CN115490665A - Spiro compounds and their use in organic electroluminescent devices - Google Patents

Spiro compounds and their use in organic electroluminescent devices Download PDF

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CN115490665A
CN115490665A CN202211300710.7A CN202211300710A CN115490665A CN 115490665 A CN115490665 A CN 115490665A CN 202211300710 A CN202211300710 A CN 202211300710A CN 115490665 A CN115490665 A CN 115490665A
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aryl
heteroaryl
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王湘成
何睦
王鹏
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Shanghai Yaoyi Electronic Technology Co ltd
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention discloses a spiro compound and application thereof in an organic electroluminescent device, wherein the spiro compound has a structure shown as a formula (1), X 1 Selected from O, S, N (R) a ) Or C (R) a R b )，Y 1 、Y 2 Independently selected from hydrogen, deuterium, fluorine, CF 3 、CN、NO 2 Substituted or unsubstituted C6-C30 aryl, C5-C30 heteroaryl, C (= O) (R) c )、N(R c R d )、Si(R c R d R e )、P(＝O)(R c R d ) Or S (= O) 2 (R c )，R 1 、R 2 Selected from substituted or unsubstitutedSubstituted aryl, heteroaryl, alkyl or heteroalkyl radicals or R 1 And R 2 The A and the B are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or a ring structure shown in a formula (2), and the material serving as a functional layer for the OLED device can improve the luminous efficiency and the service life of the device.

Description

Spiro compounds and their use in organic electroluminescent devices
Technical Field
The invention relates to the field of organic luminescent materials, in particular to a spiro compound and application thereof in an organic electroluminescent device.
Background
Organic Light Emitting Diodes (OLEDs), because of their characteristics of self-luminescence, solid state, flexibility, high efficiency, high pixel density, etc., are widely used in various display devices, such as consumer displays for mobile phones, watches, etc., medical displays, vehicle displays, industrial control displays, VR/AR, etc. The current vacuum evaporation material method is a commonly used OLED device manufacturing process, vacuum evaporation is to continuously evaporate materials onto a glass substrate or a plastic substrate for a device, and the materials are heated for hundreds of hours. When the material molecule has a large pi-pi action, the intermolecular force is large, the material vapor deposition temperature is high, the material is easily deteriorated by heating at a high temperature for a long time, and it is generally useful to reduce the intermolecular force by using an alkyl group, but a conventional chain alkyl group such as methyl, t-butyl, etc. is useful because of the alkyl SP 3 With aryl radicals SP 2 The carbon bond (C) can be subjected to thermodynamic motions such as free rotation and vibration, and the bond is easily broken and unstable. In addition, since the alkyl bond molecules vibrate largely, the molecular properties are greatly affected, and the luminous efficiency and the service life of the device may be reduced, and the present invention has been made to improve the above problems.
Disclosure of Invention
The invention firstly discovers that the problems can be avoided by introducing non-conjugated rings such as cycloalkyl or heterocycloalkyl into a fluoranthene group, and the electronic effect of a molecular structure can be effectively adjusted due to the limitation of rotation or vibration of the cycloalkyl or heterocycloalkyl in the designed compound, so that the thermal stability of the compound is well improved, the evaporation temperature is reduced, and the service life is prolonged.
Based on the above, the invention provides a spiro compound, which has a chemical structure shown in formula (1):
Figure BDA0003904541640000011
in the formula (1), X 1 Selected from O, S, N (R) a ) Or C (R) a R b )，R a And R b Independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or R a And R b Connecting to form a ring;
Y 1 and Y 2 Independently selected from hydrogen, deuterium, fluorine, CF 3 、CN、NO 2 Substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, C (= O) (R) c )、N(R c R d )、Si(R c R d R e )、P(＝O)(R c R d ) Or S (= O) 2 (R c )，R c 、R d And R e Independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or R c 、R d And R e Any two of them are connected to form a ring, and Y 1 And Y 2 At least one group comprising a number of C atoms greater than 11;
R 1 selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C5-C30 heteroarylene, C1-C10 alkylene, or C1-C10 heteroalkylene;
R 2 selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, C1-C10 alkyl or C1-C10 heteroalkyl;
or R 1 And R 2 Connecting to form a ring;
a and B are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or a ring structure as shown in formula (2):
Figure BDA0003904541640000021
and at least one of A and B is the structure shown in (2);
in the formula (1), the heteroatom is selected from O, N, S, P, si, se or B;
in the formula (2), W is selected from any structure shown in the formula (3):
Figure BDA0003904541640000022
in the formula (3), is a site bonded to a benzene ring, Z 1 -Z 5 Each independently selected from O, S, N (R) f ) Or C (R) f R g )，R f And R g Independently selected from hydrogen, deuterium, C1-C10 alkyl or C1-C10 heteroalkyl, wherein the heteroatom is O or S.
