TWI720788B - Tertiary butyl helical bifluorene ring compound and organic light emitting element - Google Patents

Abstract

A tertiary butyl spiral double fluorene ring compound and an organic light emitting element containing the tertiary butyl spiral double fluorene ring compound. The third butyl helical bifluorene ring compound is shown in chemical formula I. The luminous efficiency of the organic light-emitting device containing the third butyl helical bifluorene ring compound of the present invention can be effectively improved.

Description

Tertiary butyl helical bifluorene ring compound and organic light emitting element

The present invention relates to a helical double fluorene ring derivative and an organic light emitting device containing the aforementioned helical double fluorene ring derivative, in particular to a t-butyl spirobifluorene compound and a t-butyl spirobifluorene compound containing the aforementioned first Organic light-emitting element of tributyl helical bifluorene ring compound.

Organic light-emitting elements (OLED) are light, thin, wide viewing angle, high contrast, low power consumption, high response speed, full-color painting and flexibility. Therefore, they are used in full-color monitors or portable electronics. The applications of devices are highly anticipated.

A typical OLED is a multilayer thin film structure formed by sequentially depositing an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode through a vacuum deposition method or a coating method. When a current is applied, the anode injects holes and the cathode injects electrons into the one or more organic layers, and the injected holes and electrons migrate to opposite charged electrodes. When an electron and a hole are confined to the same molecule, an "exciton" is formed. The exciton is a localized electron-hole pair with an excited energy state. The exciton relaxes and emits light through the luminescence mechanism. .

The existing OLED is provided with a hole or electron injection layer in order to reduce the driving voltage, so that the OLED has a multi-layer thin film structure, so as to provide a good charge transfer capability of the device. The key points to be considered for the aforementioned components also include the stability of the interface between the electrode and the organic layer and the matching of the commensurate organic materials. If a commensurate organic material and light-emitting layer are used as the hole and electron auxiliary layer (ie injection layer or transport layer), the holes and electrons can be effectively transferred to the light-emitting layer, and the electrons and holes in the light-emitting layer can be balanced Density, which in turn increases luminous efficiency.

US 7,714,145 B2 discloses that the spiral bifluorene ring derivative can be used as an effective hole transport layer when used in organic light-emitting devices. However, when applied to different light-emitting layer materials, the light-emitting efficiency of the organic light-emitting element cannot meet the requirements of actual display applications.

In view of the problem that when the existing spiral bifluorene ring derivatives are used in organic light-emitting devices, their luminous efficiency cannot meet the needs of actual display applications. Therefore, the applicant in this case first provided a tertiary butyl helical bifluorene ring compound, which can effectively improve the luminous efficiency of the organic light-emitting device.

Therefore, the first objective of the present invention is to provide a third butyl helical bifluorene ring compound.

其中， R為氫或‒NR ¹R ²；及 R ¹與R ²分別為氫、氘、經取代或未經取代的C ₁~C ₃₀烷基、C ₁~C ₃₀烷氧基、經取代或未經取代的C ₆~C ₃₀芳基、經取代或未經取代的C ₅~C ₃₀雜芳基、C ₃~C ₃₀環烷基、C ₅~C ₇雜環烷基、三C ₁~C ₃₀烷基矽烷基、三C ₆~C ₃₀芳基矽烷基、二C ₁~C ₃₀烷基C ₆~C ₃₀芳基矽烷基、C ₁~C ₃₀烷基二C ₆~C ₃₀芳基矽烷基、C ₂~C ₃₀烯基、C ₂~C ₃₀炔基、氰基、二C ₁~C ₃₀烷基胺基、二C ₆~C ₃₀芳基硼基或二C ₁~C ₃₀烷基硼基。 Therefore, the third butyl helical bifluorene ring compound of the present invention is shown in the following chemical formula I: [Chemical formula I]

