CN100421282C - Organic electroluminous device - Google Patents

Organic electroluminous device Download PDF

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CN100421282C
CN100421282C CNB2004101003516A CN200410100351A CN100421282C CN 100421282 C CN100421282 C CN 100421282C CN B2004101003516 A CNB2004101003516 A CN B2004101003516A CN 200410100351 A CN200410100351 A CN 200410100351A CN 100421282 C CN100421282 C CN 100421282C
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electroluminescent device
phosphorescence
emitter material
integer
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CN1620210A (en
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洪敏玲
柯崇文
刘醕炘
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AU Optronics Corp
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Abstract

The present invention provides an organic electroluminescence device, wherein an organic luminous layer comprises the auxiliary illuminant material and the phosphorescence main illuminant material. The phosphorescent main illuminant material is provided with silane system molecules of the chemical formula (I) such as the right formula in the formula (I). R <1>, R <2> and R <3> independently represent H or a substituent, and R <4> represents the alkyl, the alkenyl, the heteroaromatic group, or the aromatic radical with or without substituents. The Q is an integer from 0 to 4, the m is an integer from 1 to 3, and the n is an integer from 1 to 3. The M + N = 4.

Description

Organnic electroluminescent device
Technical field
The present invention relates to a kind of Organnic electroluminescent device (organic electroluminescent device), particularly a kind of host and guest's type Organnic electroluminescent device.
Background technology
Organnic electroluminescent device also is called Organic Light Emitting Diode (organic light-emitting diode; OLED), be with a kind of light-emitting diode of organic layer as active layers.Because Organnic electroluminescent device has advantages such as low voltage operating, high brightness, in light weight, wide viewing angle and high reduced value, is used in gradually in recent years on the flat panel display (flat panel display).
Fig. 1 represents traditional OLED structure, and wherein substrate 8 is for to be electrically insulated and transparent glass or plastic material, and anode 6 is to be positioned on the substrate 8, and and negative electrode 2 between insert and put organic luminous layer 4.Anode 6 and negative electrode 2 are to be connected to external power source 5.In when operation, when the bias voltage of anode 6 during greater than negative electrode 2, this diode is to be in forward bias voltage drop, so hole and electronics can be injected in the organic luminous layer 4 from anode 6 and negative electrode 2 respectively, and causes the combination again of hole-electronics, and discharges light energy.
According to hole and electronic spin attitude (spin state), the exciton that is produced by the combination again of hole and electronics can have the spin state of triplet (triplet) or singlet state (singlet).By singlet state exciton (singletexciton) produced luminous for fluorescence (fluorescence), and luminously be phosphorescence (phosphorescence) by what triplet exciton (triplet exciton) produced.The luminous efficiency of phosphorescence is three times of fluorescence.Therefore, developing high efficiency phosphor material is very important with the luminous efficiency of promoting OLED.
At present on the phosphorescence establishment of component of OLED, commonly used is with phosphorescence guest emitter collocation host emitter material 4,4 '-N, N '-two carbazyl biphenyl (4,4 '-N, N '-dicarbazole-biphenyl; CBP).CBP has the characteristics such as energy jump value of transmitting hole ability and broadness, and in the phosphorescence component internal because carrier transfer rate difference, cause carrier in conjunction with incomplete, accumulate situation and form electric charge, therefore cause phosphorescence assembly stability to decay, need other phosphor material to improve the stability of phosphorescence assembly.
Summary of the invention
In view of this, purpose of the present invention is provides a kind of host and guest's type Organnic electroluminescent device, and wherein the phosphorescence host emitter is for having the silane system molecule of chemical formula (I)
Figure C20041010035100051
In chemical formula (I), R 1, R 2And R 3For identical or different, and be H or substituting group, R 4Be alkyl, thiazolinyl, assorted aromatic radical or aromatic radical that substituting group or unsubstituted are arranged, q is 0 to 4 integer, and m is 1 to 3 integer, and n is 1 to 3 integer, and m+n=4.