Preferably, the spiro compound is selected from any one of the chemical structures shown in formulas a-H:
Figure BDA0003904541640000023
in the formula A-H, X 2 Selected from O, S, N (R) a ) Or C (R) a R b )，R a And R b Independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or R a And R b Connecting to form a ring;
X 1 、Y 1 、Y 2 a and B are as previously described;
R 3 、R 4 、R 5 and R 6 Each independently selected from hydrogen, deuterium, C1-C10 alkyl or C1-C10 heteroalkyl;
Ar 1 and Ar 2 Independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
Ar 3 and Ar 4 Independently selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C5-C30 heteroarylene;
n is 2, 3, 4 or 5;
wherein the heteroatom is selected from O, N, S, P, si, se or B.
Preferably, the spiro compound is selected from any one of the chemical structures represented by formula (4):
Figure BDA0003904541640000031
in the formula (4), W A And W B The same or different, independently selected from any structure shown in the formula (3);
*、Z 1 -Z 5 、X 1 as described above;
X 2 selected from O, S, N (R) a ) Or C (R) a R b )，R a And R b Independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or R a And R b Connecting to form a ring;
wherein the heteroatom is selected from O, N, S, P, si, se or B.
In any of the foregoing spiro compounds, the "substituted or unsubstituted C6-C30 aryl", "substituted or unsubstituted C5-C30 heteroaryl", "C1-C10 alkyl", or "C1-C10 heteroalkyl" is selected from one or a combination of two or more of the chemical structures shown in formula (5):
Figure BDA0003904541640000032
Figure BDA0003904541640000041
in formula (5), any one of the chemical structures contains a linking site;
ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
A 1 and A 2 Independently selected from hydrogen, deuterium, fluorine, CF 3 、CN、NO 2 Substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C5-C20 heteroaryl;
X 3 selected from O, S or N (R) f )，R f Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
wherein the heteroatom is selected from O, N, S, P, si, se or B.
Preferably, W and W are as defined above a Or W b One selected from the chemical structures shown in formula (6):
Figure BDA0003904541640000042
Figure BDA0003904541640000051
in the formula (6), R h Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, wherein the heteroatom is selected from O, N, S, P, si, se or B, which is a linking site.
Preferably, the spiro compound represented by formula (1) is selected from one or more of the following chemical structures:
Figure BDA0003904541640000052
Figure BDA0003904541640000061
Figure BDA0003904541640000071
Figure BDA0003904541640000081
Figure BDA0003904541640000091
Figure BDA0003904541640000101
Figure BDA0003904541640000111
Figure BDA0003904541640000121
the invention also provides application of the spiro compound in organic electroluminescent devices, for example, the spiro compound can be used as a hole transport material, a luminescent host material, an electron transport material and other functional materials of the organic electroluminescent devices.
The invention also provides an organic electroluminescent device which comprises a substrate, a first electrode, an organic functional layer and a second electrode, wherein the organic functional layer comprises at least one layer selected from a light-emitting layer, an electron transport layer or a hole transport layer, and the material of the organic functional layer comprises one or more of the spiro compounds.
The invention also provides a display or lighting device which comprises the organic electroluminescent device.
Compared with the prior art, the invention has the following beneficial effects: the spiro compound containing the non-conjugated ring can reduce the use temperature, improve the thermal stability and facilitate the improvement of a film layer compared with an aromatic spiro compound, and is used as a plurality of functional layers of an organic electroluminescent device, such as a hole transport material, a luminescent main body material, an electron transport material and the like, so that the luminous efficiency and the service life of the device are obviously improved.
