CN117256211A - Composition for organic optoelectronic device, and display device - Google Patents
Composition for organic optoelectronic device, and display device Download PDFInfo
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- CN117256211A CN117256211A CN202280032342.4A CN202280032342A CN117256211A CN 117256211 A CN117256211 A CN 117256211A CN 202280032342 A CN202280032342 A CN 202280032342A CN 117256211 A CN117256211 A CN 117256211A
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- deuterium
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- 230000005693 optoelectronics Effects 0.000 title claims abstract description 49
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 239000000126 substance Substances 0.000 claims abstract description 118
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
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- 229910052805 deuterium Inorganic materials 0.000 claims description 99
- 239000010410 layer Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 239000012044 organic layer Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- -1 dibenzofuranyl Chemical group 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 12
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
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- 125000001624 naphthyl group Chemical group 0.000 claims description 7
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- 125000001072 heteroaryl group Chemical group 0.000 description 9
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- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
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- 125000000524 functional group Chemical group 0.000 description 3
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- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 2
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- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 125000005103 alkyl silyl group Chemical group 0.000 description 2
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- 125000005104 aryl silyl group Chemical group 0.000 description 2
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to: a composition for an organic optoelectronic device, the composition comprising a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formulas 2 and 3; an organic optoelectronic device and a display device including the same. The details of chemical formulas 1 to 3 are defined in the specification.
Description
Technical Field
A composition for an organic optoelectronic device, and a display device are disclosed.
Background
An organic optoelectronic device (organic optoelectronic diode) is a device capable of converting electrical energy and optical energy into each other.
Organic optoelectronic devices can be broadly divided into two classes according to the principle of operation. One is a photoelectric device that generates electric energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, and the other is a light emitting device that generates light energy from electric energy by supplying voltage or current to the electrodes.
Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.
Among them, organic Light Emitting Diodes (OLEDs) have attracted much attention in recent years due to an increase in demand for flat panel display devices. An organic light emitting diode is a device that converts electric energy into light, and the performance of the organic light emitting diode is greatly affected by organic materials between electrodes.
Disclosure of Invention
Technical problem
One embodiment provides a composition for an organic optoelectronic device capable of realizing a low-driving, high-efficiency, and long-life organic optoelectronic device.
Another embodiment provides an organic optoelectronic device comprising a composition for an organic optoelectronic device.
Another embodiment provides a display device including an organic optoelectronic device.
Technical proposal
According to one embodiment, a composition for an organic optoelectronic device is provided that includes a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formulas 2 and 3.
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
L 1 and L 2 Each independently is a single bond or a substituted or unsubstituted C6 to C30 arylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclyl group (heterocyclic group),
R 1 to R 4 Each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C30 aryl,
Ar 6 to Ar 9 Each independently is hydrogen or a substituted or unsubstituted C6 to C30 aryl,
m1 and m4 are each independently one of integers from 1 to 4,
m2 and m3 are each independently one of integers from 1 to 3, and
chemical formula 1 satisfies both the following conditions (i) and (ii),
(i)Ar 1 and Ar is a group 2 At least one of which is a C6 to C30 aryl substituted with at least one deuterium or a C2 to C30 heterocyclic group substituted with at least one deuterium, and
(ii)R 1 to R 4 At least one of which is deuterium;
in the chemical formula 2 and the chemical formula 3,
Ar 3 to Ar 5 Each independently is a substituted or unsubstituted C6 to C20 aryl or a substituted or unsubstituted C2 to C30 heterocyclyl,
a 1 * To a 4 * Each independently is a linking carbon (C) or C-L a -R a ，
A in chemical formula 2 1 * To a 4 * Is linked to the adjacent two in formula 3,
L a and L 3 To L 6 Each independently is a single bond, a substituted or unsubstituted C6 to C20 arylene or a substituted or unsubstituted C2 to C20 heteroarylene, and
R a and R is 5 To R 12 Each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl.
According to another embodiment, an organic optoelectronic device is provided comprising an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the organic layer comprises a composition for an organic optoelectronic device.
According to another embodiment, a display device including an organic optoelectronic device is provided.
Advantageous effects
Low driving, high efficiency and long life organic optoelectronic devices can be realized.
Drawings
Fig. 1 is a sectional view illustrating an organic light emitting diode according to an embodiment.
< description of reference numerals >
100: organic light emitting diode
105: organic layer
110: cathode electrode
120: anode
130: light-emitting layer
140: hole transfer region (hole transport region)
150: electronic transmission area (electron transport region)
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the invention is not limited thereto, and the invention is defined by the scope of the claims.
As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, halogen, hydroxy, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.
In one example of the invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced with deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In specific examples of the invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In specific examples of the invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced with deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In specific examples of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.
In the present specification, "unsubstituted" means that a hydrogen atom is not replaced with another substituent but remains.
In the present specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".