Above-mentioned silane system molecule can glow with guest emitter collocation, green glow or blue light, and the guest emitter that can arrange in pairs or groups for example has chemical formula (III)
Wherein M is an atomic weight greater than 40 metal; R is at least 1 integer; S is at least 0 integer; R 5Be H or any substituting group; X is an assistant ligand; A is aromatic rings or assorted aromatic rings; B is an aromatic rings.
Description of drawings
Fig. 1 represents traditional OLED structure.
Fig. 2 represents the phosphorescence assembly profile of embodiments of the invention.
Fig. 3 represents the efficiency chart of giving out light of the phosphorescence assembly of embodiments of the invention and comparative example.
Fig. 4 represents the half life figure of the phosphorescence assembly of embodiments of the invention and comparative example.
The primary clustering symbol description
2~negative electrode;
4~organic luminous layer;
5~external power source;
6~anode;
8~substrate;
20~ito glass;
22~hole injection layer;
24~hole transmission layer;
26~luminescent layer;
28~hole barrier layer;
30~electron transfer layer;
32~negative electrode.
Embodiment
The invention provides a kind of can the collocation as the silane system molecule of phosphorescence host emitter with guest emitter, it has chemical formula (I)
Figure C20041010035100061
In chemical formula (I), R 1, R 2And R 3Be H or substituting group C independently 1-C 20Alkyl (as comprising functional groups such as methyl, ethyl, isopropyl, the tert-butyl group, n-octyl, positive decyl, n-hexyl, cyclopropyl, cyclopenta and cyclohexyl), C 2-C 20Thiazolinyl, C 2-C 20Alkynyl (as comprising functional groups such as propine and 3-pentyne), C 1-C 20Assorted alkyl, C 3-C 40Aromatic radical (as comprising functional groups such as phenol, o-methylbenzene, alkynes), C 3-C 40Assorted aromatic radical (increases atoms such as oxygen, sulphur and nitrogen on carbon atom, as comprise imidazole radicals (imidazolyl), pyridine radicals (pyridyl), furyl (furyl), piperidyl (piperidyl), benzoxazolyl (benzoxazolyl), thienyl (thienyl), triazolyl (triazolyl) and carbazyl functional groups such as (carbazolyl)), R4 is alkyl, thiazolinyl, assorted aromatic radical or the aromatic radical that substituting group or unsubstituted are arranged, q is 0 to 4 integer, m is 1 to 3 integer, n is 1 to 3 integer, and m+n=4.
R 4Can be C 1-20Alkyl, its concrete example are methyl, ethyl, isopropyl, butyl, n-octyl, positive decyl, n-hexadecyl, cyclopropane base, cyclopenta, cyclohexyl etc.Also can be C 2-20Thiazolinyl, its concrete example are vinyl, acrylic, 2-cyclobutenyl or the 3-pentenyl that substituting group or unsubstituted are arranged.Also can be C 1-50Assorted aromatic radical, can be the assorted aromatic radical that contains oxygen, sulphur and nitrogen, its concrete example is imidazole radicals (imidazolyl), pyridine radicals (pyridyl), furyl (furyl), piperidyl (piperidyl), benzoxazolyl (benzoxazolyl), thienyl (thienyl), triazolyl functional groups such as (triazolyl).Also can be C 6-30Aromatic radical, its concrete example are phenyl (phenyl), p-methylphenyl (p-methylphenyl), naphthyl functional groups such as (naphthyl).
R 2And R 3Can be independently and for H or substituting group.Perhaps, link together and form assorted aromatic rings with its carbon atom that is connected is common.
The object lesson of the phosphorescence host emitter of above-mentioned silane system molecule is as follows.
Figure C20041010035100071
Silane system molecule of the present invention can glow with guest emitter collocation, green glow or blue light, and the guest emitter that can arrange in pairs or groups for example has chemical formula (III)
Figure C20041010035100082
Wherein M is an atomic weight greater than 40 metal; R is at least 1 integer; S is at least 0 integer; R 5Be H or any substituting group such as C 1-C 20Alkyl, C 2-C 20Thiazolinyl (alkenyl), C 2-C 20Alkynyl (alkynyl), C 1-C 20Assorted alkyl, C 3-C 40Aromatic radical, C 3-C 40Assorted aromatic radical X is an assistant ligand; A is aromatic rings or assorted aromatic rings; B is an aromatic rings.
Available and of the present invention silane system molecule collocation and the object lesson of the guest emitter that glows is as follows.
Figure C20041010035100083
Figure C20041010035100091
The object lesson of the guest emitter of the collocation of available and of the present invention silane system molecule and green light is as follows.
Figure C20041010035100092
Available and of the present invention silane system molecule collocation and the object lesson of the guest emitter that glows is as follows.
Figure C20041010035100093
Below by embodiment illustrating further method of the present invention, feature and advantage, but be not to be used for limiting the scope of the invention, scope of the present invention should be as the criterion with appended claim.