Drawings
FIG. 1 is a schematic structural view of a bottom emission organic electroluminescent device in an embodiment;
FIG. 2 is a schematic structural view of a top emission organic electroluminescent device in an embodiment;
wherein: 101 a base layer; 102 a first electrode (anode); 103 a hole injection layer; 104 a first hole transport layer; 105 a second hole transport layer; 106 an organic light-emitting layer; 107 hole blocking layers; 108 an electron transport layer; 109 a second electrode (cathode); 110 of a cover layer.
Detailed Description
The synthesis method of spiro compounds in the present invention will be specifically described below with reference to synthetic examples, and compounds not mentioned in the synthesis method in the present invention are commercially available.
The A series spiro compounds are prepared by C-N coupling reaction:
synthesis example 1
Figure BDA0003904541640000131
Synthesis of A2: a2-1 (10g, 28.1mmol), A2-2 (8.0g, 28.1mmol), and tris (dibenzylideneacetone) dipalladium (Pd) were added to a three-necked flask 2 (dba) 3 (0.5g, 0.56mmol), tri-tert-butylphosphine t-Bu 3 P (0.6g, 2.8mmol), sodium t-butoxide NaOBu-t, (7.2g, 75.3mmol) was stirred in 100mL of a toluene solvent (toluene) under a nitrogen atmosphere, and the reaction mixture was heated to 110 ℃ and stirred for reaction for 3 hours. Cooling the reaction liquid to room temperature, adding 50mL of water for extraction and phase separation, evaporating a toluene phase to dryness, separating and purifying the solid by using toluene-petroleum ether for column chromatography, then carrying out vacuum concentration, and recrystallizing and purifying the concentrated solution by using toluene to obtain 12g of the A2 compound with the yield of 70.5%. LCMS (ESI ion source) M/Z:603.4; 1 H NMR(DMSO-d 6 )：δ，7.51–7.43(m,3H),7.41–7.24(m,5H),7.22–7.03(m,7H),6.92(d,1H),6.77(s,1H),1.74(s,4H),1.62(s,6H),1.57(s,6H),1.29(s,12H)。
the other a-series compounds were synthesized in the same operation as in synthesis example 1, except that the starting materials were replaced, and the yields of the starting materials and the target products in synthesis examples 2 to 16 were as shown in table 1:
TABLE 1
Figure BDA0003904541640000141
Compounds obtained in Synthesis examples 2 to 16 described above 1 H NMR is shown in Table 2:
TABLE 2
Figure BDA0003904541640000142
Figure BDA0003904541640000151
The synthesis examples of the B series spiro compounds of the present invention are as follows:
synthesis example 17
Synthesis of compound B1:
Figure BDA0003904541640000161
in a three-necked flask, B1-1 (10g, 33.4mmol), B1-2 (11.8g, 33.4mmol) and K were charged in this order 2 CO 3 (11.4g, 100.2mmol), tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 (0.76g, 0.67mmol) was added to a mixed solvent of 60mL of toluene, 10mL of water and 10mL of ethanol, and the reaction mixture was heated to reflux and stirred for 6 hours. After the reaction solution was cooled, 100mL of brine was added for extraction, the organic phase was dried over anhydrous sodium sulfate and then concentrated in vacuo, and the resulting solid was subjected to column chromatography using toluene and petroleum ether as washing solutions. Then toluene recrystallization was performed again for 2 times to obtain a solid, which was dried to obtain 14g of the compound B1 with a yield of 74%. LCMS (ESI ion source) M/Z:571.2; 1 H NMR(DMSO-d 6 ):δ8.45–8.27(m,2H),8.03–7.94(m,2H),7.90(m,1H),7.72–7.62(m,4H),7.54–7.33(m,8H),7.16(t,1H),6.71(t,1H),2.74(m,4H),1.75(m,4H),1.62(s,6H).