As used herein, when no definition is otherwise provided, "hetero" refers to one that includes one to three heteroatoms selected from N, O, S, P and Si in one functional group and the remainder is carbon.
As used herein, "aryl" refers to a group comprising at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p-orbitals that form a conjugate, e.g., phenyl, naphthyl, and the like; two or more hydrocarbon aromatic moieties may be linked by sigma bonds and may be, for example, biphenyl, terphenyl, tetrabiphenyl, and the like; and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, e.g., fluorenyl.
Aryl groups may include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings sharing pairs of adjacent carbon atoms) functional groups.
As used herein, "heterocyclyl" is a generic term for heteroaryl and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as aryl, cycloalkyl, fused rings thereof, or combinations thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.
For example, "heteroaryl" refers to an aryl group comprising at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryl groups are directly linked by a sigma linkage, or when a heteroaryl group includes two or more rings, the two or more rings may be fused. When heteroaryl is a fused ring, each ring may include one to three heteroatoms.
More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fused tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted droyl group, a substituted or unsubstituted bistriphenyl group (triphenylene group ), a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furyl group, or a combination thereof, but is not limited thereto.
More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted thiophenyl group, but is not limited thereto.
As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and holes formed in an anode can be easily injected into and transported in a light emitting layer due to conductive characteristics according to the Highest Occupied Molecular Orbital (HOMO) level.
Further, the electron characteristics refer to an ability to accept electrons when an electric field is applied, and electrons formed in the cathode may be easily injected into and transported in the light emitting layer due to a conductive characteristic according to a Lowest Unoccupied Molecular Orbital (LUMO) level.
Hereinafter, a composition for an organic optoelectronic device according to one embodiment is described.
The composition for an organic optoelectronic device according to one embodiment includes a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formulas 2 and 3.
The first compound may be represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
L 1 and L 2 Each independently is a single bond or a substituted or unsubstituted C6 to C30 arylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heterocyclyl,
R 1 to R 4 Each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C30 aryl,
m1 and m4 are each independently one of integers from 1 to 4,
m2 and m3 are each independently one of integers from 1 to 3,
Ar 6 to Ar 9 Each independently is hydrogen or a substituted or unsubstituted C6 to C30 aryl group, and chemical formula 1 satisfies both the following conditions (i) and (ii).
(i)Ar 1 And Ar is a group 2 At least one of which is a C6 to C30 aryl substituted with at least one deuterium or a C2 to C30 heterocyclic group substituted with at least one deuterium, and
(ii)R 1 to R 4 At least one of which is deuterium.
The first compound represented by chemical formula 1 has biscarbazole as a basic skeleton, and has a structure in which the benzene moiety of the carbazole is substituted with at least one deuterium and the ninth (N-direction) substituent Ar of the carbazole 1 And Ar is a group 2 Is substituted with at least one deuterium.
Since the benzene moiety of carbazole and the ninth (N-direction) substituent of carbazole are simultaneously substituted with deuterium, the zero point energy (zero point energy) and the vibrational energy of the compound can be further reduced. Therefore, the ground state energy is further reduced, and the intermolecular interaction is weakened, so that the thin film thus formed can be made amorphous, which improves heat resistance and lifetime. In other words, if this is applied, a low-driving, high-efficiency, and particularly long-life organic light emitting diode can be realized.
Depending on the linking position of carbazole, chemical formula 1 may be represented as any one of chemical formulas 1-1 to 1-10, for example.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
[ chemical formulas 1-9]
[ chemical formulas 1-10]
In chemical formulas 1-1 to 1-10,
L 1 、L 2 、Ar 1 、Ar 2 、Ar 6 to Ar 9 、R 1 To R 4 And m 1 To m 4 The same as described above.
When R is 1 When greater than or equal to 2, each R 1 May be the same or different from each other.
When R is 2 When greater than or equal to 2, each R 2 May be the same or different from each other.
When R is 3 When greater than or equal to 2, each R 3 May be the same or different from each other.
When R is 4 When greater than or equal to 2, each R 4 May be the same or different from each other.
When Ar is 6 When greater than or equal to 2, each Ar 6 May be the same or different from each other.
When Ar is 7 When greater than or equal to 2, each Ar 7 May be the same or different from each other.
When Ar is 8 When greater than or equal to 2, each Ar 8 May be the same or different from each other.
When Ar is 9 When greater than or equal to 2, each Ar 9 May be the same or different from each other.
For example, R 1 To R 4 At least two of which may be deuterium.
For example, R 1 To R 4 Each may be deuterium, m1 and m4 may each be an integer of 4, and m2 and m3 may each be an integer of 3.
For example, R 1 And R is 2 Each may be deuterium, m1 may be an integer from 1 to 4, m2 may be an integer from 1 to 3, and R 3 And R is 4 Each may be hydrogen.