Embodiment
Synthetic compound (II)
Route of synthesis is as follows.
Figure C20041010035100101
The preparation method of compound 1:
With 1 of 4.65g (19.7mmole), 3-dibromobenzene (Dibromobenzene), the oxolane of 150ml (tetrahydrofurane) is inserted in the round-bottomed bottle of 250ml under-78 ℃ with the n-butyl lithium (n-Butyllithium) of 8ml, next under nitrogen, add the dichloro diphenyl silane (dichlorodiphenylsilane) of 2g (7.9mmole) and stir, question response is finished, add the carrene (dichloromethane) of 200ml and the water of 200ml again, organic layer is separated and take out, obtain pair (3-bromophenyl)-diphenyl silanes [Bis (3-bromo-phenyl)-diphenyl silane] (compound 1) by silica gel (towards extract: ethyl acetate and n-hexane solvent) tubing string chromatography (column chromatography) again by concentrated mode.
The preparation method of compound 2:
Carbazole (carbazole) with 0.94g (5.6mmole), 0.59g t-butanols (6.1mmole) is received (Sodium t-butoxide), 0.12g three-t-butyl phosphine (Tri-t-butylphosphine) (0.6mmole), 0.034g the toluene of acid chloride (0.15mmole) (Palladium acetate) and 100ml, insert in the round-bottomed bottle of 250ml, next under nitrogen, add the compound 1 of 1.26g (2.5mmole) and stir, question response is finished under the reaction temperature of solvent refluxing, add the carrene (dichloromethane) of 200ml and the water of 200ml again, organic layer is separated and take out, obtain compound 2 by silica gel (towards extract: ethyl acetate and n-hexane solvent) tubing string chromatography (column chromatography) again by concentrated mode.
With compound (II) is that the phosphorescence host emitter prepares the OLED assembly
See also Fig. 2, with the pre-treatment of ito glass (20) process, going up evaporation thickness through the ito glass (20) of pre-treatment is the hole injection layer (22) of 60~80nm, and going up evaporation one layer thickness in hole injection layer (22) again is the hole transmission layer (24) of 20~40nm.Then, evaporation one layer thickness is compound (II) luminescent layer (26) of 20~40nm, and the phosphorescence guest emitter that mixes simultaneously.It is the hole barrier layer (28) of 10~25nm that continuation is gone up evaporation one layer thickness at luminescent layer (26), and going up evaporation one layer thickness in hole barrier layer (28) again is the electron transfer layer (30) of 30~50nm, goes up evaporation negative electrode (32) at electron transfer layer (30) at last.The result is shown in Fig. 3 curve B, and giving out light at assembly can reach 7.3cd/A aspect the efficient, and aspect the half-life, shown in Fig. 4 curve B, initial brightness is 1000nits (every square centimeter candle light), and its decline 20% is about 166 hours.
Comparative example
Assembly preparation procedure and material are roughly as embodiment, and it is CBP that difference is in the material of phosphorescence host emitter.Detailed preparation method is as described below.Through pre-treatment, is the hole injection layer (22) of 60~80nm going up evaporation thickness through the ito glass (20) of pre-treatment with ito glass, and going up evaporation one layer thickness in hole injection layer (22) again is the hole transmission layer (24) of 20~40nm.Then, evaporation one layer thickness is the CBP luminescent layer of 20~40nm, and the phosphorescence guest emitter of evaporation doping simultaneously.Continuation evaporation one layer thickness on the CBP luminescent layer is the hole barrier layer of 10~25nm, and evaporation one layer thickness is the electron transfer layer of 30~50nm on the barrier layer of hole again, at last evaporation negative electrode on electron transfer layer.The result is shown in Fig. 3 curve A, and giving out light at assembly can reach 5.5cd/A aspect the efficient, and aspect the half-life, shown in Fig. 4 curve A, initial brightness is 1000nits (every square centimeter candle light), and its decline 30% is about 162 hours.
The result of Fig. 3 and Fig. 4 shows, changes phosphorescence main light emission material layer the compound (II) of silane system molecule of the present invention into, the phosphorescence assembly of embodiments of the invention give out light efficient and half life all relatively embodiment (traditional luminescent material) be good.
Though the present invention discloses as above with preferred embodiment; right its is not in order to restriction the present invention, anyly has the knack of this operator, without departing from the spirit and scope of the present invention; change and retouching when doing, thus protection scope of the present invention when with appended claim the person of being defined be as the criterion.