the other B series compounds were synthesized according to the same operation as in synthesis example 17 except that the used raw materials were replaced, and the raw materials and the yields of the objective products used in synthesis examples 18 to 30 were as shown in table 3:
TABLE 3
Figure BDA0003904541640000162
Figure BDA0003904541640000171
The partial products obtained in the above Synthesis examples 18 to 30Compound (I) 1 H NMR is shown in Table 4:
TABLE 4
Figure BDA0003904541640000172
The synthesis examples of the C series spiro compounds of the present invention are as follows:
synthetic example 31
Synthesis of compound C3:
Figure BDA0003904541640000181
the first step, the synthesis of an intermediate C3-3:
into a three-necked flask, C3-1 (10g, 34.3mmol), B1-2 (5.6g, 33mmol) and K were sequentially added 2 CO 3 (11.2g, 99mmol), tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 (0.75g, 0.66mmol) was added to a mixed solvent of 60mL of toluene, 10mL of water and 10mL of ethanol, and the reaction mixture was heated to reflux and stirred for 6 hours. After the reaction solution was cooled, 100mL of brine was added for extraction, the organic phase was dried over anhydrous sodium sulfate and then concentrated in vacuo, and the resulting solid was subjected to column chromatography using toluene and petroleum ether as a washing solution. Then toluene recrystallization was carried out again for 2 times to obtain a solid, which was dried to obtain 9.1g of a C3-3 compound with a yield of 82%. LCMS (ESI ion source) M/Z:338.0.
second step, synthesis of compound C3:
in a three-necked flask, C3-3 (9g, 26.5 mmol), C3-4 (8.2g, 26.5 mmol) and K were sequentially added 2 CO 3 (9g, 79.6mmol), tetrakis (triphenylphosphine) palladium Pd (pph) 3 ) 4 (0.6g, 0.53mmol) was added to a mixed solvent of 50mL of toluene, 8mL of water and 8mL of ethanol, and the reaction mixture was heated to reflux and stirred for 6 hours. After the reaction solution was cooled, 100mL of brine was added for extraction, the organic phase was dried over anhydrous sodium sulfate and then concentrated in vacuo, and the resulting solid was subjected to column chromatography using toluene and petroleum ether as a washing solution. Then toluene recrystallization is carried out for 2 times to obtain solid, the solid is dried,11.7g of the C3 compound was obtained in 78% yield. LCMS (ESI ion source) M/Z:570.2.1H NMR (DMSO-d 6). Delta.8.34-8.25 (m, 2H), 8.23-8.15 (m, 2H), 8.06-8.00 (m, 1H), 7.98-7.85 (m, 2H), 7.76 (t, 1H), 7.66 (m, 1H), 7.59 (m, 1H), 7.56-7.20 (m, 8H), 6.86 (s, 1H), 6.68 (s, 1H), 4.43-4.04 (m, 4H), 1.63 (s, 6H).
Other C-series compounds were synthesized by the same operation as in synthesis example 31, except that the used starting materials were replaced, and the yields of the starting materials and the target products used in synthesis examples 32 to 41 were as shown in table 5:
TABLE 5
Figure BDA0003904541640000182
Figure BDA0003904541640000191
Partial Compounds obtained in Synthesis examples 32 to 41 1 H NMR is shown in Table 6:
TABLE 6
Figure BDA0003904541640000192
Figure BDA0003904541640000201
The spiro compound can be applied to a plurality of functional material layers such as a hole transport layer, a light emitting layer and an electron transport layer of OLED bottom light emitting and top light emitting devices, and corresponding device embodiments are given below for different functional material layers.
The bottom light emitting device refers to light emitted from the TFT substrate side (fig. 1), and the top light emitting device refers to light emitted from the TFT substrate side away (fig. 2). Top-emitting devices have a capping layer on the cathode compared to bottom-emitting devices. The light emission color of the device may be red, green, blue, white, yellow, or the like.
The configuration of the bottom emitting device may be selected from one of:
(1) anode/hole injection layer/hole transport layer 1/light emitting layer/electron transport layer 1/cathode.
(2) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light emitting layer/electron transport layer 1/cathode.
(3) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light-emitting layer/electron transport layer 1/electron transport layer 2/cathode.
(4) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light-emitting layer/electron transport layer 1/electron transport layer 2/electron injection layer/cathode.
(5) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light emitting layer/electron transport layer 1/electron transport layer 2/multilayer cathode.
(6) Anode/hole injection layer/hole transport layer 1/light-emitting layer 1/carrier generation layer/hole transport layer 2/light-emitting layer 2/electron transport layer 1/cathode.