For example, R 3 And R is 4 May each be deuterium, m3 may be an integer from 1 to 3, m4 may be an integer from 1 to 4, and R 1 And R is 2 Each may be hydrogen.
For example, R 1 And R is 4 May each be deuterium, m1 and m4 may each be an integer of 1 to 4, and R 2 And R is 3 Each may be hydrogen.
For example, R 1 To R 3 May each be deuterium, m2 and m3 may each be an integer from 1 to 3, m1 may be an integer from 1 to 4, and R 4 May be deuterium or a C6 to C30 aryl group substituted or unsubstituted with deuterium.
As an example, depending on the substitution R 1 To R 4 The substitution position of deuterium of (2) chemical formula 1 may be represented by any one of chemical formulas 1a to 1 e.
[ chemical formula 1a ]
[ chemical formula 1b ]
[ chemical formula 1c ]
[ chemical formula 1d ]
[ chemical formula 1e ]
In chemical formulas 1a to 1e, L 1 、L 2 、Ar 1 、Ar 2 And Ar is a group 6 To Ar 9 The same as described above.
Ar 6 To Ar 9 Each independently is C6 to unsubstituted substituted with hydrogen or deuteriumA C30 aryl group,
D 3 refers to the replacement of three deuterium.
For example, ar 1 And Ar is a group 2 May be phenyl substituted with at least one deuterium, biphenyl substituted with at least one deuterium, terphenyl substituted with at least one deuterium, naphthyl substituted with at least one deuterium, anthryl substituted with at least one deuterium, phenanthryl substituted with at least one deuterium, ditriphenyl substituted with at least one deuterium, fluorenyl substituted with at least one deuterium, dibenzofuranyl substituted with at least one deuterium, or dibenzothienyl substituted with at least one deuterium.
As a specific example, ar 1 And Ar is a group 2 May be phenyl substituted with at least one deuterium, biphenyl substituted with at least one deuterium, terphenyl substituted with at least one deuterium, ditriphenyl substituted with at least one deuterium, dibenzofuranyl substituted with at least one deuterium or dibenzothienyl substituted with at least one deuterium.
As a specific example, ar 6 To Ar 9 Each independently may be a C6 to C20 aryl group unsubstituted or substituted with hydrogen or deuterium.
For example, ar 6 To Ar 9 Each may be independently hydrogen, a phenyl group substituted or unsubstituted with deuterium, a biphenyl group substituted or unsubstituted with deuterium, a terphenyl group substituted or unsubstituted with deuterium, a naphthyl group substituted or unsubstituted with deuterium, a phenanthryl group substituted or unsubstituted with deuterium, an anthracyl group substituted or unsubstituted with deuterium, a ditriphenyl group substituted or unsubstituted with deuterium, or a fluorenyl group substituted or unsubstituted with deuterium.
For example, L in chemical formula 1 1 -Ar 1 And L 2 -Ar 2 Can each be independently selected from the substituents listed in groups I-1 and I-2, and L 1 -Ar 1 And L 2 -Ar 2 At least one of which may be selected from the substituents listed in group I-2.
Group I-1
Group I-2
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In groups I-1 and I-2, are connection points.
For example, chemical formula 1 may be represented by chemical formulas 1 to 8a or chemical formulas 1 to 8 e.
[ chemical formula 1-8a ]
[ chemical formulas 1-8e ]
In chemical formulas 1 to 8a and chemical formulas 1 to 8e,
L 1 、L 2 、Ar 1 and Ar is a group 2 Is the same as above and Ar 9 Is a C6 to C30 aryl substituted or unsubstituted with deuterium.
For example, ar 9 It may be a phenyl group substituted or unsubstituted by deuterium, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group substituted or unsubstituted by deuterium, a naphthyl group substituted or unsubstituted by deuterium, a phenanthryl group substituted or unsubstituted by deuterium, an anthracyl group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, or a fluorenyl group substituted or unsubstituted by deuterium.
For example, the compound for an organic optoelectronic device represented by chemical formula 1 may be one selected from the compounds listed in group 1, but is not limited thereto.
Group 1
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As a more specific example, the compound for an organic optoelectronic device according to the present invention may be represented by chemical formulas 1 to 8a,
L 1 and L 2 May be a single bond or a substituted or unsubstituted phenylene group, and
Ar 1 and Ar is a group 2 Each may be a phenyl group substituted with deuterium, a biphenyl group substituted with deuterium, a terphenyl group substituted with deuterium, or a biphenylene group substituted with deuterium.
The second compound may be represented by a combination of chemical formula 2 and chemical formula 3.
In the chemical formula 2 and the chemical formula 3,
Ar 3 to Ar 5 Each independently is a substituted or unsubstituted C6 to C20 aryl or a substituted or unsubstituted C2 to C30 heterocyclyl,
a in chemical formula 2 1 * To a 4 * Each independently is a linking carbon (C) or C-L a -R a ，
A in chemical formula 2 1 * To a 4 * Each of the two adjacent in (a) is connected to a group represented by formula 3,
L a 、L 3 to L 6 Each independently is a single bond, a substituted or unsubstituted C6 to C20 arylene or a substituted or unsubstituted C2 to C20 heteroarylene, and
R a and R is 5 To R 12 Each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl.