Claims (4)

1. Organnic electroluminescent device, it comprises a pair of anode electrode and cathode electrode, and the luminescent layer between this antianode electrode and cathode electrode, and this luminescent layer comprises guest emitter material and host emitter material, this host emitter material is for having the silane system molecule of chemical formula (II)
Figure C2004101003510002C1
2. Organnic electroluminescent device as claimed in claim 1 further comprises:
Hole injection layer is between this luminescent layer and this anode electrode;
Hole transmission layer is between this hole injection layer and this luminescent layer;
The hole barrier layer is between this luminescent layer and this cathode electrode; And
Electron transfer layer is between this hole barrier layer and this cathode electrode.
3. Organnic electroluminescent device as claimed in claim 1, wherein the guest emitter material has chemical formula (III)
Figure C2004101003510002C2
Wherein M is an atomic weight greater than 40 metal; R is a positive integer; S is 0 or positive integer; R 5Be H or substituting group; X is an assistant ligand; A is aromatic rings or assorted aromatic rings; B is an aromatic rings.
4. Organnic electroluminescent device as claimed in claim 1, the chemical formula that wherein above-mentioned guest emitter material has
Figure C2004101003510003C1
Figure C2004101003510003C2
Or
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TW201121116A (en) * 2009-08-24 2011-06-16 Du Pont Organic light-emitting diode luminaires
CN101863914B (en) * 2010-05-28 2011-12-28 武汉大学 Phosphorescent light body material and application
CN104650154B (en) * 2015-02-06 2017-09-22 中国科学院长春应用化学研究所 Dark red smooth phosphorescent iridium complex and preparation method thereof and the organic electroluminescence device using the complex

Citations (5)

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Publication number Priority date Publication date Assignee Title
US5391681A (en) * 1992-06-05 1995-02-21 Ciba-Geigy Corporation Curable compositions based on epoxy resins or mixtures of epoxy resins and polyisocyanates containing trisimidazolyl triazines
JP2002100476A (en) * 2000-07-17 2002-04-05 Fuji Photo Film Co Ltd Light-emitting element and azole compound
CN1364847A (en) * 2000-12-01 2002-08-21 佳能株式会社 Metal ligand compound, luminous device and display device
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5391681A (en) * 1992-06-05 1995-02-21 Ciba-Geigy Corporation Curable compositions based on epoxy resins or mixtures of epoxy resins and polyisocyanates containing trisimidazolyl triazines
JP2002100476A (en) * 2000-07-17 2002-04-05 Fuji Photo Film Co Ltd Light-emitting element and azole compound
CN1474826A (en) * 2000-11-30 2004-02-11 ������������ʽ���� Luminescent element and display
CN1364847A (en) * 2000-12-01 2002-08-21 佳能株式会社 Metal ligand compound, luminous device and display device
WO2004045002A1 (en) * 2002-11-08 2004-05-27 Universal Display Corporation Organic light emitting materials and devices

Non-Patent Citations (2)

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Title
DIVALENTOSMIUMCOMPLEXES:SYNTHESIS,CHARACTERIZATION,STRONGRED PHOSPHORESCENCE,ANDELECTROPHOSPHORESCENCE. BRENDEN CARLSON, GREGORY D.PHELAN,WERNERLANINSKY, LARRY DAITON, XUEZHONGJIANG, SEN LIU,AND ALEX K.-Y.JEN.AMERICAN CHEMICAL SOCIETY,Vol.124 No.47. 2002
DIVALENTOSMIUMCOMPLEXES:SYNTHESIS,CHARACTERIZATION,STRONGRED PHOSPHORESCENCE,ANDELECTROPHOSPHORESCENCE. BRENDEN CARLSON, GREGORY D.PHELAN,WERNERLANINSKY, LARRY DAITON, XUEZHONGJIANG, SEN LIU,AND ALEX K.-Y.JEN.AMERICAN CHEMICAL SOCIETY,Vol.124 No.47. 2002 *

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