Wherein, R is hydrogen or ‒NR ¹ R ² ; and R ¹ and R ² are hydrogen, deuterium, substituted or unsubstituted C ₁ ~C ₃₀ alkyl, C ₁ ~C ₃₀ alkoxy, substituted Or unsubstituted C ₆ ~C ₃₀ aryl, substituted or unsubstituted C ₅ ~C ₃₀ heteroaryl, C ₃ ~C ₃₀ cycloalkyl, C ₅ ~C ₇ heterocycloalkyl, tri-C ₁ ~C ₃₀ alkylsilyl group, tri-C ₆ ~C ₃₀ arylsilyl group, two C ₁ ~C ₃₀ alkyl group, C ₆ ~C ₃₀ arylsilyl group, C ₁ ~C ₃₀ alkyl group, two C ₆ ~C ₃₀ arylsilyl group, C ₂ ~C ₃₀ alkenyl group, C ₂ ~C ₃₀ alkynyl group, cyano group, di C ₁ ~C ₃₀ alkylamino group, di C ₆ ~C ₃₀ aryl boron group or di C ₁ ~C ₃₀ Alkyl Boronyl.

Therefore, the second object of the present invention is to provide an organic light emitting device.

Therefore, the organic light-emitting device of the present invention contains the aforementioned third butylspiral bifluorene ring compound.

The effect of the present invention is: since the third butylspiral bifluorene ring compound of the present invention has a structure as shown in Chemical Formula I, and the organic light-emitting device of the present invention contains the third butylspiral bifluorene ring compound of the present invention, therefore, the present invention The luminous efficiency of the invented organic light-emitting element can be effectively improved.

The content of the present invention will be described in detail below:

[ Tertiary butyl helical double fluorene ring compound ]

The third butyl helical bifluorene ring compound of the present invention is shown in the following chemical formula I: [Chemical formula I]

among them,

R is hydrogen or ‒NR ¹ R ² ; and

R ¹ and R ² are respectively hydrogen, deuterium, substituted or unsubstituted C ₁ to C ₃₀ alkyl, C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₆ to C ₃₀ aryl, Substituted or unsubstituted C ₅ ~C ₃₀ heteroaryl, C ₃ ~C ₃₀ cycloalkyl, C ₅ ~C ₇ heterocycloalkyl, tri C ₁ ~C ₃₀ alkylsilyl, tri C ₆ ~ C ₃₀ arylsilyl group, two C ₁ ~C ₃₀ alkyl C ₆ ~C ₃₀ arylsilyl group, C ₁ ~C ₃₀ alkyl group, C ₆ ~C ₃₀ arylsilyl group, C ₂ ~C ₃₀ alkenyl group , C ₂ ~C ₃₀ alkynyl, cyano, two C ₁ to C ₃₀ alkylamino, two C ₆ to C ₃₀ aryl boron or two C ₁ to C ₃₀ alkyl boron.

Preferably, R ¹ and R ² are respectively a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group.

、

、

、

、

、

、

、

、

、

、

、

、

、

、

或

。 More preferably, R ¹ and R ² are respectively

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

.

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

Still more preferably, the third butylspiral bifluorene ring compound of the present invention is, for example, but not limited to, the compounds listed in Table 1 below. Table 1 Compound number structure Compound number structure 1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

twenty one

twenty two

twenty three

twenty four

25

26

27

28

29

30

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

[ Organic light emitting element ]

The organic light-emitting device of the present invention contains the aforementioned tertiary butylspiral bifluorene ring compound.

Preferably, the organic light emitting device includes a substrate, an anode located on the substrate, a hole injection layer located on a side of the anode opposite to the substrate, and a hole injection layer located opposite to the anode. The hole transport layer unit on the side, a light emitting layer located on the side of the hole transport layer unit opposite to the hole injection layer, and an electron transport layer located on the side of the light emitting layer opposite to the hole transport layer unit , An electron injection layer located on the side of the electron transport layer opposite to the light-emitting layer, and a cathode located on the side of the electron injection layer opposite to the electron transport layer, wherein the hole transport layer unit includes at least two Layer hole transport layer.

The anode material can be any metal or conductive compound with high work function. The material of the anode is, for example, but not limited to, transparent metal oxide (such as ITO, IZO, SnO ₂ , ZnO, etc.), polysilicon (poly-Si), amorphous silicon (α-Si), or a combination of the foregoing. The flexible transparent substrate combined with the anode disclosed in the US Patent No. 5,844,363 can also be cited in the present invention.