The second compound may be used in the light emitting layer together with the first compound to improve light emitting efficiency and lifetime characteristics by increasing charge mobility and stability.
For example, the second compound may be represented by any one of chemical formula 2A, chemical formula 2B, chemical formula 2C, chemical formula 2D, chemical formula 2E, and chemical formula 2F.
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In chemical formulas 2A to 2F, ar 3 To Ar 5 、L 3 To L 6 And R is 5 To R 12 In the same manner as described above,
L a1 to L a4 And L is equal to 3 To L 6 Is defined as the same as the definition of (a),
R a1 to R a4 And R is R 5 To R 12 Is the same as defined in the following.
For example, ar of chemical formula 2 and chemical formula 3 3 To Ar 5 May each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted tetrabiphenyl group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group,
R a1 to R a4 And R is 5 To R 12 May each independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
In one embodiment of the present invention, formulas 2 and 2Ar in formula 3 3 To Ar 5 Each independently selected from the substituents listed in group II.
Group II
In group II, the connection points are.
In one exemplary embodiment, R a1 To R a4 And R is 5 To R 12 May independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
For example, R a1 To R a4 And R is 5 To R 12 May each independently be hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl.
In a more specific embodiment, R 5 To R 12 May each independently be hydrogen, deuterium or cyano,
wherein L is 3 To L 6 May be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted pyridylene group, and
Ar 3 to Ar 5 May each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted bistriphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.
In one embodiment of the present invention, the second compound may be represented by chemical formula 2B, wherein in chemical formula 2B, L a1 And L a2 Can be a single bond, L 3 To L 6 May each independently be a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 5 To R 12 、R a1 And R is a2 Can each independently be hydrogen, deuterium orSubstituted or unsubstituted phenyl, and Ar 3 To Ar 5 May each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
For example, the second compound may be one selected from the group 2 compounds, but is not limited thereto.
Group 2
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In a more specific embodiment of the present invention, the first compound may be represented by chemical formulas 1 to 8a, and the second compound may be represented by chemical formula 2B.
For example, the first compound and the second compound may be included in a weight ratio of 1:99 to 99:1. Within this range, the electron transport capacity of the first compound and the hole transport capacity of the second compound can be used to adjust the desired weight ratio to achieve bipolar characteristics and thus improve efficiency and lifetime. Within this range, they may be included, for example, in a weight ratio of 10:90 to 90:10, 20:80 to 80:20 (e.g., 20:80 to 70:30, 20:80 to 60:40, or 30:70 to 60:40). As a specific example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.
One or more compounds may be included in addition to the first and second compounds described above.
For example, the above-described compositions for organic optoelectronic devices may also comprise dopants.
The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red phosphorescent dopant.
The dopant is a material mixed in a small amount with a composition for an organic optoelectronic device to cause luminescence, and may generally be a material such as a metal complex that emits light by multiple excitations into a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or two or more types.
One example of a dopant may be a phosphorescent dopant, and examples of phosphorescent dopants may include organometallic compounds, including Ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd, or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by chemical formula Z, but is not limited thereto.
[ chemical formula Z ]
L 7 MX
In formula Z, M is a metal, and L 7 And X is the same or different and is a ligand that forms a complex with M.
M may be, for example, ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd or a combination thereof, and L 7 And X may be, for example, a bidentate ligand.
From L 7 And X may be selected from the formulae listed in group a, but is not limited thereto.
[ group A ]
In the group a of which the number of cells is equal,
R 300 to R 302 Each independently is hydrogen, deuterium, C1 to C30 alkyl substituted or unsubstituted by halogen, C6 to C30 aryl substituted or unsubstituted by C1 to C30 alkyl substituent, or halogen, and
R 303 to R 324 Each independently is hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF 5 A trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.
For example, a dopant represented by formula V may be included.
[ chemical formula V ]
In the chemical formula V, the chemical formula is shown in the specification,
R 101 to R 116 Each independently is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or-SiR 132 R 133 R 134 ，
R 132 To R 134 Each independently is a C1 to C6 alkyl group,
R 101 to R 116 At least one of which is a functional group represented by the formula V-1,
L 100 bidentate ligands, which are monovalent anions, which coordinate iridium via a lone pair of electrons on a carbon or heteroatom, and
m15 and m16 are each independently any one of integers from 0 to 3, and m15+m16 is any one of integers from 1 to 3,
[ chemical formula V-1]
In the formula V-1 of the present invention,
R 135 to R 139 Each independently is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or-SiR 132 R 133 R 134 ，
R 132 To R 134 Each independently is a C1 to C6 alkyl group, and
* Refers to a moiety attached to a carbon atom.
