WO2017101687A1 - 有机发光显示器件及显示装置 - Google Patents
有机发光显示器件及显示装置 Download PDFInfo
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- WO2017101687A1 WO2017101687A1 PCT/CN2016/108389 CN2016108389W WO2017101687A1 WO 2017101687 A1 WO2017101687 A1 WO 2017101687A1 CN 2016108389 W CN2016108389 W CN 2016108389W WO 2017101687 A1 WO2017101687 A1 WO 2017101687A1
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- 239000000463 material Substances 0.000 claims abstract description 60
- 230000005525 hole transport Effects 0.000 claims abstract description 44
- 238000002347 injection Methods 0.000 claims abstract description 16
- 239000007924 injection Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 230000003111 delayed effect Effects 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000013590 bulk material Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 6
- 230000000903 blocking effect Effects 0.000 abstract description 4
- 238000007725 thermal activation Methods 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- -1 aryl tertiary amine compound Chemical class 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- SZAANBOGSUKUJG-UHFFFAOYSA-N c(cc1)ccc1-c(nc1)ncc1-c1nc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)nc(-c2cnc(-c3ccccc3)nc2)n1 Chemical compound c(cc1)ccc1-c(nc1)ncc1-c1nc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)nc(-c2cnc(-c3ccccc3)nc2)n1 SZAANBOGSUKUJG-UHFFFAOYSA-N 0.000 description 1
- 0 c(cc1)ccc1-c1nc(-c2ccccc2)nc(*2c(c3c(cc4)c5ccccc5[n]3-c3ccccc3)c4-c3c2cccc3)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(*2c(c3c(cc4)c5ccccc5[n]3-c3ccccc3)c4-c3c2cccc3)n1 0.000 description 1
- BVBUDFHMPRODKB-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-[n](c(cccc2)c2c2c3)c2cc(c2c4cccc2)c3[n]4-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-[n](c(cccc2)c2c2c3)c2cc(c2c4cccc2)c3[n]4-c2ccccc2)n1 BVBUDFHMPRODKB-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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Definitions
- the present invention relates to the field of flat panel display technologies, and in particular, to an organic light emitting display device and a display device.
- organic light emitting display devices are classified into a single body device and a dual body device.
- a single-host device generally has a problem of low current efficiency and short life.
- the dual-body device is more advantageous for the regulation of carrier balance in the device than the single-body device, and the device performance is better.
- the dual-body device has high requirements on process stability, and the slight fluctuation of the ratio of the two main components in the dual-body device will greatly change the performance of the device, which is a big challenge to the yield of the product in the production line.
- An organic light emitting display device comprising:
- the functional structure layer includes a hole injection layer, a first hole transport layer sequentially stacked on the first electrode a second hole transport layer, an organic light emitting layer, an electron transport layer, and an electron injection layer;
- the highest occupied orbital energy level of the first material constituting the first hole transporting layer is smaller than the highest occupied orbital energy level of the second material constituting the second hole transporting layer;
- the triplet energy level is greater than 2.5 eV;
- the organic light emitting layer includes a light emitting material including a thermally activated delayed fluorescent material.
- the second material constituting the second hole transport layer is selected from the compounds represented by Formula 1.
- Structure 1-1 is:
- Structure 1-2 is:
- -L a is selected from an aromatic ring having 6 to 25 ring carbon atoms or an aromatic hetero ring having 5 to 25 ring atoms
- - Ar d is selected from ring carbon atoms of 6 to 25 aryl group, or hetero ring atoms is 5 to 25 aromatic group
- n is selected from 2 or 3, a plurality -Ar d each may be the same or different;
- Structural formula 1-3 is:
- L b is selected from the group consisting of an arylene group having 6 to 25 ring carbon atoms or a heteroarylene group having 5 to 25 ring atoms; L b is bonded to a ring to which R 1 is attached;
- R 1 and R 2 are each independently selected from an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, and a ring-constituting carbon atom.
- X is selected from CR 3 R 4 , NR 5 , O or S, and R 3 , R 4 and R 5 are each independently selected from an alkyl group having 1 to 15 carbon atoms or a ring-constituting carbon number of 6 ⁇ 25 aryl;
- Ar c is selected from an aryl group having 6 to 50 ring carbon atoms or a heteroaryl group having 5 to 25 ring atoms, or a structure represented by Structural Formula 1-1, Structural Formula 1-2 or Structural Formula 1-3. .
- the second hole transport layer has a thickness of 20 to 50 nm.
- the second hole transport layer has a thickness of 35 to 45 nm.
