CN109111456B - Iridium complex used as phosphorescent material, preparation method and application thereof - Google Patents

Iridium complex used as phosphorescent material, preparation method and application thereof Download PDF

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CN109111456B
CN109111456B CN201710488817.1A CN201710488817A CN109111456B CN 109111456 B CN109111456 B CN 109111456B CN 201710488817 A CN201710488817 A CN 201710488817A CN 109111456 B CN109111456 B CN 109111456B
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陈跃
丰佩川
胡灵峰
杨阳
王林
王鹏程
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Yantai Xianhua Photoelectric Material Research Institute Co ltd
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an iridium complex used as a phosphorescent material, and a preparation method and application thereof. The iridium complex with high luminous efficiency prepared by the invention can adjust the color of emitted light in a large range by adjusting the position and the type of the heteroatom. In addition, the preparation methods of the luminescent materials with different colors are basically the same, and the operation is simple. The main ligands of the iridium complexes have the same framework structure, and the light emitting color of the complexes can be adjusted in the wavelength ranges of blue green light and green light only due to different positions of heteroatoms on the main ligands and different types of the heteroatoms. The novel iridium complex has high luminous efficiency and thermal stability, and can be applied to OLED illumination and display.

Description

Iridium complex used as phosphorescent material, preparation method and application thereof
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an iridium complex used as a phosphorescent material, and a preparation method and application thereof.
Background
An Organic Light Emitting Diode (OLED) is a solid device composed of organic thin films, which can convert electrical energy into light energy. Because the OLED has the characteristics of self-luminescence, clearness, brightness, lightness, thinness, high response speed, wide visual angle, low power consumption, large applicable temperature range, simple manufacturing process and the like, the OLED becomes one of the research hotspots in the field of panel display and illumination.
The light emitting material is one of the core materials of the OLED device. Organic light emitting materials have been developed over the years, from the laboratory to the consumer market. A large number of researches show that the iridium (III) complex has the characteristics of good thermal stability, short excited state life and high luminous efficiency. The iridium (III) complex phosphorescent material is a research hotspot in the field of electroluminescence.
When the method is applied to OLED full-color display, red, green and blue OLED devices with excellent performance generally need to be obtained at the same time. The green iridium phosphorescent material widely used at present mainly adopts phenylpyridine (PPY) as a main ligand. Such materials have very good luminous efficacy, e.g. (PPY)3The maximum emission peak of a device made of the Ir complex is near 514nm, and the maximum external quantum efficiency reported at present is up to 21.7%. The properties such as emission light wavelength, material stability and the like are adjusted by modifying the phenylpyridine ligand.
Phosphorescent materials having ligands other than PPY as the main ligand are also relatively lacking. The development of green phosphorescent materials containing novel main ligand structures can enrich the types of green materials and have important significance for developing more efficient and stable green materials.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides an iridium complex used as a phosphorescent material, and a preparation method and application thereof.
The technical scheme for solving the technical problems is as follows: an iridium complex used as a phosphorescent material has a structural formula as follows:
Figure BDA0001331108100000021
wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10And R11Each independently is hydrogen, deuterium, substituted or unsubstituted alkyl, cycloalkyl, hydroxy, amino, mercapto, alkenyl, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, alkoxy, aryloxy, amino, silyl, halogen, CN, SCN, NO2、CR12R13NR14R15Or CF3Any one of (a); r12、R13、R14、R15Each independently is hydrogen, deuterium, substituted or unsubstituted alkyl, cycloalkyl, hydroxy, amino, mercapto, alkenyl, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, alkoxy, aryloxy, amino, silyl, halogen, CN, SCN, NO2Or CF3Any one of (a);
x is O, S, Se, NR16、CR17R18、SiR19R20Or GeR21R22(ii) a Wherein R is16、R17、R18、R19、R20、R21、R22Each independently is hydrogen, deuterium, substituted or unsubstituted alkyl, cycloalkyl, hydroxy, amino, mercapto, alkenyl, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, alkoxy, aryloxy, amino, silyl, halogen, CN, SCN, NO2Or CF3Any one of (a);
(L ^ Z) is an auxiliary ligand which is the same as or different from the main ligand on the left side in the structural formula;
m is greater than 0, and m is an integer; n is not less than 0 and n is an integer.
Wherein R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11And X, any two adjacent groups are linked to form a cyclic group, and the formed cyclic group may contain one or more heteroatoms.
Further, R5And R6Bridging groups linked to form- (Y) -, said Y being O, S, Se or NR23(ii) a Wherein R is23Is hydrogen, deuterium, substituted or non-substitutedSubstituted alkyl, cycloalkyl, hydroxy, alkenyl, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, alkoxy, aryloxy, silyl, halogen or CF3Any one of the above.
Further, R5And R6Connection formation- (AR)24R25) A bridging group of z-; wherein R is24And R25Each independently is hydrogen, deuterium, substituted or unsubstituted alkyl, cycloalkyl, hydroxy, amino, mercapto, alkenyl, alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, alkoxy, aryloxy, amino, silyl, halogen, CN, SCN, NO2Or CF3Any one of (a); a is C, Si or Ge; z is a radical of>0, and z is an integer.
Further, the auxiliary ligand (L ^ Z) is any one of acetylacetone, 2-picolinic acid, 2-phenylpyridine, 2,6, 6-tetramethyl-3, 5-pimelic acid, (E) -N, N' -diisopropylbenzamidine or (Z) -2, 3-diisopropyl-1, 1-diphenylguanidine.