For example, a dopant represented by formula Z-1 may be included.
[ chemical formula Z-1]
In formula Z-1, rings A, B, C and D are each independently a 5-or 6-membered carbocyclic or heterocyclic ring;
R A 、R B 、R C and R is D Each independently represents mono-, di-, tri-or tetra-substituted or unsubstituted;
L B 、L C and L D Each independently selected from direct bond (direct bond), BR, NR, PR, O, S, se, C = O, S = O, SO 2 CRR ', siRR ', geRR ' and combinations thereof;
when nA is 1, L E Selected from direct bond, BR, NR, PR, O, S, se, C = O, S = O, SO 2 CRR ', siRR ', geRR ' and combinations thereof; when nA is 0, L E Absence of; and is also provided with
R A 、R B 、R C 、R D R and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; any adjacent R A 、R B 、R C 、R D R, R and R' are optionally linked to form a ring; x is X B 、X C 、X D And X E Each independently selected from carbon and nitrogen; and Q is 1 、Q 2 、Q 3 And Q 4 Each represents oxygen or a direct bond.
The dopant according to one embodiment may be a platinum complex and may be represented by formula VI.
[ chemical formula VI ]
In the formula VI, in which the compound is a compound,
X 100 selected from O, S and NR 131 ，
R 117 To R 131 Each independently is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or-SiR 132 R 133 R 134 ，
R 132 To R 134 Each independently is a C1 to C6 alkyl group, and
R 117 to R 131 At least one of them is-SiR 132 R 133 R 134 Or tert-butyl.
Hereinafter, an organic optoelectronic device to which the aforementioned compound for an organic optoelectronic device is applied will be described.
The organic optoelectronic device may be any device that converts electric energy into light energy (or vice versa), without particular limitation, and may be, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.
An organic light emitting diode as one example of an organic optoelectronic device is described herein with reference to the accompanying drawings.
Fig. 1 is a sectional view illustrating an organic light emitting diode according to an embodiment.
Referring to fig. 1, an organic light emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110.
Anode 120 may be made of a conductor with a large work function to aid hole injection and may be, for example, a metal, metal oxide, and/or conductive polymer. Anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; combinations of metals and oxides, such as ZnO and Al or SnO 2 And Sb; conductive polymers such as poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene) (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
The cathode 110 may be made of a conductor having a small work function to aid electron injection, and may be, for example, a metal, metal oxide, and/or conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or the like, or alloys thereof; multilayer structural materials, such asLiF/Al、LiO 2 Al, liF/Ca and BaF 2 /Ca, but is not limited thereto.
The organic layer 105 may comprise the aforementioned compositions for organic optoelectronic devices.
The organic layer 105 may include the light emitting layer 130, and the light emitting layer 130 may include the aforementioned composition for an organic optoelectronic device.
The composition for an organic optoelectronic device further comprising a dopant may be, for example, a red-emitting composition (red-light emitting composition).
The light emitting layer 130 may include, as a phosphorescent host, a composition such as that used in organic optoelectronic devices.
The organic layer may include a charge transport region in addition to the light emitting layer.
The charge transport region may be, for example, hole transport region 140.
The hole transport region 140 may further increase hole injection and/or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light emitting layer 130 and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer, and at least one of the group B compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.
[ group B ]
/>
/>
/>
/>
In the hole transporting region, in addition to the above-mentioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and the like and compounds having similar structures can be used.
Further, the charge transport region may be, for example, the electron transport region 150.
The electron transport region 150 may further increase electron injection and/or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.
In particular, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130 and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer, and at least one of the compounds of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.
[ group C ]
/>
/>
/>
An embodiment of the present invention may provide an organic light emitting diode including a light emitting layer as an organic layer.
Another embodiment of the present invention may provide an organic light emitting diode including a hole transport region and a light emitting layer as an organic layer.
Another embodiment of the present invention may provide an organic light emitting diode including an electron transport region and a light emitting layer as an organic layer.
As shown in fig. 1, one embodiment of the present invention may provide an organic light emitting diode including a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130.
In another embodiment of the present invention, the organic light emitting diode may include an electron injection layer (not shown), a hole injection layer (not shown), etc. as an organic layer in addition to the light emitting layer.
The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, and then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming the cathode or the anode thereon.
The organic light emitting diode may be applied to an organic light emitting display device.
Detailed description of the embodiments
Hereinafter, embodiments are described in more detail with reference to examples. However, these embodiments are exemplary, and the scope of the claims is not limited thereto.
Hereinafter, starting materials and reactants used in examples and synthesis examples were purchased from Sigma-Aldrich co.ltd., TCI inc, tokyo chemical industry or P & H tech or synthesized by known methods, unless otherwise specified.
