4- (diphenylamino) phenol] —N, N, dimethylphenol 4, 4, monobenzidine is 60 nm thick as a hole injection layer on the substrate. Then, N, N, Ν ', Ν'-tetrakis (4-biphenol-bis) bis-4,4'-benzidine was deposited thereon to a thickness of lOnm. Next, the following compound (A-1), which is a naphthacene derivative, and the following compound (B-1), which is an indenoperylene derivative, are co-deposited at a weight ratio of 40: 0.4 as the light emitting layer, and deposited to a thickness of 40 nm. did.

[0079] [Chemical 22]

Compound (A-1) Compound (B-1)

Next, the following compound (C-1) was deposited to a thickness of 30 nm as an electron transport layer.

[Chemical 23]

Compound (C_1)

[0081] Next, lithium fluoride was deposited to a thickness of 0.3 nm, and then aluminum was deposited to a thickness of 150 nm. This aluminum Z lithium fluoride serves as the cathode. In this way, an organic EL device was produced.

When a current test was performed on the obtained device, red light emission with a driving voltage of 4. IV and a light emission luminance of 1135 cdZm ² was obtained at a current density of lOmAZcm ² and the chromaticity coordinates were (0.666, 0). 32), the efficiency was 11. 07cdZA. In addition, a continuous DC test with an initial luminance of 5000cdZm ² was conducted, and the driving time when it reached 80% of the initial luminance was 2010 hours.

[0083] Example 2

In Example 1, an organic EL device was prepared and evaluated in the same manner except that the following compound (B-2) was used instead of (B-1) as the indenoperylene derivative. The evaluation results of the obtained device are shown in Table 1.

[0084] [Chemical 24]

Compound (B-2)

[0085] Example 3-7

In Example 1, an organic EL device was prepared and evaluated in the same manner except that the following compounds (A-2) to (A-6) were used instead of (A-1). The evaluation results of the elements are shown in Table 1.

[0086] [Chemical 25]

Compound (A-2) Compound (A-3) Compound (A-4)

Compound (A-5) Compound (A-6)

[0087] Comparative Example 1

An organic EL device was prepared and evaluated in the same manner as in Example 1 except that (b-1) was used instead of (B-1) and Alq3 was used instead of (C1).

[0088] [Chemical 26]

Compound (b— 1) A 1 q 3

[0089] [Table 1]

Industrial applicability

The organic EL element of the present invention can be applied to fields such as various display devices, displays, backlights, illumination light sources, labels, signboards, interiors, etc., and is particularly suitable as a display element for a color display.

Claims

The scope of the claims

A cathode and an anode,

[Chemical 27]

[Where

Ar ² and Ar ³ are each independently a substituted or unsubstituted aromatic group or aromatic heterocyclic group, χ′-χ ¹⁸ », each independently hydrogen, halogen, alkyl group, alkoxy group, alkylthio group, Alkenyl group, alkoxy group, alkenyl group, aromatic ring-containing alkyl group, aromatic ring-containing alkyloxy group, aromatic ring-containing alkylthio group, aromatic ring group, aromatic heterocyclic group, aromatic ring oxy group, Aromatic ring thio group, aromatic alkenyl group, alkenyl aromatic ring group, amino group, carbazolyl group, cyano group, hydroxyl group, CO OR ¹ ′ (R ¹ ′ is hydrogen, alkyl group, alkenyl group, aromatic ring-containing alkyl Or —COR ² ′ (R ² ′ is hydrogen, an alkyl group, an alkenyl group, an aromatic ring-containing alkyl group, an aromatic ring group or an amino group), or OCOR ³ ′. (R ° includes alkyl, alkenyl and aromatic rings. An alkyl group or an aromatic ring group). Adjacent groups of ^1-8 may be bonded to each other to form a ring together with the carbon atom substituted. At least one of ~ 8 is not hydrogen. )

[2] The organic electoluminescence device according to [1], wherein the indenoperylene compound is a dibenzotetraphenylperifuranthene derivative.

[3] The organic electroluminescent device according to claim 1 or 2, wherein the compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms is a naphthacene derivative represented by the following formula (I): [Chemical 28]

(!)

[Wherein Q ^ Q ¹² ^, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, amino Group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 20 nuclear carbon atoms, substituted or unsubstituted Substituted aryl group having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, or substituted or unsubstituted nucleus It is a heterocyclic group having 5 to 20 atoms, and may be the same or different, and adjacent ones may form a saturated or unsaturated cyclic structure. ]

[4] In the formula ^{(I), Q \ Q 2} , Q 3 and at least one organic-elect opening device according to claim 3 Ru der aromatic hydrocarbon group Q ^4.

[5] The organic electoluminescence device according to claim 3 or 4, wherein the naphthacene derivative represented by the formula (I) has a structure represented by the following formula (Π).