The material of the cathode can be any metal or conductive compound with low work function. The material of the cathode is, for example, but not limited to Au, Al, In, Mg, Ca or similar metals or alloys. The cathode disclosed in US 5,703,436 and US 5,707,745 can also be cited in the present invention. The cathode has a thin metal layer [such as magnesium/silver (Mg:Ag)] and a transparent conductive layer covering the thin metal layer by sputtering deposition. (ITO layer).

Preferably, at least one of the anode and the cathode is transparent or semi-transparent to facilitate the penetration of the emitted light.

At least one of the hole injection layer and the hole transport layers contains the aforementioned tertiary butyl helical bifluorene ring compound.

Preferably, the hole injection layer further contains a P-type doping compound. The P-type doping compound is, for example, but not limited to, bismuth telluride, cadmium sulfide, cadmium telluride, gallium nitride, uranyl compound, titanium dioxide, zinc oxide, or a combination of the foregoing.

Preferably, the thickness of the hole injection layer ranges from 50 to 200 Å.

Preferably, the thickness of the hole transport layer adjacent to the hole injection layer is in the range of 1000 to 2000 Å, and the thickness of the hole transport layer adjacent to the light-emitting layer is in the range of 50 to 300 Å.

Preferably, the hole injection layer and the hole transport layers can also contain any existing materials that can be applied to the hole injection layer or the hole transport layer, such as but not limited to triazole derivatives, oxadiene An azole derivative, an imidazole derivative, a phenylenediamine derivative, a spiro-linked molecule derivative (such as a spiral bifluorene ring derivative), an arylamine derivative, or a combination of the foregoing.

Preferably, the light-emitting layer contains a fluorescent material and can emit fluorescence.

Preferably, the light-emitting layer contains a light-emitting dopant and a light-emitting host.

The material of the electron transport layer is, for example, but not limited to, organic alkali metal/alkaline earth metal complexes, oxides, halides, carbonates, alkali metal/alkaline earth metal salts containing at least one selected from lithium and cesium metals, or the foregoing The combination.

The material of the electron injection layer is, for example, but not limited to, alkali metal halide (such as LiF, CsF), nitrogen-containing or oxygen-containing alkali metal chelate [such as 8-quinolinolato lithium (Liq)], or the foregoing The combination.

It should be noted that structures and materials not specifically described can also be applied to the present invention. For example, the organic light-emitting device including polymer materials disclosed in the US Patent No. 5,247,190 can be cited in the present invention in its entirety. As disclosed in the US 2003/0230980 A1 patent, the n-type doped electron transport layer is doped with lithium in BPhen at a molar ratio of 1:1, and the entire content can be cited in the present invention. US 6,097,147 and US 2003/0230980 patents disclose the application and principle of each barrier layer, the entire contents of which can be cited in the present invention. The entire contents of the injection layer disclosed in the US 2004/0174116 A1 patent and the protective layer described in the same case can be cited in the present invention.

In particular, any layer in the different embodiments of the organic light-emitting element can be deposited and formed by any suitable method. As far as the organic layer is concerned, the preferred method includes the thermal evaporation method and the spray printing method disclosed in US 6,013,982 and US 6,087,196 patents, the entire contents of which can be cited in the present invention; the organic layer disclosed in US 6,337,102 B1 patent Organic vapor phase deposition (organic vapor phase deposition), the entire content of which can be cited in the present invention; the organic vapor phase deposition method disclosed in US 10/233470, the entire content of Can be cited in the present invention. Other suitable methods include spin coating and solution-based processes. The solution-based process is preferably performed in a nitrogen or inert gas environment. For other layers, the preferred method includes thermal evaporation. The preferred patterning method includes the process of mask deposition and then cold welding as disclosed in US 6,294,398 B1 and US 6,468,819 B1, and the process of integrated spray printing or organic vapor spray deposition and patterning, all of which are Can be cited in the present invention. Of course, the present invention can also use other methods to prepare organic light-emitting elements. The material used for deposition can also be adjusted to correspond to the deposition method used.