Preferably, the iridium complex has the structural formula:
Figure BDA0001331108100000031
Figure BDA0001331108100000041
the second object of the present invention is to provide a method for preparing the iridium complex, which comprises the following steps:
(1) carrying out C-N coupling reaction on the raw material I and the raw material II to obtain a main ligand;
(2) under the protection of nitrogen, dissolving a main ligand in ethylene glycol monoethyl ether, adding iridium trichloride hydrate and deionized water, and heating for reaction to obtain an iridium-chlorine bridge complex;
(3) under an alkaline condition, heating and refluxing the iridium-chlorine bridge complex and the auxiliary ligand for reaction to obtain an iridium phosphorescent material;
wherein the raw material I is 1H-indole;
the raw material II is halogenated benzofuro [2,3-c ] pyridine, halogenated benzothieno [2,3-c ] pyridine or halogenated 9-methyl-9H-pyrido [3,4-b ] indole;
the auxiliary ligand (L ^ Z) is a bidentate ligand which is the same as the main ligand on the left side in the structural formula, or is any one of acetylacetone, 2-picolinic acid, 2-phenylpyridine, 2,6, 6-tetramethyl-3, 5-pimelic acid, (E) -N, N' -diisopropylbenzamidine and (Z) -2, 3-diisopropyl-1, 1-diphenylguanidine.
The third purpose of the invention is to provide the application of the iridium complex as an electroluminescent material in an organic electroluminescent device.
The invention has the beneficial effects that: the iridium complex with high luminous efficiency prepared by the invention can adjust the color of emitted light in a large range by adjusting the position and the type of the heteroatom. In addition, the preparation methods of the luminescent materials with different colors are basically the same, and the operation is simple. The main ligands of the iridium complexes have the same framework structure, and the light emitting color of the complexes can be adjusted in the wavelength ranges of blue green light and green light only due to different positions of heteroatoms on the main ligands and different types of the heteroatoms. The novel iridium complex has high luminous efficiency and thermal stability, and can be applied to OLED illumination and display.
Drawings
FIG. 1 is a schematic diagram of an OLED structure of an organic electroluminescent material;
FIG. 2 is a graph of luminescence spectrum analysis of application examples 1 to 3;
in the figure, 1, a glass substrate; 2. an anode layer; 3. a hole injection layer; 4. a hole transport layer; 5. a light emitting layer; 6. an electron transport layer; 7. an electron injection layer; 8. a cathode layer.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
The iridium complex Ir6 is synthesized according to the following reaction equation:
(1) preparation of the Main ligand
Figure BDA0001331108100000051
(2) Synthesis of chloro-bridged dimers
Figure BDA0001331108100000061
(3) Target synthesis
Figure BDA0001331108100000062
Example 2
The iridium complex Ir7 is synthesized according to the following reaction equation:
(1) preparation of the Main ligand
Figure BDA0001331108100000063
(2) Synthesis of chloro-bridged dimers
Figure BDA0001331108100000064
(3) Target synthesis
Figure BDA0001331108100000071
Example 3
The iridium complex Ir8 is synthesized according to the following reaction equation:
(1) preparation of the Main ligand
Figure BDA0001331108100000072
(2) Synthesis of chloro-bridged dimers
Figure BDA0001331108100000073
(3) Target synthesis
Figure BDA0001331108100000074
As shown in fig. 1, the structure of an organic electroluminescent device (OLED) includes a glass substrate 1, an anode layer 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode layer 8, which are sequentially stacked and combined. The iridium phosphorescent material prepared by the invention is applied to a light emitting layer of an OLED, and the composition of each layer of the OLED in application examples 1-3 is shown in Table 1.
TABLE 1
Figure BDA0001331108100000081
Application example 1
Depositing a layer of Indium Tin Oxide (ITO) with the thickness of 100nm on a glass substrate 1 to be used as a transparent anode layer 2; NPB (N, N '-di (1-naphthyl) -N, N' -diphenyl-1, 1 '-biphenyl-4-4' -diamine) hole transport material with the thickness of 10nm is vacuum-evaporated on the transparent anode layer 2 to be used as a hole injection layer 3, wherein F4-TCNQ (2,3,5, 6-tetrafluoro-7, 7',8,8' -tetracyanoquinodimethane) is doped with 3 percent of impurities; a layer of spiro-TAD (2,2',7,7' -tetra (diphenylamino) -9,9' -spirobifluorene) with the thickness of 100nm is arranged on the hole injection layer 3 to be used as a hole transport layer 4; a layer of 40nmCBP (4,4 '-N, N' -dicarbazolylbiphenyl) is evaporated on the hole transport layer 4 in vacuum to form a light-emitting layer 5, and 6 wt% of iridium complex Ir6 is doped in the layer; and then sequentially performing vacuum evaporation on the light-emitting layer 5 to form a layer of TPQ (2,3,5, 8-tetraphenylquinoxaline) with the thickness of 30nm as an electron transport layer 6 and form Liq with the thickness of 1nm as an electron injection layer 7, and finally depositing metal aluminum (Al) with the thickness of 100nm on the electron injection layer 7 by adopting a vacuum evaporation film deposition technology to form a cathode layer 8 of the device.
The performance test shows that the maximum light-emitting wavelength of the electroluminescence spectrum of the device is 511nm, the color is green, and the maximum external quantum efficiency is 15%.
Application example 2
The same as in application example 1, except that: the light-emitting layer 5 is CBP (4,4 '-N, N' -dicarbazolylbiphenyl) with a thickness of 40nm, which is doped with 6 wt% of an iridium complex Ir 7.
The performance test shows that the maximum luminous wavelength of the electroluminescent spectrum of the device is 517nm, the color is green, and the maximum external quantum efficiency is 14%.
Application example 3
The same as in application example 1, except that: the light-emitting layer 5 is CBP (4,4 '-N, N' -dicarbazolylbiphenyl) with a thickness of 40nm, which is doped with 6 wt% of an iridium complex Ir 8.
The performance test shows that the maximum luminescent wavelength of the electroluminescent spectrum of the device is 493nm, the color is blue-green, and the maximum external quantum efficiency is 11%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (3)