[Chemical 29]

[Wherein Q ^{3 to} Q ¹² , QQ ¹⁰⁵ and. ¹ ~. ² . ⁵ each independently represents the same group as Q ^ Q ^12, and may be the same or different, and adjacent ones may form a saturated or unsaturated cyclic structure. ]

[6] In the above formula (Π), at least one of Q ¹⁰ \ Q ^1G5 , Q ^2G1 and Q ^{2 5} is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted nuclear carbon number of 6 -50 aromatic hydrocarbon group, amino group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted nuclear carbon number 6-20 aryloxy group, substituted or unsubstituted aralkyl group having 6-20 carbon atoms, substituted or unsubstituted alkenyl group having 2-20 carbon atoms, substituted or unsubstituted nucleus 7-20 carbon atoms aralkyl 6. The organic electroluminescent device according to claim 5, which is a group or a substituted or unsubstituted heterocyclic group having 5 to 20 nuclear atoms.

[7] The compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms includes an anthracene derivative represented by the following formula (3), an asymmetric anthracene derivative represented by the following formula (4), and the following formula (5): The organic electoluminescence device according to claim 1, which is an asymmetric pyrene derivative represented by the following formula, an asymmetric diphenylanthracene derivative represented by the following formula (6), or a bispyrene derivative represented by the following formula (7). [Chemical 30]

[In the formula (3), X ^{19 to} X are each a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear carbon atoms. Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted alkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 50 carbon atoms, substituted or unsubstituted Substituted aralkyl groups having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 50 carbon atoms, substituted or unsubstituted carbon atoms 1 to 50 An alkoxycarbo group, a substituted or unsubstituted silyl group, a force carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group. Ar ⁴ and Ar ⁵ are each independently a condensed aromatic group substituted or unsubstituted aromatic ring group having 10 to 50, at least one of Ar ⁴ and Ar ^5, represented by the following formula (3a) 1 A naphthyl derivative or a 2-naphthyl derivative represented by the following formula (3b).

[Chemical 31]

Y (4)

[In Formula (4), Α ¹ and Α ² are each independently a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 20 nuclear carbon atoms, and Ar ⁶ and Ar ⁷ are each independently , A hydrogen atom, or a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and R ^{8 to} R ¹⁵ each independently represent a hydrogen atom, a substituted or unsubstituted nuclear carbon number of 6 to 50 aromatic hydrocarbon ring group, substituted or unsubstituted aromatic heterocyclic group having 5 to 50 carbon atoms, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted carbon A C3-C50 alkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms Roxy group, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted Alkoxycarbonyl of 1 to 50 carbon atoms - group, a substituted or unsubstituted silyl group, a force carboxyl group, a halogen atom, a Shiano group, a nitro group or a hydroxyl group, R ¹⁶ and R ^17, each independently, hydrogen Atom, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 carbon atoms, substituted or unsubstituted aromatic heterocyclic group having 5 to 50 carbon atoms, substituted or unsubstituted 1 to 50 carbon atoms An alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, substituted or An unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxycarbon group having 1 to 50 carbon atoms, a substituted or unsubstituted group Cyril Group, carboxyl group, halogen atom, cyano group, nitro group or hydroxyl group. Ar R ¹⁶ and R ¹⁷ may be bonded to a plurality of Α ¹ or Α ² or adjacent to each other to form a saturated or unsaturated cyclic structure. However, there is no case where a group which is symmetrical with respect to the Χ-Υ axis shown on the anthracene is bonded to the 9th and 10th positions of the central anthracene. ]

[Chemical 33]

[In Formula (5), Ar ⁸ and Ar ⁹ are each a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, and L ¹ and L ² are each a substituted or unsubstituted phenylene group. A substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorenylene group, and a substituted or unsubstituted dibenzosilolylene group. m is an integer from 0 to 2, n is an integer from 1 to 4, s is an integer from 0 to 2, and t is an integer from 0 to 4. L ¹ or Ar ⁸ is bonded to any of the 1-5 positions of pyrene, and L ² or Ar ⁹ is bonded to any of the 6-10 positions of pyrene.

However, when n + t is an even number, Ar ⁸ , Ar ⁹ ,

L ² satisfies the following (1) or (2).

(2) When Ar ⁸ = Ar ⁹ and L ¹ = L ²

(2—l) m ≠ s and / or n ≠ t, or

(2-2) When m = s and n = t,

(2-2-2) 1 ^ and 1, or pyrene is, if bonded to the same position of Ar ⁸ and Ar ^9, L ¹ and L ^2, or substitution position of pyrene Ar ⁸ and Ar ⁹ Is symmetrical Never become. ]

[Chemical 34]

[In the formula (6), Ar ¹ "and Ar ¹¹ are each independently a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, and m 'and n are each 1 to It is an integer of 4. However, if m, = n, = 1, and the bonding position of Ar ^1G and Ar ^{11 to} the benzene ring is symmetrical, Ar ^1G and Ar ¹¹ are not the same m, or When n 'is an integer from 2 to 4, m and n' are different integers.