The organic light-emitting element of the present invention can be applied to a single element, and its structure can be an array configuration or an element with positive and negative poles in the X-Y coordinate of the array.

> Example >

Preparation compound 1 to 3

中間體 A1 和 A2 的製備方法 取10 g 2,2′-叔丁基-9,9′-螺二芴與100 mL醋酸加入500 mL反應瓶中。冰浴下加入10 mL溴水，加完後回至室溫反應4小時。加入水稀釋以乙酸乙酯萃取，分離出有機層，再以無水硫酸鈉乾燥，並經減壓濃縮後，以矽膠管柱純化分離出7 g中間體 A1及3 g中間體 A2。 化合物 1 的製備方法

化合物 1在1 L三口瓶中，依次加入中間體 A1:26.15g、二苯胺：16.59 g、叔丁醇鈉：9.85 g、甲苯250 g，氮氣置換三次後，加入三叔丁基膦：2.09 g、催化劑Pd ₂(dba) ₃：0.209 g。升溫回流，回流溫度約110℃。加入甲苯約100 mL、水100 mL，升溫至60~70℃，趁熱分液，除去水相。有機相用約5%的鹽酸洗滌三次，每次用量約100 mL。再水洗至中性，除去水相，有機相濃縮至較稠體系，約100 mL體積，再用約150 mL甲醇析晶，降溫至室溫(25℃及以下均可)，經過濾後得化合物 1共35.8 g。 化合物 2 的製備方法

化合物 2反應器中加入中間體 A145.2 g、N-苯基-4-聯苯39 g、甲苯500 mL通氮氣回流1小時。降溫至35℃度加入叔丁醇鈉17 g、催化劑Pd ₂(dba) ₃452 mg、三叔丁基膦甲苯溶液5.4 g。氮氣置換後，保證氮氣流持續通入，回流反應4 hr。先降溫後以矽膠短柱(50 g)處理，甲苯淋洗至TLC監測產品點較弱，加水(300 mL*3)萃取，濾液濃縮至100 mL後，控溫80℃下緩慢加入1000 mL正庚烷。當有大量固體析出時，降至室溫，經過濾後得化合物 2共78 g。 化合物 3 的製備方法

化合物 3在1 L三口瓶中，依次加入中間體 A126.37g、二-(4-聯苯)胺28.89 g、叔丁醇鈉9.98 g、甲苯250 g，氮氣置換三次後，加入三叔丁基膦2.64 g、催化劑Pd ₂(dba) ₃0.264 g。升溫回流，回流溫度約110℃。加入甲苯約100 mL、水100 mL，升溫至60-70℃，趁熱分液，除去水相。有機相用約5%的鹽酸洗滌三次，每次用量約100 mL，再水洗至中性，除去水相。有機相濃縮至較稠體系，約100 mL體積。再用約150 mL甲醇析晶，降溫至室溫(25℃及以下均可)，經過濾後得黃色化合物 3共32 g。 化合物 10 的製備方法

化合物 10反應器中加入中間體 A145.2 g、N-苯基-2-二苯並呋喃40 g、甲苯500 mL通氮氣回流1小時。降溫至35℃度加入叔丁醇鈉17 g、催化劑Pd ₂(dba) ₃452 mg、三叔丁基膦甲苯溶液5.4 g。氮氣置換後，保證氮氣流持續通入，回流反應4 hr。先降溫後以矽膠短柱(50 g)處理，甲苯淋洗至TLC監測產品點較弱，加水(300 mL*3)萃取，濾液濃縮至100 mL後，控溫80℃下緩慢加入1000 mL正庚烷。當有大量固體析出時，降至室溫，經過濾後得化合物 10共70 g。 The preparation process of compound 1-3 is prepared according to the following reaction formula 1 and the following steps. [Reaction formula 1]

Preparation method of intermediates A1 and A2 Take 10 g of 2,2'-tert-butyl-9,9'-spirobifluorene and 100 mL of acetic acid into a 500 mL reaction flask. Add 10 mL of bromine water under ice bath and return to room temperature to react for 4 hours after the addition is complete. Dilute with water and extract with ethyl acetate. Separate the organic layer, dry with anhydrous sodium sulfate, and concentrate under reduced pressure, and purify and isolate 7 g of Intermediate A1 and 3 g of Intermediate A2 with a silica gel column. Preparation method of compound 1