(7) Anode/hole injection layer/hole transport layer 1/light-emitting layer 1/carrier generation layer/hole transport layer 2/light-emitting layer 2/electron transport layer 1/electron transport layer 2/cathode.
(8) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light-emitting layer 1/carrier generation layer/hole transport layer 3/light-emitting layer 2/electron transport layer 1/cathode.
(9) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light emitting layer 1/carrier generation layer/hole transport layer 3/light emitting layer 2/electron transport layer 1/electron transport layer 2/cathode.
The configuration of the top-emitting device may be selected from one of:
(1) anode/hole injection layer/hole transport layer 1/light emitting layer/electron transport layer 1/cathode/capping layer.
(2) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light-emitting layer/electron transport layer 1/cathode/capping layer.
(3) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light emitting layer/electron transport layer 1/electron transport layer 2/cathode/capping layer.
(4) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light emitting layer/electron transport layer 1/electron transport layer 2/electron injection layer/cathode/capping layer.
(5) Anode/hole injection layer/hole transport layer 1/light emitting layer/electron transport layer 1/electron transport layer 2/multilayer cathode/capping layer.
(6) Anode/hole injection layer/hole transport layer 1/light emitting layer 1/carrier generation layer/hole transport layer 2/light emitting layer 2/electron transport layer 1/cathode/capping layer.
(7) Anode/hole injection layer/hole transport layer 1/light emitting layer 1/carrier generation layer/hole transport layer 2/light emitting layer 2/electron transport layer 1/electron transport layer 2/cathode/capping layer.
(8) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light-emitting layer 1/electron transport layer 2/carrier generation layer/hole transport layer 3/light-emitting layer 2/electron transport layer 1/cathode/capping layer.
(9) Anode/hole injection layer/hole transport layer 1/hole transport layer 2/light emitting layer 1/electron transport layer 3/carrier generation layer/hole transport layer 3/light emitting layer 2/electron transport layer 1/electron transport layer 2/cathode/capping layer.
The hole transport layer 1 is generally 40 to 150nm in thickness, and an arylamine-containing compound such as an aromatic monoamine or an aromatic polyamine is usually used. The hole transport material is required to have high hole mobility, can reduce driving voltage, has a glass transition temperature of over 100 ℃, avoids crystallization at high temperature, and can be selected from the following molecular structures:
the thickness of the hole transport layer 2 and the hole transport layer 3 is generally 3 to 150nm.
The content of the host material (host) in the luminescent material layer is larger than that of the luminescent object doping material (dopant), and the mass percentage of the object doping material in the optional luminescent material layer is 1-20%.
The guest doping material of the light emitting material may include a phosphorescent or fluorescent material or a thermally activated delayed fluorescent material, and red, green, and blue light may be selected from the above three guest doping materials.
The light emitting body may be one kind of light emitting body or two kinds of light emitting bodies.
The electron transport layer is used for transporting electrons of the cathode to the luminescent layer, and generally adopts a material with hole transport capability, and the thickness is 10-50 nm.
The covering layer is formed on the side of the semitransparent cathode of the OLED display panel, which is far away from the substrate, so that the light output efficiency can be improved. The thickness is generally 50 to 90nm, for example, 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm, etc., and the light transmittance between 450 to 650nm is not less than 65%, for example, 68%, 69%, 73%, 77%, 79%, 83%, 88%, 93%, etc.
Device example 1
In this embodiment, a compound A2 is used as a material of the hole transport layer 1 104, and a blue light device (bottom emission) manufacturing method is taken as an example, and the preparation process is as follows:
a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003904541640000221
With a hole-transporting material A2
Figure BDA0003904541640000222
The mixed material of (3) as the hole injection layer 103 was mixed at a ratio of 3
Figure BDA0003904541640000223
A first hole transport layer 104 was obtained, and then a compound having a thickness of 20nm was evaporated
Figure BDA0003904541640000224
A second hole transport layer 105 was obtained, and then a light emitting host material was vapor-deposited at a vapor deposition rate of 95
Figure BDA0003904541640000225
And a light-emitting material
Figure BDA0003904541640000226
30nm, fabricating a blue light emitting unit 106, and evaporating to deposit 10nm
Figure BDA0003904541640000227
The hole blocking layer 107 was formed, and then evaporated at an evaporation rate of 4
Figure BDA0003904541640000228
And with
Figure BDA0003904541640000229
An electron transport layer 108 having a thickness of 30nm was formed, and then magnesium silver (mass ratio 1.