R ²⁶ and R ²⁷ are each independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or An unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted carbon number 5 to 50 aryloxy group, substituted or unsubstituted carbon number 5 to 5 A arylthio group of 0, a substituted or unsubstituted alkoxycarbon group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; ]

(A ³ ) ― (X ²² ) ― (Ar ¹² ) ― (Y ¹ ) ― (B ¹ ) (7)

e f g h l

[8] The organic electroluminescent device according to claim 1 or 2, wherein the compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms is a compound represented by the following formula (8).

X ^23- (Y ² ) (8)

[9] X ²³ in formula (8) is, naphthacene, pyrene, benzo-anthracene, pentacene, dibenzoanthracene, benzopyrene, Benzofunore old Ren, Funore old Ranten, Benzofunore old Lante down, naphthyl fluoranthene, dibenzo fluorene, dibenzopyrene 9. The organic electroluminescent device according to claim 8, wherein a compound having a carbocycle having 4 or more carbocycles, which is selected as a group force of dibenzofluoranthene and isennaphthylfluoranthene.

[10] Compound power represented by the above formula (8) Naphthacene derivative, anthracene derivative, benzoanthracene derivative, dibenzoanthracene derivative, pentacene derivative, bisanthracene derivative, pyrene derivative, bispyrene derivative, benzopyrene derivative, dibenzopyrene derivative , Fluorene derivatives, benzofluorene derivatives, dibenzofluorene derivatives, fluoranthene derivatives, benzofluoranthene derivatives, dibenzofluoranthene derivatives, naphthylfluoranthene derivatives, acenaphthylfluoranthene derivatives, diaminoanthracene derivatives, naphtho 9. The organic electroluminescent device according to claim 8, which is at least one compound selected from the group consisting of a fluoranthene derivative, a diaminobylene derivative, a diaminoperylene derivative, a dibenzidine derivative, an aminoanthracene derivative, an aminobilene derivative and a dibenzothalicene derivative. .

[11] The organic electoluminescence device according to any one of [1] to [10], wherein the light emitting layer contains the indenoperylene compound and a compound having a condensed aromatic ring having 10 to 50 nuclear carbon atoms.

12. The organic elect according to any one of claims 1 to 11, wherein the organic thin film layer includes an electron transport layer, and the electron transport layer contains an aromatic hydrocarbon compound represented by the following formula (9). Mouth luminescence element.

A ⁴ -B ² (9)

[In the formula (9), A ⁴ is an aromatic hydrocarbon group having 2 or more carbon rings, and B ² is a substituted or unsubstituted heterocyclic group. )

[13] Formula A ⁴ (9) is, anthracene, Fuenantoren, naphthacene, pyrene, Tarisen, Ben zo anthracene, pentacene, dibenzoanthracene, benzopyrene, fluorene, benzofluorene, fluoranthene, benzofluoranthene, naphthoquinone source fluoranthene 13. The organic electroreductive element according to claim 12, which is a heterocyclic compound having in its molecule one or more skeletons selected from the group consisting of: dibenzofluorene, dibenzopyrene and dibenzofluoranthene.

[14] The organic electoluminescence device according to [12] or [13], wherein the compound power is a nitrogen-containing heterocyclic compound represented by the formula (9).

[15] The organic electoluminescence device according to claim 14, wherein the nitrogen-containing heterocyclic compound is a compound represented by the following formula (10) or formula (11).

[Chemical 35]

[In the formula, each R ²⁶ is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted group. An alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, k is an integer of 0 to 4, and R ²⁷ is a substituted or unsubstituted carbon group having 6 to 60 carbon atoms. R ²⁸ is an aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms. Hydrogen atom, substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or substituted or Unsubstituted carbon number 1 to 20 alkoxy groups, L ³ represents a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted quinolylene group, or A substituted or unsubstituted fluorenylene group, and Ar ¹³ is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted quinolinylene group. . ]

[16] The nitrogen-containing heterocyclic compound has one or more skeletons in which the group power of pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinoxaline, atalidine, imidazopyridine, imidazopyrimidine, and phenantoral linker is also selected. The organic electoluminescence device according to claim 14, which is a compound.

17. The organic electroluminescent element according to any one of claims 1 to 16, wherein the emission color is orange to red. [18] The light emitting layer contains a dopant material, the concentration of the dopant material occupied in the luminescent layer is 0.1 to 10 weight ^_0/0 organic elect port Ruminessen scan device according to any one of claims 1 to 17 is .

[19] The organic electroreductive element according to [18], wherein the concentration of the dopant material is 0.5 to 2% by weight.