Compound 1 was added to a 1 L three-necked flask, followed by Intermediate A1 : 26.15g, diphenylamine: 16.59 g, sodium tert-butoxide: 9.85 g, and toluene 250 g. After nitrogen replacement for three times, add tri-tert-butyl phosphine: 2.09 g , Catalyst Pd ₂ (dba) ₃ : 0.209 g. Increase the temperature to reflux, and the reflux temperature is about 110°C. Add about 100 mL of toluene and 100 mL of water, raise the temperature to 60~70°C, separate the liquid while it is hot, and remove the water phase. The organic phase was washed three times with about 5% hydrochloric acid, with a dosage of about 100 mL each time. Then wash with water until it is neutral, remove the water phase, concentrate the organic phase to a thicker system with a volume of about 100 mL, then use about 150 mL of methanol to crystallize, cool to room temperature (25°C and below), and filter to obtain the compound 1 A total of 35.8 g. Preparation method of compound 2

The compound 2 reactor was charged with 45.2 g of intermediate A1 , 39 g of N-phenyl-4-biphenyl, and 500 mL of toluene and refluxed with nitrogen for 1 hour. Cool to 35°C and add 17 g of sodium tert-butoxide, catalyst Pd ₂ (dba) ₃ 452 mg, and 5.4 g of tri-tert-butylphosphine toluene solution. After nitrogen replacement, ensure the continuous flow of nitrogen flow and reflux for 4 hr. After lowering the temperature, treat with a short silica gel column (50 g), wash with toluene until the TLC monitoring product point is weak, add water (300 mL*3) for extraction, and then concentrate the filtrate to 100 mL, then slowly add 1000 mL positive at 80°C. Heptane. When a large amount of solid precipitated, it was cooled to room temperature, and 78 g of compound 2 was obtained after filtration. Preparation method of compound 3

Compound 3 was placed in a 1 L three-necked flask, and 26.37g of Intermediate A1 , 28.89 g of bis-(4-benzyl)amine, 9.98 g of sodium tert-butoxide, and 250 g of toluene were added in sequence. After nitrogen replacement for three times, tri-tert-butyl was added. Phosphine 2.64 g, catalyst Pd ₂ (dba) ₃ 0.264 g. Increase the temperature to reflux, and the reflux temperature is about 110°C. Add about 100 mL of toluene and 100 mL of water, increase the temperature to 60-70°C, separate the liquid while it is hot, and remove the water phase. The organic phase was washed three times with about 5% hydrochloric acid, with an amount of about 100 mL each time, and then washed with water to neutrality, and the water phase was removed. The organic phase is concentrated to a thicker system, about 100 mL in volume. Then use about 150 mL of methanol to crystallize, and cool to room temperature (25°C or below). After filtration, a total of 32 g of yellow compound 3 is obtained. Preparation method of compound 10

Add 45.2 g of Intermediate A1 , 40 g of N-phenyl-2-dibenzofuran, and 500 mL of toluene into the reactor of compound 10 and reflux with nitrogen for 1 hour. Cool to 35°C and add 17 g of sodium tert-butoxide, catalyst Pd ₂ (dba) ₃ 452 mg, and 5.4 g of tri-tert-butylphosphine toluene solution. After nitrogen replacement, ensure the continuous flow of nitrogen flow and reflux for 4 hr. After cooling down, it is treated with a short silica gel column (50 g). Toluene is eluted until the TLC monitoring product point is weak. Add water (300 mL*3) for extraction. After the filtrate is concentrated to 100 mL, slowly add 1000 mL positive Heptane. When a large amount of solids precipitated, the temperature was lowered to room temperature, and a total of 70 g of compound 10 was obtained after filtration.

> Application example 1>

Organic light emitting element

Referring to FIG. 1, the organic light emitting device of this application example 1 includes a substrate 80, an anode 10, a hole injection layer 20, a hole transport layer unit 30, a light emitting layer 40, an electron transport layer 50, and an electron injection Layer 60 and a cathode 70.