- the luminescent host material comprises a green photothermally activated delayed fluorescent material.
- the luminescent host material is selected from the group consisting of compounds represented by Formula 2,
- the structure of the ring A is as shown in the structural formula 2-1.
- Structure 2-1 is:
- Ring A is fused to an adjacent ring;
- X is selected from N or CH, wherein at least one X is selected from N;
- Ar 1 , Ar 2 , and Ar 3 are each independently selected from a non-fused ring aromatic hydrocarbon substituent, or are not thick.
- R is selected from a H atom or a monovalent substituent.
- the luminescent host material is selected from the group consisting of compounds of the formula
- the luminescent host material comprises a red light thermally activated delayed fluorescent material.
- the first hole transport layer has a thickness of 1 to 40 nm.
- the present invention also provides a display device comprising the organic light emitting display device provided by the present invention.
- the organic light-emitting display device of the present invention adopts two layers of hole transport layers, wherein the second hole transport layer functions as an electron blocking layer and an optical compensation layer, and is delayed from thermal activation in the organic light-emitting layer
- the combination of fluorescent materials enhances the current efficiency and lifetime of the organic light-emitting display device.
- FIG. 1 is a schematic structural view of an organic light emitting display device according to a preferred embodiment of the present invention.
- FIG. 2 is a schematic structural view of an organic light emitting display device of Comparative Example 1.
- an organic light emitting display device 100 includes a first electrode 110, a second electrode 120, and a functional structure layer 130 between the first electrode 110 and the second electrode 120.
- the first electrode 110 is an indium tin oxide electrode
- the second electrode 120 is a silver electrode.
- the first electrode 110 and the second electrode 120 are not limited to the above electrodes, and may be He electrodes.
- the organic light-emitting display device 100 in the present embodiment is a top emission, and in order to further optimize the performance, a circular polarizer layer 190 is further disposed on a side of the second electrode 120 away from the functional structure layer 130.
- the circular polarizer layer 190 may not be provided.
- the functional structure layer 130 includes a hole injection layer 131 sequentially stacked on the first electrode 110, a first hole transport layer 1321, a second hole transport layer 1322, an organic light emitting layer 133, an electron transport layer 134, and Electron injection layer 135.
- the material and thickness of the hole injection layer 131, the electron transport layer 134, and the electron injection layer 135 are not particularly limited, and materials and thicknesses well known to those skilled in the art may be used, and details are not described herein.
- the primary role of the first hole transporting layer 1321 is hole transport, and the second hole transporting layer 1322 serves as an electron blocking layer and an optical compensation layer in addition to hole transport.
- the material of the second hole transport layer 1322 has a triplet energy level greater than 2.5 eV.
- the highest occupied orbital energy level of the material of the second hole transport layer 1322 is greater than the highest occupied orbital energy level of the material of the first hole transport layer 1321.
- the material of the first hole transport layer 1321 is selected from the group consisting of NPB.
- the material of the first hole transport layer 1321 is not limited to NPB, and may be other hole transport materials.
- the first hole transport layer 1321 has a thickness of 1 to 40 nm, more preferably 5 to 20 nm.
- the material of the second hole transport layer 1322 is an aryl tertiary amine compound.
- the material of the second hole transport layer is selected from the compounds represented by Formula 1.
- Structure 1-1 is:
- Structure 1-2 is:
- -Ar d is selected from a self-substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms;
- n is selected from 2 or 3, a plurality of -Ar d They can be the same or different;
- Structural formula 1-3 is:
- -L b is selected from substituted or unsubstituted arylene groups having 6 to 25 ring carbon atoms or substituted or unsubstituted heteroarylene groups having 5 to 25 ring atoms; L b and R 1 The connected ring is connected by a single button;
- R 1 and R 2 are each independently selected from an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, and a ring-constituting carbon atom.
- X is selected from CR 3 R 4 , NR 5 , O or S, and R 3 , R 4 and R 5 are each independently selected from a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or substituted or An unsubstituted aryl group having 6 to 25 ring carbon atoms;
- Ar c is selected from substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms, or substituted or unsubstituted heteroaryl groups having 5 to 25 ring atoms, or structural formula 1-1, structural formula 1-2 or structural formula 1-3.
- the material of the second hole transporting layer is preferably a compound of the following formula:
- the second hole transport layer 1322 has a thickness of 20 to 50 nm, more preferably 35 to 45 nm.
- the organic light-emitting layer 133 comprises a light-emitting host material, and the light-emitting host material is a heat-activated delayed fluorescent material.