(preparation of Compounds for organic optoelectronic devices)
The compounds presented as more specific examples of the compounds of the present invention are synthesized by the following steps.
(Synthesis of first Compound)
The compounds presented as more specific examples of the compounds of the present invention are synthesized by the following steps.
Synthesis example 1: synthesis of Compounds 1-38
[ reaction type 1]
The first step: synthesis of Compound Int 1
The compound Int 1 was synthesized by referring to the method disclosed in korean laid-open No. 10-2016-0049842.
And a second step of: synthesis of Compounds 1-38
30g (0.0535 mol) of compound Int 1,40 g (0.267 mol) of trifluoromethanesulfonic acid and 282g (3.35 mol) of D are introduced 6 Benzene, then stirred at 10 ℃ for 24 hours. Subsequently, purified water is added thereto, followed by saturation with K 3 PO 4 And (5) neutralizing the solution. The organic layer was concentrated and purified by column to give 18g of compounds 1-38 (white solid, LC-mass Mz 578.79, C42H10D18N 2).
Comparative synthesis example 1: synthesis of Compound Y1
[ reaction type 2]
35g (0.095 mol) of (phenyl-4-boric acid) -9H-carbazole, 17g (0.105 mol) of bromobenzene-D are introduced 5 3.3g (0.0028 mol) Pd (PPh) 3 ) 4 32.7g (0.237 mol) of K 2 CO 3 120ml of purified water and 320ml of THF, and then refluxed with stirring. When the reaction was completed, purified water was added thereto after cooling to separate an organic layer, and the organic layer was concentrated. The concentrated product was subjected to column purification to obtain 25g of Int 2 (molecular weight: 324.43).
20g (0.062 mol) of Int 2 were dissolved in 200ml of DMF and 11.5g (0.065 mol) of NBS was slowly added thereto at 0 ℃. The obtained mixture was stirred at room temperature to complete the reaction, and purified water was added thereto to produce a solid. The solid was subjected to column purification to obtain 23g of Int 3 (molecular weight: 403.33).
Into which 20g (0.0496 mol) of Int 3, 22g (0.06 mol) of phenyl-9H-carbazole-3-borate and 1.72g (0.0015 mol) of Pd (PPh) were introduced 3 ) 4 13.7g (0.099 mol) of K 2 CO 3 50ml of purified water and 165ml of THF, and reflux was stirred. When the reaction was completed, purified water was added thereto after cooling to separate an organic layer, and then the organic layer was concentrated. The concentrated product was subjected to column purification to obtain 11.5g of compound Y1 (molecular weight: 565.72).
Comparative synthesis example 2: synthesis of Compound Y2
[ reaction type 3]
47g (0.281 mol) of carbazole, 50g (0.310 mol) of bromobenzene-D are introduced 5 53g (0.028 mol) of CuI, 58g (0.42 mol) of K 2 CO 3 5g (0.028 mol) of 1, 10-phenanthroline and 560ml of DMF are stirred at reflux. When the reaction was completed, after cooling to room temperature, a solid was produced by adding purified water thereto. The solid was subjected to column purification to obtain 62g of Int 4 (molecular weight: 248.33).
62g (0.25 mol) of Int 4 are added to DMF and dissolved therein. Subsequently, 45g (0.25 mol) of NBS was slowly added thereto at 0℃and then stirred at room temperature to complete the reaction. Subsequently, purified water was added to the reaction solution to produce crystals, and the solid was subjected to column purification to obtain 80g of Int 5 (molecular weight: 327.23).
80g (0.245 mol) of Int 5, 120g (0.27 mol) of 4-biphenyl-carbazole-3-boronate, 68g (0.49 mol) of K are introduced 2 CO 3 14g (0.0122 mol) Pd (PPh) 3 ) 4 320ml of purified water and 490ml of THF, and was refluxed with stirring. When the reaction was completed, the organic layer was extracted by adding purified water thereto, and then concentrated. The mixture was subjected to column purification to obtain 90g of compound Y2 (molecular weight: 565.72).
(Synthesis of the second Compound)
Synthesis example 2: compounds of formula (I)Synthesis of B-12
[ reaction type 4]
The first step: synthesis of intermediate M-2
11, 12-indolino [2,3-a ]]Carbazole (78.35 g,305.69mmol, CAS number 60511-85-5), 3-bromobiphenyl (59.38 g,254.74 mmol), naOt-Bu (26.93 g,280.22 mmol), and Pd 2 (dba) 3 (7 g,7.64 mmol) was suspended in 1,400ml of toluene, and P (t-Bu) was added thereto 3 (3.64 ml,15.28 mmol) and then refluxed with stirring for 12 hours. Subsequently, distilled water was added to the reaction solution to separate the mixture. The obtained product was purified by a silica gel column to obtain intermediate M-2 (68.7 g, 57%).