The anode 10 is located on the substrate 80, and the material is indium tin oxide (ITO) with a thickness of 1350 Å.

The hole injection layer 20 is located on the side of the anode 10 opposite to the substrate 80, has a thickness of 100 Å, and contains a P-type dopant compound (compound DP, purchased from Novaled) and a compound doped with 3% by volume. HT1 (purchased in Merck).

The hole transport layer unit 30 is located on a side of the hole injection layer 20 opposite to the anode 10, and includes a first hole transport layer 30a and a second hole transport layer 30b. The first hole transport layer 30a is located on a side of the hole injection layer 20 opposite to the anode 10, has a thickness of 1100 Å, and contains a compound HT1. The second hole transport layer 30b is located on the side of the first hole transport layer 30a opposite to the hole injection layer 20, has a thickness of 200 Å, and contains compound 1.

The light-emitting layer 40 is located on the side of the hole transport layer unit 30 opposite to the hole injection layer 20, has a thickness of 250 Å, and contains a 3% volume ratio light-emitting dopant BD (purchased from Idemitsu) and Light-emitting body BH (purchased from Idemitsu).

The electron transport layer 50 is located on the side of the light emitting layer 40 opposite to the hole transport layer unit 30, has a thickness of 250 Å, and contains a compound ET doped with 40% by volume of lithium quinolate (Liq) (purchased from Toray) .

The electron injection layer 60 is located on the side of the electron transport layer 50 opposite to the light emitting layer 40, has a thickness of 10 Å, and contains lithium fluoride (LiF).

The cathode 70 is located on the side of the electron injection layer 60 opposite to the electron transport layer 50, has a thickness of 1000 Å, and contains aluminum (Al).

The order of the layers in the organic light-emitting element of the present invention can also be reversed to that shown in FIG. 1. In the reverse structure, one or more layers can be added or removed as needed.

The organic light emitting element of Application Example 1 can be expressed as follows. ITO(1350Å)/DP:HT1(5%,200Å)/HT1(1100Å)/Compound 1 (100Å)/BD:BH(3%,250Å)/Liq:ET(40%,250Å)/LiF(10Å) /Al(1000Å)

> Application example 2~3 And comparative application examples 1>

Organic light emitting element

The organic light-emitting elements of Application Examples 2 to 3 and Comparative Application Example 1 are similar to Application Example 1, and the difference is that the hole injection layer 20 and the first hole transport layer 30a of Application Examples 1 to 3 and Comparative Application Example 1 It is different from the spiral bifluorene ring derivative used in the second hole transport layer 30b (sorted in Table 2 below). Table 2 Spiral Bifluorene Ring Derivatives Used Hole injection layer First hole transport layer Second hole transport layer Application example 1 Compound HT1 Compound HT1 Compound 1 Application example 2 Compound 3 Compound 3 Compound HT2 Application example 3 Compound 10 Compound 10 Compound HT2 Comparative application example 1 Compound HT1 Compound HT1 Compound HT2

The structures of compounds HT1, HT2, BH, BD and ET are as follows.

> Driving voltage and luminous efficiency of organic light-emitting elements >

The light-emitting properties of the organic light-emitting devices in Application Examples 1 to 3 and Comparative Application Example 1 were measured at room temperature. The resulting driving voltage (voltage) and luminous efficiency (Cd/A) are summarized in Table 3. table 3 Spiral double fluorene ring compound used Luminous properties Hole injection layer First hole transport layer Second hole transport layer voltage Cd/A Application example 1 Compound HT1 Compound HT1 Compound 1 +0.17V +5% Application example 2 Compound 3 Compound 3 Compound HT2 +0.00V +17% Application example 3 Compound 10 Compound 10 Compound HT2 +0.23V +17% Comparative application example 1 Compound HT1 Compound HT1 Compound HT2

It can be seen from Table 1 that when at least one of the hole injection layer and the hole transport layer in the organic light emitting element contains the third butylspiral bifluorene ring compound of the present invention (application examples 1 to 3), the organic light emitting element The increased luminous efficiency percentages are all greater than 0, that is, the luminous efficiency of the organic light-emitting device can be effectively improved.