- the organic light-emitting display device of the present invention is preferably a green light device, that is, the light-emitting host material is a green light-thermally-activated delayed fluorescent material.
- the luminescent host material is selected from the compounds represented by Formula 2,
- the structure of the ring A is as shown in the structural formula 2-1.
- Structure 2-1 is:
- Ring A is fused to an adjacent ring;
- X is selected from N or CH, wherein at least one X is selected from N; and
- Ar 1 , Ar 2 , and Ar 3 are each independently selected from substituted or unsubstituted non-fused ring aromatic hydrocarbons.
- R is selected from a H atom or a monovalent substituent.
- the luminescent host material is selected from one of the compounds of the following structural formula
- the luminescent host material is not limited to the compound of the above formula, and may also be a compound of the following formula:
- the organic light-emitting layer 133 generally also includes a dye.
- Dyes may be selected from dyes well known to those skilled in the art.
- the organic light-emitting layer has a thickness of 10 to 40 nm.
- the organic light emitting display device of the present invention is not limited to a green light device, and may be a red light device or a blue light device.
- the above organic light-emitting display device employs two layers of hole transport layers, wherein the second hole transport layer functions as an electron blocking layer and an optical compensation layer, and is matched with a thermally activated delayed fluorescent material in the organic light-emitting layer, thereby improving the organic light-emitting display.
- Current efficiency and lifetime of the device And there is no increase in difficulty in the process relative to the prior art.
- the present invention also provides a display device comprising the organic light emitting display device provided by the present invention.
- a top-emitting green single-body device as shown in FIG. 1, includes a first electrode 110, a hole injection layer 131, a first hole transport layer 1321, and a second hole transport layer 1322 in order from bottom to top.
- the first electrode 110 is an indium tin oxide electrode and has a thickness of 40 nm.
- the material of the hole injection layer 131 is HAT and has a thickness of 10 nm.
- the material of the first hole transport layer 1321 is NPB and has a thickness of 20 nm.
- the material of the second hole transport layer 1322 is a material of the following structural formula and has a thickness of 40 nm.
- the material of the organic light-emitting layer 133 is a material of the following structural formula and has a thickness of 30 nm.
- the electron transport layer 134 is a co-evaporated layer of Bphen and Liq having a thickness of 30 nm.
- the material of the electron injecting layer 135 is a silver alloy and has a thickness of 2 nm.
- the second electrode 120 is a silver electrode and has a thickness of 16 nm.
- the material of the optical coupling layer 190 is Alq 3 and has a thickness of 65 nm.
- the top-emitting green single-body device 100' has only one hole transport layer 132, and the material of the hole transport 132 and the second hole transport layer of Embodiment 1. The materials are the same.
- the hole injection layer has two layers, that is, a first hole injection layer 1311 and a second hole injection layer 1312.
- the second hole injecting layer serves as an optical compensation layer and has a thickness of 35 nm.
- the material of the second hole injecting layer was 4,4,4-tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine (m-MTDATA).
- Comparative Example 1 The difference from Comparative Example 1 is that the material of the hole transport layer is NPB.
- the life decay test was performed at an initial luminance of 10 Knit, and the brightness was attenuated to the initial 97%.
- Example 1 The devices of Example 1 and Comparative Example 1-2 were subjected to voltage, current efficiency, CIE-x, CIE-y, and lifetime detection, respectively, and the test structure is shown in Table 1.
- the device of Example 1 has a significant improvement over the device of Comparative Example 1 or 2 regardless of current efficiency, CIE-x, CIE-y, and lifetime.
- the device current efficiency of Example 1 was 11.2% higher than that of the device of Comparative Example 2, the lifetime was improved by 225 hours, and the lifetime was almost doubled.
- the device current efficiency of Example 1 was 10% higher than that of the device of Comparative Example 1, the lifetime was improved by 165 hours, and the lifetime was almost doubled.