And a second step of: synthesis of intermediate M-3
2, 4-dichloro-6-phenyl-1, 3, 5-triazine (74.50 g,329.56 mmol) and 4-biphenylboronic acid (55.47 g,280.12 mmol) were dissolved in a mixed solution of 0.7L Tetrahydrofuran (THF) and distilled water (3:1), and sodium t-butoxide (68.32 g,494.34 mmol) was added thereto, followed by stirring and refluxing for 12 hours. After cooling and layering the reaction solution, the organic layer was collected and concentrated. The concentrated residue was purified by a silica gel column to obtain intermediate M-3 (75.9 g, 67%).
And a third step of: synthesis of Compound B-12
Using intermediate M-2 and intermediate M-3, compound B-12 was obtained in the same manner as in the method of synthesizing intermediate M-2.
(manufacture of organic light-emitting diode)
Example 1
The glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate is ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and dried, and then transferred to a plasma washer by using oxygen plasmaThe cleaning was performed for 10 minutes and then transferred to a vacuum depositor. Using the prepared ITO transparent electrode as an anode, compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on an ITO substrate to formA thick hole injection layer and depositing compound A on the hole injection layer to +.>To form a hole transport layer. Depositing a compound B on the hole transport layer to +.>To form a hole transport auxiliary layer. On the hole transport auxiliary layer, the compounds 1 to 38 and the compound B-12 obtained in the above synthesis examples were simultaneously used as hosts in a weight ratio of 4:6 by vacuum deposition, and 10wt% of PhGD was doped as a dopant to form>A thick light emitting layer. Subsequently, compound C is deposited on the light-emitting layer to form +.>A thick electron transport auxiliary layer and simultaneously vacuum depositing compound D and Liq in a weight ratio of 1:1 to form +.>A thick electron transport layer. Will->LiQ and>sequentially vacuum deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light emitting diode.
The structure is ITO/compound A (3% NDP-9 doped)，) Compound A->Compound BEML [90wt% host (Compound 1-38: compound B-12=4:6 w/w): 10wt% PhGD]/>Compound C->Compound D, liQ->/LiQ/>/Al/>
Compound a: n- (biphenyl-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine
Compound B: n, N-bis (9, 9-dimethyl-9H-fluoren-4-yl) -9, 9-spirodi (fluoren) -2-amine
Compound C:2- [3'- (9, 9-dimethyl-9H-fluoren-2-yl) [1,1' -biphenyl ] -3-yl ] -4, 6-diphenyl-1, 3, 5-triazine
Compound D:2- (biphenyl-4-yl) -4- (9, 9-diphenyl-9H-fluoren-4-yl) -6-phenyl-1, 3, 5-triazine
[PhGD]
Comparative examples 1 to 3
Organic light emitting diodes according to comparative examples 1 to 3 were manufactured in the same manner as in example 1, except that the main body was changed as shown in table 1.
Evaluation
(1) Measuring current density variation according to voltage variation
The current value flowing through the cell device in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to provide a result.
(2) Measuring brightness change according to voltage change
The luminance was measured by using a luminance meter (Minolta Cs-1000A) while increasing the voltage of the organic light emitting diode from 0V to 10V.
(3) Measuring luminous efficiency
By using the brightness and the current density from the items (1) and (2), a current density (10 mA/cm 2 ) Light-emitting efficiency (cd/A) under the light-emitting efficiency.
(4) Measuring lifetime
The result is by dividing the luminance (cd/m 2 ) Maintained at 24000cd/m 2 And measuring the time for which the luminous efficiency (cd/a) was reduced to 95%.
The values shown in table 1 are relative values based on the values of comparative example 2, respectively.
TABLE 1
Referring to table 1, the life characteristics of the organic light emitting diode according to the embodiment of the present invention were significantly improved as compared to the organic light emitting diode according to the comparative example. While the present disclosure has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments. On the contrary, it is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.
Claims (12)
1. A composition for an organic optoelectronic device comprising
A first compound represented by chemical formula 1
A second compound represented by a combination of chemical formula 2 and chemical formula 3:
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
L 1 and L 2 Each independently is a single bond or a substituted or unsubstituted C6 to C30 arylene group,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heterocyclyl,
R 1 to R 4 Each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C30 aryl,
Ar 6 to Ar 9 Each independently is hydrogen or a substituted or unsubstituted C6 to C30 aryl group, and
m1 and m4 are each independently one of integers from 1 to 4,
m2 and m3 are each independently one of integers from 1 to 3, and
chemical formula 1 satisfies both the following conditions (i) and (ii),
(i)Ar 1 and Ar is a group 2 At least one of which is a C6 to C30 aryl substituted with at least one deuterium or a C2 to C30 heterocyclic group substituted with at least one deuterium, and
(ii)R 1 to R 4 At least one of which is deuterium;
in the chemical formula 2 and the chemical formula 3,
Ar 3 to Ar 5 Each independently is substituted or unsubstitutedA C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
a 1 * To a 4 * Each independently is a linking carbon (C) or C-L a -R a ，
A in chemical formula 2 1 * To a 4 * Is linked to the adjacent two in formula 3,
L a 、L 3 to L 6 Each independently is a single bond, a substituted or unsubstituted C6 to C20 arylene or a substituted or unsubstituted C2 to C20 heteroarylene, and
R a and R is 5 To R 8 Each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl.