Device examples 2 to 5 were prepared using compounds A9, a19, a76, a84 of the invention and comparative compound 1:
Figure BDA00039045416400002210
instead of A2 of device example 1, the other materials remained unchanged.
The device test adopts a Keithley power supply and MS-75 spectral radiometer combined test device. The voltage and the efficiency are 10mA/cm 2 Voltage (V) and current efficiency (in Cd/A) at time, lifetime of 10mA/cm 2 The time required for the luminance to decay to 95% of the initial luminance at the time of current was as shown in table 7:
TABLE 7
Figure BDA00039045416400002211
Figure BDA0003904541640000231
Device example 6
In this embodiment, compound a12 is used as a material of the hole transport layer 2, and taking a method for manufacturing a green device (bottom emission) as an example, the preparation process is as follows:
forming a transparent anode ITO film layer on a glass substrate 101The thickness was 150nm, and the first electrode 102 was obtained as an anode, followed by vapor deposition
Figure BDA0003904541640000232
And hole transport material
Figure BDA0003904541640000233
The hole injection layer 103 was prepared by mixing the materials (1) and (2) at a mixing ratio of 3
Figure BDA0003904541640000234
A first hole-transporting layer 104 was obtained, and then a 60nm thick compound A12 of the present invention was evaporated
Figure BDA0003904541640000235
The second hole transport layer 105 was obtained, and then a 40nm compound was evaporated at an evaporation rate of 45
Figure BDA0003904541640000236
And
Figure BDA0003904541640000237
the green light emitting unit 106 is manufactured, and then vapor deposition is performed to 10nm
Figure BDA0003904541640000238
Forming a hole blocking layer 107, and then evaporating
Figure BDA0003904541640000239
And
Figure BDA00039045416400002310
the electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4.
Device examples 7 to 15 were prepared using compounds a27, a39, a45, a55, a64, a96, a107, a112, a128 of the invention and comparative compound 2:
Figure BDA0003904541640000241
and comparative compound 3:
Figure BDA0003904541640000242
instead of a12 of device example 6, as the second hole transport layer 105.
The device test adopts a Keithley power supply and MS-75 spectral radiometer combined test device. The voltage and the efficiency are 10mA/cm 2 Voltage (V) and current efficiency (in Cd/A) at time, and a lifetime of 10mA/cm 2 The time required for the luminance to decay to 95% of the initial luminance at current was as shown in table 8:
TABLE 8
Figure BDA0003904541640000243
Device example 16
In this embodiment, a compound B1 is used as a material of the electron transport layer 108, and taking a blue light device (bottom emission) manufacturing method as an example, the preparation process is as follows:
a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003904541640000244
And hole transport material
Figure BDA0003904541640000245
The mixed material of (3) was mixed as the hole injection layer 103 at a mixing ratio of 3
Figure BDA0003904541640000251
A first hole transport layer 104 was obtained, and then a compound having a thickness of 20nm was evaporated
Figure BDA0003904541640000252
A second hole transport layer 105 was obtained, and then a light emitting host material was evaporated at an evaporation rate of 95
Figure BDA0003904541640000253
And a luminescent material
Figure BDA0003904541640000254
30nm, fabricating a blue light emitting unit 106, and evaporating to deposit 10nm
Figure BDA0003904541640000255
The hole-blocking layer 107 was formed, and then the compound B1 of the present invention was evaporated at an evaporation rate of 4
Figure BDA0003904541640000256
And
Figure BDA0003904541640000257
an electron transport layer 108 having a thickness of 30nm was formed, and then magnesium silver (mass ratio 1.
Device examples 17 to 29 were prepared using compounds B3, B11, B23, B35, B41, B44, B49, B60, B67, B86, B97, B109, B112 of the present invention and comparative compound 4:
Figure BDA0003904541640000258
and comparative compound 5:
Figure BDA0003904541640000259
instead of B1 of device example 16, the other materials remained unchanged.
The device test adopts a keithley power supply and MS-75 spectral radiometer combined test device. The voltage and the efficiency are 10mA/cm 2 Voltage (V) and current efficiency (in Cd/A) at time, and a lifetime of 10mA/cm 2 The time required for the luminance to decay to 95% of the initial luminance at current was as shown in table 9:
TABLE 9
Figure BDA0003904541640000261
Device example 30
In this embodiment, a compound C1 is used as a light emitting host material and a light emitting guest material for the light emitting layer 106, and taking a blue light device (top emission) manufacturing method as an example, the preparation process is as follows:
a light-impermeable reflective anode Ag/ITO film layer with a thickness of 100nm/15nm was formed on a glass substrate 101 to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003904541640000262
And hole transport material
Figure BDA0003904541640000263
The mixed material of (3) was mixed as the hole injection layer 103 at a mixing ratio of 3
Figure BDA0003904541640000264
A first hole transport layer 104 was obtained, and then a compound having a thickness of 20nm was evaporated
Figure BDA0003904541640000265
A second hole transport layer 105 was obtained, and then the light-emitting host material C3 of the present invention was evaporated at an evaporation rate of 95
Figure BDA0003904541640000271
And a light-emitting guest material
Figure BDA0003904541640000272
30nm, fabricating a blue light emitting unit 106, and then evaporating to deposit 10nm
Figure BDA0003904541640000273
The hole blocking layer 107 was formed, and then a compound was evaporated at an evaporation rate of 4
Figure BDA0003904541640000274
And with
Figure BDA0003904541640000275
Forming a layer with a thickness of 30nmAfter the sub-transport layer 108, magnesium silver (mass ratio 1
Figure BDA0003904541640000276
A capping layer 110 is formed.
Device examples 31 to 40 were prepared using compounds of the invention C9, C20, C25, C36, C45, C59, C68, C74, C85, C101 and comparative compound 6:
Figure BDA0003904541640000277
and comparative compound 7:
Figure BDA0003904541640000278
instead of C3 of device embodiment 30, the other materials remain unchanged.
The device test adopts a keithley power supply and MS-75 spectral radiometer combined test device. The voltage and the efficiency are 10mA/cm 2 The voltage (V) and current efficiency at that time are expressed in terms of the ratio of the color coordinate CIEy (in Cd/A/CIEy), and the results are shown in Table 10:
TABLE 10
Figure BDA0003904541640000279
Figure BDA0003904541640000281
From the above results, it can be seen that the spiro compound of the present invention has the advantages of good thermal stability improvement, evaporation temperature reduction, and prolonged service life due to the limitation of rotation or vibration of cycloalkyl or heterocycloalkyl, and as a plurality of functional layers of an organic electroluminescent device, such as a hole transport material, a luminescent host material, an electron transport material, etc., the device has significantly improved luminescent efficiency and service life.

Claims (10)

1. A spiro compound having a chemical structure represented by formula (1):
Figure FDA0003904541630000011
in the formula (1), X 1 Selected from O, S, N (R) a ) Or C (R) a R b )，R a And R b Independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or R a And R b Connecting to form a ring;
Y 1 and Y 2 Independently selected from hydrogen, deuterium, fluorine, CF 3 、CN、NO 2 Substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, C (= O) (R) c )、N(R c R d )、Si(R c R d R e )、P(＝O)(R c R d ) Or S (= O) 2 (R c )，R c 、R d And R e Independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl or R c 、R d And R e Any two of them are connected to form a ring, and Y 1 And Y 2 At least one group comprising a number of C atoms greater than 11;
R 1 selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C5-C30 heteroarylene, C1-C10 alkylene, or C1-C10 heteroalkylene;
R 2 selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, C1-C10 alkyl or C1-C10 heteroalkyl;
or R 1 And R 2 Connecting to form a ring;
a and B are independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or a ring structure as shown in formula (2):
Figure FDA0003904541630000012
and at least one of A and B is the structure shown in (2);
in the formula (1), the heteroatom is selected from O, N, S, P, si, se or B;
in the formula (2), W is selected from any structure shown in the formula (3):
Figure FDA0003904541630000013
in the formula (3), is a site bonded to a benzene ring, Z 1 -Z 5 Each independently selected from O, S, N (R) f ) Or C (R) f R g )，R f And R g Independently selected from hydrogen, deuterium, C1-C10 alkyl or C1-C10 heteroalkyl, wherein the heteroatom is O or S.