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Abstract
Description
Claims (12)
- 一种有机发光显示器件,包括:第一电极;第二电极;以及功能结构层,其位于第一电极和第二电极之间,其中,所述功能结构层包括顺序地层叠在所述第一电极上的空穴注入层、第一空穴传输层、第二空穴传输层、有机发光层、电子传输层、以及电子注入层;其中,构成所述第一空穴传输层的第一材料的最高已占轨道能级小于构成所述第二空穴传输层的第二材料的最高已占轨道能级;所述第二材料的三线态能级大于2.5eV;所述有机发光层包括发光主体材料,所述发光主体材料包括热激活延迟荧光材料。
- 根据权利要求1所述的有机发光显示器件,其特征在于,所述第二空穴传输层的材料选自通式1所表示的化合物,其中,—Ara的结构如结构式1-1或1-2所示,其中,—La选自成环碳原子数为6~25的芳香族环、或成环原子数为5~25的芳香族杂环;—Ard选自成环碳原子数为6~25的芳基、或成环原子数为5~25的杂芳基;n选自2或3,多个—Ard分别可以相同也可以不同;—Arb的结构如结构式1-3所示,结构式1-3为:其中,—Lb选自成环碳原子数为6~25的亚芳基或成环原子数为5~25的杂亚芳基;Lb与R1所连接的环单键连接;R1和R2分别独立地选自碳原子数为1~15的烷基、碳原子数为2~15的烯基、成环碳原子数为3~15的环烷基、成环碳原子数为6~25的芳基、成环原子数为5~25的杂芳基、由碳原子数为1~15的烷基形成的三烷基甲硅烷基、由成环碳原子数为6~25的芳基形成的三芳基甲硅烷基、由碳原子数为1~15的烷基和成环碳原子数为6~25的芳基形成的烷基芳基甲硅烷基、咔唑基、卤素原子或氰基,o选自0~3的整数,p选自0~4的整数,相邻的多个R1之间和R2之间、以及R1和R2可以相互键合而形成环,X选自CR3R4、NR5、O或S,R3、R4和R5分别独立地选自碳原子数为1~15的烷基或成环碳原子数为6~25的芳基;Arc选自成环碳原子数为6~50的芳基、或成环原子数为5~25的杂芳基,或由结构式1-1、结构式1-2或结构式1-3表示的结构。
- 根据权利要求1所述的有机发光显示器件,其特征在于,所述第二空穴传输层的厚度为20~50nm。
- 根据权利要求1所述的有机发光显示器件,其特征在于,所述第二空穴传输层的厚度为35~45nm。
- 根据权利要求1所述的有机发光显示器件,其特征在于,所述发光主体材料包括绿光热激活延迟荧光材料。
- 根据权利要求1所述的有机发光显示器件,其特征在于,所述发光主体材料包括红光热激活延迟荧光材料。
- 根据权利要求1-8中任一项所述的有机发光显示器件,其特征在于,所述第一空穴传输层的厚度为1~40nm。
- 根据权利要求1-8中任一项所述的有机发光显示器件,其特征在于, 在所述第二电极上远离所述功能结构层130的一侧还设有圆偏光镜层190。
- 根据权利要求1-8中任一项所述的有机发光显示器件,其特征在于,所述有机发光层的厚度为10~40nm。
- 一种显示装置,其特征在于,包括权利要求1-8中任一项所述的有机发光显示器件。
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US15/781,446 US20200203618A1 (en) | 2015-12-15 | 2016-12-02 | Organic light-emitting display device and display apparatus |
EP16874744.2A EP3392911B1 (en) | 2015-12-15 | 2016-12-02 | Organic light-emitting display device and display apparatus |
KR1020187018243A KR102103874B1 (ko) | 2015-12-15 | 2016-12-02 | 유기 발광 디스플레이 기기 및 디스플레이 장치 |
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CN109659442A (zh) * | 2018-12-13 | 2019-04-19 | 云谷(固安)科技有限公司 | 一种有机电致发光器件和显示装置 |
CN110911572A (zh) * | 2019-11-25 | 2020-03-24 | Tcl华星光电技术有限公司 | 一种有机发光显示器件及其制备方法 |
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EP3598516B1 (en) * | 2017-03-15 | 2024-01-31 | Hodogaya Chemical Co., Ltd. | Organic electroluminescent element |
CN111225905B (zh) * | 2018-02-13 | 2023-09-05 | 株式会社Lg化学 | 杂环化合物及包含其的有机发光器件 |
US20210171963A1 (en) | 2018-07-26 | 2021-06-10 | Daewoong Pharmaceutical Co., Ltd. | Recombinant yeast strain having sterol productivity, preparation method therefor and use thereof |
CN111384280B (zh) * | 2018-12-29 | 2021-05-18 | Tcl科技集团股份有限公司 | 一种量子点发光二极管及其制备方法 |
CN111662312B (zh) * | 2020-06-08 | 2023-08-11 | 武汉天马微电子有限公司 | 一种化合物、热激活延迟荧光材料及其应用 |
CN111943961B (zh) * | 2020-08-26 | 2021-07-27 | 山西穿越光电科技有限责任公司 | 基于吩嗪-噻吩-二氰基的有机电致发光化合物及应用 |
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CN106887444B (zh) | 2020-01-10 |
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