1. An iridium complex used as a phosphorescent material is characterized by having a structural formula as follows:
Figure FDA0002622473770000011
2. a process for preparing an iridium complex according to claim 1, which comprises the steps of:
(1) carrying out C-N coupling reaction on the raw material I and the raw material II to obtain a main ligand;
(2) under the protection of nitrogen, dissolving a main ligand in ethylene glycol monoethyl ether, adding iridium trichloride hydrate and deionized water, and heating for reaction to obtain an iridium-chlorine bridge complex;
(3) under the alkaline condition, heating and refluxing the iridium-chlorine bridge complex and acetylacetone to react to obtain an iridium complex;
wherein the raw material I is 1H-indole;
the raw material II is
Figure FDA0002622473770000012
3. Use of an iridium complex according to claim 1 as an electroluminescent material in an organic electroluminescent device.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011238944A (en) * 2011-06-28 2011-11-24 Konica Minolta Holdings Inc Organic electroluminescent device and display using the same
CN102449107A (en) * 2009-04-06 2012-05-09 通用显示公司 Metal complex comprising novel ligand structures
CN103102371A (en) * 2011-11-15 2013-05-15 通用显示公司 Heteroleptic iridium complex
CN103450891A (en) * 2013-09-24 2013-12-18 安徽工业大学 Iridium complex phosphorescent material taking fluorinated fluoropyridine carboxylic acid as auxiliary ligand and preparation method thereof
US20140209873A1 (en) * 2013-01-30 2014-07-31 Soung-Wook KIM Organometallic complex and organic light-emitting diode including the same
CN104650151A (en) * 2013-11-15 2015-05-27 环球展览公司 Organic Electroluminescent Materials And Devices

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102449107A (en) * 2009-04-06 2012-05-09 通用显示公司 Metal complex comprising novel ligand structures
JP2011238944A (en) * 2011-06-28 2011-11-24 Konica Minolta Holdings Inc Organic electroluminescent device and display using the same
CN103102371A (en) * 2011-11-15 2013-05-15 通用显示公司 Heteroleptic iridium complex
US20140209873A1 (en) * 2013-01-30 2014-07-31 Soung-Wook KIM Organometallic complex and organic light-emitting diode including the same
CN103450891A (en) * 2013-09-24 2013-12-18 安徽工业大学 Iridium complex phosphorescent material taking fluorinated fluoropyridine carboxylic acid as auxiliary ligand and preparation method thereof
CN104650151A (en) * 2013-11-15 2015-05-27 环球展览公司 Organic Electroluminescent Materials And Devices

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