In summary, since the third butylspiral bifluorene ring compound of the present invention has the structure shown in Chemical Formula I, and the organic light-emitting device of the present invention contains the third butylspiral bifluorene ring compound of the present invention, therefore, the present invention The luminous efficiency of the organic light-emitting element can be effectively improved, so it can indeed achieve the purpose of the invention.

However, the above are only examples of the present invention. When the scope of implementation of the present invention cannot be limited by this, all simple equivalent changes and modifications made in accordance with the scope of the patent application of the present invention and the content of the patent specification still belong to This invention patent covers the scope.

10: anode 20: Hole injection layer 30: Hole transport layer unit 30a: The first hole transmission layer 70: cathode 30b: The second hole transport layer 40: luminescent layer 50: electron transport layer 60: Electron injection layer 80: substrate

Other features and effects of the present invention will be clearly presented in the embodiments with reference to the drawings, in which: FIG. 1 is a schematic cross-sectional view illustrating the structure of the organic light emitting device of Application Example 1. FIG.

10: anode

30b: The second hole transport layer

20: Hole injection layer

40: luminescent layer

30: Hole transport layer unit

50: electron transport layer

30a: The first hole transmission layer

60: Electron injection layer

70: cathode

80: substrate

Claims (7)

A third butyl helical double fluorene ring compound, as shown in the following chemical formula I: [chemical formula I]

Wherein, R is hydrogen or ‒NR ¹ R ² ; and R ¹ and R ² are hydrogen, deuterium, substituted or unsubstituted C ₁ ~C ₃₀ alkyl, C ₁ ~C ₃₀ alkoxy, substituted Or unsubstituted C ₆ ~C ₃₀ aryl, substituted or unsubstituted C ₅ ~C ₃₀ heteroaryl, C ₃ ~C ₃₀ cycloalkyl, C ₅ ~C ₇ heterocycloalkyl, tri-C ₁ ~C ₃₀ alkylsilyl group, tri-C ₆ ~C ₃₀ arylsilyl group, two C ₁ ~C ₃₀ alkyl group, C ₆ ~C ₃₀ arylsilyl group, C ₁ ~C ₃₀ alkyl group, two C ₆ ~C ₃₀ arylsilyl group, C ₂ ~C ₃₀ alkenyl group, C ₂ ~C ₃₀ alkynyl group, cyano group, di C ₁ ~C ₃₀ alkylamino group, di C ₆ ~C ₃₀ aryl boron group or di C ₁ ~C ₃₀ Alkyl Boronyl. The third butyl helical bifluorene ring compound according to claim 1, wherein R ¹ and R ² are respectively substituted or unsubstituted C ₆ to C ₃₀ aryl groups, or substituted or unsubstituted C ₅ ~C ₃₀ heteroaryl. The third butyl helical bifluorene ring compound according to claim 2, wherein R ¹ and R ² are respectively

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. The third butyl helical double fluorene ring compound according to claim 3, wherein the third butyl helical double fluorene ring compound is

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. An organic light-emitting element comprising the third butyl helical bifluorene ring compound according to claim 1. The organic light emitting device according to claim 5, wherein the organic light emitting device comprises a substrate, an anode on the substrate, a hole injection layer on a side of the anode opposite to the substrate, and a hole injection layer on the side of the substrate. The hole injection layer is opposite to the hole transport layer unit on one side of the anode, a light emitting layer is located on the side of the hole transport layer unit opposite to the hole injection layer, and one is located on the light emitting layer opposite to the hole transport An electron transport layer on one side of the layer unit, an electron injection layer on the side of the electron transport layer opposite to the light-emitting layer, and a cathode on the side of the electron injection layer opposite to the electron transport layer, wherein, The hole transport layer unit includes at least two hole transport layers, and at least one of the hole injection layer and the hole transport layers contains the third butyl helical bifluorene ring compound. The organic light-emitting device according to claim 6, wherein the hole injection layer further contains a P-type doping compound.

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