2. The composition for an organic optoelectronic device according to claim 1, wherein
The first compound is represented by any one of chemical formulas 1-1 to 1-10:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
[ chemical formulas 1-9]
[ chemical formulas 1-10]
In chemical formulas 1-1 to 1-10,
L 1 、L 2 、Ar 1 、Ar 2 、Ar 6 to Ar 9 、R 1 To R 4 M 1 To m 4 As described in claim 1.
3. The composition for an organic optoelectronic device according to claim 1, wherein
Ar of chemical formula 1 1 And Ar is a group 2 Is phenyl substituted with at least one deuterium, biphenyl substituted with at least one deuterium, terphenyl substituted with at least one deuterium, naphthyl substituted with at least one deuterium, anthryl substituted with at least one deuterium, phenanthryl substituted with at least one deuterium, ditriphenyl substituted with at least one deuterium, fluorenyl substituted with at least one deuterium, dibenzofuranyl substituted with at least one deuterium, or dibenzothiophenyl substituted with at least one deuterium.
4. The composition for an organic optoelectronic device according to claim 1, wherein
L of chemical formula 1 1 -Ar 1 And L 2 -Ar 2 Each independently selected from the substituents listed in groups I-1 and I-2, and
L 1 -Ar 1 and L 2 -Ar 2 At least one of the substituents listed in group I-2:
group I-1
Group I-2
In groups I-1 and I-2, are connection points.
5. The composition for an organic optoelectronic device according to claim 1, wherein the first compound is represented by chemical formulas 1 to 8 a:
[ chemical formula 1-8a ]
In the chemical formulas 1 to 8a,
L 1 、L 2 、Ar 1 and Ar is a group 2 As defined in claim 1.
6. The composition for an organic optoelectronic device according to claim 1, wherein the first compound is one selected from the compounds listed in group 1:
group 1
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
7. The composition for an organic optoelectronic device according to claim 1, wherein
The second compound is represented by any one of chemical formula 2A to chemical formula 2F:
/>
in chemical formulas 2A to 2F,
Ar 3 to Ar 5 、L 3 To L 6 And R is 5 To R 12 As described in claim 1,
L a1 to L a4 And L is equal to a Is the same as defined in the specification, and
R a1 to R a4 And R is R a Is the same as defined in the following.
8. The composition for an organic optoelectronic device according to claim 1, wherein
R in chemical formula 2 and chemical formula 3 5 To R 12 Each independently of the other is hydrogen, deuterium or cyano,
L 3 to L 6 Is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted pyridylene group, and
Ar 3 to Ar 5 Each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted bistriphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.
9. The composition for an organic optoelectronic device according to claim 1, wherein
The first compound is represented by chemical formulas 1-8a, and
the second compound is represented by chemical formula 2B:
[ chemical formula 1-8a ]
In the chemical formulas 1 to 8a,
L 1 and L 2 Is a single bond or a substituted or unsubstituted phenylene group, and
Ar 1 and Ar is a group 2 Each of which is a phenyl group substituted with deuterium, a biphenyl group substituted with deuterium, a terphenyl group substituted with deuterium or a biphenylene group substituted with deuterium,
[ chemical formula 2B ]
In the chemical formula 2B, the chemical formula,
L a1 and L a2 Is a single bond,
L 3 to L 6 Each independently is a single bond or a substituted or unsubstituted C6 to C12 arylene group,
R 5 to R 12 、R a1 And R is a2 Each independently is hydrogen, deuterium, cyano or substituted or unsubstituted phenyl, and
Ar 3 to Ar 5 Each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted biphenylene group.
10. An organic optoelectronic device comprising
An anode and a cathode facing each other,
at least one organic layer between the anode and the cathode, and
the organic layer comprises the composition for an organic optoelectronic device of any one of claims 1 to 9.
11. The organic optoelectronic device of claim 10, wherein
The organic layer includes a light emitting layer, and
the light emitting layer comprises the composition for an organic optoelectronic device.
12. A display device comprising the organic optoelectronic device of claim 10.
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| KR1020220082644A KR20230007960A (en) | 2021-07-06 | 2022-07-05 | Composition for organic optoelectronic device and organic optoelectronic device and display device |
| KR10-2022-0082644 | 2022-07-05 | ||
| PCT/KR2022/009716 WO2023282603A1 (en) | 2021-07-06 | 2022-07-06 | Composition for organic optoelectronic device, organic optoelectronic device and display device |
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