2. The spiro compound according to claim 1, wherein said spiro compound is selected from any one of the chemical structures represented by formulas a to H:
Figure FDA0003904541630000021
in the formula A-H, X 2 Selected from O, S, N (R) a ) Or C (R) a R b )，R a And R b Independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or R a And R b Connecting to form a ring;
X 1 、Y 1 、Y 2 a and B are as defined in claim 1;
R 3 、R 4 、R 5 and R 6 Each independently selected from hydrogen, deuterium, C1-C10 alkyl or C1-C10 heteroalkyl;
Ar 1 and Ar 2 Independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
Ar 3 and Ar 4 Independently selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C5-C30 heteroarylene;
n is 2, 3, 4 or 5;
wherein the heteroatom is selected from O, N, S, P, si, se or B.
3. The spiro compound according to claim 1, wherein said spiro compound is selected from any one of the chemical structures represented by formula (4):
Figure FDA0003904541630000022
Figure FDA0003904541630000031
in the formula (4), W A And W B The same or different, independently selected from any structure shown in the formula (3);
*、Z 1 -Z 5 、X 1 as claimed in claim 1;
X 2 selected from O, S, N (R) a ) Or C (R) a R b )，R a And R b Independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or R a And R b Connecting to form a ring;
wherein the heteroatom is selected from O, N, S, P, si, se or B.
4. The spiro compound according to any one of claims 1 to 3, wherein the "substituted or unsubstituted C6-C30 aryl", "substituted or unsubstituted C5-C30 heteroaryl", "C1-C10 alkyl" or "C1-C10 heteroalkyl" is selected from one or a combination of two or more of the chemical structures represented by formula (5):
Figure FDA0003904541630000032
Figure FDA0003904541630000041
in formula (5), any one of the chemical structures contains a linking site;
ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
A 1 and A 2 Independently selected from hydrogen, deuterium, fluorine, CF 3 、CN、NO 2 Substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C5-C20 heteroaryl;
X 3 selected from O, S or N (R) f )，R f Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl;
wherein the heteroatom is selected from O, N, S, P, si, se or B.
5. Spiro compound according to claim 1 or 3, characterized in that W, W a Or W b One selected from the chemical structures shown in formula (6):
Figure FDA0003904541630000042
Figure FDA0003904541630000051
in the formula (6), R h Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, wherein the heteroatom is selected from O, N, S, P, si, se or B, which is a linking site.
6. The spiro compound according to claim 1, wherein the spiro compound represented by formula (1) is selected from the following chemical structures:
Figure FDA0003904541630000052
Figure FDA0003904541630000061
Figure FDA0003904541630000071
Figure FDA0003904541630000081
Figure FDA0003904541630000091
Figure FDA0003904541630000101
Figure FDA0003904541630000111
Figure FDA0003904541630000121
7. use of the spiro compound according to any one of claims 1 to 6 in an organic electroluminescent device.
8. An organic electroluminescent device comprising one or more of the spiro compounds according to any one of claims 1 to 6.
9. The organic electroluminescent device according to claim 8, comprising a substrate, a first electrode, an organic functional layer and a second electrode, wherein the organic functional layer comprises at least one of a light-emitting layer, an electron transport layer or a hole transport layer, and the material thereof comprises one or more spiro compounds according to any one of claims 1 to 6.
10. A display or illumination apparatus comprising the organic electroluminescent device according to claim 8 or 9.
CN202211300710.7A 2022-10-24 2022-10-24 Spiro compounds and their use in organic electroluminescent devices Pending CN115490665A (en)

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KR20140074858A (en) * 2012-12-10 2014-06-18 에스에프씨 주식회사 An electroluminescent compound and an electroluminescent device comprising the same
KR20220074408A (en) * 2020-11-27 2022-06-03 주식회사 엘지화학 Polycyclic compound and organic light emitting device comprising same

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Publication number Priority date Publication date Assignee Title
KR20140074858A (en) * 2012-12-10 2014-06-18 에스에프씨 주식회사 An electroluminescent compound and an electroluminescent device comprising the same
KR20220074408A (en) * 2020-11-27 2022-06-03 주식회사 엘지화학 Polycyclic compound and organic light emitting device